goreamarrerorealestate.com Search Results

$699,000

End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

3 Beds ⋅ 3 Baths ⋅ 1046647 MLS

End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

49 Millstream Court, Pawling

$695,000

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

4 Beds ⋅ 2 Baths ⋅ 1047901 MLS

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$995,000

Set on over 3 beautiful acres, this spacious 4-bedroom, 3-full-bath home offers an impressive blend of classic character, generous living spaces, and modern conveniences. A welcoming wraparound front porch leads to a grand entry foyer with an open staircase and views to the second floor. The main level features a formal Living Room and Dining Room, both enhanced by large bowed windows, along with a comfortable front Sitting Room. The heart of the home is the expansive eat-in Kitchen, complete with center island, stainless steel appliances, and sliding glass doors leading to the rear deck. A spectacular Great Room boasts soaring ceilings, a fireplace, and additional sliders to the deck, creating an ideal space for entertaining or relaxing. A front mudroom entry, convenient Laundry Room, full tiled Bath with walk-in shower, and hardwood floors throughout complete the main level. The oversized garage offers both a double and single garage door for exceptional parking and storage. Upstairs, three spacious Bedrooms feature hardwood floors and double-door closets. The luxurious Primary Suite offers vaulted ceilings, beautiful bowed front windows, his-and-hers walk-in closets, a large linen closet, and a massive Primary Bath with dual vanities, Jacuzzi tub, and walk-in shower. A large Bonus Room with hardwood floors provides flexible space for an office, media room, playroom, or additional living area. The open upper hallway overlooks the Great Room below, adding to the home's dramatic sense of space. Additional highlights include an expansive unfinished basement, walk-up attic, central air, and central vacuum. Set amid peaceful acreage with plenty of room to enjoy the outdoors, this exceptional home offers space, privacy, and versatility both inside and out.

4 Beds ⋅ 3 Baths ⋅ 1045580 MLS

Set on over 3 beautiful acres, this spacious 4-bedroom, 3-full-bath home offers an impressive blend of classic character, generous living spaces, and modern conveniences. A welcoming wraparound front porch leads to a grand entry foyer with an open staircase and views to the second floor. The main level features a formal Living Room and Dining Room, both enhanced by large bowed windows, along with a comfortable front Sitting Room. The heart of the home is the expansive eat-in Kitchen, complete with center island, stainless steel appliances, and sliding glass doors leading to the rear deck. A spectacular Great Room boasts soaring ceilings, a fireplace, and additional sliders to the deck, creating an ideal space for entertaining or relaxing. A front mudroom entry, convenient Laundry Room, full tiled Bath with walk-in shower, and hardwood floors throughout complete the main level. The oversized garage offers both a double and single garage door for exceptional parking and storage. Upstairs, three spacious Bedrooms feature hardwood floors and double-door closets. The luxurious Primary Suite offers vaulted ceilings, beautiful bowed front windows, his-and-hers walk-in closets, a large linen closet, and a massive Primary Bath with dual vanities, Jacuzzi tub, and walk-in shower. A large Bonus Room with hardwood floors provides flexible space for an office, media room, playroom, or additional living area. The open upper hallway overlooks the Great Room below, adding to the home's dramatic sense of space. Additional highlights include an expansive unfinished basement, walk-up attic, central air, and central vacuum. Set amid peaceful acreage with plenty of room to enjoy the outdoors, this exceptional home offers space, privacy, and versatility both inside and out.

139 S Harmony Road, Pawling

$800,000

Set above Whaley Lake, this beautiful 3 bedroom and 2 bathroom rustic contemporary woodland retreat is ready for its next chapter. There are so many opportunities to be had at this property with almost 7 private acres, lake access, and hiking trails! The possibilities are endless. The large back deck is perfect for entertaining or just simply relaxing. The family room views of the lake provide calm and serenity. The lower level is the perfect space for a movie room or play room. A commuters dream with close proximity to 84 and the MTA train line, you get peace and privacy without being too far from NYC! Original classic features and many recent upgrades like a 6 year old roof and new well pump, this property is ready for you to call it home!

3 Beds ⋅ 2 Baths ⋅ 1045275 MLS

Set above Whaley Lake, this beautiful 3 bedroom and 2 bathroom rustic contemporary woodland retreat is ready for its next chapter. There are so many opportunities to be had at this property with almost 7 private acres, lake access, and hiking trails! The possibilities are endless. The large back deck is perfect for entertaining or just simply relaxing. The family room views of the lake provide calm and serenity. The lower level is the perfect space for a movie room or play room. A commuters dream with close proximity to 84 and the MTA train line, you get peace and privacy without being too far from NYC! Original classic features and many recent upgrades like a 6 year old roof and new well pump, this property is ready for you to call it home!

1095 Route 292, Holmes

$599,000

Set on over an acre and a half of pure enchantment, this charming predominantly one-level ranch-style home offers thoughtfully designed living space in a private and whimsical setting. A long paved driveway leads to the home, which sits high and well back from the road, creating a sense of seclusion from the moment you arrive. The backyard is truly an oasis, surrounded by lush landscaping, vibrant perennial gardens framed by a stone wall, and a recently renovated Lazy L heated inground pool. Whether envisioned as a weekend getaway or year-round sanctuary, this property offers outdoor living and relaxation at its finest. While the home presents a modest profile from the outside, the interior reveals a stylishly renovated kitchen featuring a center island with seating, crisp white cabinetry, quartz countertops, stainless steel gas range, refrigerator, dishwasher and microwave, subway tile backsplash, abundant storage, floating shelves, and a charming picture window with bench seating and storage below. The view of the pool from the kitchen is so picturesque, it feels like a living work of art. A wide hallway leads to an intimate dining room and a dramatic living room with vaulted ceiling and corner fireplace surrounded by stone. Another hallway leads to two bedrooms, including a comfortable second bedroom with pool views and a serene primary suite. The primary bedroom features French doors opening to a private deck, a bath with potential to expand by incorporating space from the adjacent walk-in closet, and three additional closets. A recently renovated hall bath with walk-in shower, full-size stacked washer and dryer tucked into a convenient laundry closet, and five additional closets of varying sizes complete the main level. From the living room, steps lead to a private third bedroom with charming sloped ceilings. Outside, the magic truly unfolds. The deck off the kitchen is an inviting spot for morning coffee, al fresco dining, or sunset cocktails. The heated inground pool is surrounded by a spacious patio finished with an exceptional concrete coating system, offering plenty of room for lounge chairs and patio furnishings. A stone patio provides the perfect setting for the gazebo, furnished for relaxing and entertaining. Beyond the gate, a custom circular fire pit creates a wonderful gathering place beneath the stars. The pool area is thoughtfully fenced, while a detached one-car garage and separate shed provide additional storage for gardening tools and equipment. Just under four miles from the charming Village of Pawling, you'll have easy access to fine dining, casual eateries, boutique shops, pubs, and the seasonal farmers market. Outdoor enthusiasts will appreciate nearby Lakeside Park, Pawling's town park, the Appalachian Trail, and the Dutchess Rail Trail, now conveniently accessible via the newly completed connector. Golf enthusiasts can choose between the public Dutcher Golf Course and the private Quaker Hill Country Club. For commuters, the Pawling Metro-North station is less than 10 minutes away, providing an approximately 90-minute train ride to New York City. A captivating private retreat with exceptional outdoor living, this enchanting property offers the perfect blend of tranquility, style, and convenience. Be sure to click the virtual tour icon and use your mouse to experience a full 360-degree tour of the sensational backyard and pool area.

3 Beds ⋅ 2 Baths ⋅ 1042803 MLS

Set on over an acre and a half of pure enchantment, this charming predominantly one-level ranch-style home offers thoughtfully designed living space in a private and whimsical setting. A long paved driveway leads to the home, which sits high and well back from the road, creating a sense of seclusion from the moment you arrive. The backyard is truly an oasis, surrounded by lush landscaping, vibrant perennial gardens framed by a stone wall, and a recently renovated Lazy L heated inground pool. Whether envisioned as a weekend getaway or year-round sanctuary, this property offers outdoor living and relaxation at its finest. While the home presents a modest profile from the outside, the interior reveals a stylishly renovated kitchen featuring a center island with seating, crisp white cabinetry, quartz countertops, stainless steel gas range, refrigerator, dishwasher and microwave, subway tile backsplash, abundant storage, floating shelves, and a charming picture window with bench seating and storage below. The view of the pool from the kitchen is so picturesque, it feels like a living work of art. A wide hallway leads to an intimate dining room and a dramatic living room with vaulted ceiling and corner fireplace surrounded by stone. Another hallway leads to two bedrooms, including a comfortable second bedroom with pool views and a serene primary suite. The primary bedroom features French doors opening to a private deck, a bath with potential to expand by incorporating space from the adjacent walk-in closet, and three additional closets. A recently renovated hall bath with walk-in shower, full-size stacked washer and dryer tucked into a convenient laundry closet, and five additional closets of varying sizes complete the main level. From the living room, steps lead to a private third bedroom with charming sloped ceilings. Outside, the magic truly unfolds. The deck off the kitchen is an inviting spot for morning coffee, al fresco dining, or sunset cocktails. The heated inground pool is surrounded by a spacious patio finished with an exceptional concrete coating system, offering plenty of room for lounge chairs and patio furnishings. A stone patio provides the perfect setting for the gazebo, furnished for relaxing and entertaining. Beyond the gate, a custom circular fire pit creates a wonderful gathering place beneath the stars. The pool area is thoughtfully fenced, while a detached one-car garage and separate shed provide additional storage for gardening tools and equipment. Just under four miles from the charming Village of Pawling, you'll have easy access to fine dining, casual eateries, boutique shops, pubs, and the seasonal farmers market. Outdoor enthusiasts will appreciate nearby Lakeside Park, Pawling's town park, the Appalachian Trail, and the Dutchess Rail Trail, now conveniently accessible via the newly completed connector. Golf enthusiasts can choose between the public Dutcher Golf Course and the private Quaker Hill Country Club. For commuters, the Pawling Metro-North station is less than 10 minutes away, providing an approximately 90-minute train ride to New York City. A captivating private retreat with exceptional outdoor living, this enchanting property offers the perfect blend of tranquility, style, and convenience. Be sure to click the virtual tour icon and use your mouse to experience a full 360-degree tour of the sensational backyard and pool area.

140 Hurds Corners Road, Pawling

$655,000

Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

3 Beds ⋅ 3 Baths ⋅ 1041481 MLS

Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

12 Rebecca Drive, Pawling

$589,000

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 1037637 MLS

Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$1,400,000

Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.

4 Beds ⋅ 3 Baths ⋅ 1037768 MLS

Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.

392 Old Quaker Hill Road, Pawling

$639,000

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

4 Beds ⋅ 4 Baths ⋅ 1035919 MLS

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

3846 Route 55, Pawling

$525,000

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

3 Beds ⋅ 3 Baths ⋅ 1033232 MLS

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

66 Reservoir Road, Pawling

$225,000

Discover the opportunity to build your custom home on this exceptional 8.44-acre homesite in Brady Brook Falls, an established community of estate properties nestled in Pawling's scenic countryside. Offering a beautiful mix of open areas and mature woodlands, the property provides a peaceful setting with plenty of space to create the home you've envisioned. Much of the preparation has already been completed, making it easy to begin your project. The lot is ready to build with an approved site plan, Board of Health approval for a septic system, and building plans that have already been approved by the HOA Architectural Review Committee. Buyers may choose to use the approved plans or submit their own custom design for architectural review. Residents of Brady Brook Falls enjoy approximately 100 acres of shared open space with trails for walking, hiking, and other passive outdoor recreation, creating a unique balance of natural beauty and thoughtfully planned community living. This property requires no fill for septic and is fully staked out including septic, well and driveway. Conveniently located just minutes from the Village of Pawling, you'll enjoy easy access to charming shops, restaurants, the seasonal farmers market, golf courses, and the Metro-North train station, offering a convenient connection to New York City. Whether you're ready to build immediately or planning for the future, this is a rare opportunity to own one of the area's premier building lots with valuable approvals already in place.

1029622 MLS

Discover the opportunity to build your custom home on this exceptional 8.44-acre homesite in Brady Brook Falls, an established community of estate properties nestled in Pawling's scenic countryside. Offering a beautiful mix of open areas and mature woodlands, the property provides a peaceful setting with plenty of space to create the home you've envisioned. Much of the preparation has already been completed, making it easy to begin your project. The lot is ready to build with an approved site plan, Board of Health approval for a septic system, and building plans that have already been approved by the HOA Architectural Review Committee. Buyers may choose to use the approved plans or submit their own custom design for architectural review. Residents of Brady Brook Falls enjoy approximately 100 acres of shared open space with trails for walking, hiking, and other passive outdoor recreation, creating a unique balance of natural beauty and thoughtfully planned community living. This property requires no fill for septic and is fully staked out including septic, well and driveway. Conveniently located just minutes from the Village of Pawling, you'll enjoy easy access to charming shops, restaurants, the seasonal farmers market, golf courses, and the Metro-North train station, offering a convenient connection to New York City. Whether you're ready to build immediately or planning for the future, this is a rare opportunity to own one of the area's premier building lots with valuable approvals already in place.

14 Akindale Road, Pawling

$249,000

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1 Beds ⋅ 1 Baths ⋅ 1031078 MLS

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1555 Route 292, Holmes

$1,475,000

**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

4 Beds ⋅ 5 Baths ⋅ 1029458 MLS

**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

7 Herd And Tanner Road, Holmes

$749,900

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

4 Beds ⋅ 4 Baths ⋅ 1029051 MLS

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

26 E Forest Trail, Holmes

$1,150,000

Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings. Designed with today's lifestyle in mind, the open-concept floor plan is filled with natural light and offers an effortless flow for both everyday living and entertaining. At the heart of the home, the dramatic vaulted family room with a gas fireplace opens to a sun-filled eat-in kitchen featuring a large center island, abundant cabinetry, and direct access to a covered porch—creating the perfect setting for seamless indoor-outdoor living. The thoughtfully designed main-level primary suite is privately situated away from the secondary bedrooms and offers a luxurious escape with a spacious walk-in closet and spa-inspired bath. Two additional bedrooms and a full bath complete the first floor, although the floor plan can easily be customized to create a second primary suite with a sitting area, accommodate multi-generational living, or provide dedicated home office space. The second level expands the home's versatility with plans for a fourth bedroom, full bath, an optional fifth bedroom or office, and a generous bonus room ideal as a media room, fitness studio, recreation room, playroom, or additional living space. The flexibility of the design allows you to tailor the home to your lifestyle. Quality finishes include hardwood flooring, high ceilings, energy-efficient insulation, central air conditioning, a welcoming Trex front porch, and an attached three-car garage. Although privately tucked away, the property is just minutes from the charming Village of Pawling, Metro-North, shopping, restaurants, major commuter routes, and the area's many hiking trails, golf courses, and cultural attractions. Whether you're searching for a full-time residence or a refined country retreat, this exceptional to-be-built home presents a rare opportunity to create a custom residence where privacy, elegance, and convenience come together. Photos include virtual renderings and images of a recently completed similar home and are for illustrative purposes only. Finishes, specifications, and features are subject to change during construction.

5 Beds ⋅ 4 Baths ⋅ 1024239 MLS

Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings. Designed with today's lifestyle in mind, the open-concept floor plan is filled with natural light and offers an effortless flow for both everyday living and entertaining. At the heart of the home, the dramatic vaulted family room with a gas fireplace opens to a sun-filled eat-in kitchen featuring a large center island, abundant cabinetry, and direct access to a covered porch—creating the perfect setting for seamless indoor-outdoor living. The thoughtfully designed main-level primary suite is privately situated away from the secondary bedrooms and offers a luxurious escape with a spacious walk-in closet and spa-inspired bath. Two additional bedrooms and a full bath complete the first floor, although the floor plan can easily be customized to create a second primary suite with a sitting area, accommodate multi-generational living, or provide dedicated home office space. The second level expands the home's versatility with plans for a fourth bedroom, full bath, an optional fifth bedroom or office, and a generous bonus room ideal as a media room, fitness studio, recreation room, playroom, or additional living space. The flexibility of the design allows you to tailor the home to your lifestyle. Quality finishes include hardwood flooring, high ceilings, energy-efficient insulation, central air conditioning, a welcoming Trex front porch, and an attached three-car garage. Although privately tucked away, the property is just minutes from the charming Village of Pawling, Metro-North, shopping, restaurants, major commuter routes, and the area's many hiking trails, golf courses, and cultural attractions. Whether you're searching for a full-time residence or a refined country retreat, this exceptional to-be-built home presents a rare opportunity to create a custom residence where privacy, elegance, and convenience come together. Photos include virtual renderings and images of a recently completed similar home and are for illustrative purposes only. Finishes, specifications, and features are subject to change during construction.

Lot 5 A S White Rock Road, Holmes

$879,800

Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Once a horse farm, this unique home offers enchanting landscapes that surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... 08/26 New Sub-Zero state of the art Cove dishwasher, 2 year warranty. Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

3 Beds ⋅ 3 Baths ⋅ 1021432 MLS

Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Once a horse farm, this unique home offers enchanting landscapes that surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... 08/26 New Sub-Zero state of the art Cove dishwasher, 2 year warranty. Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

57 S White Rock Road, Holmes

$629,900

**Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC*** Featuring a brand new roof, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the Hudson Valley has to offer. Are you a runner or a walker? This house in conveniently located moments from the local rail trail as well! Swings set and soccer nets in the backyard are a welcoming site to the kiddos. Sellers used to have a pool on the right side of the home. Electric still exists. Inside, you’ll find gleaming hardwood floors, elegant crown molding, two fireplaces, and central air. The thoughtfully designed kitchen features concrete countertops, tile flooring, radiant heat floors in the kitchen and mudroom, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. BRAND NEW ROOF! The screened-in porch is the perfect place to enjoy morning coffee or unwind while overlooking the lake. A spacious open-air deck provides even more room for barbecues, outdoor dining, and entertaining. Gather around your private fire pit or enjoy the community fire pit with neighbors and friends. Reserve the community pavilion for your own lake front party while the kids play in the water and build sandcastles. Sunset Lake residents also enjoy access to a private sandy community beach and pavilion. Spend summer days swimming, fishing, kayaking, or paddleboarding, then enjoy ice skating when winter transforms the lake. The property also offers the potential for a private dock, subject to applicable community and municipal approvals. An invisible fenced yard provides a secure outdoor space for pets, while high-speed internet makes working from home easy. The attached two-car garage offers plenty of room for vehicles, kayaks, paddleboards, and other recreational equipment. Located in the Pawling School District and just minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking trails, golf courses, wineries, breweries, farms, and Interstate 84. Whether you’re searching for a year-round home or a weekend escape, 45 Willow Lake offers the opportunity to enjoy lakefront living in every season. Some photos have been virtually edited.

3 Beds ⋅ 3 Baths ⋅ 1017740 MLS

**Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC*** Featuring a brand new roof, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the Hudson Valley has to offer. Are you a runner or a walker? This house in conveniently located moments from the local rail trail as well! Swings set and soccer nets in the backyard are a welcoming site to the kiddos. Sellers used to have a pool on the right side of the home. Electric still exists. Inside, you’ll find gleaming hardwood floors, elegant crown molding, two fireplaces, and central air. The thoughtfully designed kitchen features concrete countertops, tile flooring, radiant heat floors in the kitchen and mudroom, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. BRAND NEW ROOF! The screened-in porch is the perfect place to enjoy morning coffee or unwind while overlooking the lake. A spacious open-air deck provides even more room for barbecues, outdoor dining, and entertaining. Gather around your private fire pit or enjoy the community fire pit with neighbors and friends. Reserve the community pavilion for your own lake front party while the kids play in the water and build sandcastles. Sunset Lake residents also enjoy access to a private sandy community beach and pavilion. Spend summer days swimming, fishing, kayaking, or paddleboarding, then enjoy ice skating when winter transforms the lake. The property also offers the potential for a private dock, subject to applicable community and municipal approvals. An invisible fenced yard provides a secure outdoor space for pets, while high-speed internet makes working from home easy. The attached two-car garage offers plenty of room for vehicles, kayaks, paddleboards, and other recreational equipment. Located in the Pawling School District and just minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking trails, golf courses, wineries, breweries, farms, and Interstate 84. Whether you’re searching for a year-round home or a weekend escape, 45 Willow Lake offers the opportunity to enjoy lakefront living in every season. Some photos have been virtually edited.

45 Willow Lake Drive, Holmes

$425,000

$174K PRICE IMPROVEMENT!! Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an exclusive island co-op community where properties seldom become available. From the moment you leave the mainland behind and cruise across the sparkling waters to your own private dock, you'll experience a level of peace, privacy, and seclusion that is nearly impossible to find in today's world. Surrounded by panoramic lake views and embraced by nature, this charming island getaway captures the essence of lakefront living at its finest. Wake each morning to shimmering sunrises dancing across the water, spend your days boating, swimming, fishing, or simply relaxing lakeside, and unwind in the evening as spectacular sunsets paint the sky in brilliant colors reflected across the lake's glassy surface. Inside, the home exudes warmth, comfort, and timeless lake-house charm. Thoughtfully designed for both relaxation and entertaining, the residence features two bedrooms, a spacious sleeping loft, and two beautifully renovated full bathrooms. Comfortable gathering spaces invite friends to create lasting memories, while expansive lake views serve as the backdrop to nearly every moment. Whaley Lake is one of Dutchess County's premier motorboat lakes, offering endless recreational opportunities and year-round natural beauty. Located less than 90 miles from New York City, this unique property provides the perfect weekend sanctuary, summer retreat, or lifestyle investment for those seeking a truly one-of-a-kind waterfront experience. As an added bonus, the home is being offered almost fully furnished, allowing you to begin enjoying island life immediately. Opportunities of this caliber are extraordinarily rare. This isn't simply a home—it's a lifestyle, a retreat, and a legacy property that offers an experience few will ever have the chance to own. Schedule your private showing today and discover why life on Whaley Lake is unlike anywhere else. Seller financing feasible!

2 Beds ⋅ 2 Baths ⋅ 1011452 MLS

$174K PRICE IMPROVEMENT!! Welcome to one of the Hudson Valley's most extraordinary hidden treasures—a private island retreat nestled in the heart of Whaley Lake, where every day feels like a vacation and every arrival feels like an escape from the ordinary. Accessible only by boat, this remarkable waterfront residence offers an exceptionally rare opportunity to own a piece of paradise within an exclusive island co-op community where properties seldom become available. From the moment you leave the mainland behind and cruise across the sparkling waters to your own private dock, you'll experience a level of peace, privacy, and seclusion that is nearly impossible to find in today's world. Surrounded by panoramic lake views and embraced by nature, this charming island getaway captures the essence of lakefront living at its finest. Wake each morning to shimmering sunrises dancing across the water, spend your days boating, swimming, fishing, or simply relaxing lakeside, and unwind in the evening as spectacular sunsets paint the sky in brilliant colors reflected across the lake's glassy surface. Inside, the home exudes warmth, comfort, and timeless lake-house charm. Thoughtfully designed for both relaxation and entertaining, the residence features two bedrooms, a spacious sleeping loft, and two beautifully renovated full bathrooms. Comfortable gathering spaces invite friends to create lasting memories, while expansive lake views serve as the backdrop to nearly every moment. Whaley Lake is one of Dutchess County's premier motorboat lakes, offering endless recreational opportunities and year-round natural beauty. Located less than 90 miles from New York City, this unique property provides the perfect weekend sanctuary, summer retreat, or lifestyle investment for those seeking a truly one-of-a-kind waterfront experience. As an added bonus, the home is being offered almost fully furnished, allowing you to begin enjoying island life immediately. Opportunities of this caliber are extraordinarily rare. This isn't simply a home—it's a lifestyle, a retreat, and a legacy property that offers an experience few will ever have the chance to own. Schedule your private showing today and discover why life on Whaley Lake is unlike anywhere else. Seller financing feasible!

1616 Route 292 Unit #Cottage 12, Holmes

$260,000

Build Your Dream Estate in the Heart of the Hudson Valley-Lot 5 Set amidst the natural beauty of the Hudson Valley, this exceptional 11+ acre residential parcel offers a rare opportunity to create a private luxury retreat just 75 minutes from New York City. Ideally situated between the village of Pawling and Sherman, CT, the property combines peaceful country living with convenient access to Metro-North, boutique shopping, fine dining, farmers markets, hiking trails, historic attractions, major highways, and everyday conveniences. Recently cleared and approved by the Board of Health for a 5-bedroom residence, this expansive parcel provides an ideal setting for a custom-built home. Level land providing ample space for outdoor living, recreation, gardens, or a pool create endless possibilities for designing a truly exceptional estate. For those seeking a seamless building experience, the current owners—respected local builders known for their quality craftsmanship and attention to detail—are available to assist. They can customize a home tailored to your lifestyle while helping navigate local zoning, permitting, and approval processes. Whether you're ready to break ground today or planning for the future, this premier Hudson Valley property presents a unique opportunity to build the home you've always imagined in a most desirable location.

1012082 MLS

Build Your Dream Estate in the Heart of the Hudson Valley-Lot 5 Set amidst the natural beauty of the Hudson Valley, this exceptional 11+ acre residential parcel offers a rare opportunity to create a private luxury retreat just 75 minutes from New York City. Ideally situated between the village of Pawling and Sherman, CT, the property combines peaceful country living with convenient access to Metro-North, boutique shopping, fine dining, farmers markets, hiking trails, historic attractions, major highways, and everyday conveniences. Recently cleared and approved by the Board of Health for a 5-bedroom residence, this expansive parcel provides an ideal setting for a custom-built home. Level land providing ample space for outdoor living, recreation, gardens, or a pool create endless possibilities for designing a truly exceptional estate. For those seeking a seamless building experience, the current owners—respected local builders known for their quality craftsmanship and attention to detail—are available to assist. They can customize a home tailored to your lifestyle while helping navigate local zoning, permitting, and approval processes. Whether you're ready to break ground today or planning for the future, this premier Hudson Valley property presents a unique opportunity to build the home you've always imagined in a most desirable location.

Lot 5 S White Rock Road, Holmes

$1,199,000

Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living space 1 bedroom, living room and a full bathroom above. Inside, much of the home’s original character remains with hardwood floors, crown molding, fireplaces, and hidden staircases throughout. The inviting main level features a quiet library or office with fireplace, a bright sunroom overlooking the yard and patio, a spacious living room with fireplace, and a large dining room ideal for entertaining. The kitchen is ready for your personal vision. Upstairs offers 4 unique guest bedrooms along with a spacious Primary Suite featuring hardwood floors, private staircase, large bath, and ample closet space. With room for horses, gardens, or simply enjoying the beauty and privacy of the outdoors, this special property is full of opportunity and old-world character.

5 Beds ⋅ 4 Baths ⋅ 1010537 MLS

Welcome to country living at its finest. Set on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential and timeless charm. A long tree-lined driveway leads to the 4 bedroom, 4 bathroom home surrounded by open fields, mature trees, and peaceful countryside views. The property includes a spacious 5-car garage (3 in front and additional 2 car tandum in back) with finished living space 1 bedroom, living room and a full bathroom above. Inside, much of the home’s original character remains with hardwood floors, crown molding, fireplaces, and hidden staircases throughout. The inviting main level features a quiet library or office with fireplace, a bright sunroom overlooking the yard and patio, a spacious living room with fireplace, and a large dining room ideal for entertaining. The kitchen is ready for your personal vision. Upstairs offers 4 unique guest bedrooms along with a spacious Primary Suite featuring hardwood floors, private staircase, large bath, and ample closet space. With room for horses, gardens, or simply enjoying the beauty and privacy of the outdoors, this special property is full of opportunity and old-world character.

64 S Quaker Hill Road, Pawling

$1,350,000

Multi-generational housing opportunity with 3 distinctly different homes on one property providing plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well. Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with abundant light, Formal Dining Room with chair rail accent and beautiful chandelier. Eat in Kitchen with center island, Bosch oven, stainless steel appliances with breakfast nook and bay window. Convenient First floor laundry with 2nd laundry on lower level. Sunroom with tile floor and fireplace. Primary Bedroom Suite with two walk-in closets plus private bonus space could be nursery, craft area or small office. Primary En Suite Bathroom including jetted tub, shower with ceramic tile and double vanity. 2 generous sized bedrooms with ceiling fans and more than ample closet space. Full, walk out basement with kitchenette and 2 rooms to fit your personal lifestyle or In-law Suite. Outdoor living on both upper and lower deck areas with built-in benches for entertaining and enjoying a panoramic view. Unit B: Architecturally inviting 3 bedroom, fully renovated ranch style home. Living Room boasts a cathedral ceiling, hardwood floors, exposed brick & beams and abundant light. Stairway to loft space for kids hideaway, simple storage or use your imagination. Eat in Kitchen with recessed lights. All appliances and Washer/Dryer included. Primary Bedroom Suite with En Suite Bathroom – shower with ceramic tile and built in shelving. 2 additional bedrooms with hardwood floors, ceiling fans and great closet space. Spacious deck with built in bench for relaxing or entertaining. Unit C: Contemporary modular home that is almost brand new. Open concept Living Room and Kitchen with propane heated radiant floors to keep the living space warm and cozy. Gather around the oversized island for meals and conversation. First floor bedroom and full bathroom for often sought after one floor living. Laundry Room on 1st floor with full size washer/dryer. Second floor uses electric heat, hosts 3 bedrooms and den plus another full bathroom with tub/shower and double sinks, 2 good sized linen closets and attic access for additional storage. New boiler and gutters added to home in 2025. All this on a rolling grassy 3.8 acres with large open area and fire pit - consider a pool or other outdoor games and activities. 3 car garage with deck for grilling or congregating with huge loft space for all the additional storage you’ll need. If you have the vision, this is the one!

11 Beds ⋅ 8 Baths ⋅ 1004618 MLS

Multi-generational housing opportunity with 3 distinctly different homes on one property providing plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well. Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with abundant light, Formal Dining Room with chair rail accent and beautiful chandelier. Eat in Kitchen with center island, Bosch oven, stainless steel appliances with breakfast nook and bay window. Convenient First floor laundry with 2nd laundry on lower level. Sunroom with tile floor and fireplace. Primary Bedroom Suite with two walk-in closets plus private bonus space could be nursery, craft area or small office. Primary En Suite Bathroom including jetted tub, shower with ceramic tile and double vanity. 2 generous sized bedrooms with ceiling fans and more than ample closet space. Full, walk out basement with kitchenette and 2 rooms to fit your personal lifestyle or In-law Suite. Outdoor living on both upper and lower deck areas with built-in benches for entertaining and enjoying a panoramic view. Unit B: Architecturally inviting 3 bedroom, fully renovated ranch style home. Living Room boasts a cathedral ceiling, hardwood floors, exposed brick & beams and abundant light. Stairway to loft space for kids hideaway, simple storage or use your imagination. Eat in Kitchen with recessed lights. All appliances and Washer/Dryer included. Primary Bedroom Suite with En Suite Bathroom – shower with ceramic tile and built in shelving. 2 additional bedrooms with hardwood floors, ceiling fans and great closet space. Spacious deck with built in bench for relaxing or entertaining. Unit C: Contemporary modular home that is almost brand new. Open concept Living Room and Kitchen with propane heated radiant floors to keep the living space warm and cozy. Gather around the oversized island for meals and conversation. First floor bedroom and full bathroom for often sought after one floor living. Laundry Room on 1st floor with full size washer/dryer. Second floor uses electric heat, hosts 3 bedrooms and den plus another full bathroom with tub/shower and double sinks, 2 good sized linen closets and attic access for additional storage. New boiler and gutters added to home in 2025. All this on a rolling grassy 3.8 acres with large open area and fire pit - consider a pool or other outdoor games and activities. 3 car garage with deck for grilling or congregating with huge loft space for all the additional storage you’ll need. If you have the vision, this is the one!

750 Route 292, Holmes

$2,500,000

Nestled in a tranquil and picturesque setting, this exceptional equestrian facility offers everything a rider could desire, along with a beautiful home to live in. Spanning 21 acres of mostly open land, the property features expansive pastures enclosed by charming 3-board post and rail fencing. Equestrian amenities include a main barn with 8 spacious 12x12 stalls, each with individual water, a heated tack room, wash stall, feed and storage room, a half bath, and laundry facilities. The indoor also has an additional 6 stalls and two, double run-in sheds on the backside of the barn, that could easily be moved to one of the paddocks, if wanted. Above the barn, you'll find a large space perfect for a caretaker's apartment or viewing area and huge hayloft. The property also boasts a 72x160 indoor riding ring connected to the barn with new footing, a new roof and new LED lighting, as well as a 100x200 outdoor ring equipped with ESI footing, providing an ideal environment for year-round training. Six large paddocks and an another 3+ acres that could have additional paddocks added. The charming 4,000 sq. ft. farmhouse-style home, featuring 4 bedrooms and 3.5 bathrooms, overlooks the entire facility. The home is designed for comfort and luxury, with beautiful views from every window. Outside, enjoy an in-ground pool, an one bedroom apartment above the 3-car garage, a patio with a pergola, and breathtaking sunsets. This turnkey equestrian estate is conveniently located, with easy access to I-84/684, Metro North, and just 90 minutes from New York City. Rarely does a property of this caliber, combining world-class equestrian facilities and a luxurious home, become available. Whether you’re looking to train, ride, or simply enjoy a peaceful country lifestyle, this estate offers it all. Rare Opportunity to Expand to Nearly 125 Acres An extraordinary opportunity exists for a buyer to acquire this property together with the contiguous equestrian facility located at 42-45 Blackstone Ridge, Listing #1041154. Purchased together, the two properties would create a nearly 125-acre equestrian compound with an exceptional collection of facilities. The combined properties would offer two residences, two exceptional barns, approximately 31 stalls, an indoor riding arena, an outdoor riding arena with ESI footing, extensive paddocks and turnout, miles of riding trails, and a large pond, creating an exceptional foundation for a professional training and boarding operation, multi-disciplinary equestrian center, horseman's estate, or premier private equestrian compound. The ability to combine two contiguous, established equestrian properties of this caliber is extraordinarily rare. For the serious equestrian buyer, the combined offering provides remarkable scale, infrastructure, and flexibility while maintaining the privacy and character of a spectacular Hudson Valley estate. Whether purchased individually or together with 42-45 Blackstone Ridge, this is a once-in-a-lifetime opportunity to acquire a substantial equestrian property with the acreage, facilities, and infrastructure to support virtually limitless possibilities. Schedule a showing.

4 Beds ⋅ 4 Baths ⋅ 1003257 MLS

Nestled in a tranquil and picturesque setting, this exceptional equestrian facility offers everything a rider could desire, along with a beautiful home to live in. Spanning 21 acres of mostly open land, the property features expansive pastures enclosed by charming 3-board post and rail fencing. Equestrian amenities include a main barn with 8 spacious 12x12 stalls, each with individual water, a heated tack room, wash stall, feed and storage room, a half bath, and laundry facilities. The indoor also has an additional 6 stalls and two, double run-in sheds on the backside of the barn, that could easily be moved to one of the paddocks, if wanted. Above the barn, you'll find a large space perfect for a caretaker's apartment or viewing area and huge hayloft. The property also boasts a 72x160 indoor riding ring connected to the barn with new footing, a new roof and new LED lighting, as well as a 100x200 outdoor ring equipped with ESI footing, providing an ideal environment for year-round training. Six large paddocks and an another 3+ acres that could have additional paddocks added. The charming 4,000 sq. ft. farmhouse-style home, featuring 4 bedrooms and 3.5 bathrooms, overlooks the entire facility. The home is designed for comfort and luxury, with beautiful views from every window. Outside, enjoy an in-ground pool, an one bedroom apartment above the 3-car garage, a patio with a pergola, and breathtaking sunsets. This turnkey equestrian estate is conveniently located, with easy access to I-84/684, Metro North, and just 90 minutes from New York City. Rarely does a property of this caliber, combining world-class equestrian facilities and a luxurious home, become available. Whether you’re looking to train, ride, or simply enjoy a peaceful country lifestyle, this estate offers it all. Rare Opportunity to Expand to Nearly 125 Acres An extraordinary opportunity exists for a buyer to acquire this property together with the contiguous equestrian facility located at 42-45 Blackstone Ridge, Listing #1041154. Purchased together, the two properties would create a nearly 125-acre equestrian compound with an exceptional collection of facilities. The combined properties would offer two residences, two exceptional barns, approximately 31 stalls, an indoor riding arena, an outdoor riding arena with ESI footing, extensive paddocks and turnout, miles of riding trails, and a large pond, creating an exceptional foundation for a professional training and boarding operation, multi-disciplinary equestrian center, horseman's estate, or premier private equestrian compound. The ability to combine two contiguous, established equestrian properties of this caliber is extraordinarily rare. For the serious equestrian buyer, the combined offering provides remarkable scale, infrastructure, and flexibility while maintaining the privacy and character of a spectacular Hudson Valley estate. Whether purchased individually or together with 42-45 Blackstone Ridge, this is a once-in-a-lifetime opportunity to acquire a substantial equestrian property with the acreage, facilities, and infrastructure to support virtually limitless possibilities. Schedule a showing.

5 McCarthy Road, Holmes

$725,000

1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.

3 Beds ⋅ 2 Baths ⋅ 1001208 MLS

1564 Route 292 offers a rare opportunity to own a true lakefront retreat on Whaley Lake in the heart of the Hudson Valley. Set on an oversized parcel with adjacent open space that will never be built on, the property enjoys an uncommon sense of privacy and breathing room rarely found on the lake. The home underwent a major renovation and expansion in 2007, including the addition of a second-floor loft area and full bath, blending rustic lake house charm with modern functionality. A stylish kitchen renovation completed in 2019 adds updated finishes while maintaining the relaxed character of the home. One of the property’s standout features is the walk-out lower level, which opens directly to water level, creating an effortless connection to the lake for kayaking, swimming, entertaining, or simply enjoying the view. The setting feels tucked away and peaceful, yet remains accessible to Pawling, Metro-North, and the surrounding Hudson Valley destinations. Whether you’re looking for a weekend escape from the city or a year-round waterfront home, this is the kind of authentic lake property that rarely becomes available.

1564 Route 292, Holmes

$4,750,000

Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.

8 Beds ⋅ 13 Baths ⋅ 968589 MLS

Set high atop the storied crest of Quaker Hill, Elmwood Farm is a legacy estate where Hudson Valley history, architectural grandeur, and pastoral beauty converge. Approached by a long, winding gated drive, the property reveals itself gradually across 25.5 rolling acres before arriving at a striking Elizabethan style manor that has stood watch over the surrounding countryside for generations. Quaker Hill has long been known as one of the Hudson Valley’s most distinguished enclaves. For more than a century it has quietly attracted artists, writers, diplomats, and those seeking privacy, landscape, and a connection to history. Elmwood Farm stands among the hill’s most recognizable estates, shaped by generations of stewards who helped define the character of this remarkable hamlet. Owning Elmwood Farm is not simply about acquiring a home. It is about becoming part of the long story of Quaker Hill and carrying that legacy forward. The manor itself reflects the craftsmanship and romance of another era. Leaded glass windows cast soft light throughout the interior, while hand carved pilasters and hand painted plaster ceiling motifs reveal the artistry and attention to detail that defined the estate’s original design. Dramatic rooflines with carved timber fascia and Gothic inspired spires create a striking architectural silhouette that rises above the surrounding landscape. At the center of the home, a magnificent figured oak staircase ascends through the interior, its hand carved newel posts adorned with whimsical animal figures that speak to the individuality and charm of the residence. Gracious gathering rooms anchored by ten fireplaces provide spaces that feel both intimate and grand, equally suited for quiet evenings by the fire or lively gatherings with friends. A charming upper wing with hand painted storybook murals adds an unexpected and delightful layer of character that reflects the estate’s long and colorful history. Beyond the main residence, Elmwood Farm unfolds as a true country compound. The property includes two caretaker homes, a carriage house with groom’s quarters, a yoga studio, and a greenhouse, offering extraordinary flexibility for guests, staff, creative pursuits, or wellness focused living. The grounds themselves are equally compelling. Rolling lawns, mature trees, and sweeping views across the surrounding countryside create a sense of scale and serenity that is increasingly rare in today’s world. The landscape feels timeless, a place where mornings begin with mist rising over the hills and evenings conclude with golden sunsets stretching across the valley. For the next owner, Elmwood Farm offers something truly rare. It is an opportunity to become the next steward of one of Quaker Hill’s historic estates and to preserve a remarkable piece of Hudson Valley history while shaping its next chapter for generations to come.

618 Quaker Hill Road, Pawling

$629,900

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!

57 Buhleir Road, Pawling

$1,799,000

A Quintessential Quaker Hill Estate with Guest Cottage Perched atop the storied hills of Quaker Hill, this exceptional five-acre estate embodies the romance and elegance of country living at its finest. Privately nestled amid sweeping meadows, renowned equestrian properties, and grand country estates, 43 Meeting House Road offers a rare combination of exclusivity, beauty, and refined luxury just 90 minutes from Manhattan. Thoughtfully reimagined from its original log-home roots, the residence seamlessly blends timeless character with sophisticated modern design. Wide-plank oak floors, gracious entertaining spaces, a sunlit library, and a beautifully appointed chef's kitchen with radiant-heated floors and an oversized island create an atmosphere of effortless elegance. The luxurious primary suite is a retreat unto itself, with soaring 18-foot ceilings, skylights, and a Juliet balcony overlooking rolling lawns, mature specimen plantings, and the pastoral landscape beyond. Additional ensuite bedrooms and flexible living spaces provide exceptional comfort for family and guests. Designed for an elevated indoor-outdoor lifestyle, the estate is surrounded by sweeping lawns ideal for grand-scale outdoor entertaining, garden parties, and relaxed afternoons in the countryside. Expansive decks overlook a tranquil spring-fed pond, while the resort-inspired pool area, complete with cabana, bar, and bath, evokes the atmosphere of a private countryside club. Every detail has been curated for comfort and convenience, from whole-house generators serving both residences and a heated two-car garage to integrated Sonos audio, security systems, advanced climate control, and state-of-the-art connectivity. Enhancing the estate is a beautifully renovated and completely independent two-bedroom guest cottage. Featuring its own kitchen, fireplace, lofted living area, utilities, and septic system, it offers luxurious accommodations for guests, extended family, staff, or a private home office. Rarely does a property combine such privacy, sophistication, and natural beauty. One of Quaker Hill's most compelling offerings, this remarkable estate is a turnkey country sanctuary where sweeping lawns, resort-caliber amenities, and timeless elegance create an unparalleled retreat.

5 Beds ⋅ 6 Baths ⋅ 875119 MLS

A Quintessential Quaker Hill Estate with Guest Cottage Perched atop the storied hills of Quaker Hill, this exceptional five-acre estate embodies the romance and elegance of country living at its finest. Privately nestled amid sweeping meadows, renowned equestrian properties, and grand country estates, 43 Meeting House Road offers a rare combination of exclusivity, beauty, and refined luxury just 90 minutes from Manhattan. Thoughtfully reimagined from its original log-home roots, the residence seamlessly blends timeless character with sophisticated modern design. Wide-plank oak floors, gracious entertaining spaces, a sunlit library, and a beautifully appointed chef's kitchen with radiant-heated floors and an oversized island create an atmosphere of effortless elegance. The luxurious primary suite is a retreat unto itself, with soaring 18-foot ceilings, skylights, and a Juliet balcony overlooking rolling lawns, mature specimen plantings, and the pastoral landscape beyond. Additional ensuite bedrooms and flexible living spaces provide exceptional comfort for family and guests. Designed for an elevated indoor-outdoor lifestyle, the estate is surrounded by sweeping lawns ideal for grand-scale outdoor entertaining, garden parties, and relaxed afternoons in the countryside. Expansive decks overlook a tranquil spring-fed pond, while the resort-inspired pool area, complete with cabana, bar, and bath, evokes the atmosphere of a private countryside club. Every detail has been curated for comfort and convenience, from whole-house generators serving both residences and a heated two-car garage to integrated Sonos audio, security systems, advanced climate control, and state-of-the-art connectivity. Enhancing the estate is a beautifully renovated and completely independent two-bedroom guest cottage. Featuring its own kitchen, fireplace, lofted living area, utilities, and septic system, it offers luxurious accommodations for guests, extended family, staff, or a private home office. Rarely does a property combine such privacy, sophistication, and natural beauty. One of Quaker Hill's most compelling offerings, this remarkable estate is a turnkey country sanctuary where sweeping lawns, resort-caliber amenities, and timeless elegance create an unparalleled retreat.

41 and 43 Meeting House Road, Pawling

$14,995,000

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.

4 Beds ⋅ 4 Baths ⋅ 965662 MLS

Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct access to the OTA. The stunning equine compound is presided over by a circa 1860 main estate, masterfully renovated boasting 3,942 SF, 4 bedrooms, 4 bathrooms, 9 rooms, with an in-ground pool. Designed for year-round riding, training, and boarding indoors and out. With barns, indoor and outdoor rings all developed for the unique training needs for dressage, hunter-jumper, and polo. The main barn has 32 12' x12' stalls, center aisle, matted stalls, yoked windows, fire suppression system, automatic fly control system, climate-controlled tack room with kitchen and bathroom, feed storage, office and viewing room, bathrooms, 2 hot water wash stalls with heat lamps, 4 grooming stalls, hay loft with drop to each stall, and hay conveyor. An attached 200' x 90' indoor riding ring with equestrian sand with fiber footing, sound system, and retractable windows. Adjacent to the indoor, a 220' x 100' outdoor jumping ring and a 200' x 80' outdoor dressage ring. The second largest barn has 27 12' x 12'stalls, with a 200' x 90' indoor riding ring, and a 220' x 100' outdoor jumping ring with TraveLite dust free footings. The polo barn has 14 10' x 14' yoked stalls. The pony barn has 8 10' x 12' stalls and a fire suppression system. Buildings and additional structures on the property include a gated entry and guard house, manager's house, and a renovated barn, now a stylish clubhouse, which can accommodate up to 60 people with a fireplace, full kitchen and bathrooms, a 2-bedroom apartment above and a manager's office attached. A 3-bedroom, 4 bath cape cod guest house with tennis/basketball court. 3 1-bedroom guest cottages with thatched roofs. Groom quarters, equipment barn, fire suppression building with a 50,000 gallon underground water detention tank. Automatic hot-walker for horse conditioning. Wedding barn to host special events, 15 events a year, up to 120 guests. Boma outdoor BBQ area, skeet and trap range and helipad. For those looking to build another unparalleled estate, a homesite foundation exists with an infinity edge pool with the most sublime views. Additional features include 3 ponds on the property, judges and viewing gazebos, 2-week hay storage, irrigation systems, 3 generators, 7 wells, 7 septics, and 1 fire hydrant. Two parcels, 76-acres and 171-acres create this pastoral perfection in the heart of the Hudson Valley. This premier equestrian venue presents a truly remarkable opportunity just minutes to the Village of Pawling, a quaint upstate, bucolic 18th century village. The charming village offers fine dining, fun eateries, boutique shops, antique stores, cultural attractions and a seasonal farmer's market. Pawling has its very own Metro North station stop, just 90 minutes by train or car to NYC.

15 Kirby Hill Road, Pawling

$990,000

Currently being crafted by skilled local builders and now nearing completion, this distinguished rocking-chair-porch Colonial sits gracefully on more than nine private acres, offering an exceptional blend of elegance, comfort, and modern design. With construction in its final stages, there is still time for buyers to add select personal touches and make this exceptional new home uniquely their own. Bathed in natural light, the home showcases gleaming hardwood floors, nine-foot ceilings, and a sophisticated chef’s kitchen appointed with recessed lighting, granite countertops, and a large center island that invites both culinary creativity and effortless gathering. The formal dining room provides an elegant setting for memorable celebrations and intimate dinner parties. Just beyond the kitchen, an expansive, low-maintenance Trex deck extends the living space outdoors, connecting seamlessly to the enclosed side porch and backyard. It’s an ideal retreat for al fresco dining, morning coffee, entertaining, or simply savoring the peaceful beauty of the changing seasons. The family room offers a warm and inviting ambiance centered around the glow of a gas fireplace—perfect for relaxed evenings and cozy gatherings. The finished walkout lower level adds exceptional versatility, featuring laminate flooring, nine-foot ceilings, a full bath, and an energy-efficient mini-split system. Whether envisioned as a private office, fitness studio, media lounge, recreation space, or comfortable accommodations for guests, this flexible area adapts effortlessly to your lifestyle. Upstairs, three well-appointed bedrooms and a full hall bath accompany a serene primary suite designed as a private sanctuary. A walk-in closet and luxurious en-suite bath featuring a standalone soaking tub, large glass-enclosed shower, dual vanities, and separate water closet create a spa-like experience that elevates everyday living. Thoughtful amenities throughout include nine-foot ceilings, hardwood floors, Andersen windows, central air, abundant recessed lighting, foam and batt insulation, a two-car garage, paved driveway, and a handsome bluestone walkway that complements the home’s classic Colonial architecture. The setting offers the luxury of seclusion while remaining just minutes from the charming Village of Pawling, Metro-North, major routes, shopping, restaurants, and the many cultural and natural treasures of the historic Hudson Valley. Whether envisioned as a weekend escape or a year-round haven, this nearly completed new-construction Colonial offers the increasingly rare opportunity to enjoy a beautifully designed home while still having time to influence select finishing touches—creating a home where privacy, elegance, modern comfort, and convenience come together beautifully.

4 Beds ⋅ 4 Baths ⋅ 964060 MLS

Currently being crafted by skilled local builders and now nearing completion, this distinguished rocking-chair-porch Colonial sits gracefully on more than nine private acres, offering an exceptional blend of elegance, comfort, and modern design. With construction in its final stages, there is still time for buyers to add select personal touches and make this exceptional new home uniquely their own. Bathed in natural light, the home showcases gleaming hardwood floors, nine-foot ceilings, and a sophisticated chef’s kitchen appointed with recessed lighting, granite countertops, and a large center island that invites both culinary creativity and effortless gathering. The formal dining room provides an elegant setting for memorable celebrations and intimate dinner parties. Just beyond the kitchen, an expansive, low-maintenance Trex deck extends the living space outdoors, connecting seamlessly to the enclosed side porch and backyard. It’s an ideal retreat for al fresco dining, morning coffee, entertaining, or simply savoring the peaceful beauty of the changing seasons. The family room offers a warm and inviting ambiance centered around the glow of a gas fireplace—perfect for relaxed evenings and cozy gatherings. The finished walkout lower level adds exceptional versatility, featuring laminate flooring, nine-foot ceilings, a full bath, and an energy-efficient mini-split system. Whether envisioned as a private office, fitness studio, media lounge, recreation space, or comfortable accommodations for guests, this flexible area adapts effortlessly to your lifestyle. Upstairs, three well-appointed bedrooms and a full hall bath accompany a serene primary suite designed as a private sanctuary. A walk-in closet and luxurious en-suite bath featuring a standalone soaking tub, large glass-enclosed shower, dual vanities, and separate water closet create a spa-like experience that elevates everyday living. Thoughtful amenities throughout include nine-foot ceilings, hardwood floors, Andersen windows, central air, abundant recessed lighting, foam and batt insulation, a two-car garage, paved driveway, and a handsome bluestone walkway that complements the home’s classic Colonial architecture. The setting offers the luxury of seclusion while remaining just minutes from the charming Village of Pawling, Metro-North, major routes, shopping, restaurants, and the many cultural and natural treasures of the historic Hudson Valley. Whether envisioned as a weekend escape or a year-round haven, this nearly completed new-construction Colonial offers the increasingly rare opportunity to enjoy a beautifully designed home while still having time to influence select finishing touches—creating a home where privacy, elegance, modern comfort, and convenience come together beautifully.

194 South Road, Holmes

$216,000

2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

2 Beds ⋅ 1 Baths ⋅ 931059 MLS

2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

5 Birch Drive, Holmes

$350,000

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

3 Beds ⋅ 2 Baths ⋅ 926453 MLS

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

11 Park Lane, Holmes