goreamarrerorealestate.com Search Results

$699,000

A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

3 Beds ⋅ 3 Baths ⋅ 1029600 MLS

A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.

21 Overlook Drive, Pawling

$175,000

Beautiful Private 6.4-Acre Lot in the Town of Pawling – Build Your Dream Home, Discover the perfect setting for your dream home on this beautiful, private 6.4-acre parcel in the desirable Town of Pawling. Offering peace, privacy, and a picturesque natural setting, this property is an exceptional opportunity to create your own country retreat while remaining close to the conveniences of town. Just minutes away is Metro North Train Station in the charming Village of Pawling. The village features a variety of restaurants, pubs, boutique shops, and seasonal attractions, including the popular summer farmers market. Golf enthusiasts will enjoy the Dutcher Golf Course, while Lakeside Park offers swimming, scenic walking trails, and picnic areas for outdoor recreation. For nature lovers, the renowned Appalachian Trail is nearby, providing miles of hiking and breathtaking views. During the winter months, Thunder Ridge Ski Area offers skiing and snowboarding just a short drive away. Experience the best of country living with easy access to year-round recreation, local amenities, and small-town charm.

1022374 MLS

Beautiful Private 6.4-Acre Lot in the Town of Pawling – Build Your Dream Home, Discover the perfect setting for your dream home on this beautiful, private 6.4-acre parcel in the desirable Town of Pawling. Offering peace, privacy, and a picturesque natural setting, this property is an exceptional opportunity to create your own country retreat while remaining close to the conveniences of town. Just minutes away is Metro North Train Station in the charming Village of Pawling. The village features a variety of restaurants, pubs, boutique shops, and seasonal attractions, including the popular summer farmers market. Golf enthusiasts will enjoy the Dutcher Golf Course, while Lakeside Park offers swimming, scenic walking trails, and picnic areas for outdoor recreation. For nature lovers, the renowned Appalachian Trail is nearby, providing miles of hiking and breathtaking views. During the winter months, Thunder Ridge Ski Area offers skiing and snowboarding just a short drive away. Experience the best of country living with easy access to year-round recreation, local amenities, and small-town charm.

Woodin Lane, 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. 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. 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

$360,000

This immaculate, 1,413 SF 2 bedroom, 2 1/2 bath townhome sits in the highly sought-after Cedar Valley development, less than a mile from the charming Village of Pawling. Residents here enjoy a wonderful array of amenities, including a clubhouse, inground pool, and four brand-new pickleball courts, all within a community that perfectly balances privacy and convenience. Step inside to a welcoming entry with a vaulted ceiling that sets a spacious tone. The main level flows effortlessly into an expansive open-concept living and dining area—one massive, light-filled room anchored by French doors that open to a stone patio. Beyond the patio, mature woods create a serene, natural backdrop that feels worlds away from everyday hustle. The country kitchen is warm and functional, featuring updated appliances, generous cabinetry and counter space, a convenient pantry, and a pass-through window to the dining area. A double window bathes the space in sunlight, offering the perfect spot for a breakfast table. A powder room and mechanical closet complete the thoughtfully laid out first floor. Upstairs, the primary bedroom suite provides a peaceful retreat with a large walk-in closet and an attached bath boasting a walk-in shower and linen closet. The nicely sized second bedroom offers its own attached full bath with a fitted tub. Between the two bedrooms, the washer and dryer are tucked away for everyday convenience, while pull-down attic stairs provide excellent additional storage. The home also includes two unassigned parking spots with parking available in front of the complex. Located less than a mile from the heart of the Village of Pawling, this residence puts boutique shops, fine dining, casual eateries, pubs, and the seasonal farmers market right at your fingertips. Outdoor enthusiasts will love easy access to Lakeside Park, Pawling’s town park, the Appalachian Trail, and the Dutchess Rail Trail via the newly completed connector. Golf lovers will appreciate Dutcher Golf Course just across the road. Best of all, the Pawling Metro-North station is only a little over a mile away, offering a convenient 90-minute commute to NYC. This townhome truly delivers the ideal blend of modern comfort, community amenities, and an unbeatable Hudson Valley lifestyle.

2 Beds ⋅ 3 Baths ⋅ 1028659 MLS

This immaculate, 1,413 SF 2 bedroom, 2 1/2 bath townhome sits in the highly sought-after Cedar Valley development, less than a mile from the charming Village of Pawling. Residents here enjoy a wonderful array of amenities, including a clubhouse, inground pool, and four brand-new pickleball courts, all within a community that perfectly balances privacy and convenience. Step inside to a welcoming entry with a vaulted ceiling that sets a spacious tone. The main level flows effortlessly into an expansive open-concept living and dining area—one massive, light-filled room anchored by French doors that open to a stone patio. Beyond the patio, mature woods create a serene, natural backdrop that feels worlds away from everyday hustle. The country kitchen is warm and functional, featuring updated appliances, generous cabinetry and counter space, a convenient pantry, and a pass-through window to the dining area. A double window bathes the space in sunlight, offering the perfect spot for a breakfast table. A powder room and mechanical closet complete the thoughtfully laid out first floor. Upstairs, the primary bedroom suite provides a peaceful retreat with a large walk-in closet and an attached bath boasting a walk-in shower and linen closet. The nicely sized second bedroom offers its own attached full bath with a fitted tub. Between the two bedrooms, the washer and dryer are tucked away for everyday convenience, while pull-down attic stairs provide excellent additional storage. The home also includes two unassigned parking spots with parking available in front of the complex. Located less than a mile from the heart of the Village of Pawling, this residence puts boutique shops, fine dining, casual eateries, pubs, and the seasonal farmers market right at your fingertips. Outdoor enthusiasts will love easy access to Lakeside Park, Pawling’s town park, the Appalachian Trail, and the Dutchess Rail Trail via the newly completed connector. Golf lovers will appreciate Dutcher Golf Course just across the road. Best of all, the Pawling Metro-North station is only a little over a mile away, offering a convenient 90-minute commute to NYC. This townhome truly delivers the ideal blend of modern comfort, community amenities, and an unbeatable Hudson Valley lifestyle.

16 Evergreen Way, Pawling

$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

$365,000

Spacious and affordable. This expansive ranch style home sits on an approximately 3 acres that feature beautiful mountain views from the back of the home. Due to the layout of the home the possibilities are nearly endless. It currently sits as a 3 bedroom and 3 bath home but with proper approvals additional bedrooms are possible. The are two garages on the property. The garage next to the house can fit 2 cars and a second garage behind the house can accommodate 1 car or yard equipment, etc. The price of this home reflects the need for some sweat equity in the form of a deep clean and interior paint job. With a bit of effort this home will sparkle. As an added bonus, there are approximately 97 acres held by the same owner that are contiguous to the parcel on which the house sits. That acreage can be rolled into a package deal or it will be sold off separately. Multiple offers received. Please submit highest and best offers by noon on Thursday 7/23/26

3 Beds ⋅ 3 Baths ⋅ 1026446 MLS

Spacious and affordable. This expansive ranch style home sits on an approximately 3 acres that feature beautiful mountain views from the back of the home. Due to the layout of the home the possibilities are nearly endless. It currently sits as a 3 bedroom and 3 bath home but with proper approvals additional bedrooms are possible. The are two garages on the property. The garage next to the house can fit 2 cars and a second garage behind the house can accommodate 1 car or yard equipment, etc. The price of this home reflects the need for some sweat equity in the form of a deep clean and interior paint job. With a bit of effort this home will sparkle. As an added bonus, there are approximately 97 acres held by the same owner that are contiguous to the parcel on which the house sits. That acreage can be rolled into a package deal or it will be sold off separately. Multiple offers received. Please submit highest and best offers by noon on Thursday 7/23/26

357 W Dover Road, Pawling

$575,000

Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting for gatherings. Just off the Dining Room is a spacious Laundry Room with custom built-ins, abundant storage, and a full bath with a walk-in shower. The generously sized Kitchen offers plenty of workspace, a corner breakfast bar, and access to a mudroom/enclosed porch leading to a private rear patio.Upstairs, you'll find three bright bedrooms with hardwood floors, including a spacious primary bedroom with a walk-in closet. A beautifully appointed hall bath features a classic claw-foot tub and a separate walk-in shower. Additional highlights include a one-car garage, storage shed, and a private backyard. Ideally located within walking distance to the Pawling Village shops and restaurants, Metro-North, parks, and more, this charming Victorian offers the perfect blend of historic character and everyday convenience.

3 Beds ⋅ 2 Baths ⋅ 1022255 MLS

Welcome to 17 Spring Street, a beautifully maintained 1890 Victorian in the heart of the Village of Pawling. Rich in character and timeless charm, this inviting home features hardwood floors, crown molding, and a classic rocking chair front porch. The bright Living Room opens to an elegant Dining Room with bow windows, hardwood floors, chair rail, and a chandelier, creating the perfect setting for gatherings. Just off the Dining Room is a spacious Laundry Room with custom built-ins, abundant storage, and a full bath with a walk-in shower. The generously sized Kitchen offers plenty of workspace, a corner breakfast bar, and access to a mudroom/enclosed porch leading to a private rear patio.Upstairs, you'll find three bright bedrooms with hardwood floors, including a spacious primary bedroom with a walk-in closet. A beautifully appointed hall bath features a classic claw-foot tub and a separate walk-in shower. Additional highlights include a one-car garage, storage shed, and a private backyard. Ideally located within walking distance to the Pawling Village shops and restaurants, Metro-North, parks, and more, this charming Victorian offers the perfect blend of historic character and everyday convenience.

17 Spring Street, Pawling

$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 S White Rock Road, Holmes

$619,900

TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

3 Beds ⋅ 3 Baths ⋅ 1024161 MLS

TO BE BUILT – Build your dream home in the charming Village of Pawling! Ideally located just minutes from downtown Pawling, you'll enjoy convenient access to local shops, restaurants, schools, parks, and the Metro-North train station, making commuting and everyday living a breeze. The homesite is serviced by municipal water and sewer, offering added convenience and peace of mind. Pricing and listing details, such as square footage, bedroom count, etc., is based on LMD’s Bennet model. Looking for something different? Buyers have the opportunity to select from several of our available floor plans and personalize their home with structural options and designer interior finishes to create a space that fits their lifestyle. Whether you're looking for additional living space, a first-floor owner's suite, a gourmet kitchen, or upgraded finishes throughout, our team will guide you through the customization process. Don't miss this opportunity to build a brand-new home in one of Dutchess County's most desirable communities!

Prospect Street, Pawling

$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. Enchanting landscapes 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... 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. Enchanting landscapes 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... 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

$375,000

Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer. Enjoy the sun-filled enclosed sunroom overlooking the peaceful backyard, perfect for relaxing year-round. The full bathroom includes a tub, and recent updates provide peace of mind, including a newly paved driveway (June 2026), propane furnace (2019), and new gutters (2025). Pawling Lake Estates residents enjoy access to a private beach, clubhouse, and dock, all surrounded by approximately 800 acres of protected New York State land, offering endless opportunities for hiking, fishing, kayaking, and enjoying nature. A wonderful year-round home or weekend retreat!

2 Beds ⋅ 1 Baths ⋅ 1020651 MLS

Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer. Enjoy the sun-filled enclosed sunroom overlooking the peaceful backyard, perfect for relaxing year-round. The full bathroom includes a tub, and recent updates provide peace of mind, including a newly paved driveway (June 2026), propane furnace (2019), and new gutters (2025). Pawling Lake Estates residents enjoy access to a private beach, clubhouse, and dock, all surrounded by approximately 800 acres of protected New York State land, offering endless opportunities for hiking, fishing, kayaking, and enjoying nature. A wonderful year-round home or weekend retreat!

28 Birch Terrace, Pawling

$650,000

**Lakefront Living at Its Finest on Private Sunset Lake* Newly priced at $650,000, 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. 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, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. 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. 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. A 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, cafés, 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.

3 Beds ⋅ 3 Baths ⋅ 1017740 MLS

**Lakefront Living at Its Finest on Private Sunset Lake* Newly priced at $650,000, 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. 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, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. 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. 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. A 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, cafés, 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.

45 Willow Lake Drive, Holmes

$995,000

Renovated Colonial near Quaker Hill, less than two hours from NYC and minutes from Metro-North. Board-and-batten exterior with black-trimmed windows set the tone: clean lines and deliberate detail. Inside, the kitchen anchors the main level - marble island with seating, patterned tile backsplash behind the range, double wall ovens, and a layout that opens naturally to dining and living spaces. Brick fireplace with a reclaimed wood mantel. The den, with exposed timber ceiling beams, black-framed windows on three sides, and hardwood floors, overlooks the backyard and pool. The primary suite is on the main floor, making an easy option for single-floor living, and includes luxurious private bath with a marble-topped double vanity, walk-in tile shower with steel-framed glass, freestanding soaking tub, and brass fixtures throughout. Three bedrooms upstairs, all with vaulted ceilings, share a full bath. Outside, there’s the heated gunite pool and spa with lounge surround, pool shed, basketball court, fire pit, and dining patio with stone retaining walls. The yard is open and level with room for a game of any kind, or just the quiet that brought you here in the first place.

3 Beds ⋅ 3 Baths ⋅ 1017929 MLS

Renovated Colonial near Quaker Hill, less than two hours from NYC and minutes from Metro-North. Board-and-batten exterior with black-trimmed windows set the tone: clean lines and deliberate detail. Inside, the kitchen anchors the main level - marble island with seating, patterned tile backsplash behind the range, double wall ovens, and a layout that opens naturally to dining and living spaces. Brick fireplace with a reclaimed wood mantel. The den, with exposed timber ceiling beams, black-framed windows on three sides, and hardwood floors, overlooks the backyard and pool. The primary suite is on the main floor, making an easy option for single-floor living, and includes luxurious private bath with a marble-topped double vanity, walk-in tile shower with steel-framed glass, freestanding soaking tub, and brass fixtures throughout. Three bedrooms upstairs, all with vaulted ceilings, share a full bath. Outside, there’s the heated gunite pool and spa with lounge surround, pool shed, basketball court, fire pit, and dining patio with stone retaining walls. The yard is open and level with room for a game of any kind, or just the quiet that brought you here in the first place.

6 Byrds Hill Road, Pawling

$525,000

$74K 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. And the ultimate finishing touch? Included in the sale is a stunning 2021 Nautic Star 24-foot boat powered by a 250 HP engine—your gateway to exploring the lake and making every arrival home an unforgettable experience. Private island living. Private dock. Premier lakefront location. Turnkey convenience. Included boat. 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

$74K 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. And the ultimate finishing touch? Included in the sale is a stunning 2021 Nautic Star 24-foot boat powered by a 250 HP engine—your gateway to exploring the lake and making every arrival home an unforgettable experience. Private island living. Private dock. Premier lakefront location. Turnkey convenience. Included boat. 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

$1,235,000

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

$499,000

Pure perfection! This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key with a dedicated laundry room, a linen closet, and additional closet space. Stay comfortable year-round with an efficient heat pump and central air. Outside, enjoy your private back deck overlooking just under an acre of park-like manicured lawn surrounded by a serene, partially wooded backdrop. Complete with a brand-new blacktop driveway offering plenty of parking. This gem offers easy access to I-684, I84, Thunder Ridge Ski Area, bike trails and Metro North. Just minutes from dining and shopping and a short drive to the Village of Pawling A truly turn-key property— Absolutely nothing to do but move right in and enjoy!

3 Beds ⋅ 2 Baths ⋅ 1006794 MLS

Pure perfection! This beautifully and fully renovated 3-bedroom, 2-full-bath home offers modern luxury and total peace of mind. Step inside to an open, sun-drenched living space featuring high ceilings and gleaming hardwood floors throughout. The stunning kitchen boasts sleek quartz countertops, stainless steel appliances, and a spacious pantry for all your storage needs. Convenience is key with a dedicated laundry room, a linen closet, and additional closet space. Stay comfortable year-round with an efficient heat pump and central air. Outside, enjoy your private back deck overlooking just under an acre of park-like manicured lawn surrounded by a serene, partially wooded backdrop. Complete with a brand-new blacktop driveway offering plenty of parking. This gem offers easy access to I-684, I84, Thunder Ridge Ski Area, bike trails and Metro North. Just minutes from dining and shopping and a short drive to the Village of Pawling A truly turn-key property— Absolutely nothing to do but move right in and enjoy!

358 Route 292, Holmes

$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

$600,000

Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity.

4 Beds ⋅ 3 Baths ⋅ 945476 MLS

Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space. Located just minutes from the charming town of Pawling, Metro-North, parks, schools, restaurants and shops, convenient commute to NYC while enjoying suburban tranquility. Don't miss this exceptional opportunity.

5 Red Tail Court, Pawling

$3,100,000

Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.

3 Beds ⋅ 3 Baths ⋅ 1005064 MLS

Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.

809 QUAKER HILL Road, Pawling

$2,250,000

Exceptional opportunity to own one of the most versatile and prestigious office properties in the Pawling market. Located at 515, 517 & 527 Route 22, this premier office campus offers over 11,000 SF of professional space on nearly 2 acres in a highly visible Route 22 location. Designed for flexibility and growth, the property features three levels with entrances and exits on all four sides, allowing for multiple occupancy configurations, private business operations, or a combination of owner-user and income-producing tenancy. The building offers an impressive mix of executive offices, conference rooms, kitchens, private and shared restrooms, reception areas, and multiple storage spaces above and below grade. High-end finishes, exceptional natural light, and thoughtful floor plans create an ideal environment for professional, medical, corporate, educational, creative, or administrative users. Separate utility services and multiple access points support easy subdivision and independent operation of various sections of the property. Well suited for an owner-user seeking to occupy a significant portion while generating income from additional tenants, the property also presents an outstanding investment opportunity with the ability to create multiple revenue streams. Ample parking, exterior yard areas, expansion potential, and excellent traffic exposure further enhance its appeal. Conveniently located within walking distance of shopping, restaurants, schools, and Metro-North rail service, this landmark property offers the rare combination of immediate functionality, future expansion potential, and long-term investment value. One of the most adaptable and expandable office campuses available in the Pawling submarket. Call for pricing, floor plans, and occupancy details.

1005925 MLS

Exceptional opportunity to own one of the most versatile and prestigious office properties in the Pawling market. Located at 515, 517 & 527 Route 22, this premier office campus offers over 11,000 SF of professional space on nearly 2 acres in a highly visible Route 22 location. Designed for flexibility and growth, the property features three levels with entrances and exits on all four sides, allowing for multiple occupancy configurations, private business operations, or a combination of owner-user and income-producing tenancy. The building offers an impressive mix of executive offices, conference rooms, kitchens, private and shared restrooms, reception areas, and multiple storage spaces above and below grade. High-end finishes, exceptional natural light, and thoughtful floor plans create an ideal environment for professional, medical, corporate, educational, creative, or administrative users. Separate utility services and multiple access points support easy subdivision and independent operation of various sections of the property. Well suited for an owner-user seeking to occupy a significant portion while generating income from additional tenants, the property also presents an outstanding investment opportunity with the ability to create multiple revenue streams. Ample parking, exterior yard areas, expansion potential, and excellent traffic exposure further enhance its appeal. Conveniently located within walking distance of shopping, restaurants, schools, and Metro-North rail service, this landmark property offers the rare combination of immediate functionality, future expansion potential, and long-term investment value. One of the most adaptable and expandable office campuses available in the Pawling submarket. Call for pricing, floor plans, and occupancy details.

527 Route 22, Pawling

$17,995

Opportunity awaits on Route 292 in Holmes, NY. This .25-acre vacant lot is located in an established area of Pawling with convenient access to local roads, schools, and nearby amenities. Property is being sold as-is, and buyers should perform their own due diligence regarding BOHA approval, utilities, zoning, permits, and intended use. A great entry-level land opportunity in Dutchess County at an accessible price point.

1004079 MLS

Opportunity awaits on Route 292 in Holmes, NY. This .25-acre vacant lot is located in an established area of Pawling with convenient access to local roads, schools, and nearby amenities. Property is being sold as-is, and buyers should perform their own due diligence regarding BOHA approval, utilities, zoning, permits, and intended use. A great entry-level land opportunity in Dutchess County at an accessible price point.

Rt-292, Holmes

$2,790,000

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.

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.

5 McCarthy Road, Holmes

$795,000

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

$469,900

Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal for entertaining and outdoor activities. Conveniently located right by the beautiful Whaley Lake, where you can enjoy private beaches, fishing, swimming, kayaking, boating, and motor boats are allowed. Just minutes from the charming Town of Pawling, with easy access to dining, shopping, Metro north train station, Thunder Ridge Ski Area, Trails to Walk, Bike or Hike. A wonderful opportunity to enjoy both comfort and outdoor living!

4 Beds ⋅ 2 Baths ⋅ 997863 MLS

Well maintained raised ranch offering 4 bedrooms and 2 bathrooms. This inviting home features spacious bedrooms, hardwood floors, and a bright living room filled with natural light. The finished lower level provides additional living space and laundry room, perfect for guests, a home office, or recreation. Sliding doors from the dining room lead to a deck overlooking a spacious backyard, ideal for entertaining and outdoor activities. Conveniently located right by the beautiful Whaley Lake, where you can enjoy private beaches, fishing, swimming, kayaking, boating, and motor boats are allowed. Just minutes from the charming Town of Pawling, with easy access to dining, shopping, Metro north train station, Thunder Ridge Ski Area, Trails to Walk, Bike or Hike. A wonderful opportunity to enjoy both comfort and outdoor living!

23 Lakeview Drive, Holmes

$5,000,000

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

Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- 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. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- 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 Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Is Included In The <3 Acres & Its 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!

3 Beds ⋅ 2 Baths ⋅ 992269 MLS

Super Charming Cape On An Ultra Private 2.92 Acres At The Very End Of The Dead End Street! Close To Everything -- Shopping, Schools, Train Station/Commuting, Restaurants And Still Be Tucked Into Your Own Private Haven. Flexible Floor Plan To Create Rooms For You --- 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. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Ready For Your Ideas Without Having To Start With Unfinished Space. Very Flexible Space! Both Bedrooms In The Upper Level Are Very Large and The House Has Room To Grow As Your Spatial Needs Grows -- 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 Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Summers Are The Best While Enjoying The South Facing Deck Off The Kitchen That Leads To The In-Ground Pool In The Backyard. Excited To Host Summer BBQs & Pool Parties? You Could Pack + or -- 50 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, A Camper / RV, OR For Those Fantastic Summer Parties! To The Left Of The House Is Included In The <3 Acres & Its 1 Acre Of Land That Is Part Of The Privacy. It Could Be Turned Into An Additional Detached Garages, Cute Cottage To Rent Full or Part Time (Abnb) or House an In-Law, A Garden With A Garden Potting Shed, A Work Shop, Or Whatever Your Vision Can Imagine. Cozy Up To The Fire In The Winter OR The Summer's Sun & Moon's Reflection From The Salt Water Pool As You Enjoy Your Morning Coffee & Your Evening's Glass Of Wine. Come! Relax, Unwind, & Enjoy Life!

57 Buhleir Road, Pawling

$125,000

.73 acre lot is located in the Village of Pawling! *Board of Health Approval is NOT required because the house can be hooked up to municipal water and sewer! Variance with fees is required to build. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants/pubs, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as well. You will love 200+ acre Lakeside Park! 36-acre Green Mountain Lake has a beautiful sand beach, playground, picnic area and walking trails. Nearby Dutcher Golf Course is a 9-hole beauty, the oldest public course in America! Hikers will enjoy the Appalachian Trail and Pawling Nature Reserve trails. Also nearby are Darryl's House Live Music Club & Restaurant, and Thunder Ridge Ski Area. Build your new home on this parcel! AO

991495 MLS

.73 acre lot is located in the Village of Pawling! *Board of Health Approval is NOT required because the house can be hooked up to municipal water and sewer! Variance with fees is required to build. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants/pubs, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as well. You will love 200+ acre Lakeside Park! 36-acre Green Mountain Lake has a beautiful sand beach, playground, picnic area and walking trails. Nearby Dutcher Golf Course is a 9-hole beauty, the oldest public course in America! Hikers will enjoy the Appalachian Trail and Pawling Nature Reserve trails. Also nearby are Darryl's House Live Music Club & Restaurant, and Thunder Ridge Ski Area. Build your new home on this parcel! AO

Walnut Street, Pawling

$1,799,000

Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious neighboring estates. Originally a log home, the property has been masterly reimagined for the luxury buyer into an elegant, warmly welcoming residence where fine architectural details and high-end finishes are evident at every turn. The main residence is a study in sophisticated design, anchored by wide-plank oak flooring that flows through the living room, sunroom and commanding library-style study. At the heart of the home, a modern chef’s kitchen with radient heated floors, and a generous central island that serve as the perfect stage for both grand entertaining and quiet dinners. A striking steel-clad stairwell leads to the upper level, where the primary suite serves as a private retreat with soaring 18-ft ceilings, skylights, and a Juliet balcony that overlooks a picturesque landscape of mature plantings and rolling hills. Two additional bedrooms with full baths and a large dressing room, a possible fourth bedroom, complete this level. The lifestyle extends seamlessly outdoors, where a wraparound deck overlooks a serene, spring-fed pond. For summer entertaining, a separate deck surrounds a tranquil pool area, fully equipped with a bar, cabana and bathroom. Beyond its aesthetic beauty, the home is engineered for effortless living with a heated 2-car garage, whole-house generator, central vacuum, and integrated security and Sonos systems. Complementing the main house is a charming totally separate two-bedroom guest cottage built in 1920. Fully renovated with its own full kitchen, wood burning fireplace, full bath and lofted living space, utilities, and septic system, it offers a private haven for visitors, a dedicated professional workspace or caretaker's residence. The house has state of the art wi-fi, heating and cooling systems, and an Aprilaire full-house dehumidifier that is integrated with the HVAC system. Heat coils on the gutters and parts of the roof protect the home from ice-dams. Every detail has been attended to that makes this home a true treasure. Located just minutes from the historic Village of Pawling, and under 90 minutes to Manhattan via Metro-North, this property represents the pinnacle of the Quaker Hill lifestyle—a perfect weekend retreat or a permanent paradise.

5 Beds ⋅ 6 Baths ⋅ 875119 MLS

Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious neighboring estates. Originally a log home, the property has been masterly reimagined for the luxury buyer into an elegant, warmly welcoming residence where fine architectural details and high-end finishes are evident at every turn. The main residence is a study in sophisticated design, anchored by wide-plank oak flooring that flows through the living room, sunroom and commanding library-style study. At the heart of the home, a modern chef’s kitchen with radient heated floors, and a generous central island that serve as the perfect stage for both grand entertaining and quiet dinners. A striking steel-clad stairwell leads to the upper level, where the primary suite serves as a private retreat with soaring 18-ft ceilings, skylights, and a Juliet balcony that overlooks a picturesque landscape of mature plantings and rolling hills. Two additional bedrooms with full baths and a large dressing room, a possible fourth bedroom, complete this level. The lifestyle extends seamlessly outdoors, where a wraparound deck overlooks a serene, spring-fed pond. For summer entertaining, a separate deck surrounds a tranquil pool area, fully equipped with a bar, cabana and bathroom. Beyond its aesthetic beauty, the home is engineered for effortless living with a heated 2-car garage, whole-house generator, central vacuum, and integrated security and Sonos systems. Complementing the main house is a charming totally separate two-bedroom guest cottage built in 1920. Fully renovated with its own full kitchen, wood burning fireplace, full bath and lofted living space, utilities, and septic system, it offers a private haven for visitors, a dedicated professional workspace or caretaker's residence. The house has state of the art wi-fi, heating and cooling systems, and an Aprilaire full-house dehumidifier that is integrated with the HVAC system. Heat coils on the gutters and parts of the roof protect the home from ice-dams. Every detail has been attended to that makes this home a true treasure. Located just minutes from the historic Village of Pawling, and under 90 minutes to Manhattan via Metro-North, this property represents the pinnacle of the Quaker Hill lifestyle—a perfect weekend retreat or a permanent paradise.

41 and 43 Meeting House Road, Pawling