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$699,000
3 Beds ⋅ 3 Baths ⋅ 1046647 MLS
End of a cul-de-sac, five minutes to the village of Pawling, and there's nothing left for you to fix. This colonial has been kept the way most people only promise to keep a house — brand-new kitchen with stainless appliances, granite counters, a coffee bar, and pantry storage built for real life. Three bedrooms, two and a half baths, 2,700+ square feet on a private 1.82 acres, with 9-foot ceilings and main-level hardwood floors that catch the light all day. The primary suite has its own double-door entry, a sitting room, dual closets, and a full en suite with double sinks, a jetted tub, and a separate stand-up shower. The second-floor bath, right across from the laundry closet, also offers double sinks — and laundry's upstairs, right where the bedrooms are, no hauling baskets up and down. A formal dining room that actually seats a holiday. Finished walk out basement adds to your living space for whatever you need next — office, playroom, gym. Out back, a deck with a retractable awning, so shade is never a question. A 2-car garage for everything outdoor life throws at you. New air handler, new water softener, new kitchen & appliances, new retaining wall: the expensive stuff, already done. Quiet street, real yard, move right in and make it your own. Schedule a tour today.

49 Millstream Court, Pawling
$695,000
4 Beds ⋅ 2 Baths ⋅ 1047901 MLS
Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling
$597,500
3 Beds ⋅ 3 Baths ⋅ 1047471 MLS
WELCOME TO DEERFIELD PONDS AND ALL ITS AMENITIES! THIS BEAUTIFUL COLONIAL HOME HAS SO MUCH TO OFFER, SUCH AS GORGEOUS PROPERTY WITH MATURE TREES, NUMEROUS PERENNIAL GARDENS, AND A SCENIC POND VIEW. THE COVERED FRONT PORCH WELCOMES YOU INTO THIS WONDERFUL HOME! SPECIAL FEATURES BEGIN WITH A FIRST-FLOOR PRIMARY SUITE. SPACIOUS, INVITING LIVING ROOM HAS HARDWOOD FLOORING & CROWN MOLDING, AS DOES THE LOVELY DINING ROOM. FANTASTIC KITCHEN FEATURES BEAUTIFUL CEILING-HEIGHT CABINETS, RICH GRANITE COUNTER TOPS, HARDWOOD FLOOR. GREAT FOR ENTERTAINING, THE KITCHEN IS OPEN TO THE SUNNY FAMILY ROOM, WHICH OFFERS A FIREPLACE, CROWN MOLDING AND HARDWOOD FLOOR. OFF THE FAMILY ROOM IS A DECK WITH A RETRACTABLE AWNING - A COOL SPOT ON A HOT DAY! ON THE 2ND FLOOR, YOU WILL FIND A BEAUTIFUL FULL BATH, LAUNDRY, TWO VERY NICE BEDROOMS, PLUS A DEN WITH HARDWOOD, WHICH HAS BEEN USED AS A GUEST ROOM/OFFICE. PAWLING IS A LOVELY, SOUGHT-AFTER TOWN WITH A PICTURESQUE VILLAGE, WHICH OFFERS A METRO-NORTH TRAIN STATION, RESTAURANTS, PUBS, BAKERIES, DUTCHER GOLF COURSE, QUAINT SHOPS, LIBRARY, DARYL'S HOUSE MUSIC CLUB & RESTAURANT, AND LAKESIDE TOWN PARK WITH BEACH, PICKLEBALL & PLAYGROUND. PAWLING OFFERS SOMETHING FOR EVERYONE!

41 W Deer Trail, Pawling
$995,000
4 Beds ⋅ 3 Baths ⋅ 1045580 MLS
Set on over 3 beautiful acres, this spacious 4-bedroom, 3-full-bath home offers an impressive blend of classic character, generous living spaces, and modern conveniences. A welcoming wraparound front porch leads to a grand entry foyer with an open staircase and views to the second floor. The main level features a formal Living Room and Dining Room, both enhanced by large bowed windows, along with a comfortable front Sitting Room. The heart of the home is the expansive eat-in Kitchen, complete with center island, stainless steel appliances, and sliding glass doors leading to the rear deck. A spectacular Great Room boasts soaring ceilings, a fireplace, and additional sliders to the deck, creating an ideal space for entertaining or relaxing. A front mudroom entry, convenient Laundry Room, full tiled Bath with walk-in shower, and hardwood floors throughout complete the main level. The oversized garage offers both a double and single garage door for exceptional parking and storage. Upstairs, three spacious Bedrooms feature hardwood floors and double-door closets. The luxurious Primary Suite offers vaulted ceilings, beautiful bowed front windows, his-and-hers walk-in closets, a large linen closet, and a massive Primary Bath with dual vanities, Jacuzzi tub, and walk-in shower. A large Bonus Room with hardwood floors provides flexible space for an office, media room, playroom, or additional living area. The open upper hallway overlooks the Great Room below, adding to the home's dramatic sense of space. Additional highlights include an expansive unfinished basement, walk-up attic, central air, and central vacuum. Set amid peaceful acreage with plenty of room to enjoy the outdoors, this exceptional home offers space, privacy, and versatility both inside and out.

139 S Harmony Road, Pawling
$639,000
4 Beds ⋅ 4 Baths ⋅ 1035919 MLS
Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to purchase wo additional buildable parcels are available from the same family. MLS and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

3846 Route 55, Pawling
$525,000
3 Beds ⋅ 3 Baths ⋅ 1033232 MLS
Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closets, plus 2 additional bedrooms and a full bath. The lower level offers flexible space with a summer kitchen area and a full bath, ideal for guests or extended family. Nearby, enjoy easy access to village amenities and outdoor recreation, including the Appalachian Trail, the Great Swamp, and Pawling Nature Reserve. This property combines privacy, space, and potential in a sought-after Pawling setting. Schedule an appointment today and start envisioning the possibilities.

66 Reservoir Road, Pawling
$1,475,000
4 Beds ⋅ 5 Baths ⋅ 1029458 MLS
**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

7 Herd And Tanner Road, Holmes
$749,900
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
$879,800
3 Beds ⋅ 3 Baths ⋅ 1021432 MLS
Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Once a horse farm, this unique home offers enchanting landscapes that surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... 08/26 New Sub-Zero state of the art Cove dishwasher, 2 year warranty. Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

57 S White Rock Road, Holmes
$1,350,000
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
$4,750,000
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

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.