Courtesy: Douglas Elliman Real Estate
914-273-1001
Sophisticated Contemporary Country Estate on 17+ Acres with Private Stocked Pond Welcome to 30 Harmony Rd, Pawling, NY 12564, a striking contemporary two-story residence combining modern architectural design, expansive living spaces, and unparalleled natural tranquility. Custom-built in 1987 by its current owner, this meticulously maintained estate offers approximately 3,319 square feet of thoughtfully designed living space set against a breathtaking, private country backdrop. The Residence Boasting an ideal east/northeast orientation, the home is flooded with brilliant natural light throughout the day. The modern architectural style is defined by clean lines, soaring ceilings, and a seamless flow across eight spacious rooms. • Bedrooms/Bathrooms: 4 generous bedrooms and 3.5 well-appointed bathrooms, structured perfectly for both daily comfort and effortless hosting. • Living Comfort: Equipped with central heating and air conditioning for year-round climate control, and a whole-house standby generator (installed in 2023) for ultimate peace of mind. • Convenience & Storage: A two-car attached garage offers secure parking, complemented by abundant additional storage space throughout the home. • Personalization: Offered "As-Is" in excellent, well-maintained original condition, the property comes complete with essential appliances, serving as a pristine blank canvas ready for your personal design touch. The Acreage & Outdoor Oasis Situated on an extraordinary 17.15-acre lot, this estate provides a rare level of privacy, freedom, and potential. • Water Frontage: The grounds feature a beautifully maintained garden leading down to a serene private pond. The pond is fully stocked for bass fishing, offering a peaceful waterfront retreat right in your backyard. • Expansion Potential: The massive, level acreage offers limitless possibilities to build a custom swimming pool, tennis/pickleball courts, a guest house, or equestrian outbuildings. Whether you are looking for a sophisticated full-time residence or a peaceful weekend sanctuary, this property offers a rare combination of contemporary style, spacious interiors, and quiet acreage in a highly desirable Pawling setting.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
Set amid the rolling countryside of the illustrious and highly coveted Quaker Hill in Pawling, New York, this extraordinary three-acre estate is a rare offering where historic charm, refined country living, and exceptional craftsmanship come together in remarkable fashion. Surrounded by picturesque horse farms and pastoral landscapes, this meticulously maintained property offers a lifestyle that is increasingly difficult to find. Featuring two remarkable buildings, the estate offers exceptional country living. Elegantly appointed and thoughtfully maintained, the main residence offers a beautiful blend of timeless character and modern updates. An updated kitchen and renovated bathrooms complement the home's inviting interiors, while thoughtfully designed living spaces provide an ideal setting for both intimate gatherings and gracious entertaining. The formal dining room, complete with its own fireplace, creates a warm and distinguished atmosphere for memorable occasions. The impressive great room is a true centerpiece, featuring soaring ceilings, rich natural wood, and a magnificent stone fireplace that brings warmth and character to the space. Three generously proportioned bedrooms include a beautiful en-suite primary suite. An additional bonus room, featuring natural wood details and a full bathroom, offers wonderful flexibility as guest accommodations, a home office or a creative studio. Adding another level of convenience, the main residence is equipped with an elevator. The grounds are equally captivating. A beautiful in-ground marcite swimming pool, surrounded by exquisite stonework, creates a private setting for relaxation and summer entertaining. A charming cabana completes the setting, offering the perfect place to unwind and enjoy the tranquil surroundings. Then there is The Barn, a remarkable centerpiece of the estate that is every bit as captivating as the main residence. More than a traditional barn, this extraordinary building has been tastefully renovated to create a sophisticated and inviting living environment while preserving the authentic character of its original barn-inspired design. Wide-plank floors, rough-milled beams, and beautifully executed woodwork throughout celebrate its rustic heritage while introducing an understated elegance and refinement. The open-concept main level features a kitchen, full bathroom, and expansive living space that invites entertaining, creative pursuits, or simply enjoying the peaceful surroundings. A magnificent stone fireplace rises dramatically from the main level to the second floor, where it becomes the focal point of a welcoming family room. Upstairs, a bedroom and an impressive primary suite, featuring its own balcony overlooking the property's picturesque pond, provide a truly enchanting private retreat. Above it all, a beautiful bonus cupola adds architectural distinction and completes the Barn's extraordinary character. Beyond its exceptional beauty and craftsmanship, the estate has been thoughtfully updated to provide modern comfort and reliability. Updated utilities serve the property, while each building is equipped with its own separate septic system and dedicated generator, offering independence and added peace of mind for both residences. The combination of beautifully preserved character and modern infrastructure makes this an especially appealing and turnkey country estate. Despite its wonderfully private and peaceful country setting, the estate is conveniently located just minutes from the quaint and charming Village of Pawling, where you'll discover inviting restaurants, boutique shops, local cafes and everyday conveniences. The Pawling Metro-North station, located in the heart of the village, offers Harlem Line service to Grand Central Terminal in New York City, with an approximate 90-minute train journey. Enjoy the best of both worlds—the tranquility of an exceptional country estate with the convenience of village amenities and access to the city.
Courtesy: Keller Williams NY Realty
914-437-6100
Welcome to 21 Juniper Lane, a charming 2-bedroom, 2.5-bath home located in the sought-after Cedar Valley community in Pawling. This inviting townhome lives like a single-family home and offers the perfect balance of comfort, convenience, and amenities. Step inside to find a bright and open living space designed for easy living. The home features a spacious living room, brand new Trex Deck off the living room, a functional kitchen with ample storage, a first-floor powder room, and a wood-burning fireplace for cozy winter nights. The second floor offers the Primary suite with large closets and an en-suite bathroom. Large 2nd bedroom with a 2nd bathroom ensuite and Laundry. As a Cedar Valley resident, you’ll enjoy access to wonderful community amenities, including a clubhouse, pool, and tennis courts—perfect for an active and social lifestyle. All of this is just minutes from Pawling’s charming village, Metro-North train station, dining, shopping, hiking trails, parks, and all major highways.
Courtesy: BHHS Hudson Valley Properties
845-473-1650
Make this home your own! Light & Bright end unit is a blank canvas for your personal decorating style. Spacious Living Room and open concept Dining Area offer so many possibilities. Built in window seat, French doors to patio for relaxing or summertime grilling. Attached exterior storage shed. Eat in Kitchen with oak cabinets, tile backsplash and convenient pass through to the Dining Area, which can serve as a breakfast bar too. Newer stove, refrigerator and a dishwasher that was barely used. New water heater in 2024. Central air conditioning unit only 10 years old. First floor powder room. Master Bedroom with a huge walk-in closet and en-suite bathroom has safe, walk-in shower plus it’s own linen closet. Second Bedroom and ample closet with another en-suite bathroom featuring a tub/shower. Convenient 2nd floor laundry and pull down access to attic for extra storage. Cedar Valley amenities include a pool, tennis courts and clubhouse. All just minutes from the Pawling Village center, shopping, restaurants, Metro North train station, activities and the seasonal Farmer’s Market. Come and enjoy!
Courtesy: Mark Seiden Real Estate Team
914-762-2200
A wonderful opportunity awaits in Deerfield Ponds! This inviting four-bedroom, two-and-a-half-bath home, complete with a finished basement, offers a perfect blend of classic charm, spacious living, and an exceptional lifestyle. The first floor features a welcoming family room, formal living room and dining room, and a spacious, open kitchen ideal for everyday living and entertaining. Sliding glass doors lead to the deck, providing the perfect setting to relax, dine, and enjoy the beautiful views. The finished basement offers additional versatile living space to accommodate a variety of needs. Residents of Deerfield Ponds enjoy an impressive array of community amenities, including a clubhouse, swimming pool, tennis courts, pickleball and basketball courts, fitness center, and playground. Ideally located near the village and train station, this home offers a wonderful balance of peaceful community living and convenient access to local shops, restaurants, and commuter options. This home provides the perfect setting to enjoy all that Deerfield Ponds has to offer. Don't miss your chance to make this special property your own! There are no audio recording devices inside this property.
Courtesy: McGrath Realty Inc
845-855-5550
High atop Quaker Hill, this private and secluded oasis sits on 6 acres along a quiet country road. The home rests far back at the end of a long driveway, with a stream crossing in front and woodlands, trails, and rock walls unfolding behind. Mature perennial plantings, flowering trees, and shrubs frame the grounds, while fruit-bearing trees and bushes yield pears, peaches, apples, and raspberries throughout the season. This is the first time the property has come to market. The original owners built the home with care and thoughtful detail, and the opportunity now arrives for the next stewards to carry it forward. The split-level residence offers 1,236 SF across 3 levels. The living room features accent walls of wood and brick, oversized windows, and an open connection to the dining area. Sliding glass doors open toward the greenhouse, with a side door leading to the deck. The kitchen provides space for a breakfast table or the potential to be opened fully into the living and dining spaces. Six stairs up from the living room to the 3 bedrooms, hall bath with tub, and attic access. Six stairs down from the kitchen to a 312 SF unfinished basement suited for a workbench, storage, and mechanical systems. A door from the basement connects to the 576 SF 2-car garage, with outdoor access. The grounds feel especially inviting, with a large, fenced garden, small sheds for gardening tools and lawn equipment, a chicken coop with its own fenced run, and ample parking. Acres of woodland trails and stone walls extend behind the house, offering room to explore. The setting provides privacy on coveted Quaker Hill while remaining only minutes from the Village of Pawling, with fine dining, fun eateries, boutique shops, antique stores, cultural attractions, and a seasonal farmers market. Pawling’s Metro-North station places NYC roughly 90 minutes by train or car.
Courtesy: McGrath Realty Inc
845-855-5550
Charming 3-bedroom, 2-full-bath ranch set on a level acre with a beautiful private pond. The inviting open floor plan features a bright living room with hardwood floors and large windows, flowing into the dining room with slate flooring. The kitchen offers a butcher-block peninsula with seating, farmhouse sink, propane stove, and stainless steel appliances. Sliding glass doors off the dining room lead to a spacious sunroom with new skylights, large windows, and access to the wraparound deck, perfect for relaxing or entertaining. The bedroom wing includes two bright bedrooms with hardwood floors and generous closets, a full hall bath with double sinks and a glass-enclosed shower, and a primary suite with hardwood floors, a large closet, and an en-suite bath with tub. The walkout lower level offers a spacious area currently used as a gym, laundry, and a mechanical room with a newer burner and hot water heater. An under-house one-car garage provides added convenience. Enjoy peaceful surroundings while remaining conveniently located near Route 22, I-684, I-84, Metro-North, and just two miles from the Village of Pawling with its shops, restaurants, and amenities.
Courtesy: Compass Greater NY, LLC
838-877-8283
Tucked away on five scenic acres in Pawling, this charming old farmhouse has quite the history. Originally built across the road, the house was quite literally picked up and moved across the creek to its current setting, where open lawns, mature trees, and a wooded hillside create a beautiful little world of its own. Getting here is part of the charm. Cross a small bridge over the creek that borders the front of the property, follow the driveway in, and discover a classic country farmhouse surrounded by greenery, with a generous clearing that gently rises toward the forest. The property offers a lovely mix of open space and woodland, with a rustic outbuilding tucked among the trees and plenty of room to imagine what comes next. Inside, there’s much to love. A slate-floored foyer welcomes you into the living room, where hardwood floors, warm wood trim, built-in shelving, and a substantial fireplace give the space its character. Large windows bring in beautiful natural light, while the adjoining dining room features French doors overlooking the grounds and an original wood staircase leading upstairs. The kitchen has a functional layout, ample cabinetry, and a window overlooking the backyard and wooded hillside beyond. It’s easy to picture what this space could become with a thoughtful refresh, whether that’s a few simple updates or a completely reimagined Hudson Valley farmhouse kitchen. A full bathroom, generously sized laundry room, and two additional outdoor access points round out the first floor. Upstairs, you’ll find three bright bedrooms with hardwood floors, including one with a sizable walk-in closet that could also serve as a small flex space. The second full bathroom is a delightful little time capsule, complete with vintage blue fixtures, double sinks, and a matching blue tub. Outside, the possibilities extend well beyond the house. Picture gardens, long afternoons on the lawn, an outdoor dining area, or simply enjoying the changing seasons from your own five-acre retreat. The combination of open space, surrounding woods, and creek frontage makes this a particularly special setting. With its classic farmhouse character, beautiful natural light, and wonderfully private setting, there’s already so much to appreciate here. The home would benefit from some TLC and thoughtful updates, whether your vision is to preserve its vintage charm or give it a more contemporary Hudson Valley feel. A special opportunity to make an old country house your own, with five lovely acres to enjoy along the way. Just minutes from the charming Village of Pawling and its Metro-North station, with local favorites like McKinney & Doyle, Daryl’s House for live music, and independent shops and cafes to explore. Outdoor enthusiasts will appreciate nearby access to the Appalachian Trail, Great Swamp, and Pawling Nature Reserve, while the surrounding Harlem Valley offers farm stands, scenic backroads, and endless opportunities to get outside. And with the George Washington Bridge approximately 90 minutes away, a little country living doesn’t have to mean leaving the city too far behind.
Courtesy: X-Cap Realty LLC
929-998-9227
Welcome to 18 Chestnut Lane in the Highlands of Pawling! This four-bedroom, three-bath Colonial combines spacious interiors with a private in-ground pool and sought-after community amenities. Hardwood floors flow throughout the main level, featuring a formal dining room and an open kitchen with granite countertops, stainless steel appliances, a center island, and coffee bar. The deck overlooks the backyard and private in-ground Pool, creating an inviting setting for outdoor dining and entertaining. Upstairs, the primary suite offers a tray ceiling, walk-in closet, and private bath with dual sinks, alongside three additional bedrooms and a bonus room. The full walkout basement features high ceilings, full-size windows, and possibilities for a home gym or recreation space. An attached two-car garage adds everyday convenience. Enjoy access to the Highlands’ community pool, tennis courts, and pond for kayaking and fishing. Conveniently located near the Village of Pawling’s shops, restaurants, and Metro-North station, this home offers space, recreation, and connection to all Pawling has to offer. Water & Sewer included in HOA.
Courtesy: RE/MAX Prestige Properties
914-831-3090
This distinctive contemporary Arts & Crafts home is nestled high on Quaker Hill and surrounded by approximately 2.9 acres of privacy. Tucked away in a peaceful country setting, this beautifully crafted residence offers a combination of tranquility and convenience — just minutes from Pawling Village, Metro-North, shopping, restaurants, major roads and the Connecticut border. Inside, the home reflects a rarely found level of craftsmanship. The custom interior was designed and crafted by a master cabinetmaker, with thoughtful details throughout. The spacious living room provides an inviting gathering space, while the dining room features beautiful inlaid flooring. The family room opens directly to the deck, creating an easy transition between indoor and outdoor living. The custom eat-in kitchen features maple cabinetry accented with walnut inlays, hammered-brass hardware, granite and walnut countertops, and a design that is as functional as it is beautiful. A first-floor office/guest room adds flexibility for working from home, visitors or a quiet hide-away. Upstairs, the private primary suite offers a custom-built walk-in closet, a comfortable sitting/lounge area and access to a roof deck. The primary bath is spacious with a walk-in shower. Three additional bedrooms and a full bath complete the upper level with plenty of room for family and guests. Outside, the expansive grounds provide a wonderful sense of privacy and the mature landscaping, gardens, winding walkways and outdoor living spaces create a private setting that allows you to slow down and enjoy life. Have your morning coffee surrounded by nature, dinners on the deck, gardening, entertaining friends or simply relaxing beneath the stars. The property offers the feeling of a secluded country estate while remaining remarkably accessible. Rest assured that you will not lose power during a storm as you will have your Generac generator on standby. A two-car attached garage adds everyday convenience, while the home's location puts you close to the best of Pawling and the surrounding area. Enjoy the charm of Pawling Village, local restaurants, shopping and community events, with Metro-North providing commuter rail service. Outdoor enthusiasts will appreciate the area's hiking and recreational opportunities, while the Connecticut border is only minutes away. 12 Tower Hill Road is more than a home—it is a private Hudson Valley escape with character, craftsmanship and an enviable location. Come experience the peace of Quaker Hill and discover how easy country living can be when everything you need is still close at hand.
Courtesy: RE/MAX In The City
929-222-4200
Welcome to 9 Bridle Way, a 4-bedroom, 4-bath Colonial on a 1.24-acre corner lot at the end of a quiet cul-de-sac in the Highlands at Pawling. This stunning Colonial offers roughly 4,800 sq ft of living space across three finished levels. Hardwood floors and cathedral ceilings run through the main level, which includes formal living and dining rooms, an eat-in kitchen with a sunny breakfast area, and a great room with a fireplace. A sunroom opens to the deck for easy indoor-outdoor living. A first-floor office with access to a full bath doubles as a fourth bedroom, and the mudroom/laundry connects directly to the 2-car attached garage. Upstairs, the primary suite has two walk-in closets and a tiled spa bath with a soaking tub, separate shower, and double vanity. Two more bedrooms share a full tiled bath. The finished walk-out lower level adds a family room, a bedroom, and a full bath, with full-size windows that keep it bright. Highlands residents enjoy a community pool and tennis courts. The quiet cul-de-sac setting is minutes to Pawling village and the Metro-North Harlem Line. Pawling schools. Space, light, and amenities, all in one address. Schedule your private showing today.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Welcome to Quaker Hill Estate, a circa 1800 former dairy barn on 5.4 private acres on Quaker Hill, one of Pawling's most coveted areas. Horse and sheep farms and hiking trails surround the hill, yet New York City is about 90 minutes away. Set at the end of a long drive off a quiet, well-maintained county road, the post-and-beam barn was converted into a residence around 1980 and appeared on the cover of Country Living magazine a few years later. Today it offers four bedrooms, three and a half baths, and 3,660 square feet across three levels, framed by hand-hewn timbers and wide pine floors. A two-story masonry fireplace anchors the great room, and a separate-entry guest wing, a gunite pool, and long meadow views round out the property. The barn has a rich history; it was part of the Taber farm on Quaker Hill, purchased in 1760 by Thomas Taber of Dartmouth, Massachusetts, and held by his descendants for nearly two centuries. The conversion preserved the scale and craftsmanship of the original structure, and the post-and-beam frame still shapes every room. The great room makes full use of the barn's dramatic proportions, with soaring ceilings, hand-hewn beams, and a monumental two-story masonry fireplace shared with the adjoining library. French doors open to a wraparound porch overlooking the meadows. Also on the first floor are a sunlit studio with a utility sink and a separate-entry wing with a recreation room, kitchenette, and guest bedroom opening to a stone terrace, well suited to long-term guests or in-law living. Upstairs, the kitchen, living room, and dining area form the heart of the home. Antique wood countertops, period cabinetry, and a Viking range give the kitchen both character and serious cooking function, and the dining area holds a long table for holiday gatherings by the fire. A screened porch looks across the meadows, outbuildings, and pool, a lovely spot for long summer lunches and dinners in the open air. A generous hall leads to the primary suite, a second bedroom, and a hall bath. Above, a finished attic and loft add one more quiet retreat. Outdoors, stone walls trace open meadows and partially wooded land, giving the house complete privacy. Perennial and vegetable gardens surround the house, and the gunite pool sits within fieldstone landscaping and mature plantings. A smaller barn, an attached two-car garage, a patio, and a deck complete the grounds, which draw birds, butterflies, and wildlife through every season. The current owners have invested steadily in the property, adding a new metal roof in 2015, relining the pool in 2019, replacing the septic leach field in 2020, installing solar panels in 2022, and screening the upstairs porch in 2024. Inside, the bathrooms have been retiled, the primary bath has a new tub, and the stove, refrigerator, washer, and dryer have been replaced, along with fresh paint, ceiling fans, and updated lighting. The land sits within Pawling's CD-R5 Conservation Density Residential district, with five-acre zoning. The village of Pawling is ten minutes away, with shops and restaurants that include local favorite McKinney & Doyle. The Appalachian Trail is minutes from the house for morning hikes, and the Pawling station connects to Grand Central on Metro-North's Harlem Line, with major roads close by. After more than two centuries, Quaker Hill Estate still belongs to its meadows, ready for roaring fires in winter and long porch dinners in summer.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-584-6600
Charming ranch nestled on a generous .57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachian Trail, Great Swamp, nature preserves, lakes, and parkland. Metro-North service from the Village of Pawling provides convenient access for those traveling throughout the region and into New York City.
Courtesy: Briante Realty Group, LLC
845-225-2020
This unique ranch home offers SIX bedrooms and TWO full baths. There is 2,856 sqft of living space above the walk-out basement. Generator included in sale. Sprinklers throughout the interior of the home. Upgraded and expanded Septic. Modular home. Walk out basement has plumbing set up for an apartment (bath and kitchen) but never built out. Private setting.
Courtesy: Gillian Stewart Real Estate
845-855-5092
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.
Courtesy: McGrath Realty Inc
845-855-5550
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.
Courtesy: McGrath Realty Inc
845-896-5444
Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill.
Courtesy: Exit Realty Connections
845-298-6034
Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!
Courtesy: Houlihan Lawrence Inc.
845-279-6800
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.
Courtesy: eXp Realty
888-276-0630
INTRODUCTORY 4.13% INTEREST RATE! Discover the perfect blend of small-town charm and modern living, just minutes from the picturesque Village of Pawling! Ideally located near downtown shops, restaurants, schools, parks, and the Metro-North train station, this beautiful new construction home offers both convenience and comfort. Thoughtfully designed with an impressive collection of upgrades, the Davenport will feature 9-foot first-floor ceilings, a gourmet kitchen with an expanded island, double wall ovens, 36" cooktop, and additional cabinetry, a cozy fireplace, a private study with French doors, and an enhanced owner's bath with a spacious shower and double vanity. Additional highlights include oak staircase treads, two-zone heating and cooling, and a 10' x 12' deck perfect for outdoor entertaining. Municipal water and sewer add to the convenience of this exceptional homesite. For a limited time, buyers have the opportunity to personalize their home by selecting their own interior finishes! Estimated completion is approximately 10–12 months. Don't miss your chance to make this beautiful new home your own in one of Dutchess County's most desirable locations!
Courtesy: McGrath Realty Inc
845-855-5550
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.
Courtesy: Houlihan Lawrence Inc.
914-277-8040
PRICE REDUCTION! GREAT OPPORTUNITY! If you're looking for space and the opportunity to make a home your own, this property is worth a look. The property is being offered AS-IS and will require some repairs. With its generous amount of space and potential, this could be the perfect match for a buyer looking to create a home tailored to their needs. This Squire Green home features 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. Bring your ideas and make this home your own. 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. Schedule your private showing today and come see the possibilities!
Courtesy: Serhant LLC
646-480-7665
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.
Courtesy: Berkshire Hathaway HS NE Prop.
203-744-5544
Incredibly Private & Charming Home On 2.92 Acres At The Very End Of The Dead End Road! Updated Kitchens & Baths in 2013-14 & 2025 With An Expansive Kitchen That Has Amazing Storage, Granite Countertops, 7 Foot Island w/ Even More Cabinets, and Newer Stainless Appliances. This Home Has MEGA Possibilities -- Airbnb, Potential In-Law or Both (on the side of the property & in the basement), Additional Detached Garages With Or Without a Business Office. Looking To Have A Work Shop? A Garden Or A Mini Farm? A Garden Potting Shed? Flowers OR Vegetables OR Fruit Trees? There Is Plenty Of Sun Including Space To Plant Whatever Your Heart Desires And Whatever Your Vision Can Imagine! -- A Home To Create Your Dream! Build An Adjacent Supplemental Home On The Space To The Left Of The House, Which Is Part Of The Almost 3 Acres. OR Easy Ideas In The Already Finished Basement. Live For Free OR Almost Free. The Parking Is Ideal For A Contractor or Contracting Company With All The Extra Parking and Pull Off Areas and Commercial Zoning (HB Zone) OR Someone With A Boat, Jet Skis w/ Trailers. Park + or -- 30 Cars In This Driveway Including The 2 Pave Cut-Outs Perfect For Turning Around, Parking Teenager Vehicles, Employee Vehicles As They Meet For Work, Camper / RV, OR For Those Fantastic Summer Parties! This Private Haven Is Close To Everything And Room For All -- Shopping, Schools, Train Station/Commuting, Restaurants AND Still Be Home In 5 To 10 Minutes. Flexible Floor Plan To Create Rooms For You --- A Big Dining Room Off The Kitchen W/ An Eat-In or a Quick Bite At The Island and a Family Room OR Living Room On The Other Side. Current Owners Created His & Hers Living Rooms But Either Of These Rooms Could Become Something Else. Have You Always Wanted A Media Or Game Room? The Finished Basement Is Also Ready For Your Ideas Without Having To Start With Unfinished Space. Both Bedrooms In The Upper Level Are Large and Check Out Those Unique Hardwood Floors! The House Has Room To Grow As Your Spatial Needs Grows -- The Bedroom On The Left Has 2 Very Deep Areas Currently Unfinished But Being Used As 2 Walk-In Closets. However, When It's Time To Grow, The Upstairs Could Be Turned Into A Large Primary Suite With A Bath & A Large Walk-In Closet. Excited To Host Summer BBQs & Pool Parties? There is Plenty Of Room! Enjoy The Summer's Sun OR Moon's Reflection From The Salt Water Pool As You Sip Your Morning Coffee OR Your Evening's Glass Of Wine -- On The Deck Or On The Pool's Patio. Then, Cozy Up To The Fire In The Fall & Winter. Come! Relax, Unwind, & Enjoy Life! This Is The Perfect Home!
Courtesy: Douglas Elliman Real Estate
914-234-4590
Private 5-Acre Hudson Valley Compound with Dual Residences, Pool, Pond & Long Views Description: Welcome to your ultimate year-round sanctuary and summer recreation haven, set on 5 serene acres in picturesque Pawling, NY. Offering total privacy, sweeping open views, and exceptional versatility, this rare multi-dwelling compound features two independent residences with a combined 5–6 bedrooms and 5 bathrooms. Main Residence (43 Meeting House Road): Designed for seamless indoor-outdoor living, this home offers 3–4 light-filled bedrooms and 4 full bathrooms. Warm up in the spacious living room by the classic fireplace, or step outside onto expansive two-level decks built for grand outdoor entertaining, dining, and taking in the panoramic views over the mature grounds. Second Residence / Cottage (41 Meeting House Road): Ideal as a guest house, multi-generational living quarters, or private retreat, the secondary home features 2 bedrooms, 1 full bathroom, and its own cozy living room complete with a fireplace. The Grounds & Outdoor Amenities: Unwind by your private heated swimming pool, stroll through lush lawns framed by mature plantings, or enjoy quiet reflection beside the large, peaceful pond. Whether you are hosting summer pool gatherings, cozy winter evenings by the fireside, or simply craving year-round serenity within easy reach of local amenities, this property delivers an unmatched Hudson Valley lifestyle. Schedule your private tour today!
Pawling is located in New York. Pawling, New York has a population of 8,024. Pawling is more family-centric than the surrounding county with 33.87% of the households containing married families with children. The county average for households married with children is 29.92%.
The median household income in Pawling, New York is $106,806. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Pawling is 47.9 years.
The average high temperature in July is 81.5 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 49.5 inches per year, with 49.1 inches of snow per year.
