Chatham, NY Homes for Sale with Acreage

CEDAR HILL - Architectural Country Living at its Finest - is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's

Nancy Felcetto BROWN HARRIS STEVENS HUDSON

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape. Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed

Anthony D'Argenzio Houlihan Lawrence

Charming 3-Bedroom Ranch on 14 Acres in Old Chatham, NY Discover peaceful country living at its finest in this inviting 3-bedroom ranch-style home, nestled on a sprawling 14-acre parcel in Old Chatham. Offering the perfect blend of comfort, functionality, and outdoor adventure, this property is ideal for horse enthusiasts, nature lovers, and those seeking a private retreat just minutes from

Tyler Bervy Stone House Properties, LLC

A Grand Dame in Old Chatham. Discover the joy in bringing back a classic. All the bones are solid. Five bedrooms in that rambling feel that makes farmhouses so lovable. The great room fireplace combines stone and real wood panels with views of the pond out the windows. A formal dining with wainscoting leads to a kitchen that leads out back. A second living room that could be it's own apartment.

Andrea Gabel Gabel Real Estate

Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher

Janet Kain The Kinderhook Group, Inc.

Recently renovated and thoughtfully updated, the streamside cottage and separate guest studio were once part of the historic Wigton Lester Farm, with origins dating back to the early 1800s. Nestled on 5 acres along one of the most picturesque roads in Old Chatham, the property is surrounded by open meadows, historic stone walls, and a gently winding stream that, over generations, has carved its

Michael Tellerday Houlihan Lawrence Inc.

Welcome to the original early 1800's John Jay van Valkenburgh home in the quaint and historic hamlet of Chatham Center.This three bedroom, charming two-story colonial farmhouse on 1.6 acres features original wood beams, a working fireplace with wood stove insert in the large open living room, hardwood floors and an adjoining dining room with a cast iron wood stove. A modern kitchen with

Janet Kain The Kinderhook Group, Inc.

OPEN HOUSE Sunday June 21 st 11AM-1PM In the desirable Spencertown hamlet, this ''top to bottom'' quality renovated Cape is move-in ready for summer enjoyment. Everything is new....roof, heating and AC, windows, doors, hardware, fully equipped kitchen with stainless appliances and granite countertops, flooring, lighting, bathrooms, fencing, washer and dryer and more. A fantastic location, close

Peter Newman Beach & Bartolo Realtors

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

Nikki Carchedi STONE HOUSE PROPERTIES, LLC

Open House Sunday, July 5th 11am-1pm Captivating and glorious Catskill views paired with lush rolling hills will mesmerize you from the moment you arrive. This stunning, custom-designed contemporary home with classic details is absolute perfection. Perched at the end of Lamoree Road--one of the most beautiful and undiscovered roads in Columbia County--this property offers a serene oasis in East

Peter Newman Beach & Bartolo Realtors

Set along one of the most beautiful roads in Columbia County, this extraordinary country property offers a rare convergence of architecture, design, and landscape. Surrounded by 13 gorgeous acres of rolling hillside and forest, the setting feels both cinematic and deeply peaceful. Just beyond, the road is famously home to the Chatham Sheepherding Company's iconic complex of vernacular barns and

Annabel Taylor Four Seasons Sotheby's Int.

Nestled in a serene, wooded setting, 326 Pratt Hill Road is a thoughtfully designed Cape-style home that blends rustic charm with modern comforts. Originally a quaint cabin, it has been carefully expanded over the years and now offers three bedrooms, two full bathrooms, and 8.1 private acres – perfect for a weekend escape or year-round living. The oversized living area features hardwood floors, a

Callan Bergmann Compass Greater NY, LLC

This 9.5-acre property in Chatham, NY offers exceptional potential, with multiple structures one of which is an amazing 2 story huge barn and a private pond for swimming. The tax estimate on Zillow is too high. A true diamond in the rough, the 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. Dual brick fireplaces in the living

Claudia Zucker Living Structures

Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the

Jeb Hart Licensed as Henry Hart Corcoran Country Living

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+ square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6

Margaret Guerra Trevett Group LLC

Brick House FarmTucked away in the highly sought-after Red Rock community, Brick House Farm is a rare 80-acre compound offering a distinctive blend of 19th-century character and expansive functional space. At the heart of the estate stands a classic 1810 brick home, featuring a versatile 4-bedroom, 2-bathroom layout highlighted by an extensive primary suite, rich custom woodwork, and a chef's

Rachel Haley Compass Greater NY, LLC

Tucked down a quiet country road, 2318 County Route 9 is the kind of place that feels like it's been waiting for you. Set on over five acres, this three bedroom, one bath cottage is thoughtfully designed from the inside out, every corner telling a story, every detail chosen with care.Sunlight pours through every window, framing the beauty of lush gardens and the natural world just beyond the

Shaina Marron Houlihan Lawrence Inc.

Don't overlook this peaceful escape, tucked away on nearly five wooded acres with sweeping hilltop views--yet just minutes from Ghent and Chatham. This spacious contemporary home offers both privacy and a strong connection to the surrounding natural beauty. Set at the end of a long driveway on 4.8 wooded acres, coming home feels like a retreat into peace and stillness. The well-maintained home

Darcey Volans The Kinderhook Group, Inc.

Nestled within the serene hamlet of Old Chatham, this exceptional country home offers 43 private acres with stream frontage and abundant wildlife. Thoughtfully renovated and impeccably maintained, the residence seamlessly blends timeless rural character with modern comfort. Recent enhancements include a beautifully redesigned kitchen and bath, upgraded sound attenuation for enhanced privacy, a

Mary Turoci Keyology

Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all

Nancy Felcetto Brown Harris Stevens HV LLC

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

Nikki Carchedi Stone House Properties, LLC

Camp DugwayA home that evokes the great camps of the Adirondacks within 2 hours of Manhattan. Cross the bridge over a babbling brook to a setting straight out of a Cooper novel. Three cascading waterfalls frame the view. The pond sits just off the bluestone patio. Inside a blend of craftsman style and great camp ambiance in every room. The fieldstone in the fireplace came from the land as did

Andrea Gabel Gabel Real Estate

A truly magical property tucked away at the end of a quiet country road, yet just minutes from the Village of Chatham. Set amid 10 lush and exceptionally private acres, the centerpiece of this enchanting retreat is a light-filled barn conversion featuring a soaring stone fireplace, wide-plank floors, a lofted primary suite, and a separate guest level with living room, two bedrooms, a full bath,

Lisa Bouchard Hoe The Kinderhook Group, Inc.

This 9.5-acre property in Chatham, NY offers exceptional potential, with multiple structures including a huge 2 story barn in excellent condition with a private pond. for swimming. A true diamond in the rough, the 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. Dual brick fireplaces in the living room and reading nook, a

Claudia Zucker

Located at the end of a town-maintained gravel road, this private raised ranch sits on 2.83 acres accented by a classic stone wall, offering views of the surrounding fields and woods.The first floor includes a family room, one bedroom, and a full bathroom. Upstairs, the second floor features the living room, dining area, kitchen, two additional bedrooms, a full bathroom, and a laundry room. Front

Daisy Blair Howard Hanna Capital Inc

Freshly painted and full of country charm, this inviting East Chatham home offers breathtaking long-range views, peaceful surroundings, and a quaint setting perfect for enjoying the beauty of Columbia County. Relax and take in the scenic countryside while still being conveniently located near shopping, dining, and everyday amenities. Enjoy easy access to outdoor recreation and local attractions,

Jerome Newkirk Revision Real Estate

Discover the perfect blend of privacy, space, and versatility with this custom-built 2,400 sq. ft. home nestled on 5.5 scenic acres. Featuring 3 bedrooms, 1 bath, and soaring cathedral ceilings, this one-of-a-kind property offers comfortable living with exceptional indoor and outdoor amenities. Step outside to your own private retreat, complete with an inground pool, pool house, greenhouse with a

Kimberley Willsey eXp Realty

Nestled within the serene hamlet of Old Chatham, this exceptional country home offers 43 private acres with stream frontage and abundant wildlife. Thoughtfully renovated and impeccably maintained, the residence seamlessly blends timeless rural character with modern comfort. Recent enhancements include a beautifully redesigned kitchen and bath, upgraded sound attenuation for enhanced privacy, a

Mary Turoci Keyology Realty