64 houses for sale in East Chatham

Top area builder. All brand new. Eyebrow colonial transformed in to a modern energy efficient cozy home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, smart siding. All new lighting throughout the house, new floors. All brand new appliances. Literally Brand new everything. New hot water heater tank with heat pump, water purification system. New Radon system, New wrap around deck to enjoy your backyard. Spray foam sealed insulated full basement for warmth and dryness. Bright and airy rooms with windows galore. Lots of yard and a view of the mountains. Beautiful paved driveway and access to Queechy Lake, one of the top 5 cleanest lakes in the state. Move in and live maintenance free for years. All new. Close to TSP, I 90, Hudson, Chatham, Albany. More land available to purchase. Across the road is in a conservancy to further protect against a development

A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room—an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished at

A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room-an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished at

If you love to drive long gravel roads through maplewood forests dotted with antique farmhouses and barns, we have this offering located in the corner of Columbia County that serves mountaintop views across the Hudson Valley. The impressive drive into the property through the gate is uphill past three meadows ablaze in native wildflowers across three seasons and through its own maple stock. The residence is a J. L. Ramirez, Architect PC (NYC) designed and built 4 bedroom 2.5 bathroom 3200 square foot center hall colonial with an open downstairs floor plan, high ceilings on both floors, grand porches on both front and back with sunlit, expressive Pella windows highlighting the Catskills to Berkshires views surrounding this tippy top sited spot. The estate, constructed in the year 2000, has 89 acres in total, with 20 acres mowed and lovingly maintained over 25 years to provide a lawn for lounging and entertaining. Afternoon breezes and birdwatching become the cocktail hour calling with a

Tucked away inside an exceptionally quiet, private community, and set upon more than 7 private acres, this home offers stunning vistas: every morning here begins with sunrise breaking directly over the crest of the Berkshire Mountains and ends with gorgeous colors streaking across the sky at sunset, all viewable from the entire back of the home as well as its expansive wooden deck. Inside, you'll find over 2,500 square feet of bright, open living space. The main living area flows easily, from custom chef's kitchen to columned dining area to large living room with gas fireplace, and all with those spectacular views. The main floor also houses a ½ bath as well as a laundry room and ample storage. Upstairs you will find 3 bedrooms and 2 bathrooms, including an expansive primary bathroom off the primary bedroom. The basement level features a tall, full-height finished living space, currently used as a home gym and extra sleeping space for overflow guests. The rest of the basement is framed

Open house 10/17 cancelled. There is something increasingly rare about a property that allows you to bring more of your life home. Set on 3.1 acres in Canaan, this three-bedroom, two-bath residence offers a compelling proposition for the equestrian, aspiring homesteader, or anyone drawn to a more self-sufficient way of living. A two stall horse barn and established turnout pasture mean your morning commute to the barn could simply be a walk across your own property. Keep your horses at home, trade boarding fees for independence, or reimagine the acreage with goats, chickens, a few cows, vegetable gardens, and the beginnings of your own small-scale homestead. The house itself has an unexpectedly luminous quality. Skylights and generous windows draw daylight deep into the interior, while hardwood floors and an easy, expansive layout give the home an uncontrived warmth. The sunroom is perhaps its most convivial space. Vaulted ceilings, walls of glass, a wood stove, and a wet bar create a

With lush rolling hills, long-stretching meadows, & the beautiful Kinderhook Creek running through it all, this heavenly slice of rural idyll quickly became home to grist mills, thriving trade businesses, & large farms. The largest section of the house, as it stands today, was likely built onto the original home at the turn of the 19th century by the Rider family, with the scalloped trim & other decorative millwork added towards the end of the 1800s. The entire property marks key architectural innovations & tendencies across hundreds of years. Both the barn & the farmhouse sit on beautiful, thick fieldstone foundations, with exterior elements dating from the 1700s to the early 1900s, & stone foundation ruins on the grounds remain from the original covered bridge that once connected the north & south sides of the Kinderhook Creek. Inside the house, two-foot-wide floorboards, hewn beams, & painstakingly restored Shaker hand-built cabinetry tell the story of the home's first 100 years & i

Discover the perfect blend of privacy, modern comfort, and endless possibilities on this exceptional 75.47-acre country retreat featuring trails, a scenic pond with westerly views, and breathtaking Catskill Mountain views. Whether you envision a private estate, recreational getaway, or family compound, this remarkable property offers an unparalleled opportunity. The updated single-level ranch is move-in ready and features central air conditioning, a spacious eat-in kitchen, an updated bath with a walk-in shower, and a full, dry basement with laundry and abundant storage. Live comfortably while you build your dream home overlooking the pond and mountain views, then transform the ranch into a guest house, caretaker's residence, or income-producing rental. Adding to the property's versatility are two impressive barns. Adjacent to the home is a charming 2,000-square-foot circa-1910 barn, full of timeless character and ideal for equipment, storage, or workshop space. At the highest point of

Imagine a crisp autumn morning, dew still resting on the ground. You step onto your front porch with a warm beverage in hand and take in the peaceful beauty of the surrounding countryside. For a few quiet moments, it's simply you and nature. As the cool air settles in and your drink begins to lose its warmth, you head back inside, where the woodstove keeps the living room cozy and inviting. Wander into the kitchen, finish making breakfast, and settle in to enjoy your morning in the comfort of home. Situated on approximately one acre, this three-bedroom, one-bath home offers the country setting you've been looking for while keeping you within reach of everyday destinations. East Chatham provides convenient access toward the Massachusetts border and the Berkshires, including the Pittsfield and Stockbridge areas, while Albany, Troy, and East Greenbush are also within driving distance. After a long day, pull into the attached basement garage and leave the outside world behind. As you walk

A private get away in East Chatham on 7.4 acres with fruit trees, and a terraced fire pit This 2 bedroom, 1 bath ranch home was renovated in 2008 and boosts a newer kitchen and bath There is a wood burning fireplace for cozy evenings, a 3 season sunroom and a lower level rec room. There are 2 outbuildings, one a 2 car garage with an upper unfinished loft offering many possibilities. In addition, the tiny cottage is a charming retreat with potential for an office or guests. This home wont last long on the market. Let's take a tour together and find inner peace on County Route 9. Close to Chatham, The Berkshires, Hudson and an easy Albany commute

Price improvement! At this FANTASTIC new Price you can own a slice of heaven in Columbia County! Set on an acre in Chatham, this charming three-bedroom farmhouse captures the simple pleasures of country living-morning coffee in the quiet, evenings spent at home, and plenty of space to enjoy the changing seasons. Step inside to warm and welcoming living and dining spaces, where hardwood floors lend character and a timeless farmhouse feel. The flexible first-floor bedroom can easily become a cozy guest room, private home office, den, or creative space. Upstairs, additional bedrooms offer peaceful retreats, while one-and-a-half baths and a dedicated laundry room make everyday living comfortable and convenient. Adding to the property's country character is a barn-a wonderful and increasingly coveted feature with endless possibilities. Use it for storage, a workshop, gardening supplies, outdoor gear, or imagine transforming the space to suit your own vision/ perhaps an outdoor dining space

Welcome to Pine Hollow. Set on 5.1 private acres in Old Chatham, this classic Colonial has 2,240 square feet with three bedrooms, 2.5 baths and a comfortable, gracious layout. Hardwood floors run through the main living spaces, with a generous living room, formal dining room and kitchen made for gathering. Upstairs, the primary suite has its own bath and walk-in closet, along with two additional bedrooms and a separate office space. A long driveway leads you in, crossing over a seasonal stream before reaching the house, tucked among the trees. Trails wind through the surrounding woods, with plenty of space to garden, explore or simply enjoy the peace and quiet that comes with five acres of your own. And the setting is quintessential Old Chatham. The Village of Chatham is minutes away for coffee, dinner, shops, the Crandell Theatre and PS21. Just beyond, Kinderhook, Spencertown and Austerlitz are all nearby, with Hudson and Albany an easy drive. Head east and you're quickly across the M

Welcome to the Beebe Pond House & Cabin, a breathtaking 14-acre private sanctuary offering two distinct dwellings, natural water features, and lucrative multi-house versatility. The turn-of-the-century main house blends timeless historic craftsmanship with modern energy efficiency across three bedrooms and two bathrooms. Expansive, light-filled living spaces showcase original hardwood floors, beautifully restored moldings, classic pocket doors, and a cozy kitchen. Major mechanical and functional improvements to the main home include an eco-friendly solar setup, blown-in wall insulation, a brand-new fuel tank, and newly installed electrical and custom lighting in the dedicated home office space. Situated overlooking the pond, the bohemian-inspired back cabin features two bedrooms, two bathrooms, and a custom sleeping loft crafted with high-end wood finishes and artisanal built-ins. Recent cabin enhancements offer complete peace of mind, featuring a brand-new roof, new bedroom flooring,

Tucked 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 1803 brick home, featuring a versatile 3-bedroom, 2-bathroom layout highlighted by an extensive primary suite, rich custom woodwork, and a chef's kitchen featuring an iconic Aga stove. Step outside to a private courtyard setting where a stone masonry patio leads to a saltwater swimming pool, hot tub, and a sauna. The sprawling acreage is a diverse natural landscape, offering an idyllic mix of rolling lawns, open pastures, mature woods, striking rock outcroppings, seasonal creeks and two serene ponds. Tailor-made as an unrivaled artist compound or multi-use retreat, the outbuildings include a beautifully restored antique barn, a working maple sugar shack, and a massive, finished 4,000 sq ft studio/workshop-an incredible canvas for large-scale creation, fabr

See Supplemental Remarks Welcome to Red Rock House, a remarkable architectural compound privately set on 16 acres in the historic hamlet of Red Rock in East Chatham, New York. Designed by Anmahian Winton Architects with landscapes by Studio Reed-Hilderbrand, this extraordinary retreat seamlessly blends contemporary design with the surrounding natural landscape, creating an exceptional sanctuary. A winding driveway through the forest leads to the main house and guest house, both clad in darkened cedar wood with latticed privacy screens that blend effortlessly into their surroundings. A bluestone pathway connects the structures, leading to a terraced pergola with multiple seating areas, a wood-burning fireplace, sweeping meadow views, and a 60-foot heated saltwater pool. Just beyond, a secluded cottage overlooks a rushing creek, while a woodland trail leads to an elevated treehouse-perfect for yoga, meditation, or quiet reflection. Spanning three levels, the main house is a masterclass i

Surrounded by nature with 21 acres of private trails to roam. This architecturally striking 3BR/2BA home features a soaring cathedral-ceiling great room opening to a wrap deck, plus a lower-level hangout space perfect after a day outdoors. Central air, efficient propane systems, and an oversized 2-car garage make it easy to enjoy in every season. Minutes to Queechy Lake, Chatham, Hudson, the Berkshires, and skiing just 15 miles away. A private retreat with huge redecorating potential. Ideal for year-round adventure or a high-demand AirBnB escape. Short notice showings possible. Fiber optic high speed internet. 35-year architectural shingle guarantee (6-10yrs left). Decks 4-5yrs old. Mailbox end of driveway

New price! Open house sunday, november 8 from 2-4pm! Located just minutes from the Village of Chatham, this solidly built mid-century ranch sits on a manageable half-acre lot and offers sweeping views of the Taconic foothills from the dining room, family room and deck. With only 1 owner in the last 58 years, this 3 bed / 2 bath home has been well cared for, with classic features such as a wood burning fireplace and cedar closets as well as modern amenities such as central AC, electric blinds and a whole house generator. Downstairs, the basement expands your living space with a dedicated rec room, alongside a laundry area equipped with w/d, a double utility sink and an extra freezer. An integrated 2 car garage rounds out the home. Outside, the grounds feature beautifully established perennial gardens accented by custom stone walls as well as an outdoor potting shed tucked under the deck. Just over 2 hours from NYC and Boston and nearby everything that makes Columbia County and the Berks

Tucked 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 1803 brick home, featuring a versatile 3-bedroom, 2-bathroom layout highlighted by an extensive primary suite, rich custom woodwork, and a chef’s kitchen featuring an iconic Aga stove. Step outside to a private courtyard setting where a stone masonry patio leads to a saltwater swimming pool, hot tub, and a sauna. The sprawling acreage is a diverse natural landscape, offering an idyllic mix of rolling lawns, open pastures, mature woods, striking rock outcroppings, seasonal creeks, and two serene ponds. Tailor-made as an unrivaled artist compound or multi-use retreat, the outbuildings include a beautifully restored three-story antique barn offering approximately 3,600 square feet of versatile space, a working maple sugar shack, and a massive, finished 4,000

OPEN HOUSE 10/24 11am-1pm Million-dollar views, peaceful surroundings, and room to breathe! This charming two bedroom log home has been lovingly enjoyed by the same family for 43 years. Located off a quiet dead end country road, in a private 5+ acre setting with compelling, magnificent views. Superb location only five minutes to Chatham Village, 25 minutes to Hudson or Great Barrington

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom home captures breathtaking, uninterrupted views of the Catskill Mountains and Hudson Valley, with spectacular sunsets, endless skies, and exceptional stargazing. Designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, butler's bar, and custom cabinetry by renowned Vormer Cabinetry of Hillsdale. High-performance Pella windows frame the panoramic views, while a dramatic stone fireplace with a reclaimed wood mantel anchors the great room. A marble gas fireplace adds warmth to the den. The primary suite enjoys stunning views and includes a spa-inspired bath, laundry, and generous closet space. A spacious two-car garage offers abundant storage for outdoor gear, perfectly complementing the property's proximity to Queechy Lake, Stockbridge Bowl, and year-ro

Extensively renovated in 2024, this exceptional year-round Queechy Lake retreat offers a rare combination of lifestyle, privacy, and income potential with a very active summer and winter activities in the lake or on the ice! Spanning three finished levels, the property features a total of 5 bedrooms and 2 full bathrooms. Thoughtful renovations throughout deliver a truly move-in-ready home with modern updates, quality finishes, and brand-new furnishings included. Designed for flexibility, the home offers versatile multi-unit living with two kitchens and separate owner or guest access-ideal for rental income, multi-generational living, or use as a single five-bedroom residence. The first-floor unit includes two bedrooms, one full bath, and a fireplace, while the second and third floors comprise a spacious three-bedroom, one-bath unit. Enjoy deeded private beach and boat launch access for easy lake living, all in a high-demand, year-round location just minutes from Jiminy Peak. Ideally si

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, and laundry. The owners built and have lived here for 52 years, giving constant care and maintenance to the place they loved. The mature gardens are simply breathtaking, with vibrant perennial beds, specimen trees, and beautifully landscaped grounds creating a storybook setting throughout the property. A detached two-car garage includes a spacious apartment above, ideal for guests, extended family, or creative use. Completing the estate is a large workshop/studio offering endless possibilities. Enjoy the peace and seclusion of your own private hideaway while remaining just five minutes from Chat

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatheri

Commanding one of the highest residential elevations in the Hudson Valley, this extraordinary custom residence enjoys breathtaking, uninterrupted views across the Catskill Mountains and Hudson Valley, offering spectacular sunsets, endless skies, and extraordinary stargazing from the privacy of your own mountaintop retreat. Thoughtfully designed for luxurious everyday living and effortless entertaining, the home features a chef's kitchen appointed with premium Bosch, Sub-Zero, and other high-end stainless steel appliances, a gas cooktop, a handsome butler's bar, and exceptional custom cabinetry and built-ins handcrafted by renowned local artisan Vormer Cabinetry of Hillsdale. Superb craftsmanship is evident throughout, complemented by high-performance insulated Pella windows that enhance comfort and energy efficiency while framing the spectacular views. The dramatic great room is anchored by a striking stone fireplace with a reclaimed wood mantel, while a marble gas fireplace with a woo

Remember that time when' Thats what you'll say, what your kids will say, what your grandkids will say because thats what a lakefront property creates. It's a camp built for summer. A bunkhouse upstairs, a huge deck and a dock for your boat. You'll swim and boat on one of the cleanest lakes in NY. You'll learn why they call it Last Ray Bay. You'll enter a craft in the regatta and put on a funny sailor cap. And thru the years you'll never stop remembering that time when

Simply Enchanting! Charming 1830s farmhouse in a magical country setting. Tucked off a quiet country road, this is truly a home for all seasons. Cozy up to the fireplace in winter, watch the snow gently fall from the sunroom. Create a feast in the country kitchen, then gather in the diningroom or out on the screened porch which leads to a large deck-the resident great blue heron may even grace you with a fly-over. Sit streamside in the gazebo and enjoy the soothing sounds of the waterfall. With wideboard floors, built-ins, and period appointments throughout, this home exudes warmth and character. Mechanicals are all up to date and a whole house generator gives you peace of mind. The two story antique barn with loft offers great space for storage or hobbies. Fine dining, recreational activities like skiing and hiking, and cultural venues like Tanglewood are all just a short distance away

Back on the Market and at a new price! This beautifully maintained single-family home blends classic charm with modern updates including a brand new radon remediation system and whole house UV light water treatment system! Featuring 2 bedrooms, 2 baths plus an extra room perfect for an office, this house includes gleaming wood floors and a newer kitchen designed for easy entertaining. Outdoor enthusiasts will value the Queechy Lake rights for boating, swimming and lakeside relaxation. With comfortable living spaces, a 1 car garage and attractive outdoor amenities, this property is an ideal full-time home or seasonal escape. Please note. The new price reflects the fact that a new septic is needed. Additionally the deck over the septic has been removed to allow access to the tank. The 80K price reduction allows the new owner to remedy the current setup

Welcome to Peggy's Cottage. The owner, a cellist, originally chose this Queechy Lake home for its proximity to Tanglewood and the cathedral ceilings in the family room, which serves as her music room. She quickly grew to love the lake community's friendly neighbors, trails, and private beach. This two-story, year-round lake home sits on a level. 36 acre lot, offering rare privacy with lovely gardens, a latticed entertainment deck, and two sheds. Relax in the living room in front of the stone fireplace, perfect for a quiet conversation or reading. Step into the spacious family/music room and enjoy movie night and the view of the gardens. The open kitchen and dining area connect to a first-floor bedroom with laundry and a full bath. Upstairs, you will find two large bedrooms with skylights and generous closets, including a primary bedroom with an ensuite bath and a Juliette balcony. The second bedroom accesses the bath via a hall entry. Key updates include a new roof (2025) and boiler (1

Seven vehicle spaces, over five acres, and your own private retreat: Car enthusiasts, hobbyists, and anyone craving room to spread out, this unique property deserves a closer look! Set on approximately 5.3 picturesque acres, this one-of-a-kind property offers a rare combination of garage space, flexible living areas, and outdoor amenities that make everyday living feel like a getaway! The standout feature? Exceptional vehicle capacity, including an attached garage and a substantial detached, insulated garage with electricity, ideal for those who need space for vehicles, equipment, projects, or hobbies! And there's so much more. Enjoy summer days by the inground pool, entertain poolside, or simply unwind surrounded by beautiful, mature landscaping. The grounds feature a greenhouse, fruit trees, grape arbor, pool house, and basketball court, offering plenty of room to enjoy the outdoors. Inside, cathedral ceilings and flexible living spaces offer room to work, create, relax, and make the

Price reduction! Welcome home to your year-round vacation. The moment you step inside this newly remodeled double-wide, you'll feel the care and craftsmanship that went into every detail. Hardwood floors greet you, ceramic tile with a beautiful medallion anchors the mudroom, and tongue-and-groove pine boards glow in the living and dining rooms. The kitchen is stocked with new and newer appliances, including a standout refrigerator. Your main bedroom suite is a retreat all its own-Pergo flooring, a spacious closet, a bidet, and a luxurious shower with multiple heads and a rainfall feature. The living/dining area stretches wide, filled with natural light and warmed by a gas fireplace. Look out the patio doors and you'll see the backyard that makes this home truly special. Step outside to a full outdoor cooking setup-massive grill, storage cabinets, outdoor kitchen space-and a modular pool house and sunroom for shade, rain, or gathering with friends and family. With two additional bedroom