89 houses for sale in Old Chatham

Completely reimagined and ready for its next chapter. This beautifully renovated 3-bedroom, 2-bath home has been rebuilt from the inside out, blending classic village character with modern efficiency and designer finishes. The bright, open kitchen anchors the home with crisp white cabinetry, a spacious island, and a layout designed for everyday living and entertaining. Enjoy energy-efficient upgrades, air conditioning, and the timeless appeal of a welcoming front porch. Ideally located a stone's throw from Main Street in the Village of Valatie, you'll be moments away from local restaurants, cafés, boutiques, and community events, while the nearby Albany-Hudson Electric Trail offers miles of scenic walking and biking. This is more than a renovation-it's a fresh start in one of Columbia County's most desirable small-town communities. Move in, unpack, and enjoy! (Mailboxes are being relocated)

Perched above the tranquil waters of Kinderhook Lake, The Lady of the Lake is one of Columbia County's most unforgettable homes-a thoughtfully restored former church transformed into a design-forward retreat where historic architecture meets modern luxury. Rich with character and reimagined with an exceptional eye for design, this three-bedroom, two-bath residence effortlessly blends original architectural details with warm, contemporary interiors. With wood beams and natural light framed by peaceful lake views, every space has been carefully curated to feel both timeless and inviting. At the heart of the home, the beautifully renovated kitchen flows seamlessly into open living and dining spaces designed for gathering, entertaining, and slowing down. Every finish has been intentionally selected, creating layered interiors that feel sophisticated yet not overly fussy. One of the home's most spectacular features is the newly added screened-in porch overlooking Kinderhook Lake. Whether it

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

Welcome to easy, maintenance-free living in Valatie! This beautifully appointed 2-bedroom, 2.5-bathroom townhouse offers the perfect combination of comfort, style, and convenience in a desirable no-maintenance community. Step inside to an inviting open floor plan highlighted by soaring cathedral ceilings, beautiful hardwood flooring, and an abundance of natural light. The spacious living room features a cozy propane fireplace, creating a warm and welcoming gathering space. The large kitchen is sure to impress with generous granite countertops, plenty of cabinetry, and an open connection to the dining and living areas-perfect for entertaining or everyday living. Each spacious bedroom offers the luxury and privacy of its own en-suite bathroom. A dedicated home office area provides the ideal spot for working remotely, managing household affairs, or creating a quiet reading nook. From the dining area, step outside to your own private patio oasis-a wonderful place to enjoy morning coffee, d

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

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

Welcome to Sutherland Estate, a private country compound set on more than 56 acres of rolling meadows, gardens, ponds, with Catskill Mountain views. A long paved drive leads to this elegantly designed 5,760-square-foot home, inspired by classic Greek Revival architecture and recently renovated from top to bottom with refined, high-end craftsmanship. The home features a standing-seam metal roof, radiant heated bathroom floors, energy-efficient heat pumps, a whole-home generator, and a fully integrated smart home system for lighting, temperature, and security. Recent upgrades include newly refinished white oak hardwood floors, new luxury vinyl plank basement flooring, a refreshed lighting plan with recessed fixtures and designer pieces from Arteriors and Hinkley, updated Lutron switches and outlets, new HVAC registers and vents, fresh paint, new baseboards, and updated hardware. The main level offers bright, connected gathering spaces with sweeping views of the ponds and Catskill Mountai

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

A new price adjustment now makes this a bargain for your home in Chatham! Open house Saturday, October 3 from 12-2PM! 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 Bost

Adorable, tastefully renovated cottage on a quiet side street within close proximity to Kinderhook Lake and the Empire State Rail Trail. This easy to care for home offers an array of upgrades. Including a new kitchen with a gorgeous farmhouse sink, new wainscoted bathroom, new split system for heating and cooling and a brand new deck for après dining and relaxing. There is ample parking and plenty of room for a garage or studio. Less than 10 minutes to groceries, farmers markets, dining, theatre, parks and museums. 25 minutes to the cultural hub of Hudson, and 25 minutes to Albany. Whether as a full-time home or weekend escape, this delightful cottage is the perfect place to relax, unwind, and enjoy all the area has to offer

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

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

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

Tucked away at the end of a long approach and surrounded by 13.24 acres of pure Hudson Valley beauty, this exceptional A-frame retreat offers the ultimate escape for those seeking peace, privacy, and a connection to nature. Whether you're searching for a full-time residence or a weekend sanctuary, this property delivers the perfect blend of rustic charm and modern comfort. The dramatic great room is the heart of the home, featuring soaring cathedral ceilings, walls of glass that frame the changing seasons, and a stunning stone fireplace with a wood stove insert that creates the perfect gathering place after a day outdoors. The chef's kitchen is thoughtfully designed with a gas cooktop, built-in double ovens, Hi-Mac solid surface countertops, and generous workspace for entertaining. The adjoining dining area is surrounded by oversized picture windows, bringing the outdoors in with breathtaking woodland views. Convenient first-floor living includes a spacious bedroom, full bath, and laun

Experience modern elegance in this newly remodeled property in North Chatham, New York, with beautiful lake views. This home features a sleek, updated kitchen and a well-designed bedroom with a balcony that welcomes natural light and scenic vistas. Enjoy the perfect blend of privacy and style in this lovely residence! A great opportunity to live in a peaceful community close to Kinderhook Lake

This stunning Colonial boasts 4 bedrooms, 2-1/2 baths, gorgeous hardwood floors, a recently renovated kitchen and IG pool. The first floor features a formal LR and DR, along with a spacious eat-in kitchen adjoined by a FR with woodstove. A half-bath with laundry is also conveniently located on the main level. The second floor offers a primary BR ensuite with full bath, three additional BR's and a full guest bath. Additional highlights include a two-car attached garage and a partially finished basement (approximately 500 sf) Municipal water and sewer. Situated in Valatie, this property offers easy access to several weekly farmers' markets and local shopping. Just a half-hour drive to Albany and approximately 2-1/2 hours to Boston and NYC

Opportunity awaits on beautiful Kinderhook Lake! This 900 sq ft home offers stunning water views and sits on a spacious yard, making it the perfect blank canvas to create your dream lakeside retreat. Whether you're looking for a weekend getaway, your year round home, or a great investment property, the potential here is unlimited. Property is being sold as-is and will require renovation; cash or renovation financing only (will not qualify for FHA or VA). Bring your vision and make this lakeside gem your own!

Walk through the front door, and it's easy to forget what this building has been. Instead, you begin thinking about what it could become. Long before the property became known as Kinderhof, it began its story as a distinguished country estate and working farm, remaining a familiar Columbia County landmark for generations. Over the years, it welcomed countless people while quietly preserving the craftsmanship, scale, and architectural character of another era. Today, those details still shine through. Original fireplaces, vintage tile, beautiful masonry, generous rooms, and timeless architectural features offer a glimpse into the property's past. Beyond the main residence, several historic estate outbuildings remain, including what is believed to have been the original carriage barn, a historic corn crib, and a charming storybook structure with its distinctive arched brick entry. Thought to have served the estate during its agricultural years, perhaps as a caretaker's cottage, farm offi

Own a piece of history in this beautifully maintained 4-bedroom, 2-bath Center Hall Colonial in the East Greenbush School District. This exceptional home blends timeless character with modern updates, featuring wide-plank pine floors, hardwood floors, fireplaces, chandeliers and a striking Palladian window. The spacious, flowing floor plan is perfect for both everyday living and entertaining. Enjoy your morning coffee on the enclosed rear porch overlooking a private backyard with a koi pond and colorful gardens. Wood and oil heat provide flexible heating options. The impressive 1,540-square-foot detached barn-style garage includes a heated loft, offering outstanding space for a workshop, studio, home office or recreation area. A rare opportunity to own a historic Nassau home filled with warmth, charm and versatility. 3D tour attached

This serene 5-acre property boasts open meadows and mature trees, offering a tranquil retreat that feels a world away, yet remains highly accessible to the best of the Hudson Valley and Berkshires. Its proximity to the Taconic State Parkway and Interstate 90 ensures an easy retreat from both New York City and Boston. Locally, you'll delight in the charming town of Chatham's cafes, restaurants, bars, and a burgeoning art museum scene, with Queechy Lake just a 10-minute drive away. Popular destinations like Hudson and Great Barrington are also a short beautiful drive away. Inside, discover the ease of single-floor living, featuring a spacious living room with a high vaulted ceiling and a warming wood-burning fireplace. The perfectly updated kitchen is both tasteful and functional, complemented by three generously sized bedrooms and two full bathrooms. The full-footprint basement, partially finished, presents an excellent opportunity to create additional bedrooms, home theater or even a s

Welcome to this charming single-level 1914 Craftsman Bungalow, lovingly maintained by the same family for three generations and privately situated on 2.5 secluded acres at the end of a long circular driveway. Rich in character and warmth, this well-cared-for home offers 1,496 square feet of living space, beautiful original chestnut woodwork, built-in bookcases, and beautifully refinished parquet hardwood floors throughout the main level. The remodeled kitchen features oak flooring and blends seamlessly with the home's timeless appeal, while the updated full bath adds modern convenience. The combined living and dining area is the heart of the home, featuring a beautiful brick wood-burning fireplace with a classic mantel, creating a warm and inviting gathering space. A bright four-season porch provides the perfect spot to relax and enjoy the peaceful surroundings year-round. Designed for convenient one-level living, the main floor offers two bedrooms, a full bath, a home office, and an a

Lovingly maintained and beautifully situated on a corner lot in the highly desirable Holly Hill Estates, this raised ranch offers the perfect blend of comfort, space, and convenience. Featuring four bedrooms and two full bathrooms, this home boasts bamboo flooring throughout the main living areas and ceramic tile in both bathrooms. The spacious kitchen is equipped with granite countertops and a generous dining area, making it ideal for everyday living and entertaining. The expansive lower-level family room offers endless possibilities, with plenty of space for a pool table, seating area, game room, or home theater. A stunning brick fireplace with a wood-burning insert creates a warm and inviting atmosphere. The lower level also includes a guest bedroom and a full bathroom, providing flexibility for visitors or extended family. Step outside from the dining area to the screened-in porch, where you can relax while overlooking the fully fenced backyard featuring an above-ground pool and st

Lovingly maintained and beautifully situated on a corner lot in the highly desirable Holly Hill Estates, this raised ranch offers the perfect blend of comfort, space, and convenience. Featuring four bedrooms and two full bathrooms, this home boasts bamboo flooring throughout the main living areas and ceramic tile in both bathrooms. The spacious kitchen is equipped with granite countertops and a generous dining area, making it ideal for everyday living and entertaining. The expansive lower-level family room offers endless possibilities, with plenty of space for a pool table, seating area, game room, or home theater. A stunning brick fireplace with a wood-burning insert creates a warm and inviting atmosphere. The lower level also includes a guest bedroom and a full bathroom, providing flexibility for visitors or extended family. Step outside from the dining area to the screened-in porch, where you can relax while overlooking the fully fenced backyard featuring an above-ground pool and st

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

Located only 30 minutes from the Hudson Amtrak Train Station this 9.5-acre property in Chatham, NY offers exceptional potential one of which could be an organic farm. With multiple structures there are endless possibilities. An amazing 2 story huge barn would work for an artist/actor or musician studio and wouild also work for horses. There is a private pond for swimming, kayajing and fishing. The tax estimate on Zillow is incorrect and should read 6,195 dollars, The 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. There are dual brick fireplaces in the living room and reading nook, a formal dining room, and a 3-season porch which add to its historic country charm. The property also includes a small unfinished house without a well or septic, ideal for use as an ADU, additional studio, guest house, or artist studio. A smaller barn also features a hayloft and has been used for storage. Although the vegetation is curre

Open House Saturday 9/10 11-1:00 pm. New Lower Price! Bonnie lea estates! Welcome to an unrivaled 3,000+ sq ft Colonial masterpiece set on 1.27 acres with jaw-dropping pastoral views in the highly desired Ichabod Crane S. D. Immaculately maintained and artfully upgraded, this 5+ Bedroom and 2.5 bathroom residence blends custom craftsmanship and a breathtaking outdoor sanctuary in one of the locals' favorite walkable neighborhoods! Step inside to pristine hardwood floors throughout, central AC, livingroom, office space and a showstopping family room featuring radiant-heated custom slate floors, a wood burning fireplace w/newer exhaust liner, storage closets & a 1st flr washer & dryer. A massive, expanded addition tailored for your cozy family gatherings. A perfect space for your holiday dining table seating 24+ guests! The remodeled eat-in kitchen showcases custom wood cabinetry, solid granite counters & stainless steel appliances. Upstairs a large primary bedroom & bathroom share in th

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

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

Welcome to 52 Church Street, a c. 1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect for an in-law suite or separate apartment. Upstairs four large bedrooms with generous closet spaces share a full bath. Tasteful wallpaper and decorative finishes combine with hardwood floors to provide charm throughout. Outside, an expansive deck runs the length of the exterior, giving way to a large fenced-in yard. A new hot tub and sauna offer moments of respite while the gas firepit ensures guests will be entertained well into the evening. A separate garage offers off-street parking and additional space suitable for a workshop and / or storage. Numerous updates include — but are not limited