Refine Search
Sort by
15 Maiden Lane, Chatham
$320,000
4 Beds ⋅ 3 Baths ⋅ 202629658 MLS
**NOT A DRIVE-BY!** Discover the space, privacy, and convenience of Village of Chatham living! Tucked away on a quiet dead-end street, this remarkably spacious 4-bedroom, 3-full-bath home with a den offers so much more than meets the eye. Beautifully maintained and in fantastic condition, the home features a primary suite, newer flooring, granite countertops, stainless steel appliances, and a roof just 5 years young. The versatile floor plan includes a spacious mudroom and a fully finished walkout basement featuring a large family/recreation room plus two additional flexible rooms ideal for home offices, hobbies, or guest accommodations. Enjoy outdoor living on the expansive two-level deck overlooking a lovely yard, plus convenient off-street parking. All this in a desirable Chatham Village location, just minutes from Main Street's charming shops, restaurants, cafés, and local entertainment. Enjoy the peaceful setting of a tucked-away neighborhood with the convenience of village amenities nearby. Located in Columbia County, NY, this move-in-ready home delivers exceptional space, versatility, and location. **Much larger than it appears—this one truly must be seen to be appreciated!** none

15 Maiden Lane, Chatham

1432 Rte 295, Canaan
$249,000
2 Beds ⋅ 1 Baths ⋅ 202628630 MLS
Welcome to this charming 1850 post-and-beam country retreat set on 5 peaceful acres in the heart of East Chatham. Rich with character and surrounded by nature, this inviting 2-bedroom home blends historic warmth with flexible modern living--perfect for full-time residents, weekenders, and anyone seeking a creative escape minutes from the Berkshires. Inside, exposed beams, wide plank floors, and sunlit rooms create an atmosphere that feels instantly grounding. The layout offers comfortable everyday living with opportunities to personalize through light cosmetic updates, allowing buyers to add their own style without taking on major renovation projects. A standout feature of this property is the detached, heated ''bungalow/flex space'', equipped with 50-amp service and electric baseboard heat. This versatile building is ideal for an art studio, private office, home gym, wellness space, or a remote-work retreat--a rare amenity that expands how you live, create, and work. Outside, the acreage offers privacy, wooded buffers, and room to explore, garden, or simply enjoy the quiet rhythm of country life. Located along scenic Route 295, you're minutes to Queechy Lake, the Taconic, I-90, and the cultural and outdoor experiences of the Berkshires. A character-rich home with land, lifestyle appeal, and a multi-purpose heated space--this is a special opportunity in one of Columbia County's most sought-after rural corridors. Close to the Berkshires Ski Resorts, Taconic Parkway, I-90. Come see!

1432 Rte 295, Canaan

42 White Mills Road, Chatham
$519,000
3 Beds ⋅ 1 Baths ⋅ 202628567 MLS
Modest and unassuming from the front but bright and expansive in the rear, this old mill home dating back to 1878 offers a surprising amount of space across 1800 square feet. Like many old mill homes in the area, this one has been expanded several times over the past 150 years and is now a bright, light filled home with 3 bedrooms, 1 bath, hardwood floors, open kitchen, 1st floor den/office, and 2nd floor flex room. Although there is currently only 1 large bathroom, there is space to add a 2nd bath on the 2nd floor. This home has been meticulously cared for by the same family since 1974 and is ready for its next chapter. You'll enter thru the 3 season porch off the driveway and come into a large tiled foyer/mudroom before stepping down into the open kitchen, dining and living area. An entire corner of windows and skylights fill this space with light. Step out onto the large party deck right off the kitchen and dining room and enjoy the expanded living space in the summer months for dinner parties, BBQs, and stargazing at night. The back yard is private, spacious, mostly level, and gets lots of sun. Plenty of space for a garden and/or a pool. Across the yard, you'll see the large 2 bay garage and 2 story converted barn sitting at the rear of the 1 acre property. This building is insulated, has propane heat and power and was previously used as a workshop but could easily be finished for an office or art studio or even additional living space. An antique outhouse sits behind it. The rear of the property abuts the rail line, but don't let that deter you. There are no crossing nearby, so horns are rare and the trains have to move pretty slowly as they approach the bridge over Pond Hill Rd. Only 1.5 miles to Main Street Chatham with its charming shops, restaurants, Crandell Theatre, the future Shaker Museum and only a 3 minute drive to The Chatham Berry Farm and Greenhouse Cidery in the other direction. 27 minutes to Hudson Amtrak station and 30 minutes to Albany.

42 White Mills Road, Chatham

23 Frog Alley, Chatham
$735,000
3 Beds ⋅ 3 Baths ⋅ 202628565 MLS
Welcome to Wilbor Farmhouse, a circa 1875 Victorian on 1.4 acres in the historic hamlet of Old Chatham. A wraparound covered porch, decorative wood brackets, and custom shutters give the house its period charm, and original wide-plank pine floors carry that history inside. Fully restored from top to bottom, it offers three bedrooms, 2.5 baths, and a large yard. A wood stove warms the sitting room, and the all-new kitchen, with energy-efficient appliances and custom solid wood cabinetry, opens to a deck for summer dinners. Once a bed and breakfast, the house is a short walk from the Old Chatham Country Store, ten minutes from Chatham's thriving arts scene, and thirty minutes from vibrant Hudson, with Amtrak service to New York City.

23 Frog Alley, Chatham

147 Rock City Road, Chatham
$3,595,000
6 Beds ⋅ 5 Baths ⋅ 202628091 MLS
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 attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook--and a short drive to Lenox, Stockbridge, and Great Barrington--the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.

147 Rock City Road, Chatham

341 White Mills Road, Valatie
$549,000
3 Beds ⋅ 3 Baths ⋅ 202627870 MLS
Set on 5 serene acres, this bright 3 bedroom, 3 bath residence offers generous room sizes and a peaceful, private setting within a short bike ride of town. The home features a woodstove fireplace in the dining area and a 3 flue chimney ready for a second fireplace. A full length deck spans the entire home, inviting outdoor living and quiet enjoyment. The substantial 34x24 detached building provides exceptional potential for a studio or additional workspace. A property with light, privacy, and versatile amenities. Presently the young grand daughter is in process of moving .. be ready to see boxes and the like - otherwise an exceptionally beautiful home. Occupants require 24-48 hour notice minimum. Note actual vs AI Enhanced photos. Central A/C and automatic whole-house generator among amenities.

341 White Mills Road, Valatie

1941 State Route 66, Ghent
$399,000
3 Beds ⋅ 2 Baths ⋅ 202627783 MLS
Move-in ready with a fully renovated interior for under $400K! This beautiful three-bedroom, two-bath ranch on a one-acre lot delivers exceptional value. The interior is completely updated, featuring a bright, modern kitchen with quartz countertops and all-new stainless-steel appliances, plus the everyday convenience of main-floor laundry with a brand-new washer and dryer. Downstairs, an enormous unfinished walkout basement pairs perfectly with the attached oversized two-car garage-both offering incredible storage and potential. Nestled in a highly convenient corridor, this turn-key home is just 10 minutes from the Taconic State Parkway, 15 minutes from downtown Hudson and the Amtrak station, and an easy commute to Albany and the Berkshires. Enjoy the very best of local culture right around the corner. Spend your weekends exploring Art Omi, catching a show at the Ghent Playhouse, or visiting the Hudson-Chatham Winery. Grab morning coffee and fresh scones at the historic Bartlett House, or pick up local goods at the Liberty Farms Organic Farm Store. With the diverse dining and shopping of both Hudson and Chatham just 10 to 15 minutes away, you get the perfect balance of country peace and vibrant town life. Enjoy the peace of mind of an updated home with endless potential and unmatched convenience. All you have to do is move in!

1941 State Route 66, Ghent

67 River Street, Chatham
$125,000
202625080 MLS
Beautiful 8.5-acre piece of land composed of 2 parcels with an exceptional location near the Village of Chatham. The property includes approximately 1.8 acres within the Village, with municipal water and sewer located just up the road, offering convenient access to utilities. The land features plenty of cleared, usable acreage with room to build your dream home, create a small farm, or enjoy your own private country setting--subject to town approvals. A perc test has already been completed, adding valuable peace of mind for future planning. Enjoy the best of both worlds: peaceful open space with the Village of Chatham close by, providing convenient access to local shops, restaurants, services, and community amenities. A wonderful opportunity to create your ideal home or homestead in a beautiful, convenient Chatham location. Listing contains 2 parcels: 56.-1-39 and 56.18-1-4.

67 River Street, Chatham

5 Link Road, Ghent
$549,000
2 Beds ⋅ 2 Baths ⋅ 202624945 MLS
Blacksmith House, once called The Town Ax, is a Ghent farmhouse rebuilt and renovated so its history comes with modern ease. Roughhewn beams from the original structure run through every room. A wood stove sits in the original stone hearth and anchors the living room. The eat-in kitchen mixes knotty pine, granite, and stainless steel. The main-floor bath keeps a clawfoot tub. Upstairs are two bedrooms and a bath, with a washer and dryer in the second-floor hallway closet. The primary suite has its own private balcony. A skylit third floor works as guest space, a studio, or an office. The property sits on two parcels totaling 2.06 acres of private, wooded land. From a full-width front porch, you look over a grand stone staircase, wildflower plantings, and a four-person barrel sauna. The home is currently operated as a short-term rental. Buyers should verify the Columbia County STR registration, occupancy tax obligations, and zoning before relying on this use. Art OMI and Ten Barn Farm are minutes away. New York City is two and a half hours by car, or take Amtrak to Hudson, a short drive from the door.

5 Link Road, Ghent

2640 New York 203 Stop 1, Kinderhook
$699,000
3 Beds ⋅ 3 Baths ⋅ 202623239 MLS
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 laundry/mudroom--ideal after hiking your own trails or tending the property. Upstairs, a loft overlooking the great room makes an inspiring home office, reading retreat, or cozy TV lounge. The private primary suite features an en suite bath and a charming Romeo & Juliet balcony where your morning coffee comes with birdsong and uninterrupted views of nature. The finished walk-out lower level expands the living space with room for guests, recreation, or movie nights, complete with a built-in bar ready for serving craft cocktails after a day of exploring the countryside. Step outside to the expansive wrap-around deck and experience the true magic of this property. Watch deer wander through the trees, listen to the breeze rustle the leaves, and enjoy complete seclusion in every season. A whole-house generator provides peace of mind year-round, while the detached metal garage offers abundant space for vehicles, tractors, outdoor equipment, and hobbies. A must see!

2640 New York 203 Stop 1, Kinderhook

116 Ridge Road, Canaan
$1,950,000
4 Beds ⋅ 3 Baths ⋅ 202623153 MLS
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-round recreation. Smart home features include app-controlled security cameras and HVAC. Expansive decks and patios overlook the mountains, complemented by multiple fire pit and grilling areas, a heated saltwater pool, and a charming pool house with its own outdoor kitchen patio. The walkout lower level opens to an additional stone patio and fire pit. Raised garden beds, ornamental gardens, and fenced vegetable gardens with programmable drip irrigation complete the landscape. Flexible living space provides additional guest accommodations, and a whole-house generator offers year-round peace of mind. An additional five-acre parcel is included, offering the opportunity to build a guest house, studio, or office (subject to approvals). Located on privately maintained roads, this exceptional retreat offers privacy just minutes from Chatham, Hudson, and the Berkshires, with easy access to acclaimed dining, shopping, cultural destinations including Tanglewood and Jacob's Pillow, the TSP and NYC.

116 Ridge Road, Canaan

42 Queechy Lake Drive, Canaan
$699,000
202622779 MLS
Imagine serving dinners lakeside or welcoming boaters to one of the docks for a refreshing lemonade!! This is the amazing opportunity that awaits one's vision in reviving the nostalgic Backwater Grill restaurant on beautiful Queechy Lake - one of the most pristine lakes in New York state. Here sits an opportunity to cater to the residents surrounding Queechy Lake or visitors to the Hudson Valley and Berkshires. Architectural drawings are in place showcasing the layout of the kitchen, dining area and lounge. A second-floor space includes additional room for storage and an office. The gem of the design, however, is the outdoor dining deck poised on the edge of the lake. Careful work has been done to design a septic system to handle the needs of the restaurant with special consideration given to the sensitivity of being on the lake. Both DEC and the Columbia County Board of Health have approved the design with estimates for installation in place. With so much of the planning work already completed, it's time to put ''hammer to nail'' and bring an all new Backwater Grill back to the anticipating public. It's also an opportunity to compliment the work and vision taking place up the road at the former Queechy Lake Motel. What a dynamic duo for Canaan and the visiting public has never been so fortunate!

42 Queechy Lake Drive, Canaan

276 E Hill Road, Austerlitz
$950,000
202622286 MLS
Take in the feel of the Adirondacks right here in Columbia County! 75 acres of majestic hardwoods and evergreens set among running streams and rock outcrops. Total privacy and seclusion but minutes from Chatham, Hudson and all things Hudson Valley or Stockbridge, Tanglewood and all things Berkshires The preferred building site has been cleared and access from East Hill Road is in place. The drive traverses a tree-lined stream complete with ferns and boulders. And, a newly constructed steel and concrete bridge will effortlessly bring you across. Just down an incline from the building site, you'll find a rustic cabin with wood burning stove and pavilion. In addition to the natural beauty of this parcel, adjacent and with over 400 acres of preserved woodlands is land owned by New York state - forever wild. Additionally, and just to the north of the state-owned land is the Edna St. Vincent Millay Society, known as Steepletop. This parcel is over 200 acres and encompasses the poet's gardens and home. Open to the public Create a lifestyle immersed in the sound of running water and the warmth of dappled sunlight coming through the trees. A home connected to the outdoors and an outdoors connected to the beauty and serenity of nature.

276 E Hill Road, Austerlitz

1780 County Route 22, Valatie
$140,000
202620328 MLS
Opportunity awaits on this beautiful 5.8-acre parcel loaded with potential! Already cleared and featuring a roughed-in driveway, existing slab, dug well, and two septic systems, much of the groundwork has been started for you. Whether you're dreaming of building a private country estate, creating a multi-generational family compound, or exploring other possibilities, this property offers the space and flexibility to make it happen. With plenty of room to spread out and a variety of potential future uses, this is a rare chance to own acreage that's ready for your vision. Bring your ideas and imagine the possibilities! Situated in a prime location just 10 minutes from Chatham, Kinderhook or Valatie! Located in the Chatham CSD.

1780 County Route 22, Valatie

43 Frisbee Street, Chatham
$262,900
3 Beds ⋅ 1 Baths ⋅ 202620053 MLS
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 up the stairs from the garage into the kitchen, the inviting aroma of the meal you left simmering in the crockpot all day welcomes you home. Relax to the sounds of nature, enjoy a refreshing shower in the updated bath, and settle in for a comfortable evening at home. Whether you're enjoying the brilliant colors of autumn, the warmth of the woodstove on a chilly day, or the peaceful surroundings of your own acre, 43 Frisbee Street offers a place to slow down, settle in, and feel at home. Welcome to 43 Frisbee Street--cozy, comfortable, and close.

43 Frisbee Street, Chatham

3620 County Route 9, New Lebanon
$469,000
3 Beds ⋅ 2 Baths ⋅ 202619674 MLS
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.

3620 County Route 9, New Lebanon

2261 State Route 66, Ghent
$259,000
4 Beds ⋅ 2 Baths ⋅ 202615136 MLS
Tenants require 48hour notice to show and only after 10a.m. No Sunday showings preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. MUNICIPAL WATER/SEWER. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to Chatham Village/schools, 9 to Hudson/Amtrak, and a stroll to town park w/tennis courts, Bartlett House cafe and Dairy Queen. A wonderful small-town feel while being minutes from shopping and popular attractions, including bustling Warren Street, Chatham's Main Street, Omi, Hawthorne Valley Farm Store/School, libraries, MacHaydn and Crandell Theaters. Shown by Appt Only. Tenants require a minimum of 48-72 hours' notice.

2261 State Route 66, Ghent

1129 New York 295, Chatham
$475,000
3 Beds ⋅ 2 Baths ⋅ 202613968 MLS
Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum.

1129 New York 295, Chatham

1135 NY-295, Chatham
$289,000
2 Baths ⋅ 202613557 MLS
1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High visibility on main NY-MA artery. Fantastic location for studio or professional spaces incl massage, acupuncture, attorney, chiropractor, accountant. Centrally located Columbia/Albany/Berkshire counties. Fully rented: 1st flr tenant 1100 dollars/mth; 2nd flr tenant 1750 dollars/mth. 24-48hr notice required to show. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company.

1135 NY-295, Chatham

1135 New York 295, Chatham
$289,000
3 Beds ⋅ 2 Baths ⋅ 202613554 MLS
1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High visibility on main NY-MA artery. Fantastic location for studio or professional spaces incl massage, acupuncture, attorney, chiropractor, accountant. Centrally located Columbia/Albany/Berkshire counties. Fully rented: 1st flr tenant 1100 dollars/mth; 2nd flr tenant 1750 dollars/mth. 24-48hr notice required to show. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company.

1135 New York 295, Chatham

©2019 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing. Data last updated

How much is your home worth?

Get instant property value now!