Chatham Homes for Sale

Welcome to Chatham, New York—a charming village nestled in the heart of Columbia County, where scenic beauty meets a vibrant community spirit. Known for its picturesque landscapes and rich history, Chatham is not just a place to live; it's a place to thrive. One of the standout features of this delightful area is its exceptional school district, which is highly regarded for its commitment to academic excellence and holistic development.

The Chatham Central School District serves students from pre-kindergarten through high school, offering a nurturing environment that fosters creativity, critical thinking, and a lifelong love of learning. With dedicated educators and a wide range of extracurricular activities, students are encouraged to explore their passions and develop their talents. The district is known for its strong emphasis on community involvement, ensuring that parents and local residents play an active role in shaping the educational experience.

For those looking to make Chatham their home, a variety of charming homes for sale are available, each reflecting the unique character of the area. From historic properties with timeless architecture to modern builds that blend comfort and style, there’s something for everyone. Imagine waking up to the serene beauty of the Hudson Valley, enjoying local parks, and being part of a close-knit community that values education and family.

Whether you’re a first-time homebuyer or looking to relocate, Chatham offers a welcoming atmosphere and a bright future. Explore the homes for sale in this enchanting village and discover the perfect place to call your own!

Newest Chatham Homes for Sale

$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

$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

$339,800

3 Beds ⋅ 2 Baths ⋅ 202628228 MLS

1st Open House Sunday October 18 1-3PM!! East Chatham (Canaan) Starter Home with all the I wants! Sop Close to the Berkshires Ski Resorts, Takonic PKWY Lee Ma, Remodeled 3 Bedrooms 1.5 Baths w/ Open Bright Spacious Living Space, Enclosed Heated Rear Porch w/Laundry Washer & Dryer All New Appliances, Beautiful Lighting, Full Basement New Roof Windows, Electrical Box, Septic System, Bathrooms & Kitchen, Come Home Relax on this Country Style Front Porch!!! Enjoy Life!! 22 Mins to Albany & 23 mins to Lee Mass 1st Exit Off Taconic in Canaan NY Enjoy this Country Charmer for many years.

1169 NY-295, Canaan

$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

$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

$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

$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

$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

$690,000

5 Beds ⋅ 5 Baths ⋅ 202622720 MLS

Amazing Victorian style investment opportunity in Chatham, NY. Local attractions in area include Ooms Conservation area at Sutherland Pond or catching a musical at the Mac-Haydn Theatre. This Victorian Style home shows it was built in 1886. Total square footage is showing on tax records at 4,307 sq. ft. An amazing large lot of 918,680 sq. ft. An opportunity as such comes across once in a lifetime. Do not wait on this opportunity. AS-IS SALE property. The Buyer's due diligence needs to be conducted prior to bidding, as the high bidder will receive an AS-IS only contract.

1896 County Route 9, 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

$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

$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

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Chatham Homes for Sale

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