Chatham Real Estate

Welcome to Chatham, a charming village nestled in the heart of Columbia County, New York. Known for its picturesque landscapes and vibrant community, Chatham is not just a place to live; it’s a place to thrive. One of the standout features of this delightful region is the Chatham Central School District, which is renowned for its commitment to academic excellence and holistic student development.

The Chatham Central School District serves students from pre-kindergarten through high school, offering a well-rounded education that emphasizes both academics and extracurricular activities. With a dedicated team of educators, the district prides itself on fostering a nurturing environment where students can explore their passions and reach their full potential. The small class sizes ensure personalized attention, allowing teachers to tailor their instruction to meet the diverse needs of each student.

In addition to a robust curriculum, Chatham Central School District offers a variety of programs in the arts, athletics, and technology, encouraging students to develop their talents outside the classroom. The community's strong support for local schools is evident in the numerous partnerships with local organizations, which enhance educational opportunities and provide students with real-world experiences.

Families looking to settle in Chatham will appreciate not only the quality of education but also the tight-knit community atmosphere. With scenic parks, local shops, and a rich history, Chatham is a wonderful place to call home. If you’re seeking a community that values education and fosters growth, Chatham and its exceptional school district are waiting to welcome you!

Newest Listings in 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

$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

$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

$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

$857,000

202628486 MLS

Sitting on Fog Hill Road in Austerlitz is this 149.9 untouched acres of thick forest. 2 parcels with 100 acres in Austerlitz and 49.9 in Canaan. Great private spot to build your dream home or family compound. Love to hunt?? It doesn't get better than this. Wonderful mountain top views. 1,000 ft frontage with gate and trail system in place. Two tax id # - 69.-1-17 is 100 acres and 70.-1-23 is Caanan. Zoning is R2 and R4. This property is also eligible for NYS 480a Forest Program. Property is priced at latest appraisal. Electric at road.

L17 Fog Hill Road, Austerlitz

$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

$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

$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

$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

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Chatham Real Estate

Newest Listings in Chatham

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