61 houses for sale in East Chatham

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

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 open studio w/loft w/half-bath 850 dollars/mth. All photos pre-occupancy. No interior liquor store photos. Tenants must approve all showings and give access. 48HR notice minimum. By appt only. Agents pls use ShowingTime

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers. Properties not sold separately. Assessment/tax figures herein reflect total due for both properties. Photos incl Ranch house and 2 apartments pre-occupancy. 48-72 hour notice required to show. Buyer/Coop brokers must attend all appointments. Thank you for your interest

4,008+/. Sqft 1850 Greek Revival in excellent condition w/large, open, bright rooms. First level incl wood-burning fireplace in large family rm off formal LR off spacious eat-in Cherry kitchen w/Shaker cabinetry. Updated/bright lighting throughout. 2nd incl 4 large BRS or offices if rented out. 2 full and 2 half baths. HW floors throughout. Private rear deck. Post & beam barn off large parking area. In quiet New England hamlet moments to Old Chatham, Lenox/Tanglewood, chatham Village and half-hour to Capital District via I90/Parkway one mile away. Endless possibilities by Berkshires. 2 furnaces OHW heat. 1st flr additionally features Mitsubishi HV/AC system. Property leased thru Nov 2027. Arrangements for earlier availability possible but not guaranteed. 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. 48-72HR notice req. Tenants must approve. Any access/showings must be scheduled and accompanied by lis

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

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

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, the 2,267-square-foot home offers three bedrooms, 2.5 baths, and a large yard, ready for full-time living or long country weekends. Deep bay windows pour light into the formal living room, and the dining room opens to a sitting room warmed by a wood stove, a space that could easily become a first-floor primary bedroom. The new kitchen is built around a farmhouse sink and a Wolf range, with Bosch appliances, quartz counters, and custom solid wood cabinetry, and it steps out to a new deck for summer dinners. Upstairs, the primary bedroom looks toward the back of the property for privacy, and a walk-in dressing room leads to a generous bath with a soaking tub and walk-in shower. A seco

Explore the possibilities with this 22 acre property featuring a 2,000-square-foot Cape with 3 bedrooms, 2 full baths, hardwood floors, and an attached 2-car garage. A separate 28′ x 36′ heated garage provides generous space for vehicles, hobbies, or a workshop, plus a 960-square-foot, 1-bedroom apartment above with its own septic system. Live in one residence and rent the other, accommodate guests, or explore potential Airbnb use, subject to local requirements. Enjoy country living within approximately 3 hours of NYC and just 20 minutes from skiing at Jiminy Peak. Explore nearby Chatham and the Berkshires, with the Catskills offering additional options for day trips and outdoor adventures. Whether you're seeking a full-time home or a weekend escape, this property offers space, privacy, and the flexibility to live in one residence while renting the other

Tucked away on 5 acres in the heart of Old Chatham, 14 Depot Lane is a one-of-a-kind private retreat shaped by stone, water and the character of an old house that has evolved over time. Set along a wooded ridgeline, the home is surrounded by rock outcroppings, mature trees and natural landscaping, with a creek and waterfall forming a natural border of the property. It all feels wonderfully secluded yet connected to the community around it. Inside, 2,600+ sq ft is filled with warmth, texture and unique architectural details. The eat-in kitchen is a standout with wood cabinetry, tiled countertops, terracotta floors, exposed beams and a wood-burning fireplace hearth. An oversized picture window frames the rock garden, bringing the natural setting in. The dining room has its own fireplace and barrel-shaped ceiling, with doors from both the kitchen and dining room opening to a large rear deck nestled among the treetops. A spacious living room with vaulted ceiling flows into an open study, w

Love stock car racing, drag racing, or mud bogging? Or simply looking for a well-kept raised ranch with plenty of amenities? This property has something for everyone. The home offers four bedrooms and two full baths, with room for an in-law setup. Features include an electric split system for heating, a main-floor bedroom, and an oversized kitchen that opens to the dining room and overlooks the spacious backyard. The downstairs living room has a cozy fireplace. Set on a country road, the property is close to the Berkshires and Route 20, with convenient access to shopping and work

Set on eight acres, between the Hudson Valley and the Berkshires, this idyllic, light-filled house offers ample opportunity for living, work, and entertaining. With three bedrooms, four full baths, and a recent addition, the property has stunning views of the surrounding hills, a large deck, a two-car garage, a creative studio, and a picturesque pond. Enter through a breezeway with floor-to-ceiling windows and a tiled floor. The foyer leads into the living room, with a wood burning fireplace, and a large dining area. The kitchen and the adjacent great room make it easy to host gatherings. Wide-board floors are throughout the house. French doors open from the great room to the large deck outside, overlooking the pond. The first floor bedroom, which is currently used as an office, has an ensuite full bath. Upstairs, comfort and convenience are a priority for both the primary bedroom and the guest bedroom, which have ensuite bathrooms and large walk-in closets. The primary bedroom looks o

Beautifully maintained 1922 Sears Arts & Crafts bungalow where timeless craftsmanship meets thoughtful modern updates. Rich in original character and move-in ready, this exceptional home features beautiful woodwork, inviting living spaces, an updated kitchen and baths, and a charming enclosed front porch perfect for morning coffee or peaceful evenings. The true hidden gem is the quiet, private backyard sanctuary surrounded by mature landscaping, offering the perfect setting for entertaining, gardening, or simply relaxing in nature. A rare three-car garage provides outstanding space for vehicles, hobbies, storage, or a workshop. Ideally located in the heart of Columbia County, just minutes from Chatham, Hudson, and the Berkshires, with easy access to hiking, skiing, farm markets, restaurants, shopping, and year-round cultural attractions. A perfect full-time home or weekend retreat offering charm, privacy, and a lifestyle that's increasingly hard to find

Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers generous space to gather and unwind with family and friends. At its center, the kitchen and living areas are designed for connection. The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors. Stainless steel appliances and ample workspace make the kitchen as functional as it is welcoming, equally suited to large weekend meals or quiet mornings overlooking the landscape. Windows throughout frame views of pasture, pond, and sky, keeping the surrounding land present from nearly ev

Refined and classic elegance abounds in this historic and prominent Spencertown hamlet home. Built in 1810 as a fashionable Federal Style home, it featured magnificent details and craftsmanship throughout. Step back in time in this glorious and updated property. The abundance of 19th century luxury features have been lovingly restored and enhanced from the polished original flooring, window trims, the grand staircase, 3 fireplaces with original mantles and so much more. Step outside to view the pristine landscaping, which continues to evoke the home's historic character. The sun filled property and home are both formal and casual and is designed for grand entertaining and/or a quiet retreat. You will feel the warmth immediately upon entering the home. Its 3200 sq ft. Offers a spacious living room and a magnificent dining room, both anchored with original fireplaces, a glorious sun porch, a large kitchen with a full pantry, and a den with a wood burning stove. A powder room and laundry

Almost completely-refinished 3BR/2BA home on two acres within walking distance of Old Chatham Square. There are a few things on the punch list remaining inside and out, but this 1870 two story plus walk-out basement home is now effectively a 2020s home. After being brought down to the studs, it was rewired, replumbed, and finished with new windows and doors. Foam insulation was installed before the sheetrock went up, ensuring a tight home keeping sound out (I90 is nearby) and heating and cooling in (home comes with a central air compressor awaiting installation) All flooring, tiling, appliances and lighting as well as the gas furnace is less than five years old. Buyer will need to arrange for final inspections from the town building department to get a Certificate of Occupancy but, the extra effort will be well worth it

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Cedar hill. Architectural Country Living at its Finest. Is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons. From spring's first blooms and summer's golden light to autumn's rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion. With sauna and custom sleek st

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

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! Furnace is under warranty. A standout feature of this property is the detached, heated'bungalow/flex space', equipped with 50-amp service and electric baseboard heat. With TLC, this versatile building could be 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 en

Surrounded by fine estates and set along one of Old Chatham's quietest roads, this inviting family homestead offers a rare opportunity to enjoy the beauty, privacy, and tranquility of the countryside. Set on 16.5 picturesque acres of meadow, woodland, and pond, the property offers a peaceful natural setting with trails winding through the woods-ideal for exploring, relaxing, and enjoying the outdoors. The comfortable three-bedroom, two-bath home features a large family kitchen, first-floor bedroom and bath, protected by a whole-house generator. A two-car garage includes additional recreation space with a separate entrance, offering exciting possibilities for a future apartment, guest quarters, or Airbnb rental. A separate 40' x 44' pole barn with a concrete floor and tall garage doors provides exceptional versatility, whether envisioned as an artist's studio, home gym, workshop, or spacious RV storage. With its combination of open land, wooded trails, water views, and flexible outbuild

This 3/2 ranch in Chatham Central Schools has been updated and has so much to offer! On 1.89 acres in the town of Canaan, this home has a metal roof, newer siding and a generously sized outbuilding. Inside you will find a unique floorplan with a new kitchen and two remodeled baths! The primary bedroom has an ensuite bath and gorgeous wood ceiling with beams. In the same style is a family room with a woodstove, vaulted wood ceiling and a spiral staircase to the loft area. Downstairs is another large bedroom, a room for storage and your mechanicals, which includes a newer furnace. Come add your finishing touches and call this quiet country ranch home!

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

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

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 din

Wonderful 1930 grand Hudson Avenue home, set way back from road with relaxing front porch for summer evenings, from a time when trains ruled in Chatham. Center-staircase colonial with open, eat-in kitchen, Dining Room, Den, and Living Room, all with new floors. Upstairs there are three bedrooms and a studio w/separate entrance, now open to the main house but easily changed back to another apartment. Pine floors in the Living Room and Dining Room, tile in the kitchen and baths, one bed room with a walk in closet and a small BR/office down and a nice Family Room complete the main floor. Three bedrooms up the renovated oak staircase gives plenty of living space and family privacy. A cottage in rear of the parcel for guests, studio or office. Currently two legal one-bedroom units which are vacant. Walk to everything-restaurants, movies, school, church, library, main street shops, and grocery stores. Wonderful location! Easy commute to Hudson, Albany, or Massachusetts! Tax based on 828,182

Perched high on a hill above Chatham Village, this three-story home is a stunning example of modern, geometric architecture. The house has multiple decks on different levels with views of the Catskill Mountains to the West and the Taconics to the East. The center cube of the home features a soaring two-story-height wall of windows that let in natural light and views of the surrounding nature from two floors. There are two unique wings off the center with decks, balconies, and outdoor access on one side, and the showstopper round room on the other. This stunning room includes an elevated six-foot-wide fireplace, wet bar, high ceilings, and a wall of windows framing the Catskills view. The 8-acre property (4 lots) includes a spring-fed pond and is surrounded by trees, which creates a private setting for the home, while still being just a mile from Chatham Village's Main St with its charming shops, a movie theatre, and restaurants. The home has been featured in magazines and is ready for

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