East Chatham NY Real Estate & Homes for Sale

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 27 bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the region's premier full-service equestrian facility. The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations. Equestrian enthusiasts will revel in the compound's state-of-the-art amenities including a 6000 square foot heated arena with a luxurious owner's apartment and viewing area, an outdoor arena, a jump field, and 3 barns housing 26 stalls and 2 tack rooms. Five paddocks grace the property, offering ample space for horses to roam.

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim all summer in your own pond. Pull a trophy buck in the fall. Hike to the peak and back country ski down in the wintertime. Be the first to catch a trout in your own private trout stream.

Straight up the Taconic Parkway, just 2.5 hours from Midtown, your driveway is barely noticeable -- but you know what lies beyond - safety, serenity, and seclusion. Unlock the gate, drive through the woods, and prepare to experience a different kind of rush hour - tracking big buck or flushing wild pheasants or raucous turkeys. Better still, just rest and relax on your ultra-private 223+ ac retreat on the hillsides of the Hudson River. Your driveway reveals nothing to the rest of the world about the lovely accommodations that await in the custom-built, true-log home. Outdoor enthusiasts or those just looking for a unique family or group retreat in the Hudson River highlands will find it here. The grounds of the home are well-maintained with landscaping around 2 ponds, and ample parking, plus a 500 sq ft double-door equipment barn. Enter the home and take in the cathedral-like lodge with an open living-dining-kitchen space anchored by a massive 25 foot floor-to-ceiling fieldstone wood burning fireplace. True log walls and rich pinewood floors throughout the home add strength and character in every room. The kitchen, where everyone gathers, is open to this lovely space, with a great seating peninsula, ideal for travelers and wilderness voyagers to sit while the feast is prepared. 2 bdrms on main floor, off kitchen w a shared full bath. Upstairs, a master suite w private bdrm ( massive closets ), full ba, & loft overlooking fireplace. Full basement nicely finished w bonus room ideal for a pull-out couch / guest room, laundry and work area, + .5 bath. Don (or shed) camo, boots, and parkas while still in the comfort of the lower level. There is ample storage, with drive-out doors! Whole house AC. The property is tax-advantaged with ag AND NYS Section 480-a Forest protections. The main driveway covers more than a mile as it curves through the property. Miles more off-road trails provide further access to the parcels, including the 5 high-mounted blinds. Actively managed farm fields, also within the property boundaries, mean ready-made access is waiting for your next ATV adventure.Enjoy this masterpiece along the hills of the Hudson!

Welcome to Meadow Wood. This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lilypond, terraces, pastoral views, and wonderful privacy. The custom home, built by one of the region's premiere builders, has been featured in design magazines, garden tours & has received a Garden Club of America award for its ethos & thoughtful use of building materials. The house was constructed using sustainable & recycled low maintenance building materials designed to last a lifetime. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/ potting room and a studio space. The Gunite pool is surrounded by an espaliered apple tree fence & generous stone terrace. The large screened pool house includes 1/2 bath, outdoor shower, kitchenette & massive fireplace. Further from the house is the barn complex consisting of a 2 bedroom apartment with yard & patio, separate studio apartment and 4 garage bays. A barn, cutting gardens, and a separate private drive complete this part of the estate. Hidden from the road, the main house is approached by a long drive lined with mature Scarlet Oaks & daffodils. A courtyard filled with specimen crabapple trees, stone walls & walkways creates the welcome entry to this one level home.The exterior walls are planted w/ climbing hydrangea that blur the

Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of the future for generations to come. Set on 67 +/- park-like acres this property offers 3 unique residences, a mature specimen tree farm, a spring-fed pond, wooded walking trails, and captivating views of the distant mountains all just a stone's throw away to restaurants and shops. At the heart of the estate stands The Tullar House; a well-preserved and substantial 6-bedroom 5,000+ sq ft antique Dutch Gambrel dating back to 1761, reported to be the 2nd oldest house in Egremont. Retaining much of its original charm and detail, this historic jewel boasts ample-sized rooms for gatherings and entertaining, a renovated chef's kitchen, a formal dining room, 3 grand fireplaces, 2 primary suites, and plenty of room for guests. Enjoy sweeping views of the grounds from the porch laid with locally sourced marble or relish in the shade of 'The Champion', a 250+-year-old Black Walnut Tree standing as the oldest in the state and serving as a living testament to Tullar Farms' rich past. The exterior is a sight to behold with ornate and symbolic details that capture the attention of all who pass by.

GRACIOUS IN-TOWN LIVING IN THE SOUTHERN BERKSHIRES This gracious vintage home has been thoughtfully renovated and lovingly maintained by the current owners for over 20 years. High ceilings, wonderful light, spacious rooms, a ''walk to everything'' in town location, and residential/commercial zoning provide comfort and unlimited possibilities. A 1,000 sq. ft. outbuilding with water & electric service adds more potential. Beautiful period detail combines with with modern updates-crown molding, soapstone counters, farmer's sink, cherry cabinets, a built in hutch, wood & tile flooring, a South facing bay window, French doors, a large 1st floor Laundry Room, new water heater, and new septic are just the beginning. The large, private room above the Garage is an ideal Studio or Office. There is so much to enjoy here-come see for yourself!

The post-and-beam residence showcases soaring ceilings and expansive windows that frame the spectacular landscape while highlighting the architectural character throughout. Natural materials-including local woods, native stone, and artisanal steel elements-create a sophisticated dialogue between interior spaces and the surrounding countryside. The heart of the main level features a grand Great Room anchored by a floor-to-ceiling stone fireplace, flowing seamlessly into a gourmet Chef's Kitchen with double islands and custom cabinetry. An elegant staircase serves as a natural divider between living areas, while French doors open to a spacious patio overlooking the pastoral grounds, historic barns, and mountain vistas beyond. The thoughtful floor plan includes a main-level with 3 en suite bedrooms, a library, and formal sitting room accessible from the gracious entry hall. A classic New England mudroom provides practical transition space for all seasons. The second level offers 2 primary bedroom suites plus two charming office spaces with northwestern mountain views. A custom steel staircase ascends to a serene meditation loft, creating a private retreat. The finished lower level opens directly to the landscaped side yard, featuring fieldstone walls that echo the property's agricultural roots. Several outbuildings, including a substantial barn, await their next chapter and offer a blank slate for the country hobbiest.

Clarion Farm is an iconic French Country Estate & Horse Property in Salisbury, CT. It is a serenely private retreat with a 4-bedroom main house, a Studio on 16.25 acres, and a Horse Property on 30.72 acres for a total of 47 acres only a few minutes from the village of Salisbury and 15 minutes into Great Barrington. This exquisite property seamlessly blends tranquility with sophistication, creating an unparalleled living experience. Every aspect has been thoughtfully crafted to ensure maximum comfort and well-being, making it a true haven of peace and French Country Casual Luxury. All rooms are generously sized and flow beautifully into one another. The stunning private stone-walled pool courtyard is perfectly situated on the professionally landscaped property. Clarion Farm has a 12 Stall Horse Barn, a 6 Stall Barn, an Indoor 80 x180 Indoor Riding Ring, a 100 x 200 Outdoor Riding Ring, 6 Paddocks, and a 2 Bedroom Barn Apartment. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and the villages of Salisbury, CT, Millerton, NY, Great Barrington, MA, and Wassaic Train Station. This listing includes two parcels: 10 N. Beaver Dam Road (Parcel ID: 2408134) and 471 Undermountain Road (Parcel ID: 2769378), with acreage and taxes reflective of both properties.

It's no wonder why this property is the home of Berkshire county's oldest elm tree! The abundant sunshine, quietude and peace would make anybody want to set down roots and stay a while. This light filled home has refinished wood floors throughout the main level. Kitchen has granite counters, ample cabinet space, pantry and large island. As part of the open floor plan there is a bright dining room and living room area that opens to an expansive composite deck. The great room has endless mountain views, river views and a welcoming fireplace. The lower level also has a main floor bedroom, laundry, office and lots of closet space. Upstairs is the spacious primary bedroom with private bathroom and exterior balcony overlooking horse pastures. There is a third full bath, two additional bedrooms and bonus room. This property really comes alive outside! The two stall barn is in excellent condition. Stalls are 12x12 with electric and frost free hydrant, tack/feed room. Exterior access to two private paddocks that open into a lush pasture. Barn also includes equipment area, workshop and RV parking space or use this space as a run in for livestock. The home is surrounded by mature gardens and hardscapes. Walkout basement has slider to a stone patio area and a fireplace. Could be spectacular extra living space. Home is complete with an invisible fence system for your pups and whole house generator. Horse property, waterfront and views this property is it!

Nestled on a peaceful 1-acre lot, this 2 bedroom, 2 bath Cape provides warmth, character, and opportunity! A spacious kitchen, with adjoining pantry, and dining area provides plenty of room for gathering. The inviting living room features exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry and full bath, while upstairs boasts a large bedroom, another full bath and a versatile landing area. Outside you will find an oversized shed with ample storage, perfect for tools, equipment or hobby space. With major updates already done by the owners of 23 years, this home is ready for your personal touch. A little vision and TLC can transform it into the perfect starter home, cozy getaway or AirBnB! A short drive to Great Barrington. Don't miss out! Newly adjusted price.

Discover the perfect fusion of classic allure and modern comfort at this Twin Lakes Retreat, a beautifully updated lake cottage nestled in the serene Twin Lakes area. This idyllic haven boasts deeded path to a private dock on the area's largest lake, setting the stage for an unforgettable summer filled with motor boating, swimming, fishing, and waterskiing. As you step onto the property, you're greeted by a large screen porch that invites you to relax and enjoy the tranquil surroundings. Inside, the open floor plan exudes an airy and inviting atmosphere, complemented by a cozy fireplace that anchors the living space. The tasteful updates harmonize with the cottage's quintessential charm, ensuring every corner feels both fresh and timeless. The heart of the home, a thoughtfully designed kitchen, features new appliances that echo the essence of a bygone era without sacrificing functionality. Upstairs, the primary bedroom is a retreat with an ensuite bath, while two additional bedrooms share a full bath, offering comfort and privacy for family and guests alike. Modern conveniences have been seamlessly integrated, including Anderson double-pane windows, and the convenient second-floor washer/dryer. Additional luxuries include a generator for peace of mind, a four-person sauna for relaxation, an outdoor shower and new split heat/cooling units for year-round comfort.

Enter through the Mahogany front door to the 1st floor featuring Fir wood floors, crown molding, and 11' ceilings setting the tone for this luxury home. The living room offers a fieldstone wood-burning fireplace, coffered ceilings, and sliding glass doors to a Lakeview porch. Adjacent is a kitchen with Shaker cabinetry, quartz countertops, a tiled backsplash, high-end appliances, and a central island. The butler's pantry adds convenience with an ice maker, dishwasher, and extra storage. Outdoor spaces include a dining porch with a fireplace, a screened porch, and an expansive open-air porch with Mahogany decking and stainless-steel railings. Upstairs, two serene primary suites feature lake views, vaulted ceilings, walk-in closets, and luxurious en-suite baths with soaking tubs, oversized showers, and quartz vanities. A media room and two additional en-suite bedrooms with lake views and elegant finishes complete the 2nd level. The finished lower level includes a mudroom, laundry room, game room, multipurpose space, and full bath, with walk-out access to the lake and a state-of-the-art, salt water, self-cleaning, heated gunite pool. Additional features include a boat launch and lakeside gazebo on Twin Lakes. The property also boasts a heated two-car attached garage as well as a 4-bay detached garage, perfect for your car collection, the ultimate party barn or sports or court venue. 13 heat zones, 6 cooling zones, radiant heat throughout, granite accents, & an irrigation system.

A remarkable opportunity to combine residencial on the second floor with commercial on the main floor in an excellent location with plenty of private parking. The kitchen is set up for the discerning chef , a large dining room, a bedroom/office and living room with a propane fireplace completes the first floor. The gorgeous hardwood floors throughout the house have just been finished and the house is in pristine shape for the next owner. Finally, there is central air on the second floor to complete the full package!

Embrace the pinnacle of grand lakeside living in this Salisbury residence, where Adirondack inspiration meets modern sophistication on the edge of East Twin Lake. This home is a testament to visionary design and impeccable craftsmanship, nestled on 2 acres with a private sandy beachfront. The expansive Great Room, with its walnut floors, oak paneling, and regal coffered ceiling, is a celebration of artisanal detail and serene lake views. The second floor is a retreat of luxury, offering a grand Primary suite, two additional ensuite bedrooms, and a laundry room for utmost convenience. The third floor extends the living space with a flexible area for entertainment or guest quarters. The outdoor experience is enhanced by a gazebo with a fireplace and an infinity spa, all set against the dramatic backdrop of the lake and mountains. This home's grandeur is matched by its robust infrastructure, ensuring a legacy of beauty and comfort, all within easy reach of superior private schools and only two hours from NYC. Full Bath included with the flex space on the third floor. The basement has approx. 2500 sq ft of partially finished space with a full bath, laundry connections, and a boat garage. Sale of house is on 2.0 acres, and additional land is available. 24 hour minimum notice required for showings. Buyer POF required in advance for showings. Video/Audio surveillance in use.

Once a grand residential home, this property boasts spacious interior space that could easily be brought back to its residential roots and is just awaiting for its next chapter. With a large lot, towns water and sewer, off-street parking, and multiple entry points, the flexible layout can accommodate various configurations. The property also features a charming lawn area with mature plantings, a full bath on the main floor, and a half bath upstairs, serving the 11 multi-purpose rooms throughout. Whether envisioned as a business space or restored to a residential home, the possibilities are vast. The property is equipped with an automatic generator. All proposed uses must be presented to planning and zoning.

Charming 5-Bedroom Village Colonial in the Heart of North Canaan Located in a desirable sidewalk neighborhood, this beautifully renovated Village Colonial combines classic charm with modern updates. The home features newly updated electrical and plumbing systems, replastered and lathed walls, freshly refinished main-level floors, all-new bathrooms, and a fully remodeled kitchen. Freshly painted throughout, it is ready for you to move right in. From the spacious front porch, enter into a gracious foyer and enjoy an open, airy layout perfect for family living and entertaining. Large, sun-filled rooms lead to a modern kitchen with direct access to a deck and lower patio, ideal for outdoor dining. A versatile first-floor study creating a great home office space. The walk-up attic provides potential for additional living space or a creative studio. The beautifully landscaped backyard is a private oasis with a lawn, gardens, mature fruit trees, and year-round flowering plants. Conveniently located close to ski resorts in Massachusetts and within walking distance to local amenities like the pharmacy, post office, library, grocery stores, playgrounds, and a lifeguarded town beach, this home can be both a tranquil retreat and easy access to everything you need. Make this charming home yours today! The owner has completed beautiful renovations throughout the home, enhancing both its charm and modern functionality. Room sizes are approximate. New furnace installed 1/15/25

Charming Antique Retreat with Modern Comforts Nestled on a generous 1.15-acre parcel, this enchanting antique home offers a blend of cozy warmth and modern hospitality. The residence boasts a newly added living room, complete with a welcoming fireplace that sets the stage for intimate gatherings and tranquil evenings. Featuring 3 bedrooms and 2 full baths, this home is perfectly suited for comfortable living or as a cherished weekend getaway. The full dining room invites memorable meals and celebrations, while the seamless flow to the living areas ensures that hosts and guests alike feel connected. Step outside through the living room to discover a lovely patio, an idyllic spot for outdoor relaxation and entertaining amidst the natural beauty of the property. The home's location affords easy access to the charming town of Salisbury and the cultural allure of the Berkshires, making it a prime choice for those seeking a serene lifestyle with convenience to local amenities.

MOTIVATED SELLERS! Charming and cozy two-bedroom, one-bath cottage situated in the picturesque Catskills region, ideal for those seeking a simple life or a weekend getaway. Spanning 750 sq ft, this well-maintained home offers single-floor living, making it accessible and convenient, The cottage features two comfortable bedrooms, providing ample space for family or guests. This home has seen numerous enhancements, ensuring both comfort and efficiency, including: Upgraded electrical system, including electric baseboard heat for the entire house; improved insulation for improved efficiency; brand new kitchen appliances; new pellet stove; new plumbing for kitchen and bathroom, including a new, on-demand water heater; and a new and improved laundry room with new laundry appliances. Nestled in the scenic Catskills, this property is ideally located near ski resorts and various tourist attractions, making it a perfect escape for both winter sports enthusiasts and summer adventurers. The cottage promotes a simple, peaceful lifestyle, ideal for those looking to unwind from the hustle and bustle of city life. The single-floor layout enhances livability, perfect for individuals of all ages. 231 Stone Bridge Rd is a delightful cottage that combines modern comforts with the beauty of nature. With its strategic location near recreational activities and recent updates that enhance functionality, this property is a fantastic opportunity for anyone looking to embrace the charm of Catskill living.

Idyllic cabin in the woods set on 14 acres amongst long pines, a large barn w/horse stalls. 2 hours from NYC, 6 miles to NY State hiking trails, 15 minutes to the Windham Mountain Ski slopes, and less than 30 minutes to HunterMountain ski slopes, The property is bordered by a beautiful mountain stream & the Agroforestry Model Forest, which includes 147 acres of marked hiking trails. The cabin provides cozy charm with modern comfort--including a cook's kitchen with Thermador appliances, 2 renovated baths, 3 bedrooms and a separate office space (possible 4 th bedroom), living room with barn doors, family room w/soapstone wood stove, three covered porches and an open deck, 4 zone hw ht. They have put in new basement windows and door to the backyard, restored the front and rear deck support systems, installed a security system. system and smart home devices, barn doors on the living room, a new washer and dryer, a French drain in front of the house and just re-stained the exterior and decks along with landscaping around the home. This is no ordinary cabin in the woods''

Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the beautiful long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Study off of Primary Bedroom. Second bedroom on main level has been recently reconfigured. Another great entertaining space is located downstairs including a large area perfect for games, exercise or media room with kitchenette. A THIRD bedroom was recently created near a recently renovated full bath. 3 car heated garage with massive storage space upstairs. 45KW generator. For the HORSE ENTHUSIAST, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

Introducing: Milly. Understated yet evokes a simple elegance. Tucked on a quiet in-town side street in sought after Salisbury, just moments from the White Hart. Completely updated and one story living makes it easy to say yes to this sweet abode. When you step into the living room you notice how this home has been meticulously maintained. Fresh, crisp white paint adorns the walls, the floors also just tastefully refinished. The dining room offers a large sliding door that provides ample light as well as access to additional entertaining spaces on the newly built deck and patio. The kitchen features all new appliances and freshly painted cabinets. The three bedrooms in the house share a recently updated full bath. One of a kind touches inside the home include custom doors with bohemian accents. Newly installed central AC makes the home even more comfortable. Welcome your friends to dine inside or out on the deck or beautiful stone patio. The mature landscaping attracts pollinators, watch hummingbirds from your stone patio. A darling chicken coop as well as a shed provide endless possibilities. The large basement provides ample storage. Close to all the Berkshires and the Litchfield Hills has to offer.