Chatham NY Real Estate & Homes for Sale

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.

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.

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.

SERENITY, PRIVACY and DRAMATIC VIEWS Located only a few minutes from the hamlet of Copake, NY and off a quiet country road, this private haven is set on a stunning 20 acres with rolling meadow and dramatic mountain views. The inside of the late mid-century home offers the same serenity and drama as its setting. The great room with its soaring 25 ft ceiling is flanked by a massive stone chimney and fireplace on one side and a wall of windows on the other, taking full advantage of the incredible views. The house still retains much of its original charm and character, which one could embrace or put their own stamp on. The kitchen is open to the dining area with its own stone fireplace. There are three large bedrooms and two full and one half bathrooms. The lower level has the third wood burning fireplace and walk out access to the yard and pool. A large deck looks out at the view and also has access to the in-ground pool. The property has multiple other potential building sites all with equally wonderful views, should one want a studio, guest house or the potential to subdivide. There are paths cut through the rolling 20 acres and frontage on the Roeliff Jansen Kill, a 56 mile long, meandering stream that feeds the Hudson River. Some updates are needed, but a new septic was recently installed and this incredible setting makes it worth the effort.

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!

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!

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.

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''

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.

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.

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.

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.

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!

Large Ranch with open floor plan and four bedrooms. Eat in Kitchen with plenty of cabinets. Home is handicap accessible with a roll in shower. Family room with plenty of windows to let the natural light in. Built in cabinets in the Living room. Exterior offers large lot, plenty of parking and a shed.

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.

Discover your dream ski home in a prime location minutes to Bellleayre Ski Center! This completely renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and proximity to the slopes. Step inside to an open-concept living space designed for seamless entertaining and cozy gatherings. The centerpiece of the living area is an impressive floor to ceiling stone fireplace, providing warmth and ambiance, complemented by a wood-burning stove for those chilly winter nights. The updated kitchen boasts modern appliances, an island/breakfast bar, and ample storage, making meal prep a joy. The spacious bedrooms feature plenty of natural light, with the primary suite offering a private retreat and a beautifully updated en-suite bathroom. Move-in ready, this home has been thoughtfully designed with high-quality finishes and meticulous attention to detail. Whether you re relaxing after a day on the slopes or enjoying the scenic surroundings, this home offers year-round comfort and convenience. A deck and several outbuildings add to the value of the move-in ready home. Don t miss this opportunity to own a turnkey property just minutes to skiing, dining, and outdoor Catskill adventures. 2.5 hours from NYC and close to the Trailways Bus route! Schedule your showing today!

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

Meet Elizabeth: placed in the heart of Salisbury, this house is all about lifestyle. Situated in the center of town, this home offers both elegance and serenity in one effortless swoop. The wraparound porch beckons you to entertain behind a distinguished evergreen hedge, ensuring ultimate privacy. Upon entering, you are immediately struck by the home's beauty and understated elegance. The living room features a wood-burning fireplace adorned with artful hand-painted tiles, flanked by built-in bookshelves-providing ample space for your book and art collection. Wide-plank floors lead you into the kitchen, which was renovated in 2016. Designed for both function and efficiency, the kitchen boasts granite countertops, Wolf propane range,hewn beams, custom linen Roman shades, and ample pantry space. Adjacent to the kitchen is a generously sized laundry room with a sink. The dining room's most defining feature is its tall tray ceiling, which adds a sense of elegance and spaciousness. A Danish fireplace framed by stones sourced from a Brownstone in Lee, MA provides the perfect remedy for chilly New England days. A separate entrance connects the home to the studio (flex space), where tall ceilings and abundant light-both natural and track-create an inspiring atmosphere. Double doors lead outside to the manageable backyard, which is partially fenced and includes a meditation labyrinth. Recently renovated and thoughtfully maintained, this house includes 3 bedrooms and 2 full baths

This historic 1845 Greek Revival estate, set on 11 acres of coveted Belgo Road in Lakeville, CT, offers a stunning blend of traditional design and modern conveniences. Fully restored in 2018, the primary residence features four ensuite bedrooms and is surrounded by bucolic views from each side. The first floor opens with an elegant entrance, leading to well-proportioned living areas that showcase meticulous craftsmanship. Award-winning landscaped gardens, designed by Renee Byers, create a seamless flow between indoor and outdoor spaces, featuring specimen trees, magnificent hardscaping, and kitchen and cutting gardens. The backyard invites relaxation with a swimming pool and outdoor shower, while the patio overlooks a wildflower meadow-perfect for entertaining and dining al fresco. A 3-bay garage, built in 2016, includes a sun-filled loft with high ceilings, oversized windows, and a bedroom with a full bath and kitchenette, adding versatility to the property. Sustainable features such as solar panels and an electric vehicle charger offer modern efficiency. The property is adjacent to Taconic State Park, part of one of the largest unfragmented forests between Virginia and Maine. A converted barn with two separate apartments and its own driveway provides ideal spaces for hosting guests or rental opportunities. Experience the best of country living in Litchfield County! Nearby amenities include Lakeville Lake, the towns of Salisbury, Sharon, and Millerton, a train to NYC.

Cozy Salisbury Edge-of-Town Farmhouse - This 3-bedroom Farmhouse with a Garage is in a Commercially Zoned edge-of-town location just down the street from the Scoville Memorial Library, the grocery market, restaurants and shops, and the Bike Path which runs from the east side of Salisbury to near Lakeville Lake. Town Water and Town Sewer provide this property with endless opportunities!

Design and build your dream home with Welcome. This 10.29-acre land parcel is virtually staged here with Welcome's to-be-built Modern Cabin 3 home model, but it also pairs with several other Welcome models. Customize your new home-fully online-with guaranteed pricing. Timing is estimated at 12 - 18 months from start of construction to move-in. Buildability and pricing have been confirmed by Welcome, with a promise of no overages or surprise costs during construction. The Modern Cabin 3 by Welcome is a luxurious spin on the traditional cabin. It features 3 bedrooms and 2 full bathrooms, as well as an array of luxury amenities to meet the needs of even the most discerning owner. The open-concept kitchen and living area provide easy access to the rear deck, offering an ideal space for entertaining or unwinding. Upstairs, the loft space adds a touch of versatility and provides ample room for creative expression and personal design. Once you've made your design selections and have an accepted offer on both the construction costs and the land, Welcome handles everything else, from permitting through construction and everything in between. (See MLS #24018662 for land-only information.)

A wonderfully built home privately set atop a knoll with sensational (expandable if desired) distant views to the South and West, over the nearby hills, and into NY state. All on one floor, it was superbly built, with premium quality materials and mechanicals. It has a new roof, along with new flooring in many rooms, other interior decorative touches. It has an excellent living design, all on one floor, with wide hallways and doorways. There is a lot of invisible and perhaps overbuilt quality, from a concrete based foundation and, main level under-flooring, to its interior, from the basement to the roof. The site is sun filled and so is the residence, being built, and designed, with large windows and ceiling skylights, both to 'capture' the sun in the cold months, and 'deflect' it in the warm months. Every room has individual heating controls for the radiant heating that exists throughout the home. The home is fully airconditioned, and also is outfitted with business grade (by Comcast) whole house communication equipment, enabling excellent connectivity in every room. The land has a suitable location for a pool, if desired, but is otherwise easy to maintain in its current state. The cavernous basement is ideal for storage, a home theatre, or other, non-storage uses, with large spaces for any such use. There is a ground level exit. Rooms, hallways, and doors are all sized for easy movement throughout the home.

Welcome to 36 Lincoln City. A beautiful, modern and chic renovation in bucolic Salisbury, CT. This remodel includes custom cabinetry, a high end kitchen with stainless appliances, and all new mechanicals to include HVAC. This stunning home has 3 bedrooms all in-suite with tiled showers. A powder room and mudroom/laundry area are located on the first floor. A large covered deck on the back of the house has views of the expansive lawn and seasonal town views. The house is near The Hotchkiss School, Salisbury School, Indian Mountain School and is conveniently located near Salisbury Central School.