Wooded Rural building site minutes away from Otis center; close to Skiing, Resturants, and more. This 2 acre lot is a fresh slate to build a small Cabin or country getaway; Great area to catch nature all around you. Stone walls that boarder the property will ensure your boundry lines and privacy from neighboring lots. Maintained road with no assoication fee, enjoy all the peace and quiet the Berkshires has to offer!

Serene Sandisfield Setting! This 8+acre parcel enjoys a lovely combination of level areas, gentle slopes, historic stone walls and seasonal streams. Beautiful mature trees yet not overpopulated. Perfect to build your Berkshire country dream home. Power is at the street located conveniently at each corner of the lot.

Ideal Location Near Amenities + Peaceful, Private SettingA wonderful opportunity to own one of the largest available building lots in the desirable Otis Wood Lands community -- 2.853 acres of mostly level, wooded land offering both privacy and convenience.Perfectly situated close to the lake, clubhouse, pool, tennis and pickleball courts, and fitness center, this property provides easy access to all the community's amenities while still feeling tucked away in nature. Driveway already in place, and high-speed fiber internet is available at the street -- ready for your dream home to take shape.Whether you're looking to upgrade, downsize, or design a Berkshire getaway that fits your lifestyle, Otis Wood Lands offers the ideal balance of natural beauty and active living.

Prime Location + Privacy + Fiber Internet at the StreetA rare opportunity to build your Berkshire dream home on one of the largest lots ever offered in Otis Wood Lands -- 3.029 acres of peaceful, gently rolling terrain in a premier location close to all community amenities.This property offers excellent privacy while keeping you just minutes from the lake, clubhouse, pool, tennis and pickleball courts, and fitness center. Driveway already cut and high-speed fiber internet available at the street make this an ideal site to start your build right away.Whether you've enjoyed Otis Wood Lands for years and are ready for more space and privacy, or you're discovering it for the first time, you'll find a vibrant, well-managed community that beautifully blends recreation and nature.

Exceptional Privacy + Premier Location Near All Community AmenitiesAn extraordinary chance to own both of the largest building parcels ever offered in Otis Wood Lands -- nearly 6 acres of pristine, gently rolling land. Together, these adjoining lots provide an unmatched sense of space, privacy, and flexibility to create your ultimate Berkshire escape.Ideally situated close to the lake, clubhouse, pool, tennis and pickleball courts, and fitness center -- you'll enjoy easy access to every community amenity while still feeling surrounded by nature. Driveways are already in place, and high-speed fiber internet is available at the street, making it easier than ever to start building.Design one expansive estate or create two separate retreats -- the possibilities are endless.

A charcoal board-and-batten house on a wooded knoll in Sandisfield, two acres, nearly finished. Dark hardwood floors, a kitchen with butcher block and quartz, a navy vanity with marble and brass, a teal pendant over a wood-topped island. A bedroom, a finished loft, a full basement the same footprint as the house. The septic design is permitted for three bedrooms and the leach field installation is the primary remaining item before a Certificate of Occupancy, though buyers should satisfy themselves as to what else may be required. The price reflects where things stand. Own land in the Berkshires, twenty minutes from Great Barrington, for a number that actually makes sense. Read the whole story.

Bright, fresh and fabulous, this hip, rustic getaway is perched on a hill with forest and pond views. Open living-dining-kitchen, wonderful screened porch, two bedrooms and a bath on the first floor. Upstairs, an airy loft features plenty of windows and cathedral ceiling. Many improvements include updated electric & roof. Enjoy this lovely spot, with hiking trails to a fire pit for star-gazing. Peaceful location on quiet country road near York Lake(5min), Sandisfield State Forest (13 min), Riiska Brook Orchards(3min) for apple & blueberry picking. Inn on the Green and Gedney Farm(8 min),New Marlborough Reserve for hiking (7min,),Southfield Store for Coffee,Breakfast or Lunch (10 min) Butternut Ski Area (20 min) are just down the road. Escape to this terrific property!

Step into the timeless character and charm of this remarkable historic property, built in 1750 and set on four picturesque acres. Blending centuries-old craftmanship with thoughtfully updated modern amenities, this special home offers a rare opportunity to enjoy historic living without sacrificing today's comforts. The home features three classic farmhouse bedrooms including a first-floor primary with a fireplace. There are two modern bathrooms, each tastefully updated with tile showers and one with a jetted tub. The bright, open kitchen is warm and inviting, with beautiful light-wood counters, counter-height coffee bar and ample space for hosting and creating. The dining area accommodates a large farmhouse table, perfect for family gatherings.

Contemporary two-bedroom home privately situated on just over two wooded acres with a spacious lawn. The main level features an open-concept kitchen and living area with cathedral ceilings, two bedrooms, a full bath, and an open loft ideal for a home office or additional living space. The finished lower level offers a flexible living area that could serve as a guest room or bedroom, a full bath, and a kitchenette with sink that also functions as a convenient mudroom. Electric heat, a wood stove for supplemental warmth, and a mini-split providing heat and A/C on the main level ensure year-round comfort. Additional features include new exterior decks, 200-amp electrical service, ample basement storage, and an automatic generator.

Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with space above for artist's studio. An easy-to-maintain property. Association amenities include tennis/pickleball courts, pool, fitness room, clubhouse, playground, lake and beach area. $4,000 reserve fund fee due from buyer at closing. Wood stove disconnected prior to closing.

Privacy, space, and the beauty of the Berkshires come together at 125 Town Hill Road. Set on nearly 3 wooded acres in the peaceful town of Sandisfield, this 4-bedroom, 3-bath contemporary offers a private retreat surrounded by nature. The home features comfortable living spaces, a screened porch, spacious deck, finished walk-out lower level, and a private tennis court. Enjoy the serenity of country living while being conveniently located near lakes, hiking, skiing, restaurants, galleries, and the charming towns of the southern Berkshires. A special setting for a year-round home or Berkshire getaway.

This 1,320-square-foot contemporary retreat at 311 Tamarack Trail is refreshed and ready for immediate move-in. Tucked away in the private Otis Wood Lands community, the home borders protected state forest land, offering a serene and private wooded setting for your seasonal escape. The interior features a bright, open-concept layout with soaring vaulted ceilings, skylights, and expansive windows that bring the beauty of the forest indoors. For effortless year-round comfort, the home is equipped with a brand-new pellet stove and high-efficiency mini-split units in every room for customized heating and cooling.

Little Acorn House - a warm and inviting Otis Wood Lands Contemporary with three bedrooms and three full bathrooms. The dappled morning light brightens the open kitchen/living/dining area. A spacious four-season room, bedroom and full bath complete the main floor. Second floor includes two bedrooms and a full bathroom. Walk-out lower level with great game room space, office/den and full bathroom. New roof 08/2026. Association amenities include pool, tennis/pickleball courts, fitness room, lodge, playground, beach, and lake for non-motorized boats. $4,000 reserve fund fee due from buyer at closing. Dishwasher does not work. Wood stove disconnected prior to closing.

Discover the epitome of lakeside living in this exceptional 4-bedroom, 2-bath home nestled in the desirable Otis Wood Lands community. This fully furnished residence seamlessly combines comfort and entertainment, featuring bright, spacious rooms and an expansive deck perfect for relaxation or hosting gatherings. Enjoy modern conveniences such as energy-efficient heat pumps, remote-controlled security systems, and Alexa-compatible features, all designed to enhance your lifestyle. Step outside to find a private beach and swimming area just moments away, ideal for launching your canoe or kayak. The community offers a wealth of recreational amenities, including a lodge for social events, a fitness center, tennis and pickleball courts, and a heated outdoor pool.

Beautiful property in a bucolic setting with sprawling front flower gardens! The main floor boasts a first floor primary with en suite bath, open kitchen with fireplace, dining room with built ins and access to the oversized deck, great room with beautiful wood floors and doors that lead to the serene screened porch, cozy den with fireplace, office/flex space and half bath. The second level includes two guest bedrooms and a full bath with washer and dryer. Truly a special offering.

At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground up, wide softwood floors, working brick fireplace, cast-iron clawfoot tub, first-floor primary opening through French doors to a stone patio, stairs to lawn and river. Kitchen and dining open to a deck over the water. Quarry-granite three-car garage, studio cottage with grandfathered footprint, and a second river parcel with 19th-century mill history included. Flood Zone A12; elevation certificate available. READ MORE

Welcome to 365 Deer Run, a beautifully refreshed four bedroom, 3.5-bathroom home tucked into the sought-after Otis Woodlands community. Inside, 2,297 square feet of cedar-wrapped warmth unfolds beneath cathedral ceilings and skylights, with east-facing windows that bring beautiful morning light into the home throughout the year. A window-lined three-season porch extends the living space and offers an inviting place to linger through spring, summer, and fall. The home is designed for both comfort and ease, with features including soapstone countertops, gas heat with Nest controls, a private sauna, and a brand-new roof. Thoughtfully updated and move-in ready, it offers the rare combination of character, modern comfort, and minimal fuss.

Light, airy & effortlessly inviting this 4 bedroom & 3 full bath home is made for Berkshire Living. Walls of windows & a sun filled sunroom bring the surrounding woodlands into nearly every room, while a brand new oversized deck sets the stage for long summer dinners & relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking & easy entertaining. Spacious interior rooms, abundance of natural light & multiple gathering spaces make this an exceptional year round retreat. Then there's the Otis Wood Lands lifestyle w/ an incredible array of amenities including a private lake, clubhouse, swimming pool, tennis/pickleball & playground. It's the perfect pairing of a beautiful home & a welcoming community offering everything you need to relax, play and entertain.

Otis Wood Lands lakefront Contemporary on OWL Lake with four bedrooms and three full bathrooms. Open kitchen/dining/living area with views of the lake. Spacious, two-level screened-in porch with deck access. First-floor primary suite with private deck access, and two additional bedrooms and full bathroom on the main level. Large lower level with walk-out access and fourth bedroom. Community amenities include pool, tennis/pickleball courts, lodge, playground, beach and community lake for non-motorized boats. Reserve fund fee of $4,000 due from buyer at closing. Woodstove disconnected prior to closing.

Cross the charming historic-style covered bridge and enter a world of privacy, nature, and endless possibilities. This remarkable 94-acre sportsman's estate offers river frontage on the Farmington River, expansive woods, trails, and room to roam. At the heart of it all is a spacious split-level home with 3 bedrooms and 2.5 baths, featuring fresh paint, new flooring, and a new roof. A 5-bay barn/garage provides incredible space for vehicles, equipment, hobbies, and toys. A separate mobile home offers flexible additional space for a studio, guest quarters, office, or creative retreat. Whether you're seeking a private Berkshire escape, outdoor adventure, or simply a place where the woods are truly your own, 132 North Main Road is a rare opportunity to own your very own Hundred Acre Wood!