113 properties for sale in Otis Wood Lands

Light, airy and effortlessly inviting this 4 bedroom and 3 full bath home is made for Berkshire Living. Walls of windows and 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 and relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking and easy entertaining. Spacious interior rooms, abundance of natural light and 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 and playground. It's the perfect pairing of a beautiful home and a welcoming community offering everything you need to relax, play and entertain

Welcome to this inviting Lindal Cedar home, nestled in the sought-after Otis Wood Lands community. Open-concept kitchen/living/ dining area with soaring cathedral ceiling, a wall of windows with serene wooded views and easy access to the cedar deck-perfect for relaxing or entertaining. Lovely screened-in porch offers additional space to enjoy the peaceful setting. Main level includes 2 BRs and full bath. Upstairs, a spacious loft area leads to the primary suite. Unfinished, walk-out lower level, with radiant heat, provides potential for an office, rec room, or additional living space. Enjoy the many amenities of Otis Wood Lands: pool, tennis/pickleball courts, fitness room, lodge, playground, Owl Lake for non-motorized watercraft, and beach area. $4K reserve fund fee due from buyer at closing

Light, airy and effortlessly inviting this 4 bedroom and 3 full bath home is made for Berkshire Living. Walls of windows and 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 and relaxing afternoons. A separate grilling deck offers the perfect spot for outdoor cooking and easy entertaining. Spacious interior rooms, abundance of natural light and 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 and playground. It's the perfect pairing of a beautiful home and a welcoming community offering everything you need to relax, play and entertain

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

If your dream is to have a Berkshire country getaway that is large enough to have the whole family come and enjoy. We can make your dream come true. Imagine sitting on your very private deck sipping on your morning coffee with only the sights and sounds of nature waking with you. Minutes to Jacobs Pillow Dance Festival and a short country ride to Tanglewood. Indian Lake is right there for a refreshing swim, a paddle, or a game of tennis. Come and start your Berkshire memories with Family and friends

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

Newly remodeled homeNew siding, insulation, electrical, hvac, plumbing, windows etc. Granite, tile, 2 beds, loft 2 bath, walk In closet, WaterviewsA chance to own a house in the berkshires

Welcome to Merritt Farm - The original home built in 1780 oozes with charm. Front of the house faces south with a large heated sun porch flanking the west side overlooking the pool and tennis court. The main floor rambles with a front parlour, a keeping room off the kitchen with back stair, formal dining and office. In 2008 a large studio addition was added with a first floor primary, full basement and heating system supplying the kitchen and boot room with radiant heat as well as the studio. Second floor has two additional bedrooms, one with a large deck over the sunporch and a generous hall bath. Over 35 acres with mature landscaping, gunite pool and tennis court nicely tucked away this property is set up to be the modern homestead

Newly remodeled homeNew siding, insulation, electrical, hvac, plumbing, windows etc. Granite, tile, 2 beds, loft 2 bath, walk In closet, WaterviewsA chance to own a house in the berkshires

Tucked away in the desirable Klondike Camp Resort, this well-maintained 1987 KROPF EXECUTIVE MANSION vinyl-sided park model mobile home offers the perfect seasonal retreat with added space and privacy. Featuring a large 12x24 expansion, this property provides comfortable living with 1 bedroom and 1 full bath, complemented by updated flooring throughout. Set on a private 0.33-acre corner lot, the property includes two storage sheds and a spacious deck-ideal for grilling and relaxing outdoors. The home is being offered fully furnished, with all appliances included, making it truly move-in ready for immediate enjoyment. Enjoy a short walk or quick golf cart ride to the resort's many amenities, including a clubhouse, in-ground solar-heated pool, tennis and pickleball courts, and playground. Cash only

Welcome to Merritt Farm - The original home built in 1780 oozes with charm. Front of the house faces south with a large heated sun porch flanking the west side overlooking the pool and tennis court. The main floor rambles with a front parlour, a keeping room off the kitchen with back stair, formal dining and office. In 2008 a large studio addition was added with a first floor primary, full basement and heating system supplying the kitchen and boot room with radiant heat as well as the studio. Second floor has two additional bedrooms, one with a large deck over the sunporch and a generous hall bath. Over 35 acres with mature landscaping, gunite pool and tennis court nicely tucked away this property is set up to be the modern homestead

Big, 2800 square foot log home privately set on a seven plus acres. The great room, framed with massive log timbers, opens onto the large deck leading to the hot tub and fire pit. Kitchen features include granite and butcher block counters and an eat in island. Two bedrooms - each with private half baths - plus a full bath in the hallway complete the main level. The upper level loft is used as an office and extra sleeping area. The primary bedroom, cathedral ceiling, walk in closet, has an ensuite bath with soaking tub and separate shower. The game room on the lower level can also be used as an overflow sleeping area with the full bath including a jet tub and sauna. Laundry area, mud room, garage access and utility room Are located n this level. The 7+ acre lot includes a surveyed 2nd lot

Big, 2800 square foot log home privately set on a seven plus acres. The great room, framed with massive log timbers, opens onto the large deck leading to the hot tub and fire pit. Kitchen features include granite and butcher block counters and an eat in island. Two bedrooms - each with private half baths - plus a full bath in the hallway complete the main level. The upper level loft is used as an office and extra sleeping area. The primary bedroom, cathedral ceiling, walk in closet, has an ensuite bath with soaking tub and separate shower. The game room on the lower level can also be used as an overflow sleeping area with the full bath including a jet tub and sauna. Laundry area, mud room, garage access and utility room Are located n this level. The 7+ acre lot includes a surveyed 2nd lot

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

9 PRIVATE ACRES, 2,700 SQ. FT. OF LIVING SPACE and EVEN MORE POTENTIAL!If you've been searching for a home that offers space, privacy, beautiful scenery, and room to grow, this is one you won't want to miss! Nestled on 9 breathtaking acres, this beautifully maintained home features 3 spacious bedrooms, each with its own private en-suite bathroom, offering the perfect combination of comfort and privacy.But what truly makes this property stand out is its incredible versatility! In addition to the existing living space, you'll find 2 additional rooms that offer exciting potential for future bedrooms, home offices, or hobby spaces. The basement and spacious attic above the garage provide even more possibilities for additional usable space or storage!Whether you're looking for room to spread out, work from home, entertain, or simply enjoy the peace and privacy of your own acreage, this property has so much to offer.With this much space and potential, you truly have to see it in person to ap

Sixty wooded acres at the end of a quiet, town maintained dead-end road, rising behind and beside a circa 1840 farmhouse with room for everyone. In the Berkshires that combination rarely comes up, and even more rarely under $800,000. The original house and its addition are seamlessly joined, each with its own entrance and stairway: five bedrooms and five private baths upstairs, plus a sixth full bath off the dining room. Wood burning fireplaces, two screened porches, a tennis court, and handsome stonework inside and out. Old cart roads wind through the woods toward a nineteenth century quarry, with room to hike, ski, garden, and roam from the back door. Newer windows, insulation, and Hardie board siding mean the big work is done. Five bedrooms, sixty acres, one dead-end road. Come walk it. Sixty wooded acres at the end of a quiet, town maintained dead-end road, rising behind and beside a circa 1840 farmhouse with room for everyone. In the Berkshires, that combination rarely comes up, a

Built in 1951, this charming 2-bedroom, 1-bath cottage offers the perfect opportunity to enjoy all that Otis Reservoir has to offer. Located at the end of a quiet dead-end street, this property sits on a larger lot with plenty of privacy and room to expand. The open floor plan creates a comfortable and inviting living space, while the existing 2-car garage provides excellent storage and parking. A major highlight is the deeded rights and private dock on Otis Reservoir, offering easy access to boating, swimming, fishing, and relaxing by the water. Whether you're looking for a weekend getaway, summer retreat, or a property with potential for future expansion, this cottage provides a wonderful foundation in a desirable waterfront community. Make this property your own !

EXCEPTIONAL WATERFRONT RETREAT ON TRANQUIL HAYES POND!Nestled on over 3 private acres w/an extraordinary 650 feet of frontage on Hayes Pond,this exceptional waterfront retreat offers sweeping elevated views,a private dock, sandy beach, and direct access to swimming, kayaking, and fishing.Designed to embrace its stunning natural setting,the home features expansive windows and multiple outdoor living spaces, including a wraparound deck, waterside gazebo, and screened porch w/hot tub connection-perfect for entertaining or relaxing in every season.The bright open-concept interior includes 4 bedrooms and 3 full baths,highlighted by a dramatic great room w/ knotty pine ceilings,a wood-burning stove w/stone hearth, and direct deck access overlooking the water.The spacious primary suite also opens to the deck and features its own and features its own wood-burning stove and en suite bath.The walkout lower level offers additional living space w/ a family room,full bath,and two and two bedrooms i

Tucked into the woods of Sherwood Greens and just a short walk to Long Bow Lake's private beach, this home is the kind of Berkshire retreat you have been looking for. Set on 2.35 acres with privacy on both sides, it offers the peaceful, tucked-away feeling of a cabin in the woods while remaining just minutes from Lee and the Berkshires' renowned cultural attractions, including Jacob's Pillow, Tanglewood, and the area's vibrant restaurants, shops, and hiking trails. One of the community's greatest attractions is Long Bow Lake itself, a quiet non-motorized lake enjoyed by kayakers, canoeists, paddleboarders, and those seeking a more peaceful pace. Inside, cathedral ceilings, warm pine walls, and a wood stove create an inviting atmosphere that feels instantly welcoming. Offering 1,764 square feet, the spacious living room opens to the dining area, creating a comfortable gathering space filled with natural light and character. Sliding glass doors lead to a brand-new deck overlooking the su

Beautiful contemporary home with views of Long Bow Lake in the desirable Sherwood Greens Community! This property features an amazing wrap-around deck and large yard. You will fall in love with the open floor plan and recently renovated kitchen with tiled floors. The first floor also offers a bathroom with shower and lovely screened porch off the living room. Upstairs you'll find a loft space with picture windows overlooking the lake, as well as two bedrooms and a full bathroom. This is your Berkshire Dream Home

Come see this cheerful, modernized ranch, renovated with the utmost care by its architect owner over a ten year span. Deeded beach and lake access within walking distance. Plenty of room for all with two bedrooms on the main level, a recently finished family room off the kitchen and dining room areas plus a second living room. New slate and gleaming hardwood flooring- real! - throughout the main level. The completely renovated main bathroom features wood wainscotting, tile floors and jet tub. The walkout lower level opens onto the back yard with 2 storage sheds and fire pit. The large 27'x17' game room, with a wall of windows facing the back yard, could be used for multiple purposes: entertaining, pool table, overflow sleeping, etc. Also on the lower level: laundry/half bath, utility rm and work rm. Over the past 10 years the following improvements have been made: New Roof New Heating system Whole house dehumidifier New Plumbing system with dedicated pex piping to all fixtures coming f

Escape to the beauty of the Berkshires with this charming 3-bedroom, 2-bath retreat near Otis Reservoir! This inviting home features soaring vaulted ceilings, abundant natural light, a stunning stone fireplace, spacious bedrooms, a versatile loft, and a bright kitchen perfect for gathering. Relax on the front porch, enjoy evenings around the fire pit, and take advantage of the storage shed for all your outdoor gear. With deeded rights to Otis Reservoir, you'll enjoy easy access to boating, fishing, swimming, and year-round recreation. Currently operating as a successful Airbnb offering excellent income potential. Whether you're looking for a vacation getaway, investment property, or full-time residence, this home is a must-see. Please note: As an active short-term rental, all showings require confirmation. A group showing will be scheduled, with the date to be announced

Berkshire County Lakefront cottage, fully furnished and just 30 minutes to Tanglewood!Near Lee and Lenox, this Berkshires waterfront cottage offers two bedrooms and a full bath on the main level, plus a bonus room in the lower-level walkout. An open floor plan-kitchen, dining, and living-opens to a screened-in porch with western views over Little Robin Lake. Enjoy the quiet of this no-motor lake: kayak, swim off your dock, or fish until sunset. Evening dinners or a glass of wine belong on the expansive lower stone patio. A gentle slope leads to lake access and an expansive shoreline-ideal for a fire pit and s'mores-plus an attached garage for winter storage of boats and water gear. Hike October Mountain State Forest and Becket Quarry, ski Otis Ridge or Canterbury Farm, and reach Lee and Lenox restaurants, Tanglewood, and Jacob's Pillow in minutes

Be the first to live in this newly built split-entry home in Becket. Located in the Sherwood Forest community, it is just a few minute walk away from the private beach and lake. A private, fenced-in yard with gated access welcomes you on arrival. Exterior highlights include a deck overlooking serene wooded views and a covered patio below-perfect for outdoor entertaining. The main level offers an open-concept layout with a light-filled living room flowing into the dining area and kitchen. The kitchen features an island, new stainless steel appliances, shaker cabinets, and quartz countertops. This level also includes two bedrooms and a full bath. The partially finished lower level provides additional living space with a bonus room, a full bath with laundry, and interior access to the attached one-car garage. Additional features include vinyl-plank flooring throughout, tile-finished bathrooms, a subway-tiled bathtub on the main level, and a high-efficiency hybrid heat-pump water heater

Beautiful Amish 2021 built log sided home for the ultimate weekend getaway set on a private 3/4 acre lot. Move in ready - all interior and exterior furniture to remain. Beautiful outdoor living space with a masonry fireplace under a timber framed pavilion. Very energy efficient cabin, cool in the summer, cozy in the winter. Energy features include solar panels on the roof, mini splits for heat and AC, charging station for EV, ceiling fans plus a wood stove in the living area. For feature list please refer to supplement or documents tab. Amish Built Settler Log Cabin 2 bedroom, 1 bath, 952 sq ft with Amish Built Outdoor Pavilion fireplace, patio, 192 sq ft Electrical professional install to the pavilion with lighting and outdoor chandelier Washer-Dryer stacked unit-set in closet Leaf guards on gutters Solar Front porch, storage chest for cushions-pavilion's furniture Wood stove- potbelly Timber frame outdoor living space with fireplace, wrap around wicker seating, outdoor dining wicker

Turnkey Berkshire cottage on Shales Brook, completely reimagined from top to bottom. This stylish two-bedroom, two-bath retreat pairs thoughtful design with an idyllic waterside setting, just around the corner from Jacob's Pillow and approximately 10 minutes from downtown Lee. Nearly every element of the home has been renewed, including the kitchen, bathrooms, plumbing, electrical, septic system, heating system and hot water system. The bright, open living space features wood floors, a beautifully renovated kitchen with custom cabinetry finished in a rich Farrow and Ball green, and a striking vintage copper Malm wood-burning stove that adds warmth and character. Two king-size bedrooms and two beautifully updated baths create a comfortable and functional layout. A screened-in porch and spacious deck extend the living space outdoors, surrounded by mature trees and the peaceful sounds of nature. One of the property's most special features is its frontage on Shales Brook. Relax on the scre

A rare Berkshire investment and development opportunity! This c.1780 colonial estate on 1.1 acres offers 8,200 total SF: a 4,200 SF main residence plus two 2,000 SF barns, indoor heated pool and sauna complex. Previous designer-led conversion plans outlined a 5-bedroom all-ensuite layout, upgraded pool wing, and adaptive barn reuse for a luxury short-term rental. Area comps achieve $1,500-$1,800/night rates with substantial multi-million dollar post-renovation equity potential. Moments to Lake Garfield town beach and less than 15 minutes to downtown Great Barrington. All projections, designs, and revenue figures are conceptual/illustrative; buyer and buyers agents encouraged to perform their own due diligence. BEING SOLD AS-IS. There will be no negotiating price or repairs after inspection

Sometimes fairy tales do come true. Tucked away on five private acres in Monterey, this singular handcrafted Berkshire cottage feels as though it emerged from a storybook. Natural-edge wood siding, steep rooflines, a massive fieldstone chimney and a tower-like upper level rise from a landscape of hydrangeas, woodland and a grape-covered arbor. Inside, the house is an irresistible mix of rustic character and thoughtful updates. Original wood floors, reclaimed hand-hewn beams, paneled walls, arched doors and unexpected architectural details give each room its own identity. The dramatic great room is the heart of the house, where soaring volume, exposed beams, richly paneled walls and an immense fieldstone fireplace create a space that feels far removed from everyday life. French doors open to a stone patio, while an open staircase rises through the room to the upper level, adding to the home's storybook quality. A sun-filled pink living room offers a dreamy contrast - soft, light-filled

Spacious Berkshire Contemporary with Pool in Becket Woods! Set on more than five acres in Becket's premier residential community, this inviting contemporary offers spacious living areas, an inground pool, hot tub, and plenty of room for family and guests. The surrounding woodlands provide a peaceful setting, while Becket Woods' swimming pond, hiking trails, tennis, pickleball, and basketball courts offer recreation just beyond your doorstep. Inside, soaring wood ceilings, exposed beams, and expansive windows bring natural light and views of the surrounding landscape into the great room. A stone fireplace provides a focal point, with the kitchen and dining area opening directly to the main living space. A glass door leads to a spacious deck with a hot tub and seating area. Radiant-heated tile floors add warmth and comfort to the main living area. Three first-floor bedrooms include a generous primary suite with a soaking tub. Upstairs, a second primary suite is joined by two flexible bon

A private Berkshire lodge with room for everyone. Set on 4.89 acres in Becket Woods, this five-bedroom, four-bath home offers more than 4,000 square feet of living space across three finished levels. It is an ideal retreat for gathering family and friends, with ample space for everyone to spread out. At the center of the home is a dramatic two-story great room, where a massive stone fireplace rises through the soaring wood-paneled space. Large arched windows fill the room with natural light and views of the surrounding trees, while the open loft above adds to the lodge-like scale and character. The bright kitchen opens directly to the great room and features a Viking range, butcher-block island, generous workspace, and an eat-in area. An adjoining dining area leads to the screened porch, while the great room opens to an expansive deck overlooking the lawn and surrounding woods. Together, the spaces make it easy to move between indoors and out through the warmer months. A spacious first