68 houses for sale in Montville, Sandisfield town Berkshire County Massachusetts

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

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

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

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 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

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

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 !

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

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

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

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

A rare opportunity on Lake Garfield, this mid-century A-frame and two-story barn are being offered for the first time since the home was built in 1965. Renovated over the years, the home features a dramatic cathedral-ceilinged great room with a wood-burning fireplace, a wonderful kitchen with butcher-block countertops, three bedrooms, two full baths, and a comfortable TV room in the second-floor loft. The property comprises two separate parcels: one with the house and barn, and the other providing direct waterfront access. Long considered one of the Berkshires' most desirable lakes, Lake Garfield has been the setting for generations of cherished summer memories. Now, a new owner has the opportunity to create a distinctive lakeside compound and begin a tradition of their own

The original Tryon Hotel - circa 1840 has the charm of age with the palette of a modern residence. The entry is off the front porch, perfect for mornings basking in the sun and evenings watching the life around. Porch comes into the kitchen area with good working space and open to the dining room with gas fireplace. Large back living room with mini-split gives generous square footage to the first floor. The front living room has built-ins and is flooded with light. A first floor bedroom and en suite full bath complete this floor. The second floor meanders as only an old house can, there are 4 bedrooms, a large hall bath and an office space. A brand new fence surrounds the backyard giving a lovely amount of privacy in this quintessential village home - moments to the library and town beach

Perched on Mount Hunger is this lovely, private, contemporary four-bedroom, three-bath home located near Lake Garfield, of which there are winter views. The current owners added a huge, beautiful living/dining room with a fieldstone fireplace, cathedral ceiling and huge windows. The renovated kitchen has granite counters with a Viking cooktop and Bosch double wall ovens. A first floor primary suite is complimented by a den and a three-season porch. The second floor holds two guest bedrooms and a guest bath, while the lower walk-out level has a fourth bedroom, a family room, laundry and utility room and a storage room with built-in shelving. Located well off the road with air conditioning, an outdoor shower and fiber internet. A true Berkshire country home with the best town beach nearby

Discover this spacious and impeccably maintained, privately sited home spanning three levels, designed for both everyday living and effortless entertaining. The open-concept living, dining, and kitchen area features a soaring wood vaulted ceiling, handsome stone fireplace, lots of glass, screened porch and a newly renovated deck overlooking a peaceful backyard with historic stone walls and woodlands. A newer addition offers a generous office or den above the attached garage. The first or lower level provides a private retreat for guests or children. Located in the sought-after Harrington Woods community, residents enjoy a shared pool, tennis and pickleball court, and a welcoming neighborhood, all just minutes from Great Barrington, Otis Reservoir, Monterey Town Beach, and Jacob's Pillow

A One-of-a-Kind Berkshires Retreat Step into a truly singular Berkshires property where visionary architecture meets peaceful country living. Inspired by the groundbreaking principles of Buckminster Fuller, this striking geodesic dome is a rare and captivating home, set on more than 6 private, wooded acres along a quiet country road. Constructed from a network of interlocking triangles, the geodesic design creates a remarkably strong, lightweight structure while maximizing interior space. Inside, the open-concept layout feels airy and expansive, with abundant natural light, two bedrooms, one full bath, and a cozy pellet stove complemented by electric heat for year-round comfort. Nature is at your doorstep. Less than a half-mile- just a 5 minute walk- two-minute drive-from beautiful Hayes Pond, the property offers easy access to swimming, fishing, and kayaking. Hopbrook flows through the property, adding another peaceful element to this private woodland setting. A versatile auxiliary bu

Set on nearly six wooded acres, this beautifully maintained center-hall Colonial offers privacy, comfort, and exceptional outdoor living. Recent improvements include mechanicals, roof (2022), and landscaping (2023). The renovated kitchen features quartz countertops, stainless appliances, and a breakfast bar. Spacious, sun-filled rooms, a primary suite, two full baths, first-floor powder room, and expansive lower level provide plenty of space. Outside, enjoy a heated saltwater in-ground pool, fenced backyard, composite deck, and two-car garage. Surrounded by mature trees and charming stone walls, this move-in-ready retreat offers the perfect blend of modern updates and peaceful country living, all conveniently located near skiing and area amenities!

COMMANDING VIEWS OVER LAKE GARFIELD WITH A STUNNING MOUNTAIN BACKDROP, this beautifully updated home offers charm with modern refinement. Original architectural character has been thoughtfully preserved, while expansive windows fill the home with light and frame the breathtaking scenery. Recently renovated chef's kitchen, first floor primary bedroom, and loads of closet space address today's needs. And could there be any better spot to watch sunsets than the expansive front porch? What's more, a well-appointed suite in the separate carriage house offers flexible space for guests, a home office, or artist's studio. Features include eight private acres, high speed internet, low Monterey taxes, and proximity to the Monterey bathing beach and the incomparable tomatoes at Anna's farm stand

Jaw-dropping water and sunset views from every room define this beautiful contemporary overlooking Lake Garfield. Offered fully furnished, this Berkshire retreat features a chef's kitchen flowing into a light-filled great room and screened porch. Four bedrooms - including an ensuite primary - plus a spacious family room offers plenty of room to gather. Linger on the screened porch, entertain on 2 decks, or unwind in the hot tub as the sun sets over the water. Privately sited on 2.5 acres, this is refined Berkshire living - a truly magical place to escape, gather and enjoy

Loads of room for family and friends in this semi-private country home near The Old Inn on the Green and The Southfield Store Cafe. The first floor features spacious living areas, including a living room with a wood-burning fireplace, a large eat-in kitchen and dining area, and a paneled den, along with an attached two-car garage. Two of the six bedrooms are on this level, including the primary and an adjacent bedroom currently used as a home office. The adjoining room offers the potential to create an expansive en-suite bath and walk-in closet. Upstairs are four generously sized bedrooms, a full bath, and a large laundry room. A full basement provides ample storage and houses a new Buderus boiler. Set well back from the road, the property enjoys a large, private backyard

Just beyond New Marlborough Village this architectural gem showcases 5,653 square feet of superior craftsmanship along the Umpachene River. Built in 1989, this 5-bedroom home was designed by internationally renowned architect Paul Bierman-Lytle, a pioneer in sustainable development and healthy home design known for championing non-toxic climate adaptive building materials. Distinctive circular towers, curved walls, arched windows and premium natural finishes harmonize with the surrounding natural landscape. The grand foyer opens to an expansive kitchen, living, and dining space anchored by a striking Finnish soapstone wood stove and marble fireplace. A sun-filled breakfast room leads to a greenhouse atrium and an impressive indoor pool pavilion, fully heated for year-round enjoyment. On the second floor the generous primary suite enjoys its own private balcony, an adjoining sitting room (or bedroom), two walk-in closets and an impressive art nouveau inspired bath with ornate custom cab

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 and 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 and 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!

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. The kitchen has been thoughtfully refreshed for the modern cook, featuring a brand-new built-in oven and microwave alongside stainless steel appliances. The three-bedroom, two-bathroom floor plan is supported by a septic system installed just three years ago, providing peace of mind for the long term. Designed for summer enjoyment, the outdoor space includes a deck with a direct p

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!

Brand new, never occupied, pristine new build on over 4 acres in beautiful Sandisfield. This home was built with a keen eye for detail and a focus on beautiful finishes and materials that harmonize with the landscape. Bright, airy, and filled with positive energy, the space invites you in and makes you feel right at home. There are soaring ceilings in the great room and a cozy gas fireplace, which leads to a stone patio overlooking the peaceful woodland setting. A cook's kitchen with stunning marble counters, stainless steel appliances and a walk through pantry will awaken your inner chef. Each floor has a full bath, providing options for a first floor bedroom if so desired. Upstairs, there is a large loft space with tons of light, and a lovely primary bedroom with luxurious ensuite bath. A spacious second floor laundry room adds to the convenience of the home. This home was built with comfort and efficiency in mind. There is a whole house passive air exchange system, tight insulation

Otis Wood Lands lakefront Contemporary 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

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 The river is twenty feet from the back door. Not a view of the river, not near the river. The river, close enough that you fall asleep to it in summer and wake to it in winter, when the ice shelf forms

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

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