99 houses for sale in 01244

Offering the rare and coveted 'lake life' on Lake Buel, this unique property presents an extraordinary opportunity to establish your own Berkshire footprint on an expansive 2-acre parcel. Comprising 90% sun-drenched, open meadow, the large lot serves as the ultimate blank canvas with potential for a stunning architectural expansion, a custom family compound, or agricultural designs. While the existing cottage provides a peaceful, private retreat set back from the road, the true crown jewel is the property's dedicated lake access-offering the right to install your own private dock or boat slip on one of the Berkshires premier motorized lakes. Bring your vision to this exceptional property and start living the Berkshire lakeside dream today

Move right into this beautifully renovated mid-century Cape, where modern updates blend seamlessly with timeless charm. Designed for easy single-floor living, this bright and airy home features an open-concept kitchen, dining, and living area that creates an inviting space for both everyday living and entertaining. The living room is highlighted by a soaring cathedral ceiling and abundant natural light, enhancing the home's spacious feel.The thoughtfully designed layout includes a private primary suite with an en suite bath,offering comfort and convenience. French doors open from the living room to a rear deck overlooking a fire pit area, creating the perfect setting for outdoor gatherings, relaxing evenings, and enjoying the surrounding landscape.Ideally located just minutes from downtown Great Barrington, Ski Butternut, and the public boat launch at Lake Buel, this move-in-ready home provides easy access to the best of the Berkshires, from outdoor recreation to dining, shopping, and

Step into a canvas of timeless character in this Historic Colonial, originally built and occupied by Nathaniel Austin,a surveyor who was instrumental in mapping and settling Berkshire County, situated in the town of Sheffield. This 5-bedroom, 2-bathroom residence offers a rare opportunity to restore a piece of Berkshire County history while imprinting your own vision on its enduring architecture. Location and Lifestyle* Tree-lined driveway, a short stroll to the village green, markets, dining, and outdoor recreation. Proximity to the Housatonic River, lakes, and scenic trails, inviting year-round strolling, hiking, and local exploration. Easy access to regional attractions, farms, and cultural events that define the area's heritage. Exterior and Structural Potential* Traditional Colonial silhouette with original exterior detail awaiting revival. clapboard siding offers excellent restoration potential. Generous lot space with room for landscaping, a garden, or outdoor living areas once

Charming rustic 3-bedroom, 1.5-bath home located on a picturesque country road in the Village of Southfield. Full of character and warmth, this inviting property offers a peaceful setting just minutes from the Southfield Store. With both residential and commercial zoning, it presents a unique opportunity for a primary residence, home-based business, or investment. Enjoy the charm of country living with the flexibility to suit a variety of needs in one of the area's most desirable village locations. There is also a huge garage on the property

Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra storage. Inside, enjoy abundant natural light in the glassed-in sunroom or relax on the multiple porches and decks. A key feature is the large, private in-law apartment, perfect for multi-generational living or rental income. Ideally located in the heart of Sheffield village, you'll enjoy the comforts of downtown just steps from your doorstep

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound

Tucked into the rolling hills of Great Barrington just minutes from downtown and the slopes of Ski Butternut, The Turning Point is a storied 3,600-square-foot Berkshire landmark operating as an active short-term rental. Steeped in history dating back to its 1800s stagecoach tavern roots, the property showcases an enduring dual-facade of classic New England brick and weathered clapboard. Inside, original period charm takes center stage with wide-plank wood floors and glowing fireplaces, perfectly paired with a rare, substantial footprint featuring 7 generous bedrooms and 6.5 bathrooms. Designed for effortless hosting, this expansive retreat offers an incredible canvas for a lucrative rental investment, a boutique bed-and-breakfast, or a magnificent private country compound

Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn, perfect for soccer or croquet, and a private dock for paddle boats, fishing and watching out for the resident Bald Eagle! The house sits on 4.49 acres and also includes 4 additional lots for a total of almost 13 acres

Jaw-dropping water and sunset views from every room define this beautifully renovated contemporary overlooking Lake Garfield. Offered fully furnished and turnkey, with an exceptional rental history, it presents a rare opportunity as both a sophisticated Berkshire retreat and proven income-producing property. A beautifully appointed chef's kitchen flows into the light-filled great room and the screened porch. Four bedrooms include an ensuite primary. Linger on the screened porch, entertain on the expansive deck, or relax in the hot tub as the sun sets over the lake. Privately sited on 2.5 acres, this is refined Berkshire living at its best. 'Truly a Magical Place' (Air BnB Guest) Perched above Lake Garfield with breathtaking water and sunset views, this completely renovated contemporary offers effortless Berkshire living. A stunning chef's kitchen with gorgeous countertops opens to a light-filled great room, creating an inviting space for gathering and entertaining. Four bedrooms includ

Jaw-dropping water and sunset views from every room define this beautifully renovated contemporary overlooking Lake Garfield. Offered fully furnished and turnkey, with an exceptional rental history, it presents a rare opportunity as both a sophisticated Berkshire retreat and proven income-producing property. A beautifully appointed chef's kitchen flows into the light-filled great room and the screened porch. Four bedrooms include an ensuite primary. Linger on the screened porch, entertain on the expansive deck, or relax in the hot tub as the sun sets over the lake. Privately sited on 2.5 acres, this is refined Berkshire living at its best. 'Truly a Magical Place' (Air BnB Guest) Perched above Lake Garfield with breathtaking water and sunset views, this completely renovated contemporary offers effortless Berkshire living. A stunning chef's kitchen with gorgeous countertops opens to a light-filled great room, creating an inviting space for gathering and entertaining. Four bedrooms includ

Welcome to 19 Buckingham Lane, a completely turnkey, beautifully curated waterfront retreat designed by internationally acclaimed interior designer Jess Cooney of Jess Cooney Interiors. Offered fully furnished, this newly renovated home sits directly on the shores of Lake Garfield and features four bedrooms and three baths across three levels. Soft earth tones, richly textured wood finishes on floors, walls and ceilings, and elegant stone surfaces create a relaxed yet sophisticated atmosphere for lakefront living. Tucked into a private cove, it offers exceptional peace and seclusion while the expansive deck provides the perfect setting for entertaining with sweeping water views. And if you don't own a boat, you're in luck-one is included with the

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

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking

The Hatfield House: A rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility. Plans for new 2nd floor bathroom! Set on 1.5 acres with protected wetland views, commercial/residential zoning allows for gallery, studio, office, or home business use inside the adjacent 1,200 sq ft three-bay barn with electricity. Unusual space and privacy adds versatility for a Main Street location. Formerly a famous antiques destination, this property combines history, functionality, and long-term value just a quick drive from downtown Great Barrington

Privately set on just under 7 acres, this beautifully renovated home offers the perfect combination of tranquility, privacy, and convenience. A meticulously paved circular driveway leads through elegant, iron fencing to the level, beautifully landscaped property. The home offers approximately 2,800 square feet of thoughtfully updated living space, with 3 to 4 bedrooms and 2 full baths across two spacious levels. Natural light fills the interior, highlighting beautiful wood floors throughout and adding to the warm, inviting atmosphere. Skylights bring even more light into the home, while the oversized deck provides an ideal setting for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. An oversized two-car garage offers generous parking and storage. Tucked away in a completely private setting yet just minutes from town, this exceptional property is approximately two minutes from Sheffield's Cobble and the Appalachian Trail, offering easy access to hiking, nature, an

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm-exposed beams, three original fireplaces, and gorgeous antique floors-seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch. Sun-filled living spaces feature vaulted ceilings and exposed beams. The chef's kitchen boasts premium appliances and a walk-in pantry. A versatile ground floor offers guest quarters or a private suite with full bath and separate entry. Upstairs, retreat to a luxurious master suite with spa-like bath, cedar walk-in closet, and beamed ceilings, plus two additional bedrooms and a spacious landing perfect for a hom

This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added. Step inside to find timeless Colonial charm-exposed beams, three original fireplaces, and gorgeous antique floors-seamlessly paired with an expansion which added a large family room with a fourth fireplace, finished basement storage, mudroom, and partially screened wraparound porch. Sun-filled living spaces feature vaulted ceilings and exposed beams. The chef's kitchen boasts premium appliances and a walk-in pantry. A versatile ground floor offers guest quarters or a private suite with full bath and separate entry. Upstairs, retreat to a luxurious master suite with spa-like bath, cedar walk-in closet, and beamed ceilings, plus two additional bedrooms and a spacious landing perfect for a hom

JUST REDUCED TO $429,000! Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a.50-acre commercially zoned lot just a 5 minute drive to downtown Great Barrington, the property offers outstanding live/work, investment, or business potential. The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and garage. A brand-new adjoining apartment includes a beautifully finished kitchen with granite countertops, full bath, washer/dryer, and private backyard access deal for rental income, extended family, Airbnb, or professional office use. Additional updates include a new 3-bedroom septic system and new roof, backyard fence and new grass

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

A rare opportunity awaits in the heart of historic Sheffield. This exceptional multi-unit property, originally a classic 1740s farmhouse, has been thoughtfully converted into a lucrative income-producing asset while retaining its timeless New England charm. Perfectly positioned just south of Great Barrington, it offers both tenants and owners a convenient commute to local attractions, work, and restaurants. Nestled amidst beautiful, well-maintained grounds, this residence exudes curb appeal. The apartments have all been thoughtfully updated and come equipped with outdoor space, access to laundry facilities, and exceptional parking

JUST REDUCED TO $429,000! Completely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a.50-acre commercially zoned lot just a 5 minute drive to downtown Great Barrington, the property offers outstanding live/work, investment, or business potential. The 2,258 sq. ft. main residence features 3 spacious bedrooms, a large new kitchen, full bath, washer/dryer, and garage. A brand-new adjoining apartment includes a beautifully finished kitchen with granite countertops, full bath, washer/dryer, and private backyard access deal for rental income, extended family, Airbnb, or professional office use. Additional updates include a new 3-bedroom septic system and new roof, backyard fence and new grass

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Welcome home to NEWGRANGE. 1920's era Manor House with lake frontage on Lake Garfield. Over 10,000 square feet of living on 7.7 Acres. Complete the restoration and enjoy original Stone Fireplaces, comfortable Living spaces, formal Dining and 10 Bedrooms. Write that novel in the paneled Office, Library or Sunroom, create delicacies in the Country Kitchen, or shoot a round of pool in the Billiard Room. When you are done, meander to your private Dock on 165 feet of glorious private lakefront. Guest House, Pond, and Gardens originally designed by Frederick Law Olmstead. Close to town, Skiing, Shopping, Dining and Tanglewood. Low, low Monterey taxes. This one-of-a-kind property is meant for enjoying all that the Berkshires has to offer

THE ULTIMATE FOUR SEASON BERKSHIRE RETREAT- Tucked away on 3.6 serene acres, this bright and airy single-level home is the perfect year-round escape. This completely renovated home offers an open concept main living area including the dining room, efficient eat-in kitchen with stainless steel appliances and family room with wood stove, perfect for relaxation and entertaining. Two additional guest rooms and a den. The newly completed primary suite boasts a beautiful bathroom and an oversized walk-in closet versatile enough for a home office. Outside, the private grounds feature a dining patio, fire pit, gazebo and shed. Located just minutes from the slopes of Ski Butternut and downtown Great Barrington, this turnkey property also features a proven track record as a short and long term rental MORE Propane has been added with additional plumbing to set up gas powered cooking if desired and possibility to convert wood stove to a gas option. House plumbed for forced air system. The Master S