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43 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$750,000
3 BD | 2 BA
Residential - Single Family

Don't miss this hard to find single floor living opportunity in the highly sought after town of Stockbridge. Offering nearly 2500 sq ft of thoughtful living space, this 3 bedroom, 2 full bath home blends main level convenience and genuine rustic warmth and modern versatility. Inside the home features multiple cozy heat sources for New England winters, including a classic wood burning fireplace as well as two seperate wood stoves. Outside, the property sits on almost 6 acres of private land just 3 minutes from downtown Stockbridge. Open lawn areas offer plenty of room for vibrant flower beds, rich vegetable gardens, or custom outdoor entertaining spaces. Complete with an oversized garage providing ample room for vehicles, storage or workshop. Close to everything the Berkshires offer.


40 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$759,000
4 BD | 3 BA
Residential - Single Family

Styled, spacious, and serene, this exceptional French Country-inspired contemporary residence offers a rare balance of peaceful seclusion and remarkable accessibility. Perfectly positioned just moments from the cultural richness of the Berkshires, idyllic New England country living, and convenient routes to both Boston and New York, it is a home that effortlessly connects tranquility with convenience. Bordering the pristine 115-year-old grounds of the historic Blandford Golf Club, the property enjoys an extraordinary setting where protected fairways create an ever-changing natural canvas and uninterrupted views stretching for miles. The approach is equally captivating, with thoughtful landscaping featuring a striking Rising Sun Redbud and elegant Yellow Magnolia.


48 Photos
ROBERTS & ASSOC. REALTY, INC
$769,000
3 BD | 3 BA
Residential - Single Family

Minutes to the vibrant town of Gt. Barrington, you'll find this immaculate move-in ready contemporary home on a quiet country road. House is set nicely back from the street; over an acre of landscaped rolling lawn and very private setting. Bluestone walk-way leads to the front entry. Step inside and find the main level featuring a delightful open plan -great room has gleaming hardwood flooring, open kitchen with soapstone counters; great welcoming space for gathering/entertaining. Dining opens to an oversized screened porch; a summer must-have in the Berkshires! Main level primary suite has updated bath w. walk-in shower. Additional bedroom/ full bath on main level. Lower-level w light-filled family room, 3rd bedroom, full bath. Central a/c. Convenient to Tanglewood, theater and more!


64 Photos
ROBERTS & ASSOC. REALTY, INC
$774,500
4 BD | 3 BA
Residential - Condo/Townhouse

Welcome home to Silver Maple Farm. Stand-alone condo in established community of 59 homes. Here you'll meet new friends and neighbors at the clubhouse with fitness center, out on the tennis/pickle-ball courts or around the pool. This Cider Lane beauty has been lovingly maintained by the original owner. Privately sited at the end of the cul-de-sac, you'll enjoy the convenience of one-level living. Main level with primary suite, guest bedroom/full bath, den w pocket door. The great room features built-ins, gas fireplace and opens to spacious screened porch and open deck to savor sights and sounds of nature. Lower level is fully finished and walk-out with two additional bedrooms, full bath and large family room. Just in time to enjoy the Berkshire fall colors as the seasons change.


32 Photos
BERKSHIRE HOMES AND CONDOS
$774,900
4 BD | 3 BA
Residential - Single Family

A UNIQUE OPPORTUNITY TO OWN A SPACIOUS LENOX HOME IN A PRIVATE, COUNTRY SETTING AT A REASONABLE PRICE. 4BR, 2.5 BATHS, WITH HARDWOOD FLOORS, OPEN KITCHEN/DINING AREA, LARGE OPEN DECK, PELLET STOVE AND AN IN-GROUND POOL. LOVELY LANDSCAPING WITH STONE WALLS, GARDENS AND OPEN LAWN AREA FOR ATHLETICS OR JUST RELAXING. GREAT CENTRAL LOCATION, A SHORT DISTANCE TO TANGLEWOOD, TOWN AND YOUR FAVORITE BERKSHIRE ATTRACTIONS AND CULTURAL EVENTS.


58 Photos
COMPASS MASSACHUSETTS , LLC GB
$775,000
4 BD | 5 BA
Residential - Single Family

Set in a peaceful West Pittsfield neighborhood, 35 Meadow Ridge is a sophisticated contemporary home with spacious thoughtfully designed living. Soaring 12 foot ceilings and cherry hardwood floors welcome you inside. The main level features a family room with built-ins, living room with gas fireplace, dining room, eat-in kitchen and access to the outdoor deck. The second floor offers an expansive primary suite, 2 additional bedrooms, 2 full baths, and flexible fourth room for use as bedroom, den or gym.A finished walk-out basement includes a family room and ensuite bedroom adding valuable space. This versatile home offers exceptional comfort and flexibility.Moments from Pittsfield State Forest, Onota Lake, downtown dining and short drive to Tanglewood. This is Berkshire living at its best!


42 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$775,000
3 BD | 3 BA
Residential - Single Family

Moments from Lake Mansfield and Main Street, this turnkey contemporary offers clean lines, natural light, and effortless Berkshire living. The main level features an open-concept floor plan anchored by a show-stopping Duvemåla tiled stove, serving as a striking centerpiece for gatherings and cozy evenings by the fire. Enjoy the convenience of a first-floor bedroom alongside one of the home's three well-appointed full baths. Upstairs, an expansive primary suite impresses with vast cathedral ceilings. The finished lower level adds a versatile bonus room, providing extra square footage for a home gym or game room. Outside, relax and entertain on the sun-soaked deck overlooking the oversized grounds of this rare double-sized parcel.


58 Photos
ROBERTS & ASSOC. REALTY, INC
$789,900
3 BD | 3 BA
Residential - Single Family

Don't miss this Lenox beauty tucked away on a quiet side street. Main level w hardwood flooring, living room with crown molding, formal dining w. large bay window, updated kitchen w extensive cabinetry. Family room w gas fireplace opens to large screened porch / patio. First floor laundry and 1/2 bath. Three bedrooms on the upper level; primary suite w adjoining dressing room/ primary bath with soaking tub and separate shower. Two additional bedrooms and full bath; all w hardwood flooring. Central a/c; natural gas heat/hot water; attached two-car garage. Easy maintenance perennial gardens with a focus on native and specimen plantings -over 100 species carefully planned to bloom continuously wowing sight and scent! Abutting preserved land with year-round brook-your own magical retreat!


57 Photos
WILLIAM RAVEIS - BERKSHIRE
$795,000
4 BD | 2 BA
Residential - Single Family

This well-loved antique home offers a rare combination of history, thoughtful updates, and natural beauty. Set on 14+ acres with sweeping westerly mountain views, Carefully maintained over the years, the property has benefited from significant improvements, including an updated foundation, electrical and plumbing systems, heating system, windows, and roof. The home offers four bedrooms, two full baths, and a full basement, providing comfortable living space with the character and charm of an earlier era. Outside, the property unfolds across fields, gardens, mature fruit trees, and open land, with direct abutting state land and access to the Appalachian Trail nearby. An oversized detached garage with a second floor offers ample room for vehicles, equipment, storage, or a workshop.


31 Photos
HELEN MULLANY REAL ESTATE, LLC
$795,000
3 BD | 2 BA
Residential - Condo/Townhouse

''ON THE HILL'' Condo at The Oakwoood! Town-House style unit in a prime location. Located in a highly desirable setting, this property offers easy access to town, putting Shops, Dining, and local amenities just minutes away. 3-Bedrooms, 2-Baths,a large Living Room with vaulted ceiling & fireplace, Enjoy the community pool and beautifully landscaped property. Have coffee on the deck and take in the Eastern Mountain View! Great in all seasons with Ski areas, hiking and cultural attractions nearby.


69 Photos
Lamacchia Realty, Inc. - Dalton
$795,000
5 BD | 4 BA
Residential - Single Family

Set within one of the Berkshires most coveted communities, 9 Eastbrook Lane is a masterclass in refined living, where thoughtful design meets impeccable care. Beautifully and intentionally sited, this distinguished residence offers 5 bedrooms, 3 full and 2 half baths across a gracious, light-filled layout designed for both elegant entertaining and everyday comfort. The stunning kitchen showcases rich maple cabinetry, a premium Viking range, dual refrigerators and exceptional workspace, perfectly suited for the discerning cook. The renovated primary bathroom evokes a true spa experience, blending luxury and serenity with timeless finishes. Every detail has been meticulously maintained, from the seamless indoor-outdoor flow to the expansive Trex decking ideal for al fresco gatherings.


66 Photos
WILLIAM RAVEIS - BERKSHIRE
$795,000
4 BD | 3 BA
Residential - Single Family

$100,000 PRICE IMPROVEMENT! Set on nearly 3 private acres in sought-after ALFORD, this 4-bedroom home blends privacy, comfort and Berkshire charm. Built by Howard Chezar with passive-solar design, the home features open living spaces, beautiful wood details and a flexible finished third-floor bonus room. Enjoy the spacious deck, in-ground pool and peaceful setting. An 8-year-young roof, low Alford taxes and a location just minutes from Great Barrington, hiking, skiing, dining and Berkshire attractions complete the package!


42 Photos
ALTON & WESTALL REAL ESTATE AGENCY, LLC
$799,000
3 BD | 3 BA
Residential - Single Family

Wonderful opportunity in on one of Williamstown's most desirable locations! Nestled in a quiet, idyllic neighborhood in the heart of town, this lovely Colonial is surrounded by mature landscaping and beautifully maintained gardens. The 3-bedroom, 2.5 bath home features a spacious dining room addition with vaulted ceilings and sliding doors that open to the outdoors, creating an inviting space for everyday living and entertaining. A charming screened-in porch overlooks the fenced garden and offers a peaceful spot to relax and enjoy the surrounding beauty. Thoughtfully maintained and beautifully situated, 40 Waterman Place offers the rare combination of a serene setting and in-town convenience, with all that Williamstown has to offer just moments away.


22 Photos
HELEN MULLANY REAL ESTATE, LLC
$799,000
3 BD | 2 BA
Residential - Single Family

Tucked away in a peaceful, private setting, this charming mid-century ranch offers easy one -level living , warm and inviting. Featuring 3 bedrooms and 2 full baths, the home combines classic character with fresh updates. New oak floors throughout, fresh interior and exterior paint create a clean, move-in ready feel. Relax by the fire or enjoy time on the screened porch or deck. Minutes to town, Taft Farm, Guido's, Skiing and other notable Berkshire attractions.


46 Photos
MACCARO REAL ESTATE
$799,000
3 BD | 3 BA
Residential - Single Family

Thoughtfully crafted custom home offering timeless New England character, quality craftmanship, and beautiful eastern mountain views. Rich natural woodwork and exposed beams create a warm, inviting atmosphere throughout. The custom kitchen with granite, marble and butcher block countertops opens to the dining area with French doors leading to a screened in sunroom. Enjoy the expansive deck, stone patio with firepit, and beautifully landscaped grounds. Spacious living and family rooms with woodburning fireplace and generous mudroom/office. Offering three bedrooms, three baths, plus a versatile creative space, studio/sitting room, endless possibilities. Minutes to downtown Lee, Stockbridge, Lenox, Tanglewood, shopping, dining and all that the Berkshires has to offer for year-round living.


36 Photos
HOUSATONIC REAL ESTATE
$799,000
4 BD | 3 BA
Residential - Single Family

Private Lake Buel access is just steps from this one-level, 4-bedroom, 3-bath ranch--your perfect year-round getaway or full-time retreat. Inside, you'll find a striking two-sided fieldstone fireplace anchoring the living and dining areas, complemented by warm wood floors that add timeless charm. Step outside to a spacious back deck overlooking your own private bird sanctuary--an ideal setting for relaxing or entertaining. Enjoy the serenity of lakeside living with plenty of space for family and guests. Complete with a deeded boat dock and storage shed, this property offers everything you need to embrace the ultimate lake lifestyle. Sackman Way is a Private dirt road with 4 houses sharing road maintenance and snow plowing.


42 Photos
LAMACCHIA REALTY, INC
$825,000
4 BD | 2 BA
Residential - Single Family

Welcome to life on beautiful Pontoosuc Lake, where breathtaking sunrise views and year-round waterfront living await. This charming, move-in-ready home offers the perfect combination of comfort, thoughtful updates, and low-maintenance living in a truly special lakefront setting. The open and airy living room features soaring vaulted ceilings, expansive windows that capture stunning lake views, abundant natural light, and a cozy gas fireplace, creating a warm and inviting space to relax or entertain. The well-designed floor plan includes spacious first-floor bedrooms with generous walk-in closets, updated bathrooms, newer flooring, Anderson windows, skylights, and multiple heating zones for added comfort.


53 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$825,000
5 BD | 3 BA
Residential - Single Family

Set on approximately 3 picturesque acres in Dalton, this beautifully restored New England farmhouse seamlessly blends rich Berkshire history with thoughtful modern updates. Once operated as both an inn and stagecoach stop, the property is filled with timeless character. The home features 5 bedrooms and 3 full baths, including a spacious first-floor primary bedroom along with an additional first-floor bedroom and two full baths, ideal for guests or convenient single-level living. Warm and inviting gathering spaces include a library, living room, family room and formal dining room all filled with natural light and historic architectural details. Cozy gas stoves in both the kitchen and family room add modern touches to the home's classic New England feel.


41 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$849,000
3 BD | 2 BA
Residential - Single Family

Beautifully updated and lovingly maintained Colonial in the heart of Great Barrington. Bright, sunny, and truly move-in ready, this inviting home offers a combination of classic charm and comfortable modern living. The first floor features a welcoming mudroom, updated kitchen, heated sunroom, dining room, living room, family room, laundry, and full bath, providing plenty of space for both everyday living and entertaining. Upstairs are three comfortable bedrooms and a second full bath. Outside, enjoy a lovely yard and charming covered porch--perfect for relaxing and enjoying the neighborhood. Ideally located with easy access to Great Barrington's vibrant town center, library, restaurants, shops, and churches. A warm and beautifully cared-for home in a wonderful convenient location.


45 Photos
WILLIAM PITT SOTHEBY'S - GT BARRINGTON
$849,000
3 BD | 4 BA
Residential - Single Family

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.

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