The Berkshires, MA Homes for Sale

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  /37

  $239,900

  • 3 Beds
  • 1.5 Baths
  • 1,568 Sq Ft

  31 Taft St, North Adams, MA 01247

  Delightful & affordable, this 3 bedroom 1, 1/2 bath condo in North Adams' desirable West End offers modern, easy living in a convenient Berkshire location. The open floor plan creates a bright & welcoming living space, perfect for everyday comfort & entertaining. 2 bedrooms are located on the 2nd floor with a full bath, and laundry, the 3rd floor loft bedroom provides added privacy & flexibility

  Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  31 Taft St, North Adams, MA 01247
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  /88

  $3,550,000

  • 6 Beds
  • 7 Baths
  • 9,254 Sq Ft

  Unlisted Address

  The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care

  Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

  Unlisted Address
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  /30

  $299,900

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  825 Thatcher House, Hancock, MA 01237

  IT DOESN'T GET ANY EASIER THAN THIS!! Own this beautiful slope facing 1 bedroom loft condo situated above the ski rental shop. Only 2 units like this exist in the Village Center! Brand new slope side deck overlooking the Berkshire Express chairlift. Newly renovated kitchen and bathroom, and freshly painted. Owner replaced heating/cooling unit and washer/dryer. Fully furnished, including new

  Kevin Moderski JIMINY REALTY

  825 Thatcher House, Hancock, MA 01237
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  /41

  $410,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  37 Corey Rd Unit 845, Hancock, MA 01237

  Perfectly positioned in the heart of Jiminy Peak Mountain Resort, this stylishly updated two-bedroom, one-bath condominium offers the ultimate slopeside lifestyle. Just steps from the lifts, you'll enjoy effortless access to one of the region's premier ski destinations while retreating to a thoughtfully designed interior that blends comfort and modern appeal. The bright, open living space is

  Brenda Durant KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

  37 Corey Rd Unit 845, Hancock, MA 01237
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  /4

  $35,000

  $5K PRICE DROP

  • Land
  • 13,068 Sq Ft
  • $116,667 per Acre

  103 Stearns Ave, Pittsfield, MA 01201

  Looking for land in West Pittsfield for your new build? This vacant lot is one of three contiguous lots located on Jones and Stearns Ave. All have public water and sewer available. The lots are zoned residential. Listed below assessed value!

  Erin Vincent BISHOP WEST REAL ESTATE

  103 Stearns Ave, Pittsfield, MA 01201
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  /71

  $725,000

  • 4 Beds
  • 2 Baths
  • 3,114 Sq Ft

  167 Bailey Rd, Lanesborough, MA 01237

  Lovingly maintained contemporary Cape set on just over an acre with beautiful mountain views, ideally located on a paved country road just minutes from everything the Berkshires has to offer. This comfortable home is surrounded by established perennial gardens and fruit trees, creating a peaceful and private setting. The front entry welcomes you into a relaxing three-season screened porch-perfect

  Erin Scott BURNHAM GOLD REAL ESTATE, LLC

  167 Bailey Rd, Lanesborough, MA 01237
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  /42

  $158,000

  • 3 Beds
  • 1.5 Baths
  • 3,450 Sq Ft

  334 Columbus Ave, Pittsfield, MA 01201

  A unique opportunity to own a work/live space. The building consists of an updated 3 bedroom house with kitchen, dining, and living room. The ''shop'' space has heat and a separate bathroom. It also boasts a detached two car garage with power. There are endless possibilities with this property. Bring your ideas and let them flow!

  Michele Purcell Lamacchia Realty, Inc.

  334 Columbus Ave, Pittsfield, MA 01201
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  /38

  $374,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,976 Sq Ft

  27 Richmond Ln, Adams, MA 01220

  OPEN HOUSE SATURDAY MAY 16TH 10AM-11:30. Completely remodeled 4-bedroom, 2-bath home offering the perfect blend of privacy, comfort, and style. With a private yard, hidden from street-view - buyers will appreciate the unique privacy this provides. Relax while enjoying the amazing mountain views and the thoughtfully designed perennial landscaping that makes for easy, low-maintenance outdoor

  Erik Pizani GREYLOCK REALTY, LLC.

  27 Richmond Ln, Adams, MA 01220
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  /60

  $5,245,000

  • 5 Beds
  • 8 Baths
  • 9,400 Sq Ft

  50 East Rd, West Stockbridge, MA 01266

  Set on 35.6 acres in the heart of Alford, this exceptional estate offers privacy, sweeping western views to the Catskills,and direct access to the Tom Ball Mountain Trail, abutting hundreds of acres of protected land. Located just minutesfrom Great Barrington and approximately 10 minutes to the Massachusetts Turnpike, the property combines seclusionwith convenient access to the region's top

  Elyse Morris ELYSE HARNEY REAL ESTATE

  50 East Rd, West Stockbridge, MA 01266
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  /17

  $365,000

  $31K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,726 Sq Ft

  15 Ballou St, North Adams, MA 01247

  Location! Location! Location! Walk to downstreet or Mass MoCA. and shopping.Lovingly cared for 4 bedroom home. Upgrades throughout including New roof, owned solar, USB ports in each room, New heating system with Mini splits, Oil tanks removed (but pipes remain should the buyer want to convert back to oil). Smart house with smart switches throughout. New HW heater and dehumidifier. One & Done

  Sandra Sorel COLDWELL BANKER REALTY

  15 Ballou St, North Adams, MA 01247
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  /50

  $695,000

  New Construction $30K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,128 Sq Ft

  18 Cross To Canaan Valley Rd, New Marlborough, MA 01259

  Set in a small country neighborhood, this stunning 4 Bedroom is perfect for entertaining friends and family. The 1st floor includes an open kitchen and dining area with granite countertops and high ceilings, a cozy sunken living room with propane fireplace, and a spacious first floor bedroom suite. Sliding French doors throughout the 1st floor bring in plenty of light and lead onto a 50' mahogany

  Vashti Poor WILLIAM RAVEIS - BERKSHIRE

  18 Cross To Canaan Valley Rd, New Marlborough, MA 01259
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  /3

  $235,000

  $40K PRICE DROP

  • Land
  • 4.37 Acres
  • $53,776 per Acre

  162 Alford Rd, Great Barrington, MA 01230

  BEAUTIFUL, PRIVATE LOT! Gently sloped and lightly wooded parcel awaits your thoughtful build. Bring your design to life at this private and convenient location. Electric has been brought to the site, perc test available. Seasonal views. Wonderful location with easy access to Great Barrington town center, shops, restaurants, hiking and skiing!

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  162 Alford Rd, Great Barrington, MA 01230
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  /2

  $179,900

  • 4 Beds
  • 1 Bath
  • 1,630 Sq Ft

  1 Albert St, Adams, MA 01220

  Great opportunity to finish this work in progress. Owner started many renovation projects including vinyl flooring and windows, kitchen remodel, siding and enclosed porch. First floor bedroom with full bath, kitchen, living room and laundry. Second floor features three bedrooms, family room and potential for second kitchen. Roof is less than 5 years old and there's natural gas to the property

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  1 Albert St, Adams, MA 01220
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  /35

  $450,000

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  149 Kittredge Rd, Pittsfield, MA 01201

  Beautifully renovated home with plenty of space for everyone. This home offers 4 bedrooms, 2.5 baths, and a huge yard. Fully finished walkout basement adds another living room, 1⁄2 bath, and 4th bedroom.

  Tanya Shepardson Lamacchia Realty, Inc.

  149 Kittredge Rd, Pittsfield, MA 01201
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  /35

  $695,000

  • 5 Beds
  • 2.5 Baths
  • 2,368 Sq Ft

  254 Bryant St, Chesterfield, MA 01012

  Tucked away on a dead-end street in the foothills of the Berkshires, this thoughtfully designed Cape offers space, flexibility, and a setting that feels like a retreat. Set back on 2.73 acres with scenic views, the open floor plan invites easy everyday living and effortless entertaining. The main level features a primary suite with a private bath, walk-in closet, and its own balcony for quiet

  Aimee Tompkins Park Square Realty

  254 Bryant St, Chesterfield, MA 01012
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  /81

  $3,995,000

  • 4 Beds
  • 4.5 Baths
  • 5,683 Sq Ft

  27 Hemlock Hill Rd, Great Barrington, MA 01230

  Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully

  Claire Pollart WILLIAM RAVEIS - BERKSHIRE

  27 Hemlock Hill Rd, Great Barrington, MA 01230
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  /5

  $495,000

  • Land
  • 19 Acres
  • $26,053 per Acre

  0 Mohawk Lake Rd, Stockbridge, MA 01262

  Wonderful opportunity to own 19 acres in Stockbridge for your dream home! The parcel features acres of deciduous trees with an abundance of peacefulness and tranquility. Gentle upward slope from the street then levels off. Providing several options for building. Freestanding fireplace/chimney remains from a former homestead. Norman Rockwell Museum, Chesterwood and Berkshire Botanical Gardens down

  Debra Petrovsky DONOVAN REAL ESTATE

  0 Mohawk Lake Rd, Stockbridge, MA 01262
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  /23

  $89,500

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240

  Totally renovated and move-in ready mobile home in Lenox! This 2-bedroom home is located on a quiet dead-end street in the Berkshire Mobile Park and offers a nice deck along with an ample side yard to enjoy. Shed in the back needs some repairs to the roof.

  Tanya Shepardson LAMACCHIA REALTY, INC

  405 Pittsfield Rd Unit Lot F2, Lenox, MA 01240
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  /34

  $264,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,085 Sq Ft

  20 Profile St, Lanesborough, MA 01237

  Enjoy the perfect blend of comfort and scenic beauty in this beautifully maintained 3-bedroom, 1-bathroom ranch. Situated to capture stunning lake views, this home offers a serene escape.The interior features a remodeled bathroom designed for relaxation, complete with a luxurious spa tub. The functional layout flows effortlessly, leading to a walk-out basement that provides excellent potential

  Timothy Johnson NOCHER REALTY

  20 Profile St, Lanesborough, MA 01237
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  /39

  $885,000

  • 2 Beds
  • 3 Baths
  • 1,753 Sq Ft

  856 Barnum St, Sheffield, MA 01257

  Modernist retreat in a pastoral Berkshire setting; an artful sanctuary where design, landscape, and light exist in quiet harmony. Designed by acclaimed architect Debra K. Reiser, this light-filled two-bedroom, three-bath home blends refined urban modernism with the stillness of the countryside. Set along a quiet dirt road beside Moon In The Pond Farm, (an eco-conscious farm) a landscape of

  Lauren Molk ELYSE HARNEY REAL ESTATE

  856 Barnum St, Sheffield, MA 01257
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  /8

  $235,000

  $15K PRICE INCREASE

  • Land
  • 3 Acres
  • $78,229 per Acre

  0 Sandisfield Rd, Monterey, MA 01245

  The beauty of Nature; 3+ wooded acres in the quaint Berkshire town of Monterey is the perfect location for your new home or weekend getaway with a blend of level and gentle sloping terrain. It's located on the border of Monterey and Sandisfield town line, private but not secluded, only 12 miles to the Town of Lee with everything it has to offer including the entrance to the Mass Pike. Once in Lee

  Wayne Ditore BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD

  0 Sandisfield Rd, Monterey, MA 01245
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  /2

  $65,000

  $35K PRICE DROP

  • Land
  • 3 Acres
  • $21,667 per Acre

  0, Lot 7 East Rd, Hawley, MA 01339

  Check out this rare opportunity to be Trailside at Berkshire East Mountain resort. Build your on-mountain dream home and be part of the year-round resort action! This lot is wooded with a south facing slope.

  Michael Pratt Coldwell Banker Community REALTORS®

  0, Lot 7 East Rd, Hawley, MA 01339
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  /38

  $274,900

  $11K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,968 Sq Ft

  254 Route 20, Chester, MA 01011

  Welcome to this historic Colonial home nestled in the center of Chester, offering charm and modern potential. Featuring 6 spacious rooms, including 3 generous bedrooms and 1.5 bathrooms, this home is ideal for Living, investors, or those seeking an Airbnb rental opportunity. Inside, enjoy the warmth of beautiful wood floors throughout most of the home, a large kitchen with ample counter and

  Dennis LeClair RE/MAX Compass

  254 Route 20, Chester, MA 01011
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  /4

  $449,900

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft

  41 Pearl St Unit 1-2, Great Barrington, MA 01230

  Welcome to 41 Pearl Street- a 1900s two-family residence nestled on a quiet street just moments from downtown Great Barrington. This spacious 4-bedroom, 2-bathroom (both sides are 2 BR/1 BA) home offers 1,964 square feet of living space on a generous 0.25-acre lot, containing that classic period charm.Step inside to discover a welcoming floor plan with ample natural light, hardwood floors, and

  David Carlson FAIRGROUND REAL ESTATE, INC

  41 Pearl St Unit 1-2, Great Barrington, MA 01230
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  /21

  $110,000

  • Land
  • 7.07 Acres
  • $15,559 per Acre

  730 Clayton Rd, Sheffield, MA 01222

  BOG LOVERS, come look. Officially designated to be a Bog, this property could be a great one to own for observing its nature views that change the year around. Whether you would want to build a home, and/or build a viewing platform for regular visits, it has 7.2 acres (see map with) about 3.5+acres in a bog like 'state', the remainder being usable for building and walking along the bog's

  Robin Leech Robinson Leech Real Estate

  730 Clayton Rd, Sheffield, MA 01222
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  /55

  $1,490,000

  $260K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  5 Glendale Rd, Stockbridge, MA 01262

  ''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

  Martha Piper THE KINDERHOOK GROUP

  5 Glendale Rd, Stockbridge, MA 01262
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  /18

  $315,000

  • Land
  • 10.52 Acres
  • $29,943 per Acre

  0 Lenox Rd Unit 249209, West Stockbridge, MA 01266

  A rare opportunity to own two lots totaling 10.6 acres in sought-after West Stockbridge. Accessed by a shared driveway, the parcels offer flexibility for a private compound or two thoughtfully sited homes. Mowed walking paths wind through groves of mature trees and the partially cleared landscape, creating a peaceful setting with a natural balance of privacy and usable space. The property

  Conor Meehan STONE HOUSE PROPERTIES, LLC

  0 Lenox Rd Unit 249209, West Stockbridge, MA 01266
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  /39

  $619,000

  • 3 Beds
  • 2 Baths
  • 2,337 Sq Ft

  196 Norfolk Rd, Sandisfield, MA 01255

  ANTIQUE CENTER HALL COLONIAL ON NEARLY AN ACRE in the charming village of Southfield. Built in 1799, this spacious historic home has high ceilings, wideboard floors, and many original details. The first floor has a living room with a wood-stove, bedroom with adjacent full bath, den/office with a wood-stove, and a large, open kitchen/dining area. Glass doors lead to a porch overlooking nearly an

  Tom Lynch COMPASS MASSACHUSETTS , LLC GB

  196 Norfolk Rd, Sandisfield, MA 01255
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  /37

  $539,900

  • 5 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  867 Notch Rd, Cheshire, MA 01225

  Home on a dream lot--over 7 secluded acres framed by mountains and backing to the Chalet Wildlife Management Area (7,000+ acres of protected state land). Enjoy total privacy, wide-open views, and dark-night skies away from city lights. Step inside to a grand entrance with a glistening chandelier. The main level features a flowing layout: a spacious kitchen with sufficient storage and generous

  Mariah Worth LAMACCHIA REALTY, INC

  867 Notch Rd, Cheshire, MA 01225
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  /18

  $2,650,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,700 Sq Ft

  8 Shamrock St, Stockbridge, MA 01262

  A UNIQUE NEW HOME UNDER CONSTRUCTION IN THE HEART OF STOCKBRIDGE, MASSACHUSETTSHistoric Living: In an era of increasingly homogenized architecture, this extraordinary timber frame Dutch house replica offers something rare: a true sense of place. Rooted in the early traditions of the surrounding Housatonic Valley, the home is a thoughtful homage to the region's European heritage--crafted with

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  8 Shamrock St, Stockbridge, MA 01262
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  /10

  $49,900

  $10K PRICE DROP

  • Land
  • 3.1 Acres
  • $16,097 per Acre

  0 Eastbrook Ln, Pittsfield, MA 01201

  **Build Your Dream Home in the Exclusive Woodmonte Community!**Welcome to this DOUBLE Lot # 148-9 Eastbrook Lane, located in the prestigious and private Woodmonte neighborhood in Pittsfield, MA. This secluded double lot, listed at $59,900, is a rare find--completely prepped, fully serviced, and ideal for building your dream home!Enjoy the convenience of immediate ''Plug & Play'' construction,

  Nathan Girard ROYAL PROPERTY GROUP

  0 Eastbrook Ln, Pittsfield, MA 01201
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  /70

  $849,000

  • 3 Beds
  • 3 Baths
  • 3,204 Sq Ft

  211 Cottage St, Housatonic, MA 01236

  Just outside the charming village of Housatonic, this extraordinary Queen Anne Victorian stands as a true architectural gem, nested amid lush gardens and beautifully landscaped grounds. From its distinctive urn shaped columns to its twin towers, gables and wrap around porch, every detail reflects the grace and grandeur of a bygone era - balanced perfectly with thoughtful modern updates. Sweeping

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  211 Cottage St, Housatonic, MA 01236
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  /29

  $729,000

  $70K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 1,028 Sq Ft

  19 Cove Ln, Hinsdale, MA 01235

  Looking to enjoy lakeside living year round?This one bedroom home sits on three contiguous lots which provide the opportunity to expand your living space in the future. It overlooks it's own private lake lot allowing you to enjoy lakefront activities and everything that Ashmere Lake has to offer The home features an open floor plan with large windows overlooking the lake. At one end of the

  Sherry Street REALTY STREET, LLC

  19 Cove Ln, Hinsdale, MA 01235
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  /50

  $665,000

  • 3 Beds
  • 2 Baths
  • 3,188 Sq Ft

  54 Pinehill Terrace, North Adams, MA 01247

  Situated in the finest location in a quiet neighborhood of very nicely kept homes, this three bedroom, two bath home offers the discerning buyer an abundance of privacy, especially with the adjacent 1.33 acre wooded parcel included in the sale. The property also abuts state land to the south, providing additional protection and enhancing the peaceful aura of the surroundings. Stately and

  Maureen Dietze ALTON & WESTALL REAL ESTATE AGENCY, LLC

  54 Pinehill Terrace, North Adams, MA 01247
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  /40

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 2,068 Sq Ft

  147 Chipman Rd, Chester, MA 01011

  Welcome home to this peaceful & serene 3 bed, 2.5 bath contemporary offering an open floor plan, main-level primary suite, & a private trail leading to the wild streambed of Glendale Brook! The main level features a spacious living rm & dining area w/ propane stove & sliders to a sunny deck, a kitchen w/ pantry closet, half bath w/ laundry, a first-floor office, & a primary bedroom w/ ensuite

  Taylor Hildack KELLER WILLIAMS REALTY

  147 Chipman Rd, Chester, MA 01011
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  /7

  $30,000

  • Land
  • 17,859 Sq Ft
  • $73,171 per Acre

  Lot 43 S Village Rd, Tolland, MA 01034

  Be part of a small community with your own ponds and beach for the hot summer months. Escape the crowded beaches to this oasis located in the Wildwood Association of Tolland, MA. On the edge of the Berkshires this rural community is still near CT and NY. This year round or seasonal location is near the happenings of the Berkshires - Tanglewood, museums, skiing. Access can be provided to the

  Sue Como Buy Rite Home

  Lot 43 S Village Rd, Tolland, MA 01034
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  /35

  $629,000

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  32 Holden St Unit 32, North Adams, MA 01247

  Sleek and sophisticated, this stunning downtown condominium in the hip arts community of North Adams is but a stone's throw from the incomparable Massachusetts Museum of Contemporary Art as well as a host of other galleries,eateries and shops. Recently thoroughly renovated with a refined richness of detail and careful preservation of some original features of the 1873 landmark building, it is

  Maureen Dietze ALTON & WESTALL REAL ESTATE AGENCY, LLC

  32 Holden St Unit 32, North Adams, MA 01247
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  /10

  $69,900

  $15K PRICE DROP

  • Land
  • 17,860 Sq Ft
  • $170,484 per Acre

  0 Umbagog St, New Ashford, MA 01237

  Nestled near the shores Pontoosuc Lake, this lot offers the perfect blend of natural beauty and convenience.With close proximity to a public playground, boat launch, and lake access, it's an ideal spot for outdoor enthusiasts and families alike.From boating and fishing in the summer to ice fishing in the winter, this location provides endless recreational possibilities.Located in an area with

  Barbara Osborne ASHMERE REALTY, INC.

  0 Umbagog St, New Ashford, MA 01237
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  /42

  $940,000

  • 5 Beds
  • 3.5 Baths
  • 3,407 Sq Ft

  100 Walling Rd, Adams, MA 01220

  A truly rare offering in Northeast Berkshire County, this thoughtfully designed custom-built home represents a unique blend of luxury, comfort, and timeless craftsmanship. Rich hardwood floors, elegant ceramic tile, and classic molding and trim create a lasting appeal throughout the home. The main residence features a spacious gourmet kitchen with a breakfast bar, ideal for both everyday living

  Jeffrey King ALTON & WESTALL REAL ESTATE AGENCY, LLC

  100 Walling Rd, Adams, MA 01220
• 

  

  /10

  $399,000

  • 22 Beds
  • 17 Baths
  • 12,442 Sq Ft

  107 Main St, Charlemont, MA 01339

  The iconic Charlemont Inn is ready for new ownership! It has been cleaned up and renovations have been started. Condo plans have been drawn up and this could be converted to condominiums, or multi unit apartments, or one glorious single family home, or a single family with an in-law suite. Original tavern also lends possibilities for commercial uses, such as tavern, brewery, restaurant, or

  Margo Van Peterson BEST OF THE BERKSHIRES REALTY

  107 Main St, Charlemont, MA 01339

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