Homes for Sale near Mt. Everett High School

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  /10

  $155,000

  • Land
  • 5.24 Acres
  • $29,580 per Acre

  104 Hupi Rd, Monterey, MA 01245

  Ready to build a new custom home with all your personal touches! Views of Lake Garfield. Close to downtown Monterey. Fresh 5 acre parcel to construct a magnificent home in the Berkshires!

  

  Cristian Sanchez

  COHEN & WHITE ASSOCIATES

  (413) 771-4725

  104 Hupi Rd, Monterey, MA 01245
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  Explore Mt. Everett High School

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  /6

  $325,000

  • Land
  • 21.7 Acres
  • $14,977 per Acre

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230

  21.7 wooded acres on one of South County's ''best-kept-secret'' back country roads, yet just minutes away from Great Barrington, Sheffield and the bucolic villages of New Marlborough. Discover nature, privacy & a unique sense of peace on this rare piece of land. The land has been perc tested, seller will provide final survey prior to closing. Map in documents shows proposed new boundaries for

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 848-6618

  0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230
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  /38

  $4,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,002 Sq Ft

  764 E Hill Rd, New Marlborough, MA 01230

  WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern

  Karen Climo William Pitt Sotheby's Int'l

  764 E Hill Rd, New Marlborough, MA 01230
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  /86

  $2,000,000

  • 5 Beds
  • 4.5 Baths
  • 4,842 Sq Ft

  173 Hillsdale Rd, Egremont, MA 01230

  Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one of the most private and extraordinary estates in the Berkshires -- a handcrafted sanctuary where the wilderness is literally your backyard. Moose, deer, bear, fox, and turtles roam master-gardened grounds tended with rare care; fruit trees, a garden pond, mature perennial beds, and lush native plantings make

  Robert Cohen eXp REALTY

  173 Hillsdale Rd, Egremont, MA 01230
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  /39

  $1,395,000 Open Sun 11AM - 1:30PM

  • 4 Beds
  • 4 Baths
  • 3,500 Sq Ft

  3 Townhouse Hill Rd, Great Barrington, MA 01230

  Well maintained and set in a prime Egremont location, this home is perched above the Egremont plain with open views. Quiet and private, yet just minutes to downtown Great Barrington, Egremont and everything the Berkshires has to offer.The main level is bright and welcoming, with an open living space centered around a wood-burning fireplace. A first-floor library adds a quiet, separate space;

  Paige Paluch WILLIAM RAVEIS - BERKSHIRE

  3 Townhouse Hill Rd, Great Barrington, MA 01230
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  /45

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,297 Sq Ft

  10 Phelps Rd, Monterey, MA 01245

  This fully renovated 3-bedroom, 2-bath home on Peppermint Brook, an estuary of Lake Garfield, offers bright, open living with a seamless indoor/outdoor feel. Renovated in 2019 with thoughtful design, it includes a sleeping loft and a flexible third bedroom that can double as a den. Launch your kayak, canoe, or paddleboard right from the backyard into the brook or to the lake. While part of Sylvan

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  10 Phelps Rd, Monterey, MA 01245
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  /7

  $159,000

  • Land
  • 3.42 Acres
  • $46,491 per Acre

  0 Mill River To Great Barrington Rd Unit 249092, New Marlborough, MA 01230

  Discover the potential of this gently sloping parcel offering privacy in a natural setting. A partially cleared section rises to a more elevated spot where you can take in the distant view and morning sun. Perc test provided., convenient location just minutes to Great Barrington, Mill River, and Southfield. Rural tranquility and accessibility to local amenities, dining and recreation.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  0 Mill River To Great Barrington Rd Unit 249092, New Marlborough, MA 01230
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  /28

  $479,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,765 Sq Ft

  107 S Main St, Sheffield, MA 01257

  OPEN HOUSE SAT 4/11 12-2PMStep into history with this iconic property known as ''The Hatfield's,'' a beloved antique landmark in Sheffield. Built in 1793, the original home showcases timeless charm and classic architecture. A late-1990s addition created a flexible two-family layout with a one-bedroom, easily converted back to a spacious 3-bedroom, 3-bath single-family home. Recent updates include

  Judi Panzano HOUSATONIC REAL ESTATE

  107 S Main St, Sheffield, MA 01257
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  /62

  $360,000 Open Sat 10:30AM - 12PM

  • 4 Beds
  • 1 Bath
  • 1,875 Sq Ft

  117 Norfolk Rd, New Marlborough, MA 01259

  Nestled in the charming village of Southfield, this inviting 4-bedroom Cape offers the convenience of first-floor living, featuring an updated kitchen that flows into the dining area, first-floor laundry, bathroom, and two bedrooms. Additionally, upstairs, you will find two walk-through bedrooms. Enjoy the outdoors from the welcoming front porch/mudroom or relax in your backyard oasis, complete

  Jessica Rizzo LAMACCHIA REALTY, INC

  117 Norfolk Rd, New Marlborough, MA 01259
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  /36

  $1,475,000

  • 1 Bed
  • 2 Baths
  • 1,296 Sq Ft

  481 Shunpike Rd, Sheffield, MA 01257

  A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

  Suzann Ward HOUSATONIC REAL ESTATE

  481 Shunpike Rd, Sheffield, MA 01257
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  /83

  $1,650,000

  • 4 Beds
  • 5.5 Baths
  • 4,355 Sq Ft

  605 Cross Road To Canaan Valley Rd, New Marlborough, MA 01259

  Once the cherished country residence of acclaimed wildlife artist & tableware designer Lynn Chase, this gracious 4-bedroom manor dates back to 1850, and had a major update in 1998. Set on 5.96 acres of rolling pasture framed by stone walls, this charming estate is spacious but manageable, complete with a garage/horse barn, larger barn, fenced paddocks, and a small pond. Rich in character and

  Claire Pollart WILLIAM RAVEIS - BERKSHIRE

  605 Cross Road To Canaan Valley Rd, New Marlborough, MA 01259
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  /75

  $3,250,000

  • 6 Beds
  • 5.5 Baths
  • 3,416 Sq Ft

  651 Hayes Hill Rd, New Marlborough, MA 01230

  Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. 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

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  651 Hayes Hill Rd, New Marlborough, MA 01230
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  /33

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 3,082 Sq Ft

  86 Main St, Sheffield, MA 01257

  SOUTH BERKSHIRE COUNTY, UPDATED VILLAGE CENTER HOME & OFFICEThis graciously restored vintage house has all the benefits of an ideal Sheffield setting with walkability to restaurants, Bushnell-Sage Library, Dewey Hall, post office, bank, and churches. With residential/commercial zoning, the house features an above-garage private large office/studio, a 1,000 sq. ft. outbuilding with plumbing and

  David Taylor ELYSE HARNEY REAL ESTATE

  86 Main St, Sheffield, MA 01257
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  /65

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 3,615 Sq Ft

  17 Cronk Rd, Great Barrington, MA 01230

  Originally built in the 1700s, this historic post-and-beam barn has been thoughtfully renovated over time while maintaining its unique character and charm. A recently installed solar energy system allows for highly efficient living with the potential for an off-grid lifestyle.The home features an open floor plan filled with natural light from numerous oversized windows. A chef's kitchen adjoins

  Suzann Ward HOUSATONIC REAL ESTATE

  17 Cronk Rd, Great Barrington, MA 01230
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  /16

  $275,000

  • Land
  • 2.1 Acres
  • $130,952 per Acre

  14 Blue Hill Rd, Monterey, MA 01245

  A 2400 sq. ft. barn in Monterey ready for residential conversion. The property has a completed, successful perc test and established access to a shared well. The project is ready for immediate architectural planning. This is a prime opportunity for a buyer looking to fast-track construction on a desirable Berkshire lot.

  Tony Segalla WILLIAM RAVEIS - BERKSHIRE

  14 Blue Hill Rd, Monterey, MA 01245
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  /25

  $799,000

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft

  1131 Norfolk Rd, Southfield, MA 01259

  Privately set down a long drive in the scenic hills of New Marlborough, this charming shingle-style home sits on over 45 acres of beautiful Berkshire countryside. Built circa 1950, the home offers more than 2,100 square feet of living space with four bedrooms and two full bathrooms. The first floor includes a living room, dining room, kitchen, mudroom, and full bath, while the second floor

  Ahliya Phillips KELLER WILLIAMS REALTY

  1131 Norfolk Rd, Southfield, MA 01259
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  /78

  $2,850,000

  • 4 Beds
  • 4 Baths
  • 5,000 Sq Ft

  201 Stratford Rd, New Marlborough, MA 01259

  Privacy and tranquility define this exceptional Berkshire retreat. Perfectly sited with generous frontage on the pristine shores of Lake Windemere, this sprawling post and beam residence offers four bedrooms and three and a half baths, blending rustic elegance with timeless comfort. Windmere Lake is a privately owned lake with only 13 homes that have access to it. Designed for gathering and

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  201 Stratford Rd, New Marlborough, MA 01259
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  /11

  $65,000

  • Land
  • 0.8 Acre
  • $81,250 per Acre

  2 North Rd, Monterey, MA 01245

  Beautifully wooded building parcel in a private community with access to Lake Buel--one of the Berkshires' premier lakes. This parcel is conveniently located just a short drive from Great Barrington, the charming village of Monterey, and the endless skiing adventures at Butternut Basin. A wonderful spot to envision your home in the hills; please note that the existing summer cottage will need to

  Lance Vermeulen LANCE VERMEULEN RE, INC

  2 North Rd, Monterey, MA 01245
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  /45

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 2,748 Sq Ft

  594 Shunpike Rd, Sheffield, MA 01257

  The Ultimate Berkshire Retreat: Designer Luxury with Versatile Income Potential.Experience the pinnacle of refined living in this ''essentially brand new'' masterpiece by Wingate Ltd. Spanning 2,748 sq. ft. across three levels, this reimagined residence sits on one of the Berkshires' most scenic corridors, surrounded by rolling dairy farms and dramatic mountain vistas.Designed for Luxury &

  John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  594 Shunpike Rd, Sheffield, MA 01257
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  /21

  $1,575,000

  • 4 Beds
  • 4.5 Baths
  • 2,835 Sq Ft

  130 East Rd, West Stockbridge, MA 01266

  Nestled in picturesque Alford, this inviting four-bedroom, 4.5-bath home blends comfort and flexibility in a serene Berkshire setting. The first-floor primary suite features a private ensuite bath, ideal for easy living. Thoughtfully designed spaces offer room for guests, work, or hobbies, while seasonal views bring natural beauty indoors throughout the year. With low Alford taxes and a peaceful

  Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  130 East Rd, West Stockbridge, MA 01266
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  /25

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,332 Sq Ft

  44 C Mount Washington Rd, Egremont, MA 01230

  With a Passing Title V, Country cottage perched atop 3.6 acres in the charming village of South Egremont. This property is set back off the road and offers privacy. The walkout lower level boasts a stone fireplace rec area/ den and garage access. The second floor has 2 bedrooms and a bath as well as living room with fireplace.

  Matt Amstead FAIRGROUND REAL ESTATE, INC

  44 C Mount Washington Rd, Egremont, MA 01230
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  /14

  $119,000

  • Land
  • 1.17 Acres
  • $101,710 per Acre

  2 Terra Ferma Dr, Egremont, MA 01230

  Build your dream home on Terra Ferma Drive--arguably the best dead-end road in the Berkshires. Located in Egremont and just a short drive to South Egremont village, Great Barrington, and Catamount Ski Area, this is the ideal location to stake your ground. The road hosts a quiet neighborhood that leads directly to state hiking trails, putting the outdoors just steps from your door. The lot is

  Lance Vermeulen LANCE VERMEULEN RE, INC

  2 Terra Ferma Dr, Egremont, MA 01230
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  /2

  $79,000

  • Land
  • 2.3 Acres
  • $34,348 per Acre

  0 Clayton Mill River Rd, New Marlborough, MA 01244

  Over 2 + acres overlooking the Konkapot River in the village of Mill River.1 mile to Umpachene Falls.

  Mary White BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  0 Clayton Mill River Rd, New Marlborough, MA 01244
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  /70

  $2,250,000

  • 4 Beds
  • 6 Baths
  • 4,846 Sq Ft

  302 Egremont Plain Rd, Great Barrington, MA 01230

  A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with the Green River just beyond.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  302 Egremont Plain Rd, Great Barrington, MA 01230
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  /8

  $235,000

  • 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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  /28

  $340,000

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

  194 Canaan Southfield Rd, Southfield, MA 01259

  Enjoy peaceful country living in this 3-bedroom, 2-bath home set on 8.6 scenic acres along the Umpachene River and surrounded by abundant wildlife. The property offers endless potential for gardening, recreation, or creating your private retreat. Solar panels are included and will be paid off at closing, providing long-term energy savings. Conveniently located near the Southfield Store, The Old

  Freddy Friedman BIRCH PROPERTIES

  194 Canaan Southfield Rd, Southfield, MA 01259
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  /28

  $495,000

  • 4 Beds
  • 2 Baths
  • 1,531 Sq Ft

  95 Water Farm Rd, Sheffield, MA 01257

  New roof, siding, and house fully painted. Newer heating system. Experience the perfect blend of modern comfort and historical charm in this beautifully maintained home. Featuring 4 spacious bedrooms and 2 baths, this home offers over 1,500 sq. ft. of living space. Enjoy the character of the 1850s with updates, including new mechanics. This home is truly move-in ready. The stonework patio

  Suzann Ward HOUSATONIC REAL ESTATE

  95 Water Farm Rd, Sheffield, MA 01257
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  /11

  $550,000

  • Land
  • 16 Acres
  • $34,375 per Acre

  0 Gould Rd, Monterey, MA 01245

  The drive to this beautiful parcel takes you off the main road, past farms, cottages, and estates--all within a mile or two. Hidden away in one of the most scenic parts of Monterey and surrounded by larger holdings and hundreds of acres of conserved, trust-protected land, this property offers peace and privacy rarely found. The land is mostly level before gently sloping down to a brook on the

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  0 Gould Rd, Monterey, MA 01245
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  /7

  $349,000

  • Land
  • 19.73 Acres
  • $17,689 per Acre

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244

  Just shy of 20 acres. Make your way to the top for views, you won't be disappointed. An abundance of wildlife, and not a building in sight. Come take a look and make this your Berkshire retreat!

  Lawrence Reilly THE KINDERHOOK GROUP

  0 Hayes Hill Rd Unit 247870, New Marlborough, MA 01244
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  /4

  $169,000

  • Land
  • 10.7 Acres
  • $15,794 per Acre

  0 Hartsville-New Marlborough Rd, New Marlborough, MA 01230

  Exceptional 10.7-Acre Wooded Lot-Subdivision Potential. Discover a rare opportunity to own 10.7 acres of serene, wooded land in the heart of New Marlborough. With 590 feet of road frontage & the possible ability to subdivide, this property offers endless options--whether you're looking to build your dream home or explore development potential. Nestled between the charming villages of New

  Paul Reed WILLIAM RAVEIS - BERKSHIRE

  0 Hartsville-New Marlborough Rd, New Marlborough, MA 01230
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  /22

  $799,000

  • Land
  • 29 Acres
  • $27,552 per Acre

  416 West Rd, Alford, MA 01266

  Experience the Berkshires Like Never BeforeNestled on West Road in Alford, this exceptional 29-acre estate offers a rare blend of natural beauty, flexibility, and investment potential. A meandering brook, Alford Brook gently courses through the property, creating serene waterside vistas and the soothing soundtrack of flowing water day and night.From the open meadows and wooded glens, enjoy

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  416 West Rd, Alford, MA 01266
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  /60

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  905 West Rd, Great Barrington, MA 01230

  Welcome to Serenity Hill.This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road.

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  905 West Rd, Great Barrington, MA 01230
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  /45

  $3,900,000

  • 10 Beds
  • 5.5 Baths
  • 7,864 Sq Ft

  535 Main Rd, Monterey, MA 01245

  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

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  535 Main Rd, Monterey, MA 01245
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  /43

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft

  166 Berkshire School Rd, Sheffield, MA 01257

  Nestled in Sheffield Village on 8+ acres, this charming New England farmhouse blends rustic character with modern comfort. Featuring 3 bedrooms, 2 baths, wood floors, beams, Great Room with a gas stove offers a warm inviting space Enjoy a country kitchen with a pantry. Screened in porch with outdoor patio, gardens, and two sheds for storage or hobbies. Perfect as a private sanctuary or Airbnb,

  Suzann Ward HOUSATONIC REAL ESTATE

  166 Berkshire School Rd, Sheffield, MA 01257
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  /29

  $365,000

  • 3 Beds
  • 1.5 Baths
  • 1,482 Sq Ft

  153 E Main St, Ashley Falls, MA 01222

  TITLE V PASSED. Mid-1960s ranch on a quiet street with nearly 1/2 acre! A perfect family home to settle down in Southern Berkshire County. Semi-finished basement is a huge bonus, plus garage and additional detached barn/workshop. Sunny, spacious and ripe with potential. Some thoughtful updates will be needed -- or move in today and make it yours!

  John Segalla HOUSATONIC REAL ESTATE

  153 E Main St, Ashley Falls, MA 01222
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  /52

  $1,900,000

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

  1269 Clayton Mill River Rd, New Marlborough, MA 01259

  Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of

  Lisa Hoe THE KINDERHOOK GROUP

  1269 Clayton Mill River Rd, New Marlborough, MA 01259
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  /11

  $395,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  1089 Canaan Southfield Rd, Southfield, MA 01259

  An enchanting parcel of land with a 2 Bedroom Ranch, in need of updates and cosmetics. The land is beautiful, 7.87 acres, with the house nicely sited up on the knoll. So much potential! There is an attached garage and full basement.The septic design is available and estimate is in hand. Being sold ''as is'', will escrow funds for the septic. A worthwhile project in a private, natural setting.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1089 Canaan Southfield Rd, Southfield, MA 01259
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  /27

  $433,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  2170 Canaan Southfield Rd, Southfield, MA 01259

  Located in the desirable Clayton section of New Marlborough, this 3-bedroom, 2-bath home offers a rare opportunity to own 7.2 acres with 383 feet of frontage on the Konkapot River. The property features a natural setting with direct river access and plenty of room to make it your own.The home has a functional layout with three bedrooms and two full baths. While move-in ready, it would benefit

  Freddy Friedman BIRCH PROPERTIES

  2170 Canaan Southfield Rd, Southfield, MA 01259
• 

  

  /32

  $745,000

  • 3 Beds
  • 2 Baths
  • 2,460 Sq Ft

  85 Main Rd, Monterey, MA 01245

  OUTSTANDING COUNTY LIVING in idyllic Monterey with its low real estate taxes and easy access to Lake Garfield and Lake Buel. Butternut Ski Area is only 5 minutes away. 8 minutes to downtown Great Barrington. This Timber Fame (open floor plan) contemporary home features beautiful (wide-plank) pinewood floors, a cathedral ceiling Great Room, and a bonus sleeping loft area. A fireplace on the main

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  85 Main Rd, Monterey, MA 01245
• 

  

  /6

  $265,000

  • Land
  • 1.97 Acres
  • $134,518 per Acre

  14 McGee Rd, Egremont, MA 01230

  Lovely building lot on a quiet road in bucolic Egremont. Well has been drilled, septic design done for two structures and power is brought to site. Truly ready for your design/build.

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  14 McGee Rd, Egremont, MA 01230

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