Homes for Sale near Mt. Everett High School

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  /40

  $499,000

  • 6 Beds
  • 2.5 Baths
  • 3,184 Sq Ft

  119 S Main St, Sheffield, MA 01257

  A unique opportunity to make this terrific property your own, with a separate bungalow apartment for income or other home business uses. Property features a 6 bedroom, 2 bath 1880's Victorian with a classic yet casual style. First floor features a sunny living room, large country kitchen, formal dining room w/ built-ins, and front parlor/bedroom. Second floor offers 5 bedrooms, 2 full baths, and

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 481-1637

  119 S Main St, Sheffield, MA 01257
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  /57

  $3,250,000

  • 6 Beds
  • 5.5 Baths
  • 4,681 Sq Ft

  1333 Norfolk Rd, Southfield, MA 01259

  Set on 11 enchanting acres in the pastoral town of New Marlborough, Massachusetts, this exceptional Berkshires estate offers a rare convergence of architectural refinement, natural splendor, and modern luxury. Designed by an architect and originally built in 1984, the main house, guest house, and pool house were all fully renovated in early 2025 to create a cohesive, contemporary compound with

  

  Selina Lamb

  BIRCH PROPERTIES

  (413) 327-9228

  1333 Norfolk Rd, Southfield, MA 01259
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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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  /77

  $4,995,000

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

  764 E Hill Rd, New Marlborough, MA 01230

  WHERE THE WORLD FALLS AWAYAt the top of East Hill Road in the Southern Berkshires, East Hill Farm stretches out over 227 acres of unspoiled beauty: forest, meadow, pond, pasture, and sky . One of the most storied and visually captivating estates in the region, it offers not just land, but peace. Not just privacy, but purpose.At its heart stands a 1798 Federal home, built when John Adams was

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  764 E Hill Rd, New Marlborough, MA 01230
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  /56

  $480,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  14 Norwalk Acres Rd, Monterey, MA 01245

  Modern Monterey Retreat on 3.5 AcresTucked away at the end of a long private drive, this recently renovated contemporary offers a rare blend of modern design and Berkshire charm. With 1,250 sq ft of living space plus a stunning 250 sq ft screened porch, the home features clean lines, natural light, and thoughtful finishes throughout.

  Timothy Dunn VENTURE REAL ESTATE, INC

  14 Norwalk Acres Rd, Monterey, MA 01245
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  /8

  $2,150,000

  • 4 Beds
  • 2 Baths
  • 1,200 Sq Ft

  199 West St, South Egremont, MA 01258

  Rare Opportunity: 185 Acres of Natural Beauty in the Southern BerkshiresWe are offering one of the largest remaining privately owned parcels of natural acreage in the Southern Berkshires 185 private acres atop a mountain in Mount Washington, Massachusetts.Surrounded by protected forestland, this extraordinary property features over 10,000 feet of road frontage in a 3-acre zoning

  David Singer Mohonk Educational and Neuropsychological Foundation

  199 West St, South Egremont, MA 01258
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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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  /52

  $1,895,000

  • 3 Beds
  • 4 Baths
  • 3,600 Sq Ft

  65 Adsit Crosby Rd, New Marlborough, MA 01230

  Nestled on 10.5 pastoral acres along the serene Konkapot River, Elegant Berkshire estate blending timeless craftsmanship with contemporary luxury. Dramatic great room with vaulted ceilings, wide-plank floors, and a grand stone fireplace opens to sweeping meadow and pool views. Featuring three bedrooms, three offices, and four baths, the home offers a luxurious primary suite, two fireplaces, and a

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  65 Adsit Crosby Rd, New Marlborough, MA 01230
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  /64

  $1,900,000

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

  71 & 73 Blunt Rd, Egremont, MA 01230

  A Truly Inspired Berkshire RetreatThe perfect home to relax, create, and be inspired! This remarkable Egremont property offers an exceptional combination of luxury, comfort, and creativity--far beyond anything else on the market.The main house features three spacious bedrooms and three full baths, with radiant in-floor heat beneath reclaimed ancient teak floors. The first-floor primary suite

  Ryan Lane GILCREST PROPERTIES

  71 & 73 Blunt Rd, Egremont, MA 01230
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  /66

  $1,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,185 Sq Ft

  124 Egremont Plain Rd, Great Barrington, MA 01230

  This beautiful home was built in 2006, and updated in 2022. The house is situated on just shy of 5 Acres in the town of Egremont. The home is flooded with sun all day, rarely needing a light on in the house. Direct access to the Green River at the edge of property to cool off on those hot summer days. A new central AC system was installed throughout home and apt A New backup generator, rain

  Lawrence Reilly THE KINDERHOOK GROUP

  124 Egremont Plain Rd, Great Barrington, MA 01230
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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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  /20

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  749 Hartsville New Marlboro Rd, New Marlboro, MA 01230

  Discover Net Zero living in this architect-designed modern home. Newly built for superior comfort and high-performance efficiency, powered by an advanced solar system with battery backup. Blending sustainability and style, this 2,600 sq ft residence features light-filled rooms, stunning Berkshire views, a dramatic entry, custom kitchen, expansive screened porch, and generous storage. The

  Jason Saphire www.HomeZu.com

  749 Hartsville New Marlboro Rd, New Marlboro, MA 01230
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  /37

  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  414 S Undermountain Rd, Sheffield, MA 01257

  Custom modern home with open plan living area, high ceilings and oversized windows everywhere bringing in tremendous natural light. One level living with large gorgeous marble kitchen, great working island and wall pantry. Guest wing off entry with two bedrooms and a hall bath. Entry hall has a powder room, hooks for coats and closet. The primary suite, on the south side, has french doors to

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  414 S Undermountain Rd, Sheffield, MA 01257
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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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  /52

  $1,149,000

  • 4 Beds
  • 2 Baths
  • 2,742 Sq Ft

  22 Sheffield Rd, Great Barrington, MA 01230

  Discover this enchanting 1900s Town Colonial, where historic charm meets modern sophistication. Nestled in a tranquil neighborhood, this home offers four spacious bedrooms, two updated full baths, and a stunning chef's kitchen, blending comfort with style. From the moment you enter through the newly renovated mudroom, you'll appreciate the original wood floors and built-in shelving that preserve

  Suzann Ward HOUSATONIC REAL ESTATE

  22 Sheffield Rd, Great Barrington, MA 01230
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  /40

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  60 Parsley Ln, Sheffield, MA 01257

  Nestled at the end of a quiet country cul-de-sac, this newly built 5-bedroom, 4.5-bath home embodies refined country living. A dramatic primary suite offers dual walk-in closets and a spa-inspired bath with soaking tub, while a first-floor ensuite bedroom enhances comfort and flexibility. The gas fireplace living room and chef's kitchen create a seamless flow for entertaining, extending to a

  Vashti Poor LANCE VERMEULEN RE, INC

  60 Parsley Ln, Sheffield, MA 01257
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  /39

  $990,000

  • 4 Beds
  • 2 Baths
  • 2,600 Sq Ft

  1131 Norfolk Rd, Southfield, MA 01259

  Secluded country home on 48 wooded acres. 4 Bedrooms/2 full baths Contemporary Lodge/Guest House, spacious open living room with massive field stone fireplace, chefs kitchen with Garland Stove.. Lovely country setting offering great privacy for one owner or potential family compound

  Matthew Marlow BERKSHIRE HOMES AND CONDOS

  1131 Norfolk Rd, Southfield, MA 01259
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  /41

  $1,275,000

  • 4 Beds
  • 5 Baths
  • 3,528 Sq Ft

  1669 Silver St, Sheffield, MA 01257

  Experience breathtaking panoramic vistas over protected land from every angle in this renovated Classic American Farmhouse. Nestled on two parcels, this residence boasts a pool, a detached garage, and gracious proportions throughout. Relax in the majestic long-range mountain vistas. The house is perfectly positioned to experience both sunrise and sunset views.Step inside to discover an

  Elyse Morris ELYSE HARNEY REAL ESTATE

  1669 Silver St, Sheffield, MA 01257
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  /11

  $999,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 6,762 Sq Ft

  67 Blunt Rd, Egremont, MA 01230

  Unbelievable opportunity! The real hard work has been done for this six thousand square foot Timber frame home with three levels on over sixteen acres of land. Lots of the finishing materials are on site and ready to be installed. Architectural plans are available. Wonderful local mountain views and a stream with pond site make this the perfect setting. Why settle for someone else's vision when

  Ryan Lane GILCREST PROPERTIES

  67 Blunt Rd, Egremont, MA 01230
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  /31

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  184 Old Hitchcock Rd, New Marlborough, MA 01230

  Tucked away deep in the quiet woods of New Marlborough, a low tax town, this distinctive property sits on 18+ very private acres. Perfect for anyone seeking true seclusion, natural beauty, and a life off the beaten trail. Surrounded by mature trees and untouched wilderness, it offers exceptional privacy and a peaceful atmosphere where the only sounds are birdsong, flowing breeze, and the soft

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  184 Old Hitchcock Rd, New Marlborough, 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 just minutes from South Egremont, 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. This lot is perced and ready to build.

  Tony Segalla 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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  /36

  $388,000

  • 3 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  2010-2012 Clayton Mill River Rd, New Marlborough, MA 01259

  Nestled in the foothills of beautiful Southern Berkshires this turn key 3 bed 1.5 ba home is flanked on its eastern & western boundaries by protected farmland. Historic Southfield Village & nearby surrounds offers a variety of venues for dining on farm to table fare, a myriad of cultural events, nearby shopping, public & private schools. Kayak, fish & play in our many lakes, rivers & streams.

  Brenda McLean WILLIAM PITT SOTHEBY'S - SALISBURY

  2010-2012 Clayton Mill River Rd, New Marlborough, MA 01259
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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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  /3

  $425,000

  • 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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  /95

  $13,500,000

  • 7 Beds
  • 9 Baths
  • 10,429 Sq Ft

  30 East Rd, West Stockbridge, MA 01266

  Majestic 71 acre Tudor Estate atop Tom Ball Mountain in the quaint hamlet of Alford, MA. Enjoy total privacy and breathtaking views from nearly every room. The main house features 5 en-suite bedrooms, a gourmet kitchen, formal living and dining rooms, den, family room, gym, billiard room and massage room. A separate 2-bedroom guest house offers beamed ceilings and full amenities. Manicured

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  30 East Rd, West Stockbridge, MA 01266
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  /23

  $495,000

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

  95 Water Farm Rd, Sheffield, MA 01257

  Open House 10-11-25, 11:00-1:00. Inside pictures to follow soon. 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 mechanicals. Freshly painted inside and out, this home is truly move-in

  Suzann Ward HOUSATONIC REAL ESTATE

  95 Water Farm Rd, Sheffield, MA 01257
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  /32

  $425,000

  • 4 Beds
  • 3 Baths
  • 1,360 Sq Ft

  1592 County Rd, Great Barrington, MA 01230

  Wonderful location, 3 bedroom, 3 bath split level. Minutes to the downtowns of Sheffield and Great Barrington. Primary with en suite bath, finished lower level with family room, artists studio plus a two car garage.

  Michael Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  1592 County Rd, Great Barrington, MA 01230
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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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  /17

  $265,000

  • Land
  • 6.79 Acres
  • $39,016 per Acre

  00 Konkapot Rd, New Marlborough, MA 01259

  The tree lined drive leads to a level, private, cleared building site on this 6.8 acre lot. Underground 200 amp service, a new well, and 4 bedroom septic fields are installed. A short stroll brings you to the association tennis courts and swimming pool. This is a rare opportunity in a very desirable Southern Berkshires location.

  David Taylor ELYSE HARNEY REAL ESTATE

  00 Konkapot Rd, New Marlborough, MA 01259
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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 LANCE VERMEULEN RE, INC

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

  $849,000

  • Land
  • 29 Acres
  • $29,276 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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  /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

  $449,000

  • 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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  /13

  $365,000

  • Land
  • 15 Acres
  • $24,333 per Acre

  0 Brewer Branch Rd, New Marlborough, MA 01244

  Bucolic New Marlborough at its best. 15 gorgeous acres with meadows, woods and Brewer Brook. Gently rolling terrain. Lovely views of the hills, fields and trees in all directions. Sits beautifully at the southwest corner of Brewer Branch and Brewer Hill Roads. This property is perfect as an estate parcel with space for a full guest house, barns or other outbuildings. It does meet the

  Sheila Thunfors STONE HOUSE PROPERTIES, LLC

  0 Brewer Branch Rd, New Marlborough, MA 01244
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  /27

  $399,000

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

  153 E Main St, Ashley Falls, MA 01222

  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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  /85

  $3,995,000

  • 5 Beds
  • 6.5 Baths
  • 6,915 Sq Ft

  662 Brewer Hill Rd, New Marlborough, MA 01230

  Iconic only begins to describe this rare union of sophistication & natural splendor. Spanning 40+ secluded acres of rolling meadows, forested trails, & sweeping mountain views, this remarkable estate has welcomed world-renowned artists & hosted unforgettable gatherings, from summer soirees to intimate retreats.At its heart is the Great House--a 6,000 sq. ft. architectural masterpiece by renowned

  Claire Pollart LANCE VERMEULEN RE, INC

  662 Brewer Hill Rd, New Marlborough, MA 01230
• 

  

  /20

  $389,000

  • 2 Beds
  • 1 Bath
  • 1,048 Sq Ft

  68 Creamery Rd, Great Barrington, MA 01230

  Sweet ranch in an unbeatable location. Located in lovely, low tax Egremont, this turn key property is minutes away from Great Barrington, New York state, and all that Berkshire County has to offer.One level living, this home includes two bedrooms, one full bath, hardwood floors and tons of light. A spacious kitchen opens into the living room, which centers around a cozy fireplace.A large,

  Lauren Rosen LANCE VERMEULEN RE, INC

  68 Creamery Rd, Great Barrington, MA 01230
• 

  

  /4

  $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 significant 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

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  1089 Canaan Southfield Rd, Southfield, MA 01259

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