Homes for Sale near John Dewey Academy

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  /3

  $349,000

  • Land
  • 73 Acres
  • $4,782 per Acre

  0 Lake Buel Rd, Great Barrington, MA 01230

  Beautiful Building Site - 72.98 acres in Great Barrington. Gently sloping land abuts the Appalachian Trail and East Mountain State Forest. Shared driveway off Aberdeen Road in New Marlborough. Cleared spot with a partially built barn/workshop on site. Rough driveway in place. Tranquil spot for your dream home!

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Lake Buel Rd, Great Barrington, MA 01230
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  /35

  $520,000

  • 3 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  220 N Plain Rd, Great Barrington, MA 01230

  An 1825 colonial has much of its original charm and features in place - wide plank floors, beamed ceiling, original hardware and fully renovated kitchen. Many new appliances, new windows, and foam insulation in the basement. The well insulated attic and walls along with a high efficiency furnace gives you modern comfort. The house is a legal two family. The Studio apartment is attached and could

  Martin Albert COMPASS MASSACHUSETTS , LLC GB

  220 N Plain Rd, Great Barrington, MA 01230
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  /47

  $1,750,000

  • 5 Beds
  • 3 Baths
  • 2,808 Sq Ft

  353 State Rd, Great Barrington, MA 01230

  The Woodlands, A RARE OPPORTUNITY TO OWN YOUR OWN 74-ACRE PRIVATE SANCTUARY IN THE HEART OF GREAT BARRINGTON.This property abuts the Thomas & Palmer Brook preserve on three sides, is a two-minute drive to Ski Butternut and five minutes to dining and shopping in downtown Great Barrington. A picturesque pond flows into a babbling brook right outside of the large cathedral-ceiling primary suite's

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  353 State Rd, Great Barrington, MA 01230
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  /32

  $695,000

  • 5 Beds
  • 2 Baths
  • 2,060 Sq Ft

  57 South St, Great Barrington, MA 01230

  A charming historic home nestled in the heart of Great Barrington, moved to it's location from Main Street in 1858. This delightful detached residence boasts 2,060 square feet of living space across 10 rooms. The living area features a wood-burning fireplace and space for formal dining. The eat-in kitchen, complete with built-ins, adds character. With four bedrooms and two baths, there's ample

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  57 South St, Great Barrington, MA 01230
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  /12

  $125,000

  • Land
  • 0.56 Acre
  • $222,027 per Acre

  Lot 1 Park St, Great Barrington, MA 01230

  Downtown Great Barrington building lot boasting a sweet water feature, town water and sewer. Located at the top of a dead-end road and just across the street from Park Street Park, this is a perfect spot to build a downtown getaway. Water feature has been delineated. Come make this property your own!

  Tony Segalla LANCE VERMEULEN RE, INC

  Lot 1 Park St, Great Barrington, MA 01230
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  /82

  $2,375,000

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

  173 Hillsdale Rd, Egremont, MA 01230

  Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlife and protected land on three sides, this one-of-a-kind, custom-built home offers extraordinary privacy and tranquility. Crafted using wood milled directly from the property, this rustic yet contemporary home boasts a wealth of unique details that highlight exceptional craftsmanship and timeless beauty.

  Robert Cohen eXp REALTY

  173 Hillsdale Rd, Egremont, MA 01230
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  /84

  $2,399,990

  • 6 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  141 Stevens Lake Way, Monterey, MA 01245

  Discover Stevens Lake! This incredible property offers you a lifestyle that is unmatched in the modern world. The residence is perched overlooking the lake to experience spectacular sunrises. Entering from the garage there is a mud/laundry room which opens to the kitchen fit for any Chef. The kitchen features granite counters, Subzero and Viking appliances, a large pantry with an additional

  Derek Strzepa NOCHER REALTY

  141 Stevens Lake Way, Monterey, MA 01245
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  /69

  $2,750,000

  • 7 Beds
  • 6 Baths
  • 7,008 Sq Ft

  300 Alcott Rd, Great Barrington, MA 01230

  Great Barrington Compound! Custom built salt box home situated the end of a town dirt road on 32 acres. Bear Town State Forest abuts the property. Heated gunite pool and stunning view of Monument Mountain. Enjoy established gardens including an apple orchard, lilies, peonies, etc. Main house with living room, library, dining room, eat in kitchen, laundry, two powder rooms, attached two car

  Patrice Melluzzo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  300 Alcott Rd, Great Barrington, MA 01230
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  /25

  $419,000

  • 4 Beds
  • 1 Bath
  • 1,337 Sq Ft

  153 State Rd, Great Barrington, MA 01230

  Neat as a pin cape walking distance to downtown Great Barrington and amenities, this home has been thoughtfully renovated top to bottom. This sweet property has 4 bedrooms, a full bath, and even a partially finished basement. The kitchen, complete with a large pantry, retains the charming mid century details, while appealing to the modern aesthetic. Outside, there is a nice flat side yard, and

  Lauren Rosen LANCE VERMEULEN RE, INC

  153 State Rd, Great Barrington, MA 01230
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  /31

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  54 Division St, Great Barrington, MA 01230

  This 1,792 sq. ft. newly renovated home is a blank canvas, awaiting your final touches! Major upgrades have already been made, including fresh paint, kitchen cabinets, and a renovated first-floor full bathroom. A brand-new septic system has also been installed, with most renovations nearly complete.What remains is the finishing work: the primary bathroom, flooring throughout the home, as well as

  John Segalla HOUSATONIC REAL ESTATE

  54 Division St, Great Barrington, MA 01230
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  /72

  $4,290,000

  • 4 Beds
  • 4.5 Baths
  • 5,800 Sq Ft

  113 Brush Hill Rd, Great Barrington, MA 01230

  THE GOAT......This exceptional Berkshire minimalistic sensation has been architecturally designed to maximize the open floor plan concept while being mindful of private work/play spaces. A showpiece with 12+ acres of privacy surrounds you while the panoramic western views in every season bring you peace and calmness. The walls of glass integrate nature and the tranquil spellbinding views with

  Mary Jane White COHEN & WHITE ASSOCIATES

  113 Brush Hill Rd, Great Barrington, MA 01230
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  /52

  $1,475,000

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

  82 West Ave, Great Barrington, MA 01230

  Classic turn-of-the-century Berkshire residence on the Hill. Rich w/ history & ready for new memories, this home is a rare gem in an ideal location. Lovingly maintained by the same family for over 60 yrs. Nestled on 1.6 acres, this 4,000 SF residence offers 5 BRs, 3.5 BAs & an abundance of historic charm. Original wood floors, high ceilings & period details fill the home, while the grand

  Claire Pollart LANCE VERMEULEN RE, INC

  82 West Ave, Great Barrington, MA 01230
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  /13

  $850,000

  • Land
  • 23 Acres
  • $37,379 per Acre

  0 Lake Buel Rd, Great Barrington, MA 01230

  Residential development opportunity! This expansive parcel offers potential for 17 building sites, ideally located just minutes from downtown Great Barrington and Butternut Ski Area. The property abuts the iconic Appalachian Trail, offering tranquil access to nature and recreation. Build a cul-de-sac community where residents can experience the best of the Berkshires--hiking, skiing, and vibrant

  Tony Segalla LANCE VERMEULEN RE, INC

  0 Lake Buel Rd, Great Barrington, MA 01230
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  /49

  $1,999,000

  • 6 Beds
  • 6 Baths
  • 4,850 Sq Ft

  71 Blunt Rd, Great Barrington, MA 01230

  Artist Retreat / Family Compound! This very special property has a lot more to offer than anything on the market with three separate living/working spaces all thoughtfully designed for inspiration and comfort! Completely remodeled from top to bottom, the main house has three bedrooms, three bathrooms and featuring in-floor radiant heat under reclaimed ancient teak floors. There is a first floor

  Ryan Lane Gilcrest Properties

  71 Blunt Rd, Great Barrington, MA 01230
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  /49

  $1,999,000

  • 6 Beds
  • 6 Baths
  • 4,850 Sq Ft

  71 Blunt Rd, Egremont, MA 01230

  Artist Retreat / Family Compound! This very special property has a lot more to offer than anything on the market with three separate living/working spaces all thoughtfully designed for inspiration and comfort! Completely remodeled from top to bottom, the main house has three bedrooms, three bathrooms and featuring in-floor radiant heat under reclaimed ancient teak floors. There is a first floor

  Ryan Lane GILCREST PROPERTIES

  71 Blunt Rd, Egremont, MA 01230
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  /26

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft

  54 Egremont Plain Rd, Great Barrington, MA 01230

  Great New England farmhouse with really nice views. Common rooms are amply sized and the kitchen great room is perfect for many different activities. Extra room on the first floor can be used as a bedroom or an office (not pictured.) Many extras - structural renovations in 2004, central air, in line generator, in ground pool, screened porch and so much charm. Nice 3.89 acre parcel with detached

  Katie Williams STONE HOUSE PROPERTIES, LLC

  54 Egremont Plain Rd, Great Barrington, MA 01230
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  /10

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  36 Egremont Plain Rd, Great Barrington, MA 01230

  Don't miss this charming 4-bed, 2-bath home with 2 first-floor bedrooms and a full bath! Offering nearly 2,100 sq. ft. of living space and almost 1 acre of flat, dry land, this home provides plenty of room to grow. The breezeway connects the 2-car garage with newer doors and electric openers. Outside, enjoy a private patio, stone wall, and a shed for extra storage. Gorgeous flowering crabapple

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  36 Egremont Plain Rd, Great Barrington, MA 01230
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  /10

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  26 Manville St, Great Barrington, MA 01230

  Modernized 3-bedroom 2-bathroom Cape home on quiet dead-end street located in a fantastic in town neighborhood. Recently renovated, the kitchen features granite countertops, subway tiles, modern fixtures, and wood floors. Downstairs offers a dining room with wood floors, large living room with wood burning fireplace, two bedrooms, and a full bathroom that boasts more of that classic black and

  David Carlson FAIRGROUND REAL ESTATE, INC

  26 Manville St, Great Barrington, MA 01230
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  /11

  $899,000

  • Land
  • 10 Acres
  • $85,619 per Acre

  55 Prospect Lake Rd, Egremont, MA 01230

  Rare Waterfront Offering on Prospect Lake - 10.5 Acres Across Four Subdivided Lots. Nestled along the tranquil shores of beautiful Prospect Lake, this extraordinary property presents a once-in-a-lifetime opportunity to own a unique and versatile slice of the Berkshires. With direct water frontage, lightly wooded acreage, and breathtaking western views, this is the perfect setting to create your

  Suzann Ward HOUSATONIC REAL ESTATE

  55 Prospect Lake Rd, Egremont, MA 01230
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  /46

  $650,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  63 Division St, Great Barrington, MA 01230

  Welcome to this beautifully updated home with frontage on the serene Williams River, just a short drive from downtown Great Barrington. Renovated in 2017, this home boasts modern convenience with cozy charm. Step inside to a bright, open kitchen featuring granite countertops, stainless steel appliances, a farmhouse sink, and Kraftmaid cabinetry. The first-floor primary suite offers peaceful

  Tony Segalla LANCE VERMEULEN RE, INC

  63 Division St, Great Barrington, MA 01230
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  /20

  $435,000

  • 3 Beds
  • 1.5 Baths
  • 1,772 Sq Ft

  26 High St, Housatonic, MA 01236

  This charming colonial home is located within walking distance of the quaint center of Housatonic Village. Situated just over the border in West Stockbridge where property taxes are more favorable. Originally constructed as one of the manager's homes for the local mills, this residence has wood floors & high ceilings creating a spacious atmosphere. The first floor features generous living room &

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  26 High St, Housatonic, MA 01236
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  /25

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  39 Christian Hill Rd, Great Barrington, MA 01230

  GREAT OPPORTUNITY FOR A SWEET FIXER-UPPER! A feel good house, that with some cosmetics, could be your happy home. So much potential, with wood floors, tall ceilings, front porch and a back deck over looking a lovely, private back yard. A good, solid house, renovation worthy. Not a drive by, interior has much to offer. Trail to Lake Mansfield and the town center within walking distance.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Christian Hill Rd, Great Barrington, MA 01230
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  /61

  $2,500,000

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

  1373 Boardman St, Sheffield, MA 01257

  The ULTIMATE LIVE-WORK-PLAY RETREATStep onto a property as striking as the Berkshires themselves--where innovative design meets natural splendor, creating an extraordinary canvas for your ideal lifestyle. The 13,738 sq ft retreat fondly known as ''The Factory'' spans 5+ acres with views of rolling hills & protected fields. 10,000 sq ft of versatile commercial and creative space below and flanked

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  1373 Boardman St, Sheffield, MA 01257
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  /5

  $1,500,000

  • Land
  • 123 Acres
  • $12,234 per Acre

  685B S Egremont Rd, Great Barrington, MA 01230

  122+ Acres of Land in Egremont & Sheffield Only. Over 700 feet of frontage on Sheffield-Egremont Rd on the Egremont / Sheffield Border. Former use as Golf Course for the Egremont Country Club. *Does not include any acreage in Great Barrington. See MLS # 241894 for the full parcel of 225 Acres.

  Steven Weisz WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  685B S Egremont Rd, Great Barrington, MA 01230
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  /4

  $69,000

  • Land
  • 3.72 Acres
  • $18,548 per Acre

  0 Greenwood Cir, Egremont, MA 01230

  Bring your creativity to build a sweet home with views of Smiley's Pond in this lovely quiet neighborhood. 3.72 acres on private drive close to the village center of South Egremont. Frontage on both Greenwood Circle and North Undermountain Road.

  Lance Vermeulen LANCE VERMEULEN RE, INC

  0 Greenwood Cir, Egremont, MA 01230
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  /40

  $1,590,000

  • 11 Beds
  • 12.5 Baths
  • 8,134 Sq Ft

  518 Main St, Great Barrington, MA 01230

  The iconic Wainwright Inn, built in 1766, is ideally located on Main Street in Great Barrington, the largest town & hub of the famous Berkshires vacation destination in Western Massachusetts. The Inn consists of a main house with 9 guest suites & a spacious owner's suite, & a carriage house with an apartment & two additional guest suites. In pristine condition, the current owners have improved

  Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

  518 Main St, Great Barrington, MA 01230
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  /6

  $175,000

  • Land
  • 2.50 Acres
  • $70,000 per Acre

  0 The Ave, Egremont, MA 01230

  Terrific low real estate tax Egremont location. Close to the center of town, the Catamount Ski Area, and very nice restaurants and shopping. Great land value.

  George Cain WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 The Ave, Egremont, MA 01230
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  /12

  $299,000

  • Land
  • 4.10 Acres
  • $72,927 per Acre

  0 Pinecrest Hill Rd, Egremont, MA 01230

  Precious 4 acre parcel along Pine Crest Hill Rd with due diligence in place for a curb cut off of Undermountain Rd (Rte 41) a short distance from So. Egremont, with its quaint New England village charm. Potential for open and elevated views; (thinkglorious sunsets!) overlooking Smiley's (Mill) Pond. Perfect for walking and enjoying nature on Pine Crest Hill. This surveyed parcel is not part of

  Thomas Doyle, Sr. BISHOP WEST REAL ESTATE

  0 Pinecrest Hill Rd, Egremont, MA 01230
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  /9

  $199,000

  • Land
  • 1.30 Acres
  • $153,077 per Acre

  1699 N Main St, Sheffield, MA 01257

  COMMERCIAL AREA ON THE SHEFFIELD/GREAT BARRINGTON LINE OFF OF BUSY ROUTE 7. SOME WETLANDS BUT A WORTHY LOCATION. NICE WITH LEVEL LAWN. THERE ARE NOT MANY LOTS LEFT ALONG THIS POPULAR COMMERCIAL CORRIDOR.

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  1699 N Main St, Sheffield, MA 01257
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  /51

  $2,975,000

  • 5 Beds
  • 5.5 Baths
  • 3,940 Sq Ft

  19 Mill Rd, Egremont, MA 01230

  Escape to Your Own Lakefront Sanctuary in the Berkshires Nestled in the heart of the picturesque Berkshires, this enchanting lakefront property offers a rare opportunity to create your dream retreat. With over 500 feet of private waterfront, this expansive estate is a haven for those seeking tranquility and natural beauty. Situated on a sprawling parcel of land, this property is perfectly

  Suzann Ward HOUSATONIC REAL ESTATE

  19 Mill Rd, Egremont, MA 01230
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  /28

  $2,975,000

  • Land
  • 60 Acres
  • $49,916 per Acre

  19 Mill Rd, Egremont, MA 01230

  Welcome to a truly unique opportunity to own a magnificent waterfront property on Prospect Lake. Roughly 500' of Lakefront Spanning an impressive 59 acres, this expansive estate offers unparalleled privacy and endless potential for those with a vision. Whether you're looking to create a private retreat, subdivide for development, or renovate the existing home, this property provides a canvas

  Suzann Ward HOUSATONIC REAL ESTATE

  19 Mill Rd, Egremont, MA 01230
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  /85

  $1,425,000

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

  124 Egremont Plain Rd, Great Barrington, MA 01230

  This home has just about everything you're looking for and more!A 4.62 acre private setting, just 5 minutes into Great Barrington and low Egremont taxes! 4 Beds & 4.5 baths with an in law loft apartment. Wide open back yard with plenty of room for a pool if you dont feel like cooling off in the crisp & refreshing Green River at the rear end of the property. First level of home has a primary suite

  Lawrence Reilly BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  124 Egremont Plain Rd, Great Barrington, MA 01230
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  /32

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 2,422 Sq Ft

  367 N Plain Rd, Housatonic, MA 01236

  1880 4 Bedroom Colonial in a beautiful Pastoral setting. Open Living and Kitchen plan.Permitted wood burning stove in living room. Second floor has 3 bedrooms, one is a generously sized en-suite. Garage was converted partially for a perfect home office or 4th bedroom. Laundry facilities and half bath located on 1st floor. Outdoor space includes a deck, a partially fenced portion of yard for a dog

  Mark Rosengren LANCE VERMEULEN RE, INC

  367 N Plain Rd, Housatonic, MA 01236
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  /16

  $315,000

  • 2,950 Sq Ft

  16 Depot St, Great Barrington, MA 01230

  Prime Commercial / Residential / Multi-Family Space in Downtown Housatonic! A chance to create a central hub for commerce and discover the endless possibilities with a versatile commercial space. Spanning 2,950 square feet, this property offers a unique opportunity to breathe new life into the area and create a thriving business hub. Ready to be transformed into a cozy coffee shop, a vibrant meat

  John Segalla HOUSATONIC REAL ESTATE

  16 Depot St, Great Barrington, MA 01230
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  /17

  $349,000

  • Land
  • 1.13 Acres
  • $308,848 per Acre

  1 Terra Ferma Dr, Egremont, MA 01230

  Nestled on the corner of Terra Ferma Drive - a dead end road community in picturesque Egremont, this partially constructed home offers a unique opportunity to finish building your dream retreat. Current builder is prepared to finish construction starting immediately after change of ownership. The house's foundation has been poured, the deck has been laid and power has been brought to the site.

  Tony Segalla LANCE VERMEULEN RE, INC

  1 Terra Ferma Dr, Egremont, MA 01230
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  /25

  $619,500

  • 3 Beds
  • 2 Baths
  • 1,631 Sq Ft

  28 Monument Valley Rd, Great Barrington, MA 01230

  Classic family home in Great Barrington. 3 Bedroom 2 Bath on almost 2 acres. First floor large Primary bedroom, wrap around porch, deck and oversized heated garage with office space above. Enjoy the Berkshires with all it has to offer; Butternut ski area around the corner, schools, Tanglewood, theaters and restaurants all conveniently located nearby.

  Mark Rosengren LANCE VERMEULEN RE, INC

  28 Monument Valley Rd, Great Barrington, MA 01230
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  /34

  $1,785,000

  • 5 Beds
  • 4.5 Baths
  • 4,632 Sq Ft

  206 Hillsdale Rd, Egremont, MA 01230

  Handsomely built with modern comfort and amenities. Meet Guests on the covered porch and welcome them into the first floor open kitchen and great room with stone fireplace. On the first floor is also the dining room, office, den, mudroom and breezy screened porch for summer drinks. First floor primary suite with sparkling ensuite bathroom and sitting room with fireplace is its own hideaway.

  Martha Piper WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  206 Hillsdale Rd, Egremont, MA 01230
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  /66

  $6,850,000

  • 5 Beds
  • 3.5 Baths
  • 3,474 Sq Ft

  77 Seekonk Cross Rd, Great Barrington, MA 01230

  Welcome to Meadow Wood This elegant property on a secluded reach of the Green River epitomizes the concept of indoor/outdoor living. The graceful and meticulously maintained 30 acre estate features specimen trees, established gardens, a lily pond, terraces, pastoral views, and privacy. In addition to the light-filled main house, the property includes the gardens, fenced fields, a 2 car garage w/

  Elvia Gignoux WILLIAM PITT SOTHEBY'S - SALISBURY

  77 Seekonk Cross Rd, Great Barrington, MA 01230
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  /43

  $725,000

  • 7 Beds
  • 6.5 Baths
  • 3,684 Sq Ft

  3 Lake Buel Rd, Great Barrington, MA 01230

  Discover the timeless allure of 'The Turning Point,' a quintessential Berkshire retreat nestled in the hills of Great Barrington. Originally a 1800's stagecoach stop, this enchanting 3600-square-foot property boasts a rich history as a thriving inn, short-term rental and home, offering 7 bedrooms and 6.5 bathrooms. Immerse yourself in its New England charm, complete with a wood stove, propane

  Tony Segalla LANCE VERMEULEN RE, INC

  3 Lake Buel Rd, Great Barrington, MA 01230
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  /63

  $5,900,000

  • 11 Beds
  • 10 Baths
  • 9,748 Sq Ft

  25 W Sheffield Rd, Great Barrington, MA 01230

  Tullar Farm represents a rare opportunity to own a piece of history where timeless elegance meets modern comfort amidst the serenity of South Egremont's charming landscape. With its rich architectural heritage, generations of proud stewardship, and unrivaled natural beauty, this distinguished estate stands as a testament to the enduring legacy of its past and the promise of future for generations

  Elyse Morris ELYSE HARNEY REAL ESTATE

  25 W Sheffield Rd, Great Barrington, MA 01230

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