Homes for Sale near Bard Academy at Simon's Rock

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  /48

  $995,000

  • 7 Beds
  • 4 Baths
  • 2,998 Sq Ft

  49 South St, Great Barrington, MA 01230

  Immaculate home on ''The Hill'' with stunning hardwood floors and abundant natural light from its many large windows. This versatile three-level property is currently enjoyed as a stately single-family residence, but can seamlessly be divided into two separate apartments, offering a range of layout options and rental income potential. The ground floor features a bright, modern kitchen, a spacious

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  49 South St, Great Barrington, MA 01230
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• 

  

  

  /58

  $1,300,000

  • 3 Beds
  • 3 Baths
  • 2,002 Sq Ft

  276 Great Barrington Rd, West Stockbridge, MA 01236

  This 52-acre homestead blends early American heritage with modern sustainability and self-sufficiency. Originally built in 1802, this stunning property offers privacy, fertile farmland, and breathtaking mountain views' including Monument Mountain/Flag Rock. Mature fruit orchard with over 15 trees: apples, peaches, pears, cherries, plums.30-tree sugar bush with a sugarhouse for maple syrup

  Keytoria Jenkins THE KINDERHOOK GROUP - PITTSFIELD

  276 Great Barrington Rd, West Stockbridge, MA 01236
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  /57

  $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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  /80

  $2,500,000

  • 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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  /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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  /61

  $1,595,000

  • 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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  /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
• 

  

  /20

  $1,229,000

  • 4 Beds
  • 4 Baths
  • 2,322 Sq Ft

  97 Brush Hill Rd, Great Barrington, MA 01230

  Berkshires Sanctuary - A Fully Renovated Retreat with Appalachian Trail Access & Nearby Three Mile Pond.Tucked away in a landscape of towering trees and rolling hills, this exquisite four-bedroom and three-bathroom, retreat has been reimagined with over $650,000 in premium renovations, offering the perfect balance of luxury and nature. With direct access to Appalachian trail and Three Mile Pond,

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  97 Brush Hill Rd, Great Barrington, MA 01230
• 

  

  /11

  $999,000 New Construction

  • 3 Beds
  • 4 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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  /33

  $515,000

  • 4 Beds
  • 3.5 Baths
  • 2,330 Sq Ft

  230 Prospect St, Great Barrington, MA 01236

  Tucked at the end of a dead-end street, this sun-drenched 4 bedroom is set on a corner lot w/ direct access to scenic trails - a rare find just minutes from local amenities. Step inside through a practical mudroom w/ a tiled floor, oversized closet, & powder room. The main level features an open-concept layout, seamlessly connecting the living, dining & kitchen w/ granite countertops and

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  230 Prospect St, Great Barrington, MA 01236
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  /28

  $555,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  36 Castle Ln, Great Barrington, MA 01230

  Charming Renovated Cottage on The Hill - Great Barrington, MADiscover this beautifully renovated Four Square-style cottage in the heart of Great Barrington's coveted ''The Hill'' neighborhood--a rare pied-a-terre offering classic charm with modern upgrades. This delightful 2-bedroom home is nestled in the Southern Berkshires, just moments from downtown, Lake Mansfield, and preserved natural

  Selina Lamb BIRCH PROPERTIES

  36 Castle Ln, Great Barrington, MA 01230
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  /28

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  17 2nd St, Egremont, MA 01230

  Welcome to the community of Prospect Lake! Just in time for summer, this freshly painted, classic four season modern lake house in Prospect Heights is ready for you to enjoy. Located on a private one acre lot just a short short distance from the water's edge with deeded access to the lake. The interior of this three bedroom two bath home is light, bright and airy with plenty of glass to bring in

  Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  17 2nd St, Egremont, MA 01230
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  /20

  $365,000

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft

  12 Manville St Unit 4, Great Barrington, MA 01230

  Bright, happy condominium in a well- maintained building walking distance to downtown and nature trails. This sweet unit is spacious and updated, with views of East Mountain and southern exposure to let the light in. Privately situated on the top floor, this feels like a quiet and peaceful oasis close to all that Great Barrington has to offer. Lofted ceilings, a well-appointed kitchen, a large

  Lauren Rosen LANCE VERMEULEN RE, INC

  12 Manville St Unit 4, Great Barrington, MA 01230
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  /21

  $365,000

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft

  12 Manville St, Great Barrington, MA 01230

  Bright, happy condominium in a well- maintained building walking distance to downtown and nature trails.This sweet unit is spacious and updated, with views of East Mountain and southern exposure to let the light in.Privately situated on the top floor, this feels like a quiet and peaceful oasis close to all that Great Barrington has to offer.Lofted ceilings, a well-appointed kitchen, a large bath

  Lauren Rosen LANCE VERMEULEN RE, INC

  12 Manville St, Great Barrington, MA 01230
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  /15

  $149,000

  • Land
  • 1.11 Acres
  • $134,233 per Acre

  10 Miller View Rd, Egremont, MA 01230

  Tucked away on a quiet cul-de-sac in the desirable Baldwin Hill area of North Egremont, this 1.1 acre building lot offers seasonal mountain views and a serene setting. Partially cleared, with a percolation test on file and easy access to an electrical transformer at the property's edge, this property is an ideal site for your future home. Conveniently situated just minutes from great Barrington,

  Vashti Poor LANCE VERMEULEN RE, INC

  10 Miller View Rd, Egremont, MA 01230
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  /39

  $695,000

  • 3 Beds
  • 1.5 Baths
  • 2,802 Sq Ft

  40 Main St, Egremont, MA 01258

  This colonial is the perfect representation of New England charm, offering a unique opportunity to experience the character of yesteryears while enjoying modern living in the heart of historic South Egremont. The inviting layout of the first floor features a spacious, open living area that seamlessly flows into a well-appointed kitchen, perfect for entertaining. A designated office space, half

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  40 Main St, Egremont, MA 01258
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  /33

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft

  115 Brush Hill Rd, Great Barrington, MA 01230

  Contemporary Design on Six Private Acres in Great Barrington!115 Brush Hill Road - a design-forward turnkey retreat in one of the Berkshires' most coveted areas.This post-mid-century contemporary blends natural materials, clean lines, and a light-filled layout with its serene, wooded surroundings.At the heart of the home is a soaring vaulted living room with exposed wood, skylights, and

  Jared Kelly WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  115 Brush Hill Rd, Great Barrington, MA 01230
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  /30

  $739,000

  • 5 Beds
  • 3 Baths
  • 3,035 Sq Ft

  133 Front St Unit 1 & 2, Great Barrington, MA 01236

  OPEN HOUSE: Sat, May 3rd 11-1PMUnique Mixed-Use Property in Downtown HousatonicPrime opportunity for investors or owner-occupants! This charming property features a successful ground-floor retail space and two spacious, income-producing 2-bedroom apartments above. Each unit includes a large kitchen, full bath, washer/dryer hookups, and an enclosed porch with town views.The commercial space has

  Judi Panzano HOUSATONIC REAL ESTATE

  133 Front St Unit 1 & 2, Great Barrington, MA 01236
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  /17

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,691 Sq Ft

  75 van Deusenville Rd, Great Barrington, MA 01230

  This sweet ranch has been in the same family for over 40 years and awaits the updates and personal touches of its next owners. Situated on a spacious & level 2.43 acre lot (ideal for gardening) this home is conveniently located on the outskirts of the village of Housatonic, just up the road from the Guthrie Center and few minutes drive to downtown Great Barrington. The home offers over 1,600 sq

  Dan Alden ALDEN COUNTRY REAL ESTATE SERVICES

  75 van Deusenville Rd, Great Barrington, MA 01230
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  /5

  $150,000

  • Land
  • 1.96 Acres
  • $76,530 per Acre

  275 Mill River Southfield Rd, New Marlborough, MA 01230

  A rare find, nearly 2 acres of flat land, ready for your dream home! Located in a peaceful setting with easy access to utilities, this property has already passed percolation testing and is fully prepared for construction. Whether you're looking to build now or invest for the future, this is a prime opportunity.

  Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  275 Mill River Southfield Rd, New Marlborough, MA 01230
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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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  /33

  $548,500

  • 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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  /30

  $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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  /26

  $450,000

  • 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
• 

  

  /27

  $349,000

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

  54 Division St, Great Barrington, MA 01230

  Opportunity to Finish Your Dream Home! This 1792 Sq Foot newly renovated home is a blank slate awaiting your final touches! With major recent upgrades, painting, new Septic System & renovations already completed, the heavy lifting is done--just add your personal style to bring it across the finish line. Offering incredible potential, this home needs bathroom installations and a kitchen, making it

  John Segalla HOUSATONIC REAL ESTATE

  54 Division St, Great Barrington, MA 01230
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  /68

  $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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  /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
• 

  

  /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
• 

  

  /25

  $390,000

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  6 Rose Ct W, Great Barrington, MA 01230

  This beautifully updated 3-bedroom, 2.5-bath condo is move-in ready and offers an exceptional living experience in a sought-after location. As you enter, you'll be greeted by an open and inviting space, featuring modern finishes and an abundance of natural light streaming through large windows. The private balcony is perfect for relaxing and taking in panoramic views of the neighborhood. The main

  India Ward NON-MEMBER / RECIPROCAL

  6 Rose Ct W, Great Barrington, MA 01230
• 

  

  /27

  $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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  /7

  $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
• 

  

  /10

  $520,000

  • 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

  $995,000

  • Land
  • 10 Acres
  • $94,762 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
• 

  

  /19

  $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
• 

  

  /47

  $3,295,000

  • 5 Beds
  • 4.5 Baths
  • 5,238 Sq Ft

  56 Crooked Hill Rd, Great Barrington, MA 01230

  Alford Stunner! Exceptionally Designed Turnkey Home with Mountain Views!Completed in 2006, this 5200+ sq ft architect-designed home comes to the market for the first time. Meticulously curated materials, interior designer finishes, and a high-end build culminate in this showpiece home on 19.3 acres, with gunite pool and pool house.Upon entry, this home exudes warmth, style, and comfort - the

  Elle Villetto WILLIAM PITT SOTHEBY'S - LENOX

  56 Crooked Hill Rd, Great Barrington, MA 01230
• 

  

  /13

  $325,000

  • Land
  • 10 Acres
  • $33,854 per Acre

  297 N Plain Rd, Housatonic, MA 01236

  Perfect for a very private family compound. GB zoning allows three dwelling units to be built by right. Cleared one acre level house site with driveway and underground utilities brought in. Over $44,000 in site improvements plus survey and perc testing. 700' of frontage on the lovely clear, Williams River including three islands. Bathe, swim, fish, tube, cold plunge, let your imagination run

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  297 N Plain Rd, Housatonic, MA 01236
• 

  

  /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 nearby Lake Mansfield, and a short walk to town center. House being

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  39 Christian Hill Rd, Great Barrington, MA 01230
• 

  

  /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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