Newest Homes for Sale in Great Barrington, MA

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  /55

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 1,860 Sq Ft

  127 Monument Valley Rd, Great Barrington, MA 01230

  Beautifully renovated New England Farmhouse with thoughtful modern updates! The home retains original character with wood floors, some exposed timber framing, and a cozy fireplace. Chef's kitchen with high end appliances for serious cooking and easy entertaining. Three comfortable bedrooms, with two additional flex spaces that work for offices, guests , den or creative studios. The screened porch

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  127 Monument Valley Rd, Great Barrington, MA 01230
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  /46

  $625,000

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

  1057 Main St, Great Barrington, MA 01236

  Great investment opportunity! A very rare property offered for the first time outside the family in over 50 years. This is a well maintained and loved four unit income property that can produce over seventy five thousand dollars per year in rents! Lifetime metal roof, freshly painted exterior, updated units are just a few of the benefits of this investment. In the bustling village of Housatonic,

  Ryan Lane GILCREST PROPERTIES

  1057 Main St, Great Barrington, MA 01236
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  /19

  $315,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  9 Forest Row, Great Barrington, MA 01230

  Immaculate ground level unit in the private country community of Forest Row., located just a few minutes from downtown Great Barrington. Forest Row is a Community Land Trust Neighborhood. Easy care one level living with an open floor plan, delightful screened porch and a patio bordered by gardens and woods, surrounded by 21 acres of protected land for your enjoyment. Carport and garden shed. Easy

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  9 Forest Row, Great Barrington, MA 01230
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  /4

  $269,900

  • Land
  • 2 Acres
  • $134,950 per Acre

  0 Pine St, Great Barrington, MA 01230

  Two-acre parcel in a quiet location, a short stroll to the Main Street. Ideal for those who seek privacy with the convenience of nearby shops, restaurants and services.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  0 Pine St, Great Barrington, MA 01230
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  /14

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,298 Sq Ft

  17 High St, West Stockbridge, MA 01236

  AFFORDABLE OPPORTUNITY TO BUILD EQUITY!This cozy fixer-upper is the perfect chance for a first time buyer to create a home of their own. With solid bones, a welcoming front porch, and a detached garage ideal for work shop or extra storage. Located in a convenient setting, it's ready for your vision. A little work could mean a big reward.Housatonic Village a few steps away. Being sold ''as-is''.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  17 High St, West Stockbridge, MA 01236
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  /33

  $779,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  165 Maple Ave, Great Barrington, MA 01230

  Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless

  Tony Segalla LANCE VERMEULEN RE, INC

  165 Maple Ave, Great Barrington, MA 01230
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  /33

  $779,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  165 Maple Ave Unit D, Great Barrington, MA 01230

  Experience the ease of downtown living in this immaculate Maple Grove condominium. Positioned just a short walk from Main Street, this residence offers immediate access to local shops, restaurants, and town amenities. The main level centers on a modern, open floor plan defined by beautiful wood floors and abundant natural light. An open kitchen anchors the living space, allowing for seamless

  Tony Segalla LANCE VERMEULEN RE, INC

  165 Maple Ave Unit D, Great Barrington, MA 01230
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  /21

  $439,000

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  115 Bridge St, Great Barrington, MA 01230

  BRIDGERTOWN CXV A great opportunity to own or invest in a 2-unit In-town property. 3 bedroom first floor with 1 bath, 2nd Floor is a spacious and light 1 bedroom, 1 bath. Hardwood floors, Updated boiler system. Just a quick stroll across the bridge and your in town for all your shopping and entertainment. This is a great chance to own and live while bringing some income in to offset expenses.

  Mark Rosengren LANCE VERMEULEN RE, INC

  115 Bridge St, Great Barrington, MA 01230
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  /58

  $1,995,000

  • 6 Beds
  • 2.5 Baths
  • 4,138 Sq Ft

  32 Benton Ave, Great Barrington, MA 01230

  Spectacular 1896 Victorian on The Hill, completely and stylishly renovated in 2025! This six-bedroom beauty seamlessly blends original floors and grand woodwork with all-new, high-efficiency systems. Key 2025 updates include full insulation, exterior paint and two new upstairs luxury baths. 2024 brought fully ducted Air Source Heat Pumps (central AC/heating) and new windows. A 2023 heat pump

  Leslie Chesloff WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  32 Benton Ave, Great Barrington, MA 01230
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  /28

  $1,200,000

  • 5 Beds
  • 3 Baths
  • 3,328 Sq Ft

  3 Pleasant View Dr, Great Barrington, MA 01230

  Rare offering of over six acres ''On the Hill'', sprawling residence with first floor primary, large eat-in kitchen with cozy fireplace.. porch-privacy-garage..open acreage bordered by woods.. walking distance to Main Street, Skiing and Lake Mansfield nearby...Five bedrooms, three baths. Formal living room.Plenty of room for expansion.

  Martha Piper THE KINDERHOOK GROUP

  3 Pleasant View Dr, Great Barrington, MA 01230
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  /43

  $595,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  6 Blue Hill Rd, Great Barrington, MA 01230

  Set on a deep, level one-acre lot, this colonial offers a nice balance of space, privacy, and neighborhood convenience. The front entry opens to an inviting staircase that leads upstairs to three bedrooms and a shared full bath. The main level includes a comfortable living room with a fireplace and back door opening to a covered porch overlooking the fenced backyard and in-ground pool.A bright

  Paige Paluch LANCE VERMEULEN RE, INC

  6 Blue Hill Rd, Great Barrington, MA 01230
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  /4

  $499,900

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

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

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

  David Carlson FAIRGROUND REAL ESTATE, INC

  41 Pearl St Unit 1-2, Great Barrington, MA 01230
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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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  /40

  $729,000

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  81 Castle Hill Ave, Great Barrington, MA 01230

  With its excellent curb appeal, charm and location, this property delivers! The inviting exterior exudes timeless appeal, while the sun-drenched three season porch provides an ideal space to relax and enjoy the southeastern mountain views.. Inside, warm and flexible living spaces, a cozy fireplace, a bright & sunny dining nook with skylight, and other rooms that easily adapt to your lifestyle

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  81 Castle Hill Ave, Great Barrington, MA 01230
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  /34

  $434,900

  • 2 Beds
  • 1 Bath
  • 1,182 Sq Ft

  245 Long Pond Rd, Great Barrington, MA 01230

  Tucked away on a quiet country road just minutes from downtown Great Barrington, this charming single-level ranch offers the perfect Berkshire retreat. Set on two private acres, the home is surrounded by mature trees and natural beauty- with nearby access to trails. Step inside to a bright interior featuring a spacious living room anchored by a beautiful stone fireplace. The kitchen offers crisp

  Jessica Rizzo LAMACCHIA REALTY, INC

  245 Long Pond Rd, Great Barrington, MA 01230
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  /32

  $1,475,000

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

  6 Thrushwood Ln, Great Barrington, MA 01230

  MOTIVATED SELLER; WILLING TO NEGOTIATE ON UPGRADES AND IMPROVEMENTS. Indulge in refined Berkshire living on an exclusive cul-de-sac, where effortless HOA services complement this exquisite new construction. Offering 4,200 sq ft of thoughtfully designed, environmentally conscious living less than a mile from downtown Great Barrington, this home is the perfect modern retreat. Enter through a

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  6 Thrushwood Ln, Great Barrington, MA 01230
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  /16

  $725,000

  • 3 Beds
  • 3.5 Baths
  • 2,560 Sq Ft

  78 State Rd, Great Barrington, MA 01230

  Investment Opportunity - 4-Unit Mixed-Use Property in Downtown Great Barrington, MAPrime downtown Great Barrington location! This well-maintained 4-unit mixed-use property includes three 1-bedroom apartments and one street-level commercial space offering excellent visibility and steady foot traffic.Two of the residential units are currently occupied by long-term tenants with strong payment

  Timothy Dunn VENTURE REAL ESTATE, INC

  78 State Rd, Great Barrington, 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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  /43

  $1,390,000

  • 5 Beds
  • 4.5 Baths
  • 2,900 Sq Ft

  228 East St, Great Barrington, MA 01230

  Great Barrington A masterful rebuild with reverence for Great Barrington's past and a bold reimagining for modern living. This 5-bedroom, 4-1/2 bath colonial sits in-town and blends historic charm with contemporary luxury for effortless, years-long comfort.Property Highlights5 Bedrooms | 4 Full Baths + 1 Half Bath**Complex rebuild from the ground up** - preserved nod to the town's heritage with a

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  228 East St, Great Barrington, MA 01230
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  /55

  $3,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,088 Sq Ft

  110 Alford Rd, Great Barrington, MA 01230

  Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure.Inside,

  Karen Climo WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  110 Alford Rd, Great Barrington, MA 01230
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  /70

  $875,000

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

  211 Cottage St, Housatonic, MA 01236

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

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  211 Cottage St, Housatonic, MA 01236
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  /26

  $425,000

  • 2 Beds
  • 1.5 Baths
  • 1,860 Sq Ft

  264 Main St Unit B, Great Barrington, MA 01230

  Imagine waking up in a sun-splashed home just steps from Great Barrington's lively Main Street--where every cafe, bookstore, and gallery feels like an extension of your neighborhood. This second-floor floor-through condo is more than a home; it's a canvas for your life.Over 1,800 sq. ft. of expansive living space unfolds with towering ceilings, oversized windows, and graceful arched doorways that

  Maggie Merelle WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  264 Main St Unit B, Great Barrington, MA 01230
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  /19

  $525,000

  • 4 Beds
  • 3.5 Baths
  • 2,184 Sq Ft

  5 Seekonk Rd, Great Barrington, MA 01230

  This is a spacious house with generously sized rooms 5 minutes from town. 4 bedrooms with 1 full bath, 2 3/4 baths and one powder room. First floor has kitchen, living room, dining room, pantry, laundry and a generous master suite with sitting area, office space and full bath. Second floor has 3 bedrooms, one with ensuite 3/4 bath. Lots of closets and plenty of storage space with basement storage

  Jason Saphire www.HomeZu.com

  5 Seekonk Rd, Great Barrington, MA 01230
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  /8

  $465,000

  • 3 Beds
  • 3 Baths
  • 2,480 Sq Ft

  497 S Main St, Great Barrington, MA 01230

  Multi-family in a convenient location, walking distance to town and shopping, bus line nearby.Well maintained. The perfect location, walking distance to restaurants and shopping, public transportation nearby.

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  497 S Main St, 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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  /37

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  6 Locust St, Great Barrington, MA 01230

  Tucked away in a walkable east-side neighborhood of Great Barrington, this custom 3-bedroom bungalow is anything but ordinary. From the moment you step inside, the care and creativity in every corner are impossible to miss--handcrafted woodwork, thoughtful built-ins, and artful finishes infuse the home with a personality all of its own.The inviting and cozy open floor plan make everyday living

  Paige Paluch LANCE VERMEULEN RE, INC

  6 Locust St, Great Barrington, MA 01230
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  /6

  $500,000

  • Land
  • 0.66 Acre
  • $757,565 per Acre

  185 A State Rd, Great Barrington, MA 01230

  A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

  Tony Segalla LANCE VERMEULEN RE, INC

  185 A State Rd, Great Barrington, MA 01230
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  /6

  $1,000,000

  • Land
  • 1.07 Acres
  • $934,583 per Acre

  185 State Rd, Great Barrington, MA 01230

  A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include two oversized curb cuts for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

  Tony Segalla LANCE VERMEULEN RE, INC

  185 State Rd, Great Barrington, MA 01230
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  /6

  $500,000

  • Land
  • 0.41 Acre
  • $1,219,485 per Acre

  185 B State Rd, Great Barrington, MA 01230

  A premier commercial development opportunity awaits at 185 State Road. Positioned directly on the bustling Route 7, this property guarantees maximum brand exposure with a daily traffic count exceeding 16,000 vehicles. Superior site logistics include an oversized curb cut for easy ingress and egress, along with ample space for on-site parking. This versatile property is engineered for success,

  Tony Segalla LANCE VERMEULEN RE, INC

  185 B State Rd, Great Barrington, MA 01230
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  /41

  $889,000

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

  11 Prospect St, Great Barrington, MA 01230

  Situated on Great Barrington's highly sought after neighborhood of 'The Hill', 11 Prospect delivers on style, convenience and of course, location! This four bedroom home with two and a half baths over three floors and hardwood floors throughout, offers lots of room for family and friends. An oversized screened in porch, attached two car garage and a finished basement are just some of the 'must

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  11 Prospect St, Great Barrington, MA 01230
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  /37

  $455,000

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft

  35 Mechanic St, Great Barrington, MA 01230

  Live in the center of Great Barrington with a private backyard of almost 3 acres on the river! This renovated farmhouse has an inviting kitchen with cozy wood stove, first floor primary suite and 2 spacious bedrooms with a shared bath on second floor. Beautiful wide-plank floors and built-ins preserve this home's history. A solar rooftop system, fully owned, brings energy efficiency and

  Christine Martin COMPASS MASSACHUSETTS , LLC GB

  35 Mechanic St, Great Barrington, MA 01230
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  /11

  $425,000

  • 1,152 Sq Ft

  11 Rowe Rd, Great Barrington, MA 01230

  FULL BUILDING PLANS INCLUDED! Privacy and big potential! Build your Berkshire dream home in the quiet Alford hills on this 2 acre parcel surrounded by trees. Foundation for a new home is already constructed with architectural plans included as an added bonus. The property includes a new septic system and well, plus 1 outbuilding and additional barn at the back of the lot.

  John Segalla HOUSATONIC REAL ESTATE

  11 Rowe Rd, Great Barrington, MA 01230
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  /43

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  2 Lake Ave, Great Barrington, MA 01230

  WONDERFUL CONTEMPORARY HOME '' ON THE HILL'' IN GB. CONSIDERED ONE OF GB'S MOST DESIRED AREAS. ENJOY THE CONVENIENCE OF BEING CENTRALLY LOCATED TO SHOPPING, RESTAURANTS, AND ENTERTAINMENT ARE JUST WALKING DISTANCE TO ONE OF NEW ENGLAND'S BEST DOWNTOWN AREAS.THIS OPEN CONCEPTED HOME OFFERS GREAT NATURAL LIGHT AND THE ABILITY AND OPPORTUNITY TO COMMUNE AND ENTERTAIN.THREE BEDROOMS- MAIN BEDROOM

  David Carlson FAIRGROUND REAL ESTATE, INC

  2 Lake Ave, Great Barrington, MA 01230
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  /23

  $125,000

  • Land
  • 0.49 Acre
  • $255,107 per Acre

  28 Pearl St, Great Barrington, MA 01230

  Nestled on a quiet dead-end street, this .49-acre parcel offers a unique combination of privacy, scenic beauty, and walk-to-town convenience. The property has been thoughtfully divided to meet local zoning requirements within the defined build envelope as shown (see documents for survey & building envelope). A 200-foot riparian buffer protects the riverfront, ensuring that no structures can ever

  

  Dan Alden

  ALDEN COUNTRY REAL ESTATE SERVICES

  (413) 408-5316

  28 Pearl St, Great Barrington, MA 01230
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  /38

  $695,000

  • 3 Beds
  • 3 Baths
  • 1,991 Sq Ft

  483 Home Rd, Great Barrington, MA 01230

  A Berkshire dream home! Nestled in a quiet private setting to enjoy the outdoors. This 3 bedroom 3 full bath home is empty and ready to go. Great lighting nice open kitchen dining/living area. Additional room can be used as a den or 1st floor bedroom. Wood stove insert for chilly fall nights while enjoying your 3 seasoned screened porch. Oversized 2 car garage. Full basement could be completed as

  Suzann Ward HOUSATONIC REAL ESTATE

  483 Home Rd, Great Barrington, MA 01230
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  /53

  $935,000

  • 4 Beds
  • 2.5 Baths
  • 2,631 Sq Ft

  20 Cooper Rd, Great Barrington, MA 01230

  This is the one you've been waiting for. A classic mid-century home on over 4 private acres, offering the ultimate Berkshire lifestyle. The bright, open-mid century floor plan provides a seamless flow, while two fireplaces add classic comfort. The home features 4 bedrooms, 3 baths, large office and a media room, offering flexibility for family and guests. Outside, your private resort awaits. A

  Tony Segalla LANCE VERMEULEN RE, INC

  20 Cooper Rd, Great Barrington, MA 01230
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  /38

  $796,000

  • 2 Beds
  • 2 Baths
  • 1,622 Sq Ft

  324 Park St, Great Barrington, MA 01230

  Architectural gem with lots of glass perched like a treehouse on the backside of Monument Mountain. The open, mid-century modern home was built in 2012 for maximum light, efficiency, and provides glittering views through the trees of the Housatonic River! 2 bedroom, 2 full baths-both ensuite + central AC, and a Scandinavian soapstone wood stove, permit included! Minutes from hiking trails, Taft

  Claudia Laslie LANCE VERMEULEN RE, INC

  324 Park St, Great Barrington, MA 01230
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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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  /69

  $2,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,445 Sq Ft

  50 Old Village Rd, Great Barrington, MA 01230

  Nestled beside 900 acres of Alford Springs Nature Preserve, this contemporary colonial is sited on 5.8 acres. Built in 2005 and fully renovated in 2021, it boasts high-efficiency HVAC and hot water, 14GW of seller-owned solar, an open main floor plan, gorgeous kitchen with top-of-the-line appliances, front porch, screened porch, large 2-car garage, and generously-sized rooms throughout. Two

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  50 Old Village Rd, Great Barrington, MA 01230
• 

  

  /40

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  212 Highland St, Housatonic, MA 01236

  Indulge in the picturesque ''ski season'' at this charming New England farmhouse. Immerse yourself in a comfortable space with a ski boot/mudroom entryway and a cozy wood stove for post-ski relaxation. Situated on a corner lot, this 3 bed/2 bath offers a rocking chair-front porch, private rear courtyard, 1 car garage. 1st floor features a spacious living room with wood floors, a primary bedroom,

  Patricia Andrew STONE HOUSE PROPERTIES, LLC

  212 Highland St, Housatonic, MA 01236

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