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Homes for Sale near Berkshire School

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  • /71

    $5,650,000

    $250K PRICE DROP
    • 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

    Lauren Molk ELYSE HARNEY REAL ESTATE

    25 W Sheffield Rd, Great Barrington, MA 01230
  • /86

    $1,950,000

    $2M PRICE INCREASE
    • 5 Beds
    • 4.5 Baths
    • 4,842 Sq Ft

    173 Hillsdale Rd, Egremont, MA 01230

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

    Robert Cohen eXp REALTY

    173 Hillsdale Rd, Egremont, MA 01230
  • /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
  • /52

    $1,085,000

    $210K PRICE DROP
    • 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
  • /39

    $1,395,000

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

    3 Townhouse Hill Rd, Great Barrington, MA 01230

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

    Paige Backhaus WILLIAM RAVEIS - BERKSHIRE

    3 Townhouse Hill Rd, Great Barrington, MA 01230
  • /60

    $1,250,000

    $100K PRICE DROP
    • 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
  • /40

    $970,000

    • 5 Beds
    • 4.5 Baths
    • 3,024 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 WILLIAM RAVEIS - BERKSHIRE

    60 Parsley Ln, Sheffield, MA 01257
  • /44

    $1,595,000

    • 4 Beds
    • 5 Baths
    • 3,933 Sq Ft

    6 Bay Ln, Sheffield, MA 01257

    Views, privacy, and frontage on Mill Pond. This custom built classic Gilligan house is the perfect home for hosting family and friends with plenty of space both inside, and out. There are 4 plus bedrooms and 5 baths, including a generous primary suite on the first floor, a large den, and a bonus room above the 2 car garage. The property includes a fenced, in- ground pool, extensive flat lawn,

    Robin Ban COMPASS MASSACHUSETTS , LLC GB

    6 Bay Ln, Sheffield, MA 01257
  • /29

    $1,024,000

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

    97 Brush Hill Rd, Great Barrington, MA 01230

    On 2.65 private acres in the Berkshires this fully renovated 4-BR 3-bath home offers a rare combination of modern luxury w/ direct access to nature. $650K + in renovations have transformed the property into a turnkey retreat for full-time living or a seasonal escape. The outdoor space features private hiking trails, a wraparound deck, upper balcony, a large upper patio & a newly resurfaced

    David White OwnerEntry.com

    97 Brush Hill Rd, Great Barrington, MA 01230
  • /69

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    249 Boardman St, Sheffield, MA 01257

    Dreamy river Colonial: tucked away on 4 beautiful acres, 1361 feet of river frontage, offering privacy and a quiet sanctuary for wildlife viewing. Main floor features an updated classic chef's kitchen that flows into a spacious Great Room w/ wood-burning fireplace, dining area, 1/2 bath, and direct access to the sun deck with sparkling river and dramatic sunset views. A breezeway connecting the

    Claudia Laslie WILLIAM RAVEIS - BERKSHIRE

    249 Boardman St, Sheffield, MA 01257
  • /26

    $965,000

    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    188 Hillsdale Rd, Egremont, MA 01230

    GORGEOUS LOW MAINTENANCE HOME IN LOW TAX EGREMONT. A move-in ready opportunity, just minutes to the NY & CT borders AND Great Barrington. This home is ready for occupancy or ideal for income producing property. Wonderful chef's kitchen with open plan Living/Dining. The upper level hosts a grand primary en- suite, with a dedicated office space and seating area, AND its own screened porch. Two

    Helen Mullany HELEN MULLANY REAL ESTATE, LLC

    188 Hillsdale Rd, Egremont, MA 01230
  • /55

    $1,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,047 Sq Ft

    3 Cornwall Dr, Great Barrington, MA 01230

    Tucked away at the end of an exclusive cul-de-sac, this luminous 4-bedroom home offers access to one of the Berkshires' most beautiful private communities. The interior is defined by an impressive great room, where soaring cathedral ceilings and a wood-burning brick fireplace create an inviting, open-air feel. At the heart of the home, the granite-clad kitchen serves as a bright culinary hub,

    Tony Segalla WILLIAM RAVEIS - BERKSHIRE

    3 Cornwall Dr, Great Barrington, MA 01230
  • /24

    $250,000

    $120K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,683 Sq Ft

    175 Main St, Sheffield, MA 01257

    Come this charming 1820 colonial located in Downtown Sheffield! This unique property features 6 bedrooms and 5 and half bathrooms. Lovely hardwood showcasing wide plank and parquet style floors encompass 3,683 square feet of living space. Plenty of off street parking due to the oversized driveway and 2 car attached garage with loft space. Full, unfinished basement can provide additional storage

    Nicholas Decaro Property Works New England

    175 Main St, Sheffield, MA 01257
  • /55

    $649,000

    • 5 Beds
    • 2.5 Baths
    • 2,750 Sq Ft

    168 Main St, Sheffield, MA 01257

    Historic village living at its finest. This expansive Turn-of-the-Century Sheffield home is rich with original detail, from its warm wood floors to a magnificent fieldstone fireplace. The property boasts a large, private yard, offering ample space for gardening, recreation, or outdoor entertainment. A substantial barn on the property provides excellent potential for a workshop, studio, or extra

    Tony Segalla WILLIAM RAVEIS - BERKSHIRE

    168 Main St, Sheffield, MA 01257
  • /47

    $779,500

    $71K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,330 Sq Ft

    138 Hillsdale Rd, Great Barrington, MA 01230

    Move-in-ready Colonial offering 3 bedrooms and 2.5 baths on a sunny, picturesque lot flanked by a beautiful stone wall, it is just seconds from the charming downtown. The main level features a living room with a striking fieldstone fireplace, formal dining room, kitchen, a spacious family room addition, an office and a full bath with a lovely soaking tub, and a powder room. The second level has

    Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    138 Hillsdale Rd, Great Barrington, MA 01230
  • /31

    $479,000

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

    107 S Main St, Sheffield, MA 01257

    The Hatfield House -- a rare 1793 Sheffield antique offering a unique renovated live/work opportunity, move-in ready; the main residence blends historic character with modern systems; including a new sealed basement. A separate one-bedroom apartment with its own entrance provides income or guest flexibility.Set on 1.5 acres with protected wetland views, commercial/residential zoning allows for

    Judi Panzano HOUSATONIC REAL ESTATE

    107 S Main St, Sheffield, MA 01257
  • /43

    $2,995,000

    • 3 Beds
    • 2 Baths
    • 2,716 Sq Ft

    25 Baldwin Hill Rd, Egremont, MA 01230

    Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front

    Gladys Montgomery WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    25 Baldwin Hill Rd, Egremont, MA 01230
  • /88

    $3,550,000

    • 6 Beds
    • 7 Baths
    • 9,254 Sq Ft

    Unlisted Address

    The thoughtfully renovated and expanded 1940s Main House is full of exceptional spaces--elegant formal dining and living rooms in front, informal sitting area and spacious eat-in kitchen at the back, stunning central stairwell, cozy den/bar, and media room. Five comfortable bedrooms, including two luxurious primary suites. Every material, sightline, and design element has been curated with care

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    Unlisted Address
  • /39

    $885,000

    • 2 Beds
    • 3 Baths
    • 1,753 Sq Ft

    856 Barnum St, Sheffield, MA 01257

    Modernist retreat in a pastoral Berkshire setting; an artful sanctuary where design, landscape, and light exist in quiet harmony. Designed by acclaimed architect Debra K. Reiser, this light-filled two-bedroom, three-bath home blends refined urban modernism with the stillness of the countryside. Set along a quiet dirt road beside Moon In The Pond Farm, (an eco-conscious farm) a landscape of

    Lauren Molk ELYSE HARNEY REAL ESTATE

    856 Barnum St, Sheffield, MA 01257
  • /14

    $119,000

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

    2 Terra Ferma Dr, Egremont, MA 01230

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

    Tony Segalla WILLIAM RAVEIS - BERKSHIRE

    2 Terra Ferma Dr, Egremont, MA 01230
  • /62

    $2,495,000

    • 5 Beds
    • 3.5 Baths
    • 6,254 Sq Ft

    84B N Undermountain Rd, Egremont, MA 01230

    Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    84B N Undermountain Rd, Egremont, MA 01230
  • /44

    $789,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,008 Sq Ft

    1 Cornwall Dr, Great Barrington, MA 01230

    Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot w/ almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many

    Stephen Schoenfeld WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    1 Cornwall Dr, Great Barrington, MA 01230
  • /10

    $329,000

    • Land
    • 8.69 Acres
    • $37,860 per Acre

    10 Mountain Rd, Mount Washington, MA 01258

    RARE OPPORTUNITY. Private parcel with open views potential, atarting from the idyllic cul-de-sac, on Mountain Rd. in Mt. Washington, MA. This exclusive, private land parcel has 8.69 level and gently rolling acres.: Septic Field has been partially installed, Well has been drilled , and rough driveway installed. Fiber Optic is available. The plans for 4BR+4BA house with an in-law suite have been

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    10 Mountain Rd, Mount Washington, MA 01258
  • /2

    $2,400,000

    • Land
    • 38.2 Acres
    • $62,827 per Acre

    3 Jenssen Rd, Egremont, MA 01230

    3 lots available to develop in EgremontParcels, 008.0-0000-0123.0, 008.0-0000-0283.0, 008.0-0000-0048.0

    Jeremy Casey SR Commercial Realty

    3 Jenssen Rd, Egremont, MA 01230
  • /4

    $425,000

    • Land
    • 17.93 Acres
    • $23,701 per Acre

    99 Creamery Rd, Egremont, MA 01230

    NORTH EGREMONT - Almost 18 elevated acres with sweeping views of the Berkshire Hills that has been surveyed, flagged with enough road frontage to subdivide once. An open meadow with woodlands as a backdrop make this parcel most desirable....a must see!

    Cortney Dupont COHEN & WHITE ASSOCIATES

    99 Creamery Rd, Egremont, MA 01230
  • /25

    $459,000

    • 3 Beds
    • 2 Baths
    • 2,258 Sq Ft

    689 N Main St, Sheffield, MA 01257

    OPEN HOUSE: Friday, May 22nd 2:00pm-3:30pmCompletely renovated and exceptionally versatile, this spacious 3-bedroom ranch is located in desirable Sheffield, MA. Set on a .50-acre commercially zoned lot just a 5 minute drive to downtown Great Barrington, the property offers outstanding live/work, investment, or business potential.The 2,258 sq. ft. main residence features 3 spacious bedrooms, a

    Judi Panzano HOUSATONIC REAL ESTATE

    689 N Main St, Sheffield, MA 01257
  • /6

    $265,000

    $30K PRICE DROP
    • Land
    • 1.97 Acres
    • $134,518 per Acre

    14 McGee Rd, Egremont, MA 01230

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

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    14 McGee Rd, Egremont, MA 01230
  • /43

    $429,000

    $46K PRICE DROP
    • 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
  • /39

    $525,000

    • 1 Bed
    • 1.5 Baths
    • 965 Sq Ft

    261 East St, South Egremont, MA 01258

    Tucked deep in the quiet beauty of Mount Washington, this enchanting cabin is owner-designed & built on approx. 10 private acres with over 600 feet of frontage on Wright Brook & surrounded by State Forest & conservancy lands. Charming open main floor with living room, kitchen, 3/4 bath & laundry lead to a cozy second-floor BR with 1/2 bath that feels like a treetop retreat. Custom-made cherry &

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    261 East St, South Egremont, MA 01258
  • /33

    $775,000

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

    86 Main St, Sheffield, MA 01257

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

    David Taylor ELYSE HARNEY REAL ESTATE

    86 Main St, Sheffield, MA 01257
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