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Homes for Sale near Undermountain Elementary School

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  • /6

    $325,000

    • Land
    • 21.7 Acres
    • $14,977 per Acre

    0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230

    21.7 wooded acres on one of South County's ''best-kept-secret'' back country roads, yet just minutes away from Great Barrington, Sheffield and the bucolic villages of New Marlborough. Discover nature, privacy & a unique sense of peace on this rare piece of land. The land has been perc tested, seller will provide final survey prior to closing. Map in documents shows proposed new boundaries for

    Agent Photo

    Dan Alden

    ALDEN COUNTRY REAL ESTATE SERVICES

    (413) 848-6618

    0 Sisson Hill Rd Unit 248042, New Marlborough, MA 01230
  • /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
  • /66

    $1,950,000

    • 5 Beds
    • 4 Baths
    • 3,404 Sq Ft

    415 Brewer Branch Rd, New Marlborough, MA 01259

    Set on 21.5 acres at the end of a long, winding private drive, this extraordinary residence is a true architectural gem--where art, landscape, and modern living converge. Originally designed by Robert McMahon and built by Lou Boxer and later reimagined through a contemporary project by Deborah Reiser of the award-winning RUR Architecture with Hird Design and Construction as the builder, the home

    Sheila Thunfors STONE HOUSE PROPERTIES, LLC

    415 Brewer Branch Rd, New Marlborough, MA 01259
  • /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
  • /36

    $1,475,000

    • 1 Bed
    • 2 Baths
    • 1,296 Sq Ft

    481 Shunpike Rd, Sheffield, MA 01257

    A total 41 acres includes a 2nd building lot of 26 acres allowing one to build ones own home with mountain views. A 36x52 work shop. One full time residence and a separate summer studio. Some land does go into New Marlborough. Surrounded by conservation land. Passive solar views facing South and West. Property has been a sculpture park for many years. Trails throughout. Views to Connecticut.

    Suzann Ward HOUSATONIC REAL ESTATE

    481 Shunpike Rd, Sheffield, MA 01257
  • /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

    Open Sun 1PM - 3PM
    • 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
  • /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

    Open Sat 11AM - 1PM
    • 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
  • /63

    $2,150,000

    • 4 Beds
    • 3 Baths
    • 3,461 Sq Ft

    304 Hickey Hill Rd, Sheffield, MA 01257

    This historic farmhouse, originally built in the 1790s, underwent a complete renovation in 2012, including a new foundation, septic system, roof, updated plumbing and electrical, 5-zone heating, central air, and other modern systems. In 2022, a new well and a boiler for radiant heat were also added.Step inside to find timeless Colonial charm--exposed beams, three original fireplaces, and gorgeous

    Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

    304 Hickey Hill Rd, Sheffield, MA 01257
  • /52

    $1,900,000

    • 4 Beds
    • 3 Baths
    • 2,976 Sq Ft

    1269 Clayton Mill River Rd, New Marlborough, MA 01259

    Welcome to your ultimate country retreat, where the charm of history meets the ease of modern living. Here, timeless beauty and serenity reign--an escape where silence is broken only by the wind in the fields and the song of birds.The 1828 brick colonial, a masterpiece of its era, has been exquisitely restored to showcase spacious, light-filled rooms that draw the outdoors in, framing views of

    Lisa Hoe THE KINDERHOOK GROUP

    1269 Clayton Mill River Rd, New Marlborough, MA 01259
  • /28

    $429,000

    • 2 Beds
    • 1 Bath
    • 520 Sq Ft

    529 Hayes Hill Rd, New Marlboro, MA 01230

    'Cosmo Cabin', a unique find in the Berkshires, is the perfect space for a quick getaway for easy, calm and uncomplicated living. Coming fully furnished, the home was tastefully renovated in the past three years from the ground up with modern finishes and thoughtful design. With intimate living spaces, the home has two bedrooms with a full bathroom any mansion would be envious of. A large

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    529 Hayes Hill Rd, New Marlboro, MA 01230
  • /42

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,725 Sq Ft

    1874 Home Rd, Great Barrington, MA 01230

    Tucked away in a peaceful Berkshire setting, this 3-bedroom, 2-bath home offers a blend of comfort, nature, and everyday convenience just minutes from downtown Great Barrington. Imagine mornings filled with natural light streaming through skylights as vaulted ceilings open the living, kitchen, and dining areas into a bright, airy gathering space designed for connection and ease.The home features

    Gabriela Dearstyne KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    1874 Home Rd, 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
  • /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
  • /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
  • /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
  • /31

    $149,000

    • 2 Beds
    • 1 Bath
    • 1,320 Sq Ft

    243 Alum Hill Rd, Sheffield, MA 01257

    Affordable opportunity in the heart of the Berkshires! Welcome to 243 Alum Hill Rd, Sheffield, MA — a double-wide mobile home offering comfortable single-level living at an attractive price point of $149,000. This property features a spacious layout with ample natural light, functional living spaces, and plenty of potential to make it your own. Enjoy the added convenience of a detached garage,

    Axel Correia Century 21 Limitless

    243 Alum Hill Rd, Sheffield, MA 01257
  • /31

    $695,000

    • 3 Beds
    • 6 Baths
    • 4,044 Sq Ft

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222

    Old Historic Village downtown location! The centrally located Post Office building constructed in 1860, presents a unique opportunity for both residential and commercial use. Its strategic location ensures consistent foot traffic, making it an invaluable cornerstone of village life. With no mail delivery service in Ashley Falls, the Post Office attracts local residents daily. This building is

    Lance Vermeulen WILLIAM RAVEIS - BERKSHIRE

    1180 Ashley Falls Rd Unit A,B,C,D,E, Sheffield, MA 01222
  • /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
  • /75

    $3,250,000

    • 6 Beds
    • 5.5 Baths
    • 3,416 Sq Ft

    651 Hayes Hill Rd, New Marlborough, MA 01230

    Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views to the northern Connecticut hills. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape

    Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

    651 Hayes Hill Rd, New Marlborough, 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
  • /57

    $875,000

    $24K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,748 Sq Ft

    594 Shunpike Rd, Sheffield, MA 01257

    Experience refined country living in this completely reimagined masterpiece by Wingate Ltd. Spanning 3 floors of gracious living space, 594 Shunpike offers architectural drama and modern efficiency on a truly scenic Berkshire corridor. Inside, a sculptural staircase leads to a sun-drenched open living area with white oak floors and a gas fireplace. This open plan flows into the chef's kitchen

    John Burns WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    594 Shunpike 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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