426

Berkshire County MA Homes for Sale with Acreage

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  • /21

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    197 Clubhouse Dr, Otis, MA 01253

    The dream of your Berkshire country getaway can become a reality and enhanced by the amenities of the Otis Woodlands. Whether it's just enjoying this country home by sitting around the fire pit or use of the tennis courts,pool,lake, or exercise room. A simple hike in the nature of the Berkshires is also right out your door.

    David St. Laurent BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS OTIS

    197 Clubhouse Dr, Otis, MA 01253
  • /41

    $580,000

    • 3 Beds
    • 2 Baths
    • 2,106 Sq Ft

    117 Strykers Rd, Florida, MA 01247

    Two homes! 11+ acres! 3 Parcels! Have you always dreamed of living a sustainable, homesteading life with your family and extended family? This property makes generational living possible! The “cabin” is 2,106 sq ft with updated bathrooms, mainfloor laundry, 2 fireplaces with wood and pellet stove inserts, primary bedroom with large cedar lined walk in closet. Impressive P&B exposed wood

    Grace Golden Equine Homes Real Estate, LLC

    117 Strykers Rd, Florida, MA 01247
  • /4

    $990,000

    • Land
    • 100 Acres
    • $9,900 per Acre

    312 County Rd, New Marlborough, MA 01230

    Imagine building your private estate on this expansive acreage nestled in the beautiful hills of New Marlborough. This remarkable property features hidden meadows and secluded clearings-perfect settings to build the home of your dreams. Rich in natural beauty, the land was placed under conservation a few years age to preserve its timeless serenity and ensure lasting peace and privacy. Don't miss

    Timothy Harrigan BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    312 County Rd, New Marlborough, MA 01230
  • /3

    $325,000

    • Land
    • 15 Acres
    • $22,049 per Acre

    0 E Alford Rd, West Stockbridge, MA 01266

    Beautiful and pristine 14.7 acre lot, family owned since 1963. 3-4 acres are an open field; a former Christmas tree farm. Rear portion of property is largely wooded with a stream. This area of East Alford Road has many million dollar plus homes. Perfect lot to build your tranquil dream home. Lot was perc tested in 2007. 10 Minutes to the center of West Stockbridge, 15 minutes to Great

    Matt DeLucia William Pitt Sotheby's International Realty

    0 E Alford Rd, West Stockbridge, MA 01266
  • /69

    $1,195,000

    • 4 Beds
    • 3 Baths
    • 3,541 Sq Ft

    1828 Flintstone Rd, Windsor, MA 01270

    Welcome to Stone Hill - Your Private Oasis with Spectacular Views overlooking the Berkshire Hill Towns. Escape to a world of tranquility and luxury where nature's beauty meets exquisite living. Nestled on a 9.45 acre property, this spectacular estate offers the ultimate retreat for those seeking privacy and serenity. Immerse yourself in the beauty of the Chalet Wildlife Management Area

    Matt Carlino MACCARO REAL ESTATE

    1828 Flintstone Rd, Windsor, MA 01270
  • /52

    $1,295,000

    • 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
  • /30

    $537,000

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    40 Ryan Rd, Washington, MA 01223

    Contemporary cape with an open, single floor design combines charm and practicality on two private acres. The walk out lower level features an expansive family room with two additional bonus rooms. Heated garage, central vac, Vt Castings wood stove, underground propane, whole house generator and a screened porch to observe the private, landscaped lawn and gardens. This beautifully designed, well

    Henry Hagenah OCTOBER MOUNTAIN REAL ESTATE

    40 Ryan Rd, Washington, MA 01223
  • /59

    $1,500,000

    • 5 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    194 Sandisfield Rd, Sandisfield, MA 01255

    A master stoneworker and his family spent a year walking 11 acres to find the one perfect spot. Then they built their dream around it - every fieldstone placed by hand from rocks cleared by 150 years of farming, hand-hewn cherry beams harvested from the land soaring above the stone-clad Great room. This rustic modern farmhouse embodies the truth that in simplicity lives beauty. The timber-framed

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    194 Sandisfield Rd, Sandisfield, MA 01255
  • /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
  • /19

    $749,500

    • 4 Beds
    • 2 Baths
    • 2,468 Sq Ft

    484 Rossiter Rd, Richmond, MA 01254

    Nestled in the Berkshires at the end of a quiet one-mile gravel road, this charming 1805 country home blends historic character with modern comfort. Featuring four spacious bedrooms, two full baths, and stained oak flooring in nearly every room, the home offers inviting living and dining spaces filled with natural light and serene views. The well-equipped kitchen opens to a cozy entryway with

    Cindy Welch LANDVEST, INC.

    484 Rossiter Rd, Richmond, MA 01254
  • /11

    $99,500

    • Land
    • 1.22 Acres
    • $81,558 per Acre

    58 Stanley Rd, Otis, MA 01253

    THE PERFECT COMBINATION OF VIEWS + PRIVACY + DEEDED WATERFRONT ACCESS ON A MOTORBOAT LAKE A SHORT DISTANCE AWAY THE BEST OF ALL WORLDS The building parcel offers distant Southwestern Views and a large level elevated site to build on. Perc test has been completed and the building site has been partially cleared. Both beautiful distant views and deeded access to Big Pond a relatively short

    Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    58 Stanley Rd, Otis, MA 01253
  • /9

    $89,000

    • Land
    • 3.82 Acres
    • $23,298 per Acre

    62 Hadsell St, New Marlborough, MA 01230

    Wonderful opportunity to build your dream Berkshire home or getaway. This picturesque property is situated on just under 4 acres off a quiet paved country road. The winding Umpachenee River backs up to the land and it's modest building envelope. Quiet and serene country living yet not far from the bustling towns of Great Barrington and Sheffield. Quick access to the Mill River general store and

    Molly Thomas COMPASS MASSACHUSETTS , LLC GB

    62 Hadsell St, New Marlborough, MA 01230
  • /11

    $35,000

    • Land
    • 2.14 Acres
    • $16,378 per Acre

    Lot 4 Ore Bed Rd, Lanesborough, MA 01237

    Just over two acres of land located in a private setting. Located just a short distance to Jiminy Peak and Pontoosuc Lake. Zoned R-A with the town, the lot is wooded but includes some level areas for a potential building site.

    Cory Evangelisto NOCHER REALTY

    Lot 4 Ore Bed Rd, Lanesborough, MA 01237
  • /44

    $685,000

    • 3 Beds
    • 3 Baths
    • 2,395 Sq Ft

    649 Hewins St, Sheffield, MA 01257

    Located on a pastoral country road in Sheffield, this thoughtfully updated early 1900s farmhouse with carriage house sits on 1 open acre with sweeping views to the west of conservation land. The home blends original character withmodern touches--vaulted ceilings, exposed beams, hard wood floors, and high-end finishes throughout. In the main house a sunlit kitchen anchors the home featuring custom

    Lauren Molk ELYSE HARNEY REAL ESTATE

    649 Hewins St, Sheffield, MA 01257
  • /61

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,410 Sq Ft

    674 Benton Hill Rd, Becket, MA 01223

    Escape to this stunning four-bedroom contemporary retreat, nestled on 4.7 serene acres along a quiet country road. The open-concept living area boasts soaring cathedral ceilings, rich hardwood floors, and French doors that lead to an expansive upper deck. The sleek kitchen features stainless appliances, quartz countertops, and a bay window with picturesque views of the wooded backyard. The

    Melinda Boos KEMPF-VANDERBURGH REALTY CONSULTANTS, INC.

    674 Benton Hill Rd, Becket, MA 01223
  • /10

    $49,497

    • Land
    • 9 Acres
    • $5,506 per Acre

    00 Surriner Rd, Becket, MA 01223

    Here's your opportunity to own an amazing 8.99-acre property nestled in the heart of Becket, MA, located in scenic Berkshire County. Tucked off Surriner Rd, this wooded lot offers privacy, natural beauty, and endless potential. Zoned Residential with no HOA restrictions and electricity nearby, it’s a great foundation for future development or a private getaway. Buyers are responsible for

    Derek Greene The Greene Realty Group

    00 Surriner Rd, Becket, MA 01223
  • /23

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 2,464 Sq Ft

    73 Blunt Rd, Egremont, MA 01230

    Tucked away on a peaceful road in charming Egremont, this exceptional new construction offers a rare blend of modern design, luxury finishes, and practical comfort. With three spacious bedrooms and 1.5 beautifully appointed baths, this home sets itself apart from the ordinary with radiant in-floor heating, soaring ceilings, and high-end craftsmanship throughout.Set on a full acre framed by mature

    Ryan Lane GILCREST PROPERTIES

    73 Blunt Rd, Egremont, MA 01230
  • /66

    $499,900

    • 3 Beds
    • 2 Baths
    • 2,453 Sq Ft

    67 Gulf Rd, Lanesborough, MA 01237

    Discover the perfect blend of privacy, comfort, and country living at this 3-bedroom, 2-bathroom home surrounded by state woodland, this property offers the peace of a secluded retreat while still just minutes from local stores and amenities.The spacious farm-style kitchen and dining area boast sweeping mountain views, A dedicated office and large bonus room provide flexible living and working

    Robin Moore 413 REAL ESTATE

    67 Gulf Rd, Lanesborough, MA 01237
  • /24

    $325,000

    • 1 Bed
    • 1 Bath
    • 1,082 Sq Ft

    961 Peru Rd, Windsor, MA 01270

    Finish this super insulated house to your liking. Seller had to quit due to personal issues. High end kitchen cabinets are bought but not installed. Tub is installed. Sheet rock needs to be taped and spackled. Rough electric and plumbing are done. Super insulated tiny house for guests or separate home office has electricity but no plumbing. All work was permitted and inspected. Please see

    Carla Ness Delap Real Estate LLC

    961 Peru Rd, Windsor, MA 01270
  • /36

    $6,250,000

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

    53 Whites Hill Rd, Egremont, MA 01230

    Set against a backdrop of sweeping mountain views, this stunning modern residence offers an unparalleled combination of privacy, energy efficiency, and understated refinement. The award-winning home is designed to passive house standards and constructed with an emphasis on durability and sustainability. Natural light streams through high-performance triple-glazed windows and floor to ceiling

    Claudia Crane COMPASS MASSACHUSETTS , LLC GB

    53 Whites Hill Rd, Egremont, MA 01230
  • /2

    $155,000

    • Land
    • 5 Acres
    • $29,580 per Acre

    104 Hupi Rd, Monterey, MA 01245

    Ready to build a new custom home with all your personal touches! Views of Lake Garfield. Close to downtown Monterey. Fresh 5 acre parcel to construct a magnificent home in the Berkshires!

    Cristian Sanchez COHEN & WHITE ASSOCIATES

    104 Hupi Rd, Monterey, MA 01245
  • /5

    $500,000

    • Land
    • 8 Acres
    • $66,667 per Acre

    71 Miner Lots 2 and 3 Rd, Lanesborough, MA 01237

    An extraordinary opportunity awaits in the heart of the Berkshires. This is not just a parcel of land; it's a launchpad for your dreams. Offering a rare combination of privacy, turn-key potential, and lifestyle flexibility, this 7.5-acre property in Lanesborough is ready for you to create your own private compound or mini-farm.Nestled on a newly paved road just off Route 7, the property features

    Keyla Girard LAMACCHIA REALTY, INC

    71 Miner Lots 2 and 3 Rd, Lanesborough, MA 01237
  • /29

    $629,000

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft

    14 Miller View Rd, Egremont, MA 01230

    The private drive into this property says it all... Set well off a quiet cul-de-sac in a sought-after Egremont neighborhood on nearly 6 acres of lush, mature landscaping, this charming raised ranch offers the perfect blend of privacy and proximity. This beautifully maintained property is neat as a pin and move-in ready. With 3 bedrooms and 2 full baths, the main level features a light-filled open

    Dana Fuchs LANCE VERMEULEN RE, INC

    14 Miller View Rd, Egremont, MA 01230
  • /34

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 3,524 Sq Ft

    1 Old Tree Farm Rd, Stockbridge, MA 01262

    Impeccably Renovated Stockbridge Country Retreat. Minutes from Stockbridge, Lenox and Tanglewood, in the heart of the Berkshires cultural corridor, a rare opportunity in a perfect setting on 4.16 level, landscaped acres. Surrounded by mature trees and curated gardens, this home blends classic design with modern updates, offering refined style throughout. White oak floors, three full baths, a gas

    Suzann Ward Housatonic Real Estate

    1 Old Tree Farm Rd, Stockbridge, MA 01262
  • /8

    $49,000

    • Land
    • 7 Acres
    • $7,089 per Acre

    Lot 19-I W Center Rd, Otis, MA 01253

    Build your dream retreat surrounded by mature trees, stone walls, and privacy. With level topography and a prime location near Hayes Pond, this property offers the perfect site to lay down your Berkshire roots!

    Tony Segalla LANCE VERMEULEN RE, INC

    Lot 19-I W Center Rd, Otis, MA 01253
  • /46

    $625,000

    • 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
  • /29

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    308 Lenox Rd, Richmond, MA 01254

    Tucked away in the desirable, low-tax community of Richmond, Massachusetts, this 3-bedroom, 2-bathroom ranch, surrounded by higher-priced properties, offers comfortable single-floor living. The open-concept living area, filled with natural light, includes a recently updated kitchen and features quartz countertops, quality stainless appliances, and ample counter space. The master suite includes a

    William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    308 Lenox Rd, Richmond, MA 01254
  • /55

    $1,675,000

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    5 Glendale Rd, Stockbridge, MA 01262

    ''Best of Berkshire Living: Gardens, Grand Trees & Income-Ready Guest Cottage''Between the Rockwell Museum and Botanical Garden, minutes from Tanglewood, this nearly 4-acre Berkshire property offers two distinct homes surrounded by heirloom trees and landscaped gardens. The 4BR, 2BA main house features a first-floor primary suite with sunroom, spacious living areas, and central A/C. The charming

    Martha Piper THE KINDERHOOK GROUP - PITTSFIELD

    5 Glendale Rd, Stockbridge, MA 01262
  • /62

    $629,000

    • 4 Beds
    • 2.5 Baths
    • 2,428 Sq Ft

    90 Via Franco, Lee, MA 01238

    OPEN HOUSE SAT 7/26/25 10:30am-12:00pm. Don't miss this exceptional opportunity to own a spacious and beautifully updated home nestled on 1.34 acres in the heart of the Berkshires. Tucked away in a private setting yet just minutes from shopping, cultural attractions, and I-90, this home offers the perfect balance of peace and convenience. Enjoy the ease of one-level living with an updated kitchen

    Cindy Carrigan LAMACCHIA REALTY, INC

    90 Via Franco, Lee, MA 01238
  • /43

    $475,000

    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    127 Old Joe Rd, Great Barrington, MA 01230

    Nestled on a quiet country road, this well-kept ranch offers the ease of single-level living with ample space to relax, entertain, and make your own. The home features an inviting floor plan with plenty of natural light and room for upgrades, allowing you to personalize each space to your taste.Enjoy seamless indoor-outdoor living with a large back deck--perfect for gatherings or quiet mornings

    Tony Segalla LANCE VERMEULEN RE, INC

    127 Old Joe Rd, Great Barrington, MA 01230
  • /56

    $3,600,000

    • 4 Beds
    • 3.5 Baths
    • 3,313 Sq Ft

    147 Hupi Rd, Monterey, MA 01245

    A rare Lake Garfield offering - this 3300sf home sits on over an acre with sweeping southerly views across the lake's widest point. The expansive great room--encompassing living, dining, and kitchen--opens to two-story lakeside decks, as do the sunroom and primary bedroom, and rooms below. Two guest bedrooms and another full bath complete the main level, which also features two built-in A/C

    Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

    147 Hupi Rd, Monterey, MA 01245
  • /9

    $89,900

    • Land
    • 23 Acres
    • $3,922 per Acre

    Lot 32 Leonhardt Rd, Becket, MA 01223

    22.92 Acres on lovely Leonhardt Road! Enchanting wooded lot. Enjoy the peaceful location while still being close to all that the Berkshires have to offer! Hike your own trails or take a short drive to many of the amazing Berkshire hiking trails. Walk down to Yokum Pond or over to Buckley Dunton for a swim.Great land and location!

    Jessie Carlino MACCARO REAL ESTATE

    Lot 32 Leonhardt Rd, Becket, MA 01223
  • /20

    $3,995,000

    • 15 Beds
    • 15 Baths
    • 11,945 Sq Ft

    615 Laurel St, Lee, MA 01238

    The Lakehouse enjoys a spectacular setting on a westerly facing cliff overlooking pristine Laurel Lake in the heart of The Berkshires. The Lakehouse is a classic three-story, shingle style mansion with 530' of lake frontage including its own dock. Built in 1903, the architecture denotes the unpretentious, timeless elegance of a turn-of-the-century lakeside cottage. There are 15 bedrooms and

    Pamela J Long EAST COAST INN BROKERS

    615 Laurel St, Lee, MA 01238
  • /45

    $139,900

    • 3 Beds
    • 1 Bath
    • 1,517 Sq Ft

    450 River Rd, Clarksburg, MA 01247

    Clarksburg, MA. IMPROVED PRICE! NOW ONLY $139,900! SELLER SAYS ''SELL!'' Less than 5 minutes to MassMoCA! 8.8 acres & a fixer-upper Bungalow across the street from the North Branch of the Hoosac River with sidewalks all the way down to The City of North Adams.1st floor offers kitchen, laundry, bath, dining room, living room & 3-season front porch. 2nd level offers 3 bedrooms. This home is

    Colleen Zajac MONARCH REALTY, INC.

    450 River Rd, Clarksburg, MA 01247
  • /42

    $465,000

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

    42 East St, Stockbridge, MA 01262

    Set on 6.4 scenic acres, this classic New England farmhouse captures the timeless spirit of Stockbridge, a town beloved for its rich history and cultural legacy. This 2-bed 2-bath home offers authentic charm, featuring beautiful hardwood floors, a spacious kitchen, family room + 1st floor full bath, and a welcoming front porch that evokes a slower, simpler time. Thoughtful updates include a newer

    Conor Meehan STONE HOUSE PROPERTIES, LLC

    42 East St, Stockbridge, MA 01262
  • /51

    $1,775,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    9 Bott Hill Rd, Egremont, MA 01230

    Stunning Post and Beam Home with Log Facade. Nestled in a park-like setting with views of Mount Washington. Outdoor Amenities Galore. Extensive patios and wraparound decks provide the perfect venues for outdoor gatherings including a private bocce ball court, outdoor hot tub, and private dog park. The first floor offers generous entertaining spaces, including two to three bedrooms that provide

    Suzann Ward HOUSATONIC REAL ESTATE

    9 Bott Hill Rd, Egremont, MA 01230
  • /56

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    6 Muddy Brook Cir, Great Barrington, MA 01230

    Stunning Contemporary Home in Great Barrington - Perfect Blend of Privacy and ConvenienceDiscover this beautifully designed 2,500 sq. ft. contemporary residence nestled in the desirable Great Barrington area. Offering 3 spacious bedroom suites , this home combines elegant style with everyday functionality.Step outside to your private fantasy backyard -- an entertainer's dream featuring a charming

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    6 Muddy Brook Cir, Great Barrington, MA 01230
  • /21

    $110,000

    • Land
    • 7 Acres
    • $15,559 per Acre

    730 Clayton Rd, Sheffield, MA 01222

    BOG LOVERS, come look. Officially designated to be a Bog, this property could be a great one to own, for observing its nature views that change the year around. Whether you would want to build a home, or build a viewing platform for regular visits, it has 7+ acres with roughly 60-70% in a bog like status, the remainder being usable for building and walking along the bog's boundaries. All earlier

    Robin Leech Robinson Leech Real Estate

    730 Clayton Rd, Sheffield, MA 01222
  • /21

    $535,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    340 Becket Rd, Otis, MA 01253

    OFFERING $10,000 closing cost credit close by 9/30! Modern ranch on 9+ acres just minutes from Otis Reservoir & Big Pond beach! Built in 2020, this 3 bed, 2 bath home is move-in ready. The open kitchen shines with granite counters, stainless appliances & a 48 inch professional gas range, flowing seamlessly into the dining & living area. The soundproofed primary suite offers a spa like bath with

    Patricia Molina CENTURY 21 NORTHEAST

    340 Becket Rd, Otis, MA 01253
  • /15

    $36,999

    • Land
    • 5 Acres
    • $6,942 per Acre

    0 Gentian Hollow, Becket, MA 01223

    Buildable, Perc Test Passed 5.33 Acres in Becket, MA | R-1 Zoning = STRs Allowed | Power at Street | No HOA restrictions | perfect for builders, Airbnb investors, or vacation home lovers. Professionally managed short-term rentals allowed! No HOA restrictions, annual fee of $1200 for maintenance of amenities and roads paid to the Becket Woods Road District. This private lot is your blank canvas

    Derek Greene The Greene Realty Group

    0 Gentian Hollow, Becket, MA 01223

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