Berkshire, MA Homes

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  /28

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  303 Lakeshore Dr, Sandisfield, MA 01255

  Experience the ultimate in lakeside living with this stunning 4-bedroom, 2-bath home in the coveted Otis Wood Lands community. This property offers a perfect blend of comfort and entertainment, featuring spacious sun-filled rooms and a sprawling deck ideal for relaxation and gatherings. Enjoy the convenience of a fully furnished home, complete with game room favorites like pool and air hockey

  

  Gary Fuls Jr

  RE/MAX TRANSITIONS

  (413) 884-5511

  303 Lakeshore Dr, Sandisfield, MA 01255
• 

  

  

  /20

  $310,000 Sold Aug 08, 2025

  • 1,494 Sq Ft
  • $207/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1780

  42 W Hubbard Rd, Sandisfield, MA 01255

  Cozy three-bedroom, 1 bath home only minutes from the center of Monterey. Built in 1780, formerly a schoolhouse. Now a lovely home set on two level acres.

  Paul Reed LANCE VERMEULEN RE, INC

  42 W Hubbard Rd, Sandisfield, MA 01255
• 

  

  

  /38

  Est $832,485 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,878 Sq Ft

  305 Sequena Dr, Sandisfield, MA 01255

  305 Sequena Dr, Sandisfield, MA 01255
• 

  

  

  /32

  $1,250,000

  • 5 Beds
  • 5.5 Baths
  • 4,645 Sq Ft

  7 Perry Rd, Sandisfield, MA 01255

  WHERE EVERY SEASON FEELS LIKE HOME16 acres at the end of a quiet country road where your shoulders drop the moment you arrive. This five bedroom retreat with over 4,600 square feet gets Berkshire living right: soaring great room with fireplace, granite kitchen, four-season sunroom, and that incredible finished lower level with radiant floors, full bar, and walkout to covered patio. Mudroom with

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  7 Perry Rd, Sandisfield, MA 01255
• 

  

  

  /10

  $125,000 Sold Aug 01, 2025

  • Land
  • 2.09 Acres
  • $59,809 per Acre

  • 31 Days On Market

  9 S Sandisfield Rd, Sandisfield, MA 01255

  This cleared and well-maintained 2-acre lot is ready for your dream home or weekend getaway. Located just 10 miles from Great Barrington and only 10 minutes from the Connecticut border this property offers both tranquility and accessibility.Key features include:4-bedroom septic system installed post 2007Drilled well with pump and spigotGravel driveway in excellent conditionUnderground electric

  Timothy Lovett COMPASS MASSACHUSETTS , LLC GB

  9 S Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /55

  Est $828,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,220 Sq Ft

  325 Lakeshore Dr, Sandisfield, MA 01255

  325 Lakeshore Dr, Sandisfield, MA 01255
• 

  

  /91

  $749,900 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,658 Sq Ft

  329 Lakeshore Dr, Sandisfield, MA 01255

  Nestled in the heart of the highly sought-after Otis Woodlands community, this spacious 4-bedroom, 3 bath lakefront home offers the perfect blend of rustic elegance and modern comfort. With over 2,600 sq ft of living space, soaring vaulted ceilings, and an open floor plan, this property is an ideal retreat for both relaxing getaways and entertaining family and friends.Enjoy the peaceful sounds of

  Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

  329 Lakeshore Dr, Sandisfield, MA 01255
• 

  

  /47

  $785,000 Sold Jul 30, 2025

  • 2,963 Sq Ft
  • $265/SF
  • 36 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2006

  11 Jamie Ln, Sandisfield, MA 01255

  Welcome to 11 Jamie Lane. This stunning contemporary home features three levels of bright, open space, perfect for modern living. Large windows flood the interiors with natural light and provide beautiful views of the fully fenced backyard. This home is designed for comfort and style with all the modern amenities like radiant heat, air conditioning and a separate building for Yoga studio,

  Eric Steuernagle FAIRGROUND REAL ESTATE, INC

  11 Jamie Ln, Sandisfield, MA 01255
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  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
• 

  

  /77

  $4,500,000

  • 5 Beds
  • 5.5 Baths
  • 4,027 Sq Ft

  19 Roberts Rd, Sandisfield, MA 01255

  Introducing 
FREE QUARTER FARMNearly 1,500 Acres | Sandisfield, the Southern Berkshires | $4,500,000Miles of private trails for hiking, hunting, fishing, horseback riding - your own wilderness preserve134+ acres not in conservation with 1,489 feet of road frontage - craft your legacy5BR/5BA timeless home built for this wildly beautiful placeStand between your home, overlooking your private

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  19 Roberts Rd, Sandisfield, MA 01255
• 

  

  /39

  $487,500 Sold Jul 25, 2025

  • 1,566 Sq Ft
  • $311/SF
  • 13 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1985

  26 Autumn Ct, Otis, MA 01253

  This recently renovated cottage is tucked away on a private cul-de-sac in ever popular Otis Wood Lands, where you'll enjoy the association's private lake, beach, clubhouse, heated pool, tennis & pickle ball courts, fitness center, and playground. With 3 bedrooms, 3 full baths, plus a bonus sleeping loft, this is a terrific vacation getaway or year-round home. The new septic, new roof, and new

  Brian Farrell STONE HOUSE PROPERTIES, LLC

  26 Autumn Ct, Otis, MA 01253
• 

  

  /3

  Not Listed For Sale

  0 New Hartford Rd, Sandisfield, MA 01255

  0 New Hartford Rd, Sandisfield, MA 01255
• 

  

  /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
• 

  

  /42

  $631,000 Sold Jul 24, 2025

  • 2,860 Sq Ft
  • $221/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1798

  191 Sandisfield Rd, Sandisfield, MA 01255

  HISTORIC JABEZ BOSWORTH INN & TAVERN: AUTHENTIC BERKSHIRE COUNTRY LIVINGSet quietly in the heart of Sandisfield, Massachusetts, the historic Jabez Bosworth House & Inn, circa 1798, offers a genuinely rare opportunity to own an iconic piece of New England history just 14 miles from the vibrant town of Great Barrington. Originally home to Revolutionary War Captain Jabez Bosworth, this Federal-style

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  191 Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /30

  Est $471,464 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft

  25 S Sandisfield Rd, Sandisfield, MA 01255

  25 S Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /62

  $499,000

  • 4 Beds
  • 3 Baths
  • 1,188 Sq Ft

  377 Highland Way, Sandisfield, MA 01255

  Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape.Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a

  Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

  377 Highland Way, Sandisfield, MA 01255
• 

  

  /32

  $835,000 Sold Jul 10, 2025

  • 1,948 Sq Ft
  • $429/SF
  • 37 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1923

  18 S Beech Plain Rd, Sandisfield, MA 01255

  VIEWS! VIEWS! VIEWS! Built in 1923, this home with stunning views brings a blend of yesteryear's charm with todays modern expectations. Set in a private location on 15 acres of natural beauty with a running brook and outbuildings that have boundless possibilities, this is the country escape most people dream of. The original home with its wide plank flooring, stone fireplace and three cosy

  Fintan Hanley COMPASS MASSACHUSETTS , LLC GB

  18 S Beech Plain Rd, Sandisfield, MA 01255
• 

  

  /25

  Est $443,121 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft

  86 West St, Sandisfield, MA 01255

  86 West St, Sandisfield, MA 01255
• 

  

  /41

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft

  132 Sandisfield Rd, Sandisfield, MA 01255

  This Greek Revival farmhouse in quaint Sandisfield blends historic charm with modern updates. The open-concept living/dining area features a bright sitting room w/ vaulted ceilings and french doors overlooking lush greenery in the peaceful backyard. The modern kitchen has marble countertops & new appliances. The largest bedroom and a full bath are on the first floor, along with laundry and ample

  Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  132 Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /29

  $350,000 Sold Jun 27, 2025

  • 2,095 Sq Ft
  • $167/SF
  • 248 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  201 N Main St, Sandisfield, MA 01255

  This comfortable contemporary four bedroom, two bath home offers privacy yet it is convenient to local restaurants, a town center, and a small winter skiing area. The relatively open floor plan features a sunroom, living room and two screened porch areas. A nice wrap around deck is another treat to be enjoyed along with a fairly spacious back yard. The to be installed four bedroom new septic

  William Morrow WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  201 N Main St, Sandisfield, MA 01255
• 

  

  /41

  Est $412,006 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  121 West St, Sandisfield, MA 01255

  121 West St, Sandisfield, MA 01255
• 

  

  /16

  $495,000

  • Land
  • 21 Acres
  • $23,239 per Acre

  0 West St, Sandisfield, MA 01255

  OWN THE ENTIRE NORTH SHORE OF a 10 ACRE POND. Tucked into the quiet SE corner of the Berkshires, this is a property where the pace of the world seems to slow. 21.3 acres in all, with nearly the entire north shore of Ida Pond--and actual ownership of the pond, historically known as Morley Swamp Reservoir, a tributary of the Buck River that flows to West Lake in Sandisfield State Forest.With

  Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 West St, Sandisfield, MA 01255
• 

  

  /22

  $260,000 Sold May 14, 2025

  • 1,600 Sq Ft
  • $162/SF
  • 14 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1974

  12 Sears Rd, Sandisfield, MA 01255

  Charming Berkshires Getaway Opportunity on 6.25 acres of picturesque countryside! All walls are out and ready for you to restore this.2bedroom w/loft and family room. Title V passed. New spring fed well, 200A electrical and 2 new wood burning fireplaces. Even potential for addt'l building lot w +/-1000ft road frontage. Bring your skills. Renovate the existing layout or add a third level for

  Teronda Ellis MyOwn REA

  12 Sears Rd, Sandisfield, MA 01255
• 

  

  /41

  Est $486,284 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,321 Sq Ft

  212 Sandisfield Rd, Sandisfield, MA 01255

  212 Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /6

  $79,900

  • Land
  • 8 Acres
  • $9,963 per Acre

  Lot 3 Town Hill Rd, Sandisfield, MA 01255

  Here it is! Bring your ideas to this tranquil ~8 acre lot that has a completed perc test in hand. This 8.024-acre wooded property boasts a mix of trees, providing a serene, natural setting ideal for a home. With gentle slopes and varying elevations and ample privacy. The diverse vegetation supports local wildlife, creating a peaceful retreat. Access to power at the street and Perced for a future

  John Stevenson RE/MAX Compass

  Lot 3 Town Hill Rd, Sandisfield, MA 01255
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  /66

  $585,000 Sold Apr 14, 2025

  • 1,600 Sq Ft
  • $366/SF
  • 185 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  21 Sandisfield Rd, Sandisfield, MA 01255

  Discover the perfect blend of contemporary style and natural beauty in this newly renovated riverfront home. With 1,600 square feet of living space, this residence features three bedrooms and two brand-new bathrooms.The hip, newly renovated kitchen is a true design statement and now opens to the great room, with its high ceilings and large windows that fill the space with natural light. The

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  21 Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /23

  Est $545,513 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft

  32 S Sandisfield Rd, Sandisfield, MA 01255

  32 S Sandisfield Rd, Sandisfield, MA 01255
• 

  

  /9

  $99,000

  • Land
  • 26 Acres
  • $3,845 per Acre

  0 W Hubbard Rd, Sandisfield, MA 01255

  Discover the possibilities nestled in the heart of the Berkshires--just 20 minutes from the charm and culture of Great Barrington. This picturesque lot offers a rare combination of natural beauty and practical readiness, with a completed perc test and engineered septic designs already in place. Whether you're envisioning a peaceful weekend escape or a cozy, year-round haven, this is the perfect

  Andreea Duta BISHOP WEST REAL ESTATE

  0 W Hubbard Rd, Sandisfield, MA 01255
• 

  

  /21

  $235,000 Sold Apr 07, 2025

  • Land
  • 5 Acres
  • $44,847 per Acre

  • 91 Days On Market

  Unlisted Address

  One-of-a-kind opportunity in the heart of the Berkshires.! Over five acres of land partially improved with a gated entry, drilled well, 864 square foot timber frame barn and custom-built fieldstone and granite gardening shed. Work with the existing barn to convert to a weekend getaway or build your own home and multi-purpose the barn.

  Pamela Roberts ROBERTS & ASSOC. REALTY, INC

  Unlisted Address
• 

  

  /62

  Est $290,999 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,373 Sq Ft

  178 New Hartford Rd, Sandisfield, MA 01255

  178 New Hartford Rd, Sandisfield, MA 01255
• 

  

  /31

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft

  309 Tamarack Trail, Sandisfield, MA 01255

  Rustic Contemporary in Otis Wood Lands that abuts the State Forest! This cozy home has an open concept kitchen/living/dining area with vaulted ceilings. Access the screened-in porch and deck from the sunken living room. Primary bedroom with skylight and deck access. Detached two-car garage with storage above. An easy-to-maintain property. Association amenities include tennis/pickleball

  Emily Piacquadio LANCE VERMEULEN RE, INC

  309 Tamarack Trail, Sandisfield, MA 01255
• 

  

  /29

  $2,050,000 Sold Mar 14, 2025

  • 3,547 Sq Ft
  • $578/SF
  • 71 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1800

  147 New Hartford Rd, Sandisfield, MA 01255

  This quintessential country property is what everyone wants. Located in the Southern Berkshires close to the towns of Great Barrington, New Marlborough and Southfield and Norfolk, CT. This sleek historic and beautifully restored home is conveniently located for skiing, hiking, arts and culture, restaurants and all other Berkshire offerings. This home is beautifully restored and includes a

  Martha Piper THE KINDERHOOK GROUP - PITTSFIELD

  147 New Hartford Rd, Sandisfield, MA 01255
• 

  

  /35

  Est $302,341 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,074 Sq Ft

  6 Roosterville Rd, Sandisfield, MA 01255

  6 Roosterville Rd, Sandisfield, MA 01255
• 

  

  /39

  $549,000

  • 3 Beds
  • 3 Baths
  • 1,864 Sq Ft

  305 Shadow Ln, Sandisfield, MA 01255

  This beautiful 3-bed, 3-bath home in the Otis Wood Lands offers modern comforts in a serene setting. The property boasts a screen porch, sun deck, and 2 wood burning fireplaces! The sunlit great room, with floor-to-ceiling windows, is perfect for entertaining with its open concept living room, dining area, and kitchen. The large primary suite features a wood burning fireplace, walk-in closet, and

  Sarah Dixon LANCE VERMEULEN RE, INC

  305 Shadow Ln, Sandisfield, MA 01255
• 

  

  /37

  $113,000 Sold Jan 23, 2025

  • 1,024 Sq Ft
  • $110/SF
  • 23 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  8 Tannery Rd, Sandisfield, MA 01255

  Welcome to this unique fixer-upper nestled on just over one acre. Featuring a convenient one-level living layout. The unfinished upstairs area provides endless possibilities for expansion. The Farmington River is located across the street. Property is being sold as is and has a failed title V. Don't miss your chance to turn this house into your dream home!

  Jessica Rizzo LAMACCHIA REALTY, INC

  8 Tannery Rd, Sandisfield, MA 01255
• 

  

  /24

  Est $473,283 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,306 Sq Ft

  47 Rood Hill Rd, Sandisfield, MA 01255

  47 Rood Hill Rd, Sandisfield, MA 01255
• 

  

  /18

  $159,000

  • Land
  • 3.22 Acres
  • $49,379 per Acre

  0 Jamie Ln, Sandisfield, MA 01245

  Discover the perfect blend of tranquility and convenience with this exceptional cleared building lot in a picturesque country setting. Boasting seasonal views and situated within a peaceful association of beautiful homes, this property is an ideal getaway spot for your dream country home.With a drilled well and a leach field for a 3-bedroom septic system installed within the last three years, you

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  0 Jamie Ln, Sandisfield, MA 01245
• 

  

  /40

  $689,500 Sold Dec 20, 2024

  • 2,850 Sq Ft
  • $242/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1978

  381 Deer Run Rd, Sandisfield, MA 01255

  Fantastic 4 BR, 2.5 Contemporary sits on a double lot and borders state forest in the Otis Wood Lands community. Spacious open kitchen/dining/living area with vaulted ceiling & woodstove. First-floor also includes primary, den, half bath, & washer/dryer area. Second floor includes 3 BRs & full bath. All three bathrooms were updated in 2013. Lower-level has two-car garage, mudroom, and

  Emily Piacquadio LANCE VERMEULEN RE, INC

  381 Deer Run Rd, Sandisfield, MA 01255
• 

  

  /17

  Est $464,665 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  98 New Hartford Rd, Sandisfield, MA 01255

  98 New Hartford Rd, Sandisfield, MA 01255
• 

  

  /56

  $4,999,999

  • 3 Beds
  • 5.5 Baths
  • 3,000 Sq Ft

  14 Sullivan Rd, Sandisfield, MA 01255

  Atwater Pond is a remarkable 321-acre waterfront retreat in southern Berkshire County. An immaculately renovated mid-century house and 1920's guest cottage sit on the edge of a 32-acre, spring-fed pond, surrounded by hundreds of acres of pristine forest. Year-round recreational opportunities abound and a 4+ mile trail system winds through the property. Additional features include multiple docks,

  Mauren White-Kirkby BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

  14 Sullivan Rd, Sandisfield, MA 01255

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