Sandisfield, MA Homes

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  /9

  $124,900

  • Land
  • 26 Acres
  • $4,850 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
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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
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  /41

  Est $503,117 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,540 Sq Ft

  26 Autumn Ct, Otis, MA 01253

  26 Autumn Ct, Otis, MA 01253
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  /31

  $499,000

  • 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 great 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. This great house won't last long! Association amenities include tennis/pickleball

  Emily Piacquadio LANCE VERMEULEN RE, INC

  309 Tamarack Trail, Sandisfield, MA 01255
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  /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
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  /38

  Est $773,995 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
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  /32

  $825,000

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  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
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  /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 WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  147 New Hartford Rd, Sandisfield, MA 01255
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  /55

  Est $747,528 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
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  /30

  $515,000

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

  132 Sandisfield Rd, Sandisfield, MA 01255

  Experience the tranquility of Sandisfield--surrounded by lakes, trails, and natural beauty--just minutes from Great Barrington, Lee, and NW Connecticut, and a little over 2 hours from Boston or NYC. This beautifully renovated 1843 Greek Revival home blends historic charm with modern comfort: 3 bedrooms, 2 updated baths, and a bright open-concept kitchen/dining/family room with marble counters,

  Helen Mullany HELEN MULLANY REAL ESTATE, LLC

  132 Sandisfield Rd, Sandisfield, MA 01255
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  /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
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  /9

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /28

  $599,000

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

  125 Town Hill Rd, Sandisfield, MA 01255

  The property is ideal for active families (with tennis and basketball on site and swimming and hiking minutes away). A quicker, more traffic free, less fussy destination than the Hamptons and tons and tons of space and fresh air! The home is just about 15 minutes from affordable family skiing and about 30 minutes from world class music at Tanglewood and dance at Jacob's Pillow. Excellent dining

  Kimberly Spencer RE/MAX COMPASS

  125 Town Hill Rd, Sandisfield, MA 01255
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  /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
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  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /44

  $595,000

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

  305 Shadow Ln, Sandisfield, MA 01255

  This beautiful 3-bed, 3-bath contemporary home in the Otis Wood Lands offers modern comforts in a serene setting. This 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 it's open concept living room, dining room, and kitchen area. The primary suite features a wood burning fireplace,

  Sarah Dixon LANCE VERMEULEN RE, INC

  305 Shadow Ln, Sandisfield, MA 01255
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  /30

  $649,000 Sold Nov 22, 2024

  • 2,053 Sq Ft
  • $316/SF
  • 3 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1984

  363 Deer Run, Sandisfield, MA 01255

  Spacious three bedroom Otis Wood Lands Contemporary with large first-floor primary suite. Living room with cathedral ceiling and propane stove, two additional bedrooms, loft, lower-level den, and three-season room. This home has been lovingly maintained. 2014 whole-house propane generator, flooring replaced in lower level (2014), replaced all porch windows & sliders (2014). Heat/AC splits in

  Emily Piacquadio LANCE VERMEULEN RE, INC

  363 Deer Run, Sandisfield, MA 01255
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  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /5

  $39,500

  • Land
  • 2.03 Acres
  • $19,458 per Acre

  Lot 5-0 Perry Rd, Sandisfield, MA 01253

  Wooded Rural building site minutes away from Otis center; close to Skiing, Resturants, and more. This 2 acre lot is a fresh slate to build a small Cabin or country getaway; Great area to catch nature all around you. Stone walls that boarder the property will ensure your boundry lines and privacy from neighboring lots. Maintained road with no assoication fee, enjoy all the peace and quiet the

  Ashley Canger FAIRGROUND REAL ESTATE, INC

  Lot 5-0 Perry Rd, Sandisfield, MA 01253
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  /44

  $910,000 Sold Nov 22, 2024

  • 2,400 Sq Ft
  • $379/SF
  • 6 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2005

  372 Deer Run, Sandisfield, MA 01255

  Inviting Otis Wood Lands home, where relaxation & nature come together. Enjoy the heated in-ground pool, lounge on the spacious deck, or relax on the large 3-season porch in this serene setting. This elegant & spacious home has a large living room with cathedral ceiling, stone fireplace & is open to the kitchen & dining area. Beautiful kitchen w/granite-topped island & top-of-the-line appliances.

  Lance Vermeulen LANCE VERMEULEN RE, INC

  372 Deer Run, Sandisfield, MA 01255
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  /3

  Not Listed For Sale

  0 New Hartford Rd, Sandisfield, MA 01255

  0 New Hartford Rd, Sandisfield, MA 01255
• 

  

  /51

  $1,145,000

  • 3 Beds
  • 2 Baths
  • 3,320 Sq Ft

  71 E Hubbard Rd, Sandisfield, MA 01255

  Welcome to a place to gather, unwind and recharge. Just 5 minutes from the heart of Monterey, this serene property spans over 13 acres of peaceful woodlands at the end of a quiet country road, providing a true haven for family and friends. Surrounded by perennial gardens, a natural pond, and an expansive forest, this home embraces both indoor and outdoor living. The Great Room is perfect for

  Vashti Poor LANCE VERMEULEN RE, INC

  71 E Hubbard Rd, Sandisfield, MA 01255
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  /57

  $375,000 Sold Nov 06, 2024

  • 1,105 Sq Ft
  • $339/SF
  • 17 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  125 West St, Sandisfield, MA 01255

  Very peaceful quiet setting. 5.6 acres with walking trails and a very beautiful mature yard. Great location, close to skiing, Tanglewood and more. Hardwood floors through out and many new or newer updates. Newer electric and oil furnace tank. This home is having a brand new septic system installed at a cost of about 35k so no worries about septic. Large basement with work area and and oversized

  Paul Clark CLARK REALTY GROUP LLC

  125 West St, Sandisfield, MA 01255
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  /30

  Est $424,526 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
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  /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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  /31

  $120,000 Sold Nov 04, 2024

  • 980 Sq Ft
  • $122/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  122 West St, Sandisfield, MA 01255

  A lovely 1960's ranch on a quiet country road. Featuring two bedrooms, full bathroom, spacious living room with wood stove and an eat-in kitchen. Propane for heating and hot water. New Roof (2023), large yard, and walk out basement. This is a convenient location within minutes to West Lake and Abbey Lake, 13 miles to Great Barrington downtown, two ski areas within close proximity, hiking, and all

  Jose Larios LAMACCHIA REALTY, INC

  122 West St, Sandisfield, MA 01255
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  /39

  Est $271,436 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  109 Sandy Brook Turnpike, Sandisfield, MA 01255

  109 Sandy Brook Turnpike, Sandisfield, MA 01255
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  /27

  $24,000

  • Land
  • 1.06 Acres
  • $22,641 per Acre

  0 Highland Way, Otis, MA 01253

  Build your own unique Berkshire dream home in one of the most desirable communities in Berkshire county.Enjoy all that Otis Woodlands has to offer all within a stroll or short drive: a private lake,exquisite clubhouse,a pool and two tennis courts.And just beyond OWL enjoy one of the largest recreational lakes in Mass, Otis Reservoir as well as gorgeous Big Pond lake.Otis Ski Ridge is minutes away

  Thom Garvey WILLIAM PITT SOTHEBY'S - LENOX

  0 Highland Way, Otis, MA 01253
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  /26

  $398,500 Sold Oct 30, 2024

  • 1,008 Sq Ft
  • $395/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  320 Highland Way, Sandisfield, MA 01255

  Contemporary vacation chalet in popular Otis Wood Lands. Sunny great room with a cathedral ceiling opens to a spacious deck. This 3BR/2B cabin is set on a hill a short walk from all of the wonderful association amenities: private lake and beach, club house and fitness center, pool, tennis and pickle ball courts. It is located near a trail into Otis State Forest with miles of hiking and cross

  Jeff Wilkinson STONE HOUSE PROPERTIES, LLC

  320 Highland Way, Sandisfield, MA 01255
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  /25

  Est $435,884 Not Listed For Sale

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

  86 West St, Sandisfield, MA 01255

  86 West St, Sandisfield, MA 01255
• 

  

  /22

  $275,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,600 Sq Ft

  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
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  /17

  $275,000 Sold Oct 28, 2024

  • Land
  • 77 Acres
  • $3,577 per Acre

  • 171 Days On Market

  Unlisted Address

  This offering presents an exceptional opportunity to acquire two meticulously surveyed land parcels located in the picturesque town of Sandisfield, just minutes away from downtown Monterey.Lot 1, spanning over 52 acres, boasts a drilled well, perc tests, and a 4-bedroom septic design, providing the groundwork for your dream home or estate. This expansive parcel offers ample space for development

  Christian Deckert WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Unlisted Address
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  /41

  Est $393,840 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
• 

  

  /39

  $289,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,334 Sq Ft

  122 Sandisfield Rd, Sandisfield, MA 01255

  Great owner occupied opportunity- as one apartment is vacant or add to your portfolio and rent all 3 apartments.This well maintained property offers a beautiful setting and many updates such as a NEW septic system 2012, blown in insulation 2013, NEW vinyl siding and windows 2020, New water filter system 2019, New water heaters from 2019-2021 and blown in insulation 2013 to name a few. 3 CAR

  122 Sandisfield Rd, Sandisfield, MA 01255
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  /38

  $539,000 Sold Oct 18, 2024

  • 1,260 Sq Ft
  • $428/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  311 Lakeshore Dr, Sandisfield, MA 01255

  Experience lakeside living in this 2 bedroom, 2 bathroom home sitting on a serene waterfront lot in the Otis Woodlands community.An impressive large fireplace serves as the heart of the open concept living space, creating a warm and inviting atmosphere for cozy nights in.The large deck that spans the back of the home is perfect for entertaining or relaxing with your morning coffee.Just a few

  Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  311 Lakeshore Dr, Sandisfield, MA 01255
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  /41

  Est $427,216 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
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  /42

  $595,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,860 Sq Ft

  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
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  /15

  $89,000 Sold Oct 11, 2024

  • Land
  • 4.29 Acres
  • $20,746 per Acre

  • 83 Days On Market

  Unlisted Address

  4+ Peaceful & Serene Acres with significant added value that will save you many thousands of dollars building your home in the Berkshires. Improvements include a rough driveway already in place; electric brought underground from the pole to the parcel; most of all there is already a drilled, 465 ft. deep well, static level just 30', and 125' of casing. 12(+) gallons per minute. As quiet as the

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  Unlisted Address
• 

  

  /23

  Est $511,382 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
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  /18

  $159,000 Under Contract

  • 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

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