Homes in ZIP Code 01255

/70
$795,000
- 3 Beds
- 4 Baths
- 2,963 Sq Ft
11 Jamie Ln, Sandisfield, MA 01255

This well-designed home offers three floors of clean and comfortable living space. A multitude of windows welcomes changing light throughout the day, and all three levels have radiant heat. The first floor is comprised of a lovely living room with gas stove, a spacious, efficient kitchen, dining area, a den/office with separate entrance and a fabulous, screened porch. Upstairs you'll find three

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

11 Jamie Ln, Sandisfield, MA 01255
/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

/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

/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
/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

/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

/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
/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

/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

/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
/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

/9
Not Listed For Sale
Unlisted Address

Unlisted Address

/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
/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

/10
Est $119,000 Not Listed For Sale
Unlisted Address

Unlisted Address

/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
/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

/7
Not Listed For Sale
Unlisted Address

Unlisted Address

/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
/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

/7
Not Listed For Sale
Unlisted Address

Unlisted Address

/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
/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

/3
Not Listed For Sale
0 New Hartford Rd, Sandisfield, MA 01255

0 New Hartford Rd, Sandisfield, MA 01255

/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
/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

/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

/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
/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

/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

/29
$360,000
- 4 Beds
- 2 Baths
- 2,095 Sq Ft
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
/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

/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

/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
/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

/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

/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
/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

/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

/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

Showing Results 1 - 40, Page 1 of 18

Massachusetts Sandisfield 01255

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