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Sandisfield, MA Homes for Sale

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  • 14 Roosterville Rd, Sandisfield, MA 01255
    14 Roosterville Rd, Sandisfield, MA 01255
    14 Roosterville Rd, Sandisfield, MA 01255
    /50

    $795,000

    • 4 Beds
    • 2.5 Baths
    • 2,516 Sq Ft

    14 Roosterville Rd, Sandisfield, MA 01255

    At the end of a quiet dead-end road in Sandisfield, this c.1892 four-bedroom farmhouse sits less than twenty feet from the Wild and Scenic West Branch of the Farmington River, a federally protected, free-flowing trout river. Four bedrooms. Two full baths plus a half. 2,516 sq ft. 4.61 acres. Beautifully transformed interior: a granite-island kitchen rebuilt from the ground up, wide softwood

    Agent Photo

    Chapin Fish

    WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    (413) 666-1562

    14 Roosterville Rd, Sandisfield, MA 01255
  • 303 Lakeshore Dr, Sandisfield, MA 01255
    303 Lakeshore Dr, Sandisfield, MA 01255
    303 Lakeshore Dr, Sandisfield, MA 01255
    /28

    $575,000

    • 4 Beds
    • 2 Baths
    • 3,218 Sq Ft

    303 Lakeshore Dr, Sandisfield, MA 01255

    Discover the epitome of lakeside living in this exceptional 4-bedroom, 2-bath home nestled in the desirable Otis Wood Lands community. This fully furnished residence seamlessly combines comfort and entertainment, featuring bright, spacious rooms and an expansive deck perfect for relaxation or hosting gatherings. Enjoy modern conveniences such as energy-efficient heat pumps, remote-controlled

    Agent Photo

    Gary Fuls Jr

    RE/MAX Transitions

    (413) 423-0842

    303 Lakeshore Dr, Sandisfield, MA 01255
  • 19 Roberts Rd, Sandisfield, MA 01255
    19 Roberts Rd, Sandisfield, MA 01255
    19 Roberts Rd, Sandisfield, MA 01255
    /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

    Agent Photo

    Chapin Fish

    WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    (413) 591-5346

    19 Roberts Rd, Sandisfield, MA 01255
  • 314 Lakeshore Dr, Sandisfield, MA 01253
    314 Lakeshore Dr, Sandisfield, MA 01253
    314 Lakeshore Dr, Sandisfield, MA 01253
    /11

    $95,000

    • Land
    • 3.03 Acres
    • $31,353 per Acre

    314 Lakeshore Dr, Sandisfield, MA 01253

    Ideal Location Near Amenities + Peaceful, Private SettingA wonderful opportunity to own one of the largest available building lots in the desirable Otis Wood Lands community -- 2.853 acres of mostly level, wooded land offering both privacy and convenience.Perfectly situated close to the lake, clubhouse, pool, tennis and pickleball courts, and fitness center, this property provides easy access to

    Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    314 Lakeshore Dr, Sandisfield, MA 01253
  • 314 & 316 Lakeshore Dr, Sandisfield, MA 01253
    314 & 316 Lakeshore Dr, Sandisfield, MA 01253
    314 & 316 Lakeshore Dr, Sandisfield, MA 01253
    /11

    $180,000

    • Land
    • 5.88 Acres
    • $30,602 per Acre

    314 & 316 Lakeshore Dr, Sandisfield, MA 01253

    Exceptional Privacy + Premier Location Near All Community AmenitiesAn extraordinary chance to own both of the largest building parcels ever offered in Otis Wood Lands -- nearly 6 acres of pristine, gently rolling land. Together, these adjoining lots provide an unmatched sense of space, privacy, and flexibility to create your ultimate Berkshire escape.Ideally situated close to the lake, clubhouse,

    Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    314 & 316 Lakeshore Dr, Sandisfield, MA 01253
  • 125 Town Hill Rd, Sandisfield, MA 01255
    125 Town Hill Rd, Sandisfield, MA 01255
    125 Town Hill Rd, Sandisfield, MA 01255
    /42

    $549,999

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

    125 Town Hill Rd, Sandisfield, MA 01255

    Currently used as an income-producing rental, 125 Town Hill Rd offers consistent cash flow with strong potential for future owner occupancy or a weekend retreat. Set on a quiet country road surrounded by woods, the property delivers the privacy with your own tennis court in your backyard and a spacious screened-in porch. Inside features a comfortable, functional layout with bright living spaces

    Adam Dingman BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY

    125 Town Hill Rd, Sandisfield, MA 01255
  • 0 N Beech Plain Rd Unit 247823, Sandisfield, MA 01255
    0 N Beech Plain Rd Unit 247823, Sandisfield, MA 01255
    0 N Beech Plain Rd Unit 247823, Sandisfield, MA 01255
    /13

    $165,000

    • Land
    • 13.33 Acres
    • $12,378 per Acre

    0 N Beech Plain Rd Unit 247823, Sandisfield, MA 01255

    Where Quiet Becomes Currency: Elevated Berkshire Land with Mountain ViewsOn a peaceful dirt road in Sandisfield, 13.33 acres of elevated woodland offer what today's buyers increasingly seek--genuine privacy, mountain views, and the kind of profound quiet that makes working from home feel like retreat. A rough driveway climbs through mature forest to an elevated clearing where previous owners

    Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    0 N Beech Plain Rd Unit 247823, Sandisfield, MA 01255
  • 0 Perry Rd, Sandisfield, MA 01253
    0 Perry Rd, Sandisfield, MA 01253
    /2

    $34,500

    • Land
    • 2.03 Acres
    • $16,995 per Acre

    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

    Eric Steuernagle FAIRGROUND REAL ESTATE, INC

    0 Perry Rd, Sandisfield, MA 01253
  • 316 Lakeshore Dr, Sandisfield, MA 01253
    316 Lakeshore Dr, Sandisfield, MA 01253
    316 Lakeshore Dr, Sandisfield, MA 01253
    /9

    $95,000

    • Land
    • 2.85 Acres
    • $33,333 per Acre

    316 Lakeshore Dr, Sandisfield, MA 01253

    Prime Location + Privacy + Fiber Internet at the StreetA rare opportunity to build your Berkshire dream home on one of the largest lots ever offered in Otis Wood Lands -- 3.029 acres of peaceful, gently rolling terrain in a premier location close to all community amenities.This property offers excellent privacy while keeping you just minutes from the lake, clubhouse, pool, tennis and pickleball

    Shannon Margraf WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    316 Lakeshore Dr, Sandisfield, MA 01253
  • 311 Tamarack Trail, Sandisfield, MA 01255
    311 Tamarack Trail, Sandisfield, MA 01255
    311 Tamarack Trail, Sandisfield, MA 01255
    /37

    $545,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    311 Tamarack Trail, Sandisfield, MA 01255

    Perfectly timed for summer in the Berkshires, this 1,320-square-foot contemporary retreat at 311 Tamarack Trail is refreshed and ready for immediate move-in. Tucked away in the private Otis Wood Lands community, the home borders protected state forest land, offering a serene and private wooded setting for your seasonal escape. The interior features a bright, open-concept layout with soaring

    Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    311 Tamarack Trail, Sandisfield, MA 01255
Massachusetts Berkshire County Sandisfield

Real Estate & Homes for Sale in Sandisfield, MA

Why Live in Sandisfield

Sandisfield, Massachusetts, is a woodland retreat in the southern Berkshires, attracting residents from large coastal cities like Boston and Manhattan due to its accessibility and natural beauty. The area features large, contemporary cabins, 1800s farmhouses, and private lakefront communities, maintaining a rural woodland atmosphere. Popular community options like Otis Woodlands offer amenities such as a private lake, beach, clubhouse, pickleball courts, and trails. Outdoor activities are abundant, with miles of trails in Sandisfield State Forest and popular spots like Clam River Reserve and Spectacle Ponds for hiking, paddling, and fishing. The area has minimal commercial activity, with local farm shops and the historic New Boston Inn providing dining and shopping options. For more extensive shopping, residents travel to nearby towns like Great Barrington and Lee, located 15 to 20 miles away. Farmington River Elementary, located about 10 miles north in Otis, is a highly rated school serving kindergarten through sixth grade. Middle and high school students often attend Southern Berkshire Public Schools, including Mount Everett Junior and Senior High in Sheffield. Sandisfield is approximately 120 miles from Boston and 135 miles from Manhattan, making it a convenient seasonal retreat. The nearest healthcare facility is Fairview Hospital in Great Barrington, about 15 miles west.

Learn more about living in Sandisfield

Frequently Asked Questions

What is the average home price in Sandisfield, MA?
Homes for sale in Sandisfield, MA have an average home price of $1,087,740.
How many homes have sold over the last 12 months in Sandisfield, MA?
16 homes have sold in Sandisfield, MA over the last 12 months.
What are the most popular zip codes in Sandisfield, MA?
The most popular zip codes in Sandisfield, MA include 01255, 01034, 01230, 01259 and 01245.
How much do you need to make to afford a house in Sandisfield?
The median home price in Sandisfield is $575,000. If you put a 20% down payment of $115,000 and had a 30-year fixed mortgage with an interest rate of 6.23%, your estimated principal and interest payment would be $2,830 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $121K a year to afford the median home price in Sandisfield. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Sandisfield, MA?
Sandisfield, MA has highly rated public and private schools. Some of the best schools in Sandisfield based on Niche Grades are Colebrook Consolidated School, Northwestern Regional High School and Woodland School. Browse all the schools in Sandisfield, MA to learn more.

Home Trends in Sandisfield, MA

On average, homes in Sandisfield, MA sell after 122 days on the market compared to the national average of 56 days. The median sale price for homes in Sandisfield, MA over the last 12 months is $549,000, up 33% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$549,000
Median Single Family Sale Price
$575,000
Average Price Per Sq Ft
$376
Number of Homes for Sale
4
Last 12 months Home Sales
16
Months of Supply
3.00
Median List Price
$575,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
33%
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