687

Windsor, MA Homes

Section Image
  • 1523 North St, Windsor, MA 01270
    1523 North St, Windsor, MA 01270
    1523 North St, Windsor, MA 01270
    /48

    $399,900 Pending

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft

    1523 North St, Windsor, MA 01270

    NEW PRICE!!! Enjoy country living just minutes from town. Enjoy the space the privacy of every inch of this 3.75 acres and your 4 bed/2 ba New England farmhouse. Large rooms, cozy wood burning fireplace in the living/dining and woodstove in your spacious renovated kitchen (2021). Lge deck to take in the views, 3/4 bath down w/laundry. Upstairs there's 4 bedrooms & a full bath, updated floors on

    Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    1523 North St, Windsor, MA 01270
  • 130 High St Hill Rd, Windsor, MA 01270
    130 High St Hill Rd, Windsor, MA 01270
    130 High St Hill Rd, Windsor, MA 01270
    /50

    $460,000 Sold Dec 19, 2024

    • 2,240 Sq Ft
    • $205/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    130 High St Hill Rd, Windsor, MA 01270

    Discover your dream home in Windsor, set on over 5 acres of serene landscape! This charming colonial has it all, nestled in a private & efficient setting, this home is ready for its next owners. Inside, enjoy freshly painted rooms, beautiful red birch hard wood floors & high efficiency wood stove. Benefit from owned solar panels and a home generator for added efficiency & peace of mind. Enjoy

    Laiken Rapisarda LAMACCHIA REALTY, INC

    130 High St Hill Rd, Windsor, MA 01270
    • 140 Hill Cemetery Rd, Windsor, MA 01270
      140 Hill Cemetery Rd, Windsor, MA 01270
      140 Hill Cemetery Rd, Windsor, MA 01270
      /34

      Est $557,574 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,260 Sq Ft

      140 Hill Cemetery Rd, Windsor, MA 01270

      140 Hill Cemetery Rd, Windsor, MA 01270
  • 1952 Old Route 9, Windsor, MA 01270
    1952 Old Route 9, Windsor, MA 01270
    1952 Old Route 9, Windsor, MA 01270
    /19

    $135,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    1952 Old Route 9, Windsor, MA 01270

    An Ideal Project for the Right BuyerThis 2-bedroom, 1-bath Cape fixer-upper is an incredible opportunity for buyers who are looking for a project that will allow them to make their mark on a home while enjoying the rewards of renovation. With its solid foundation, charming features, and endless possibilities for expansion, this property offers the perfect blank canvas to bring your vision to

    Kolleen Schmitt BISHOP WEST REAL ESTATE

    1952 Old Route 9, Windsor, MA 01270
  • 331 Shaw Rd, Windsor, MA 01270
    331 Shaw Rd, Windsor, MA 01270
    331 Shaw Rd, Windsor, MA 01270
    /18

    $17,000 Sold Dec 17, 2024

    • Land
    • 2.17 Acres
    • $7,834 per Acre
    • 7 Days On Market

    331 Shaw Rd, Windsor, MA 01270

    Mostly level and partially cleared 2.17 acre lot. Serene and tranquil surroundings. Berkshires camping retreat? Hunting getaway? Recreational? Great location to enjoy four season outdoor recreation and all that nature has to offer. Easy access to all cultural and natural amenities in and around the Berkshires!

    Deb Trzcinski Steepleview Realty

    331 Shaw Rd, Windsor, MA 01270
    • 884 Cheshire Rd, Windsor, MA 01270
      884 Cheshire Rd, Windsor, MA 01270
      884 Cheshire Rd, Windsor, MA 01270
      /4

      Est $548,568 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,042 Sq Ft

      884 Cheshire Rd, Windsor, MA 01270

      884 Cheshire Rd, Windsor, MA 01270
  • 775 North St, Windsor, MA 01270
    775 North St, Windsor, MA 01270
    775 North St, Windsor, MA 01270
    /76

    $399,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    775 North St, Windsor, MA 01270

    First time on the market is this lovely ranch style home on 2.4 acres with westerly views. Bordering state land ensuring your peace & privacy for years to come. This meticulously maintained home offers one level of living combining the perfect blend of comfort and serenity. The heart of this home is the large, inviting eat-in kitchen featuring up-to-date stainless appliances, ample cabinetry,

    Cindy Carrigan LAMACCHIA REALTY, INC

    775 North St, Windsor, MA 01270
  • 143 Windsor Bush Rd, Cummington, MA 01026
    143 Windsor Bush Rd, Cummington, MA 01026
    143 Windsor Bush Rd, Cummington, MA 01026
    /29

    $290,000 Sold Oct 16, 2024

    • 1,014 Sq Ft
    • $286/SF
    • 4 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1965

    143 Windsor Bush Rd, Cummington, MA 01026

    Country chalet on 3+ acres with fresh water pond in the Berkshires! Take advantage of this unique opportunity to own this 2 bedroom, 2 bath home with incredible storybook-like charm. Close to route 9 for easy access to the Berkshires to the west or the 5 college area to the east. State forest lands nearby for your hiking enjoyment including Windsor Jambs at Windsor State Forest located minutes

    143 Windsor Bush Rd, Cummington, MA 01026
    • 1387 E Windsor Rd, Windsor, MA 01270
      1387 E Windsor Rd, Windsor, MA 01270
      1387 E Windsor Rd, Windsor, MA 01270
      /38

      Est $594,133 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft

      1387 E Windsor Rd, Windsor, MA 01270

      1387 E Windsor Rd, Windsor, MA 01270
  • 576 North St, Windsor, MA 01270
    576 North St, Windsor, MA 01270
    576 North St, Windsor, MA 01270
    /52

    $450,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 2,444 Sq Ft

    576 North St, Windsor, MA 01270

    Look no further, this charming farmhouse nestled on almost four acres is waiting foryou. Relax on the screened back porch or have morning coffee in the skylight drenched sunroom, you may view the wildlife that travels through the state forest, which borders the property. The home features a living room fireplace, skylights and sunroom, cedar closet and central vac. The grounds offer lots of

    John Ciepiela BISHOP WEST REAL ESTATE

    576 North St, Windsor, MA 01270
  • 877 Massachusetts 9, Windsor, MA 01270
    877 Massachusetts 9, Windsor, MA 01270
    877 Massachusetts 9, Windsor, MA 01270
    /38

    $439,900 Sold Oct 15, 2024

    • 1,782 Sq Ft
    • $247/SF
    • 5 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1952

    877 Massachusetts 9, Windsor, MA 01270

    Don’t miss your chance to escape from the hubbub of life to your very own oasis set on 22+ picturesque wooded acres. The absolute BEST of what the Hilltowns and Berkshires have to offer. Sit on the Goshen stone patio and gaze into your fish pond or enjoy the stunning view of the milky way from your hot tub. This property holds unlimited potential for your garden or homestead with fruit trees,

    Holly Berry Olde Towne Realty

    877 Massachusetts 9, Windsor, MA 01270
    • 1600 North St, Windsor, MA 01270
      1600 North St, Windsor, MA 01270
      1600 North St, Windsor, MA 01270
      /57

      Est $446,291 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,680 Sq Ft

      1600 North St, Windsor, MA 01270

      1600 North St, Windsor, MA 01270
  • 102 Monahan Rd, Windsor, MA 01270
    102 Monahan Rd, Windsor, MA 01270
    102 Monahan Rd, Windsor, MA 01270
    /56

    $410,000 Sold Aug 22, 2024

    • 1,490 Sq Ft
    • $275/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 1992

    102 Monahan Rd, Windsor, MA 01270

    We are offering a Ranch style home in a peaceful country setting on a dead end road! The home is perfectly set on 8.4 acres of largely wooded land with a nicely manicured lawn that is large enough for year round enjoyment. This 3 bedroom 2 bath ranch has been tastefully renovated recently. Some of the updates include fresh paint throughout, newer laminate floors throughout and metal roof. The

    Doug Collins LAMACCHIA REALTY, INC

    102 Monahan Rd, Windsor, MA 01270
    • 733 North St, Windsor, MA 01270
      733 North St, Windsor, MA 01270
      733 North St, Windsor, MA 01270
      /39

      Est $643,899 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,350 Sq Ft

      733 North St, Windsor, MA 01270

      733 North St, Windsor, MA 01270
  • 1430 Old Route 9, Windsor, MA 01270
    1430 Old Route 9, Windsor, MA 01270
    1430 Old Route 9, Windsor, MA 01270
    /24

    $210,000 Sold Aug 14, 2024

    • 975 Sq Ft
    • $215/SF
    • 42 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1975

    1430 Old Route 9, Windsor, MA 01270

    Embrace the serenity of nature as you come home to this cozy and cute 2-bedroom, 1-bath house, that offers beautiful natural wood cathedral ceiling and many updates throughout the house. Located on a quiet paved country road with bubbling river just across the street. Nestled in a peaceful setting, but only about 15 minutes to Pittsfield shopping centers. Visit to find out if this move-in-ready

    Ann Jerebtsov LAMACCHIA REALTY, INC

    1430 Old Route 9, Windsor, MA 01270
    • 1496 North St, Windsor, MA 01270
      1496 North St, Windsor, MA 01270
      1496 North St, Windsor, MA 01270
      /42

      Est $520,939 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,241 Sq Ft

      1496 North St, Windsor, MA 01270

      1496 North St, Windsor, MA 01270
  • 1555 Bush Rd, Windsor, MA 01270
    1555 Bush Rd, Windsor, MA 01270
    1555 Bush Rd, Windsor, MA 01270
    /25

    $81,000 Sold Jul 31, 2024

    • 350 Sq Ft
    • $231/SF
    • 3 Days On Market
    • 1 Bed
    • Built 1990

    1555 Bush Rd, Windsor, MA 01270

    Discover the perfect cozy camp getaway with this 350 sq ft off-grid cottage, nestled on 3.6 acres of serene, private land. Recently updated with a new roof and fresh exterior paint in 2023, this property offers a rustic escape surrounded by nature. The interior has been completely renovated. Powered by a generator, with two 15 amp fuses and a power inlet hookup for easy connection. Property has

    1555 Bush Rd, Windsor, MA 01270
    • 105 High St Hill Rd, Windsor, MA 01270
      105 High St Hill Rd, Windsor, MA 01270
      105 High St Hill Rd, Windsor, MA 01270
      /35

      Est $495,919 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,500 Sq Ft

      105 High St Hill Rd, Windsor, MA 01270

      105 High St Hill Rd, Windsor, MA 01270
  • 696 River Rd, Windsor, MA 01270
    696 River Rd, Windsor, MA 01270
    696 River Rd, Windsor, MA 01270
    /42

    $612,000 Sold Jun 27, 2024

    • 1,596 Sq Ft
    • $383/SF
    • 18 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    696 River Rd, Windsor, MA 01270

    Horse Properties.... sometimes you have a good house and yucky barn.... sometimes a good house and barn and a lousy location. This property has the house, the barn, the location, and a few other amenities too! Located in Windsor in the ''triangle'' between Pittsfield, Williamstown and Northampton. 22 acres - frontage on the river (but not in a flood zone as per owner) on a paved and town

    Kolleen Schmitt BISHOP WEST REAL ESTATE

    696 River Rd, Windsor, MA 01270
    • 235 High St Hill Rd, Windsor, MA 01270
      235 High St Hill Rd, Windsor, MA 01270
      235 High St Hill Rd, Windsor, MA 01270
      /21

      Est $521,418 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,716 Sq Ft

      235 High St Hill Rd, Windsor, MA 01270

      235 High St Hill Rd, Windsor, MA 01270
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /3

    $25,000 Sold May 29, 2024

    • Land
    • 3.91 Acres
    • $6,394 per Acre
    • 126 Days On Market

    Unlisted Address

    Bucolic setting, located on a paved country road, 25 minutes from Pittsfield and 35 minutes to Northampton. Evergreens, spruce, cedar and hemlock dot the landscape.Across the street is the Westfield River Brook and Notchview Cross-Country Skiing is nearby.

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

    Unlisted Address
    • 344 Worthington Rd, Windsor, MA 01270
      344 Worthington Rd, Windsor, MA 01270
      344 Worthington Rd, Windsor, MA 01270
      /107

      Est $523,971 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,500 Sq Ft

      344 Worthington Rd, Windsor, MA 01270

      344 Worthington Rd, Windsor, MA 01270
  • 877 State Highway 9 --, Windsor, MA 01270
    877 State Highway 9 --, Windsor, MA 01270
    /2

    $439,900 Sold Oct 15, 2024

    • 1,782 Sq Ft
    • $247/SF
    • 69 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1952

    877 State Highway 9 --, Windsor, MA 01270

    Easy one level living with updated and kitchen and bath.

    Comparable Listing COMPARABLE LISTING ONLY

    877 State Highway 9 --, Windsor, MA 01270
    • 1540 E Windsor Rd, Windsor, MA 01270
      1540 E Windsor Rd, Windsor, MA 01270
      1540 E Windsor Rd, Windsor, MA 01270
      /52

      Est $499,371 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,080 Sq Ft

      1540 E Windsor Rd, Windsor, MA 01270

      1540 E Windsor Rd, Windsor, MA 01270
  • 249 Bates Rd, Windsor, MA 01270
    249 Bates Rd, Windsor, MA 01270
    /2

    $1,479,000 Sold Sep 26, 2024

    • 5,000 Sq Ft
    • $296/SF
    • 55 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1984

    249 Bates Rd, Windsor, MA 01270

    Discover Westview, a stunning retreat spanning 76 acres adjacent to Notchview Reservation, offering panoramic views.This contemporary hideaway boasts exceptional craftsmanship and thoughtful design.Inside, two kitchens feature expansive layouts, abundant natural light, and custom-built cabinets that adorn every room. The integration of granite, marble, and quartz countertops enhances elegance

    Elisha Poirier STONE HOUSE PROPERTIES, LLC

    249 Bates Rd, Windsor, MA 01270
    • 1256 E Windsor Rd, Windsor, MA 01270
      1256 E Windsor Rd, Windsor, MA 01270
      1256 E Windsor Rd, Windsor, MA 01270
      /34

      Est $818,843 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,102 Sq Ft

      1256 E Windsor Rd, Windsor, MA 01270

      1256 E Windsor Rd, Windsor, MA 01270
  • Unlisted Address
    Unlisted Address
    /2

    $49,900 Sold Jul 03, 2024

    • Land
    • 34 Acres
    • $1,468 per Acre
    • 9 Days On Market

    Unlisted Address

    Large lot of undisturbed raw land waiting for your vision. Property has easement on right border for Eversource.

    John Ciepiela BISHOP WEST REAL ESTATE

    Unlisted Address
    • 1411 North St, Windsor, MA 01270
      1411 North St, Windsor, MA 01270
      /2

      Est $596,071 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft

      1411 North St, Windsor, MA 01270

      1411 North St, Windsor, MA 01270
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /25

      Est $39,074 Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /11

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • 0 High Street Hill Rd Unit 73096931, Windsor, MA 01270
      0 High Street Hill Rd Unit 73096931, Windsor, MA 01270
      0 High Street Hill Rd Unit 73096931, Windsor, MA 01270
      /11

      Not Listed For Sale

      0 High Street Hill Rd Unit 73096931, Windsor, MA 01270

      0 High Street Hill Rd Unit 73096931, Windsor, MA 01270
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address
    • 140 Windigo Rd, Windsor, MA 01270
      140 Windigo Rd, Windsor, MA 01270
      140 Windigo Rd, Windsor, MA 01270
      /42

      Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      140 Windigo Rd, Windsor, MA 01270

      140 Windigo Rd, Windsor, MA 01270
    • 1136 Flintstone Rd, Windsor, MA 01270
      1136 Flintstone Rd, Windsor, MA 01270
      1136 Flintstone Rd, Windsor, MA 01270
      /4

      Est $88,714 Not Listed For Sale

      1136 Flintstone Rd, Windsor, MA 01270

      1136 Flintstone Rd, Windsor, MA 01270
    • 2065 River Rd, Windsor, MA 01270
      2065 River Rd, Windsor, MA 01270
      2065 River Rd, Windsor, MA 01270
      /31

      Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,900 Sq Ft

      2065 River Rd, Windsor, MA 01270

      2065 River Rd, Windsor, MA 01270
    • 1149 Shaw Rd, Windsor, MA 01270
      1149 Shaw Rd, Windsor, MA 01270
      1149 Shaw Rd, Windsor, MA 01270
      /53

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,238 Sq Ft

      1149 Shaw Rd, Windsor, MA 01270

      1149 Shaw Rd, Windsor, MA 01270
    • 45 Access #3 Rd, Windsor, MA 01270
      45 Access #3 Rd, Windsor, MA 01270
      45 Access #3 Rd, Windsor, MA 01270
      /5

      Est $184,179 Not Listed For Sale

      • 2 Beds
      • 1,145 Sq Ft

      45 Access #3 Rd, Windsor, MA 01270

      45 Access #3 Rd, Windsor, MA 01270
    • 2241 Massachusetts 9, Dalton, MA 01226
      2241 Massachusetts 9, Dalton, MA 01226
      2241 Massachusetts 9, Dalton, MA 01226
      /59

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,720 Sq Ft

      2241 Massachusetts 9, Dalton, MA 01226

      2241 Massachusetts 9, Dalton, MA 01226
    • 2241 Berkshire Trail Unit Trail, Dalton, MA 01226
      2241 Berkshire Trail Unit Trail, Dalton, MA 01226
      2241 Berkshire Trail Unit Trail, Dalton, MA 01226
      /42

      Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,720 Sq Ft

      2241 Berkshire Trail Unit Trail, Dalton, MA 01226

      2241 Berkshire Trail Unit Trail, Dalton, MA 01226
    • 52 Access 3b Rd, Windsor, MA 01270
      52 Access 3b Rd, Windsor, MA 01270
      52 Access 3b Rd, Windsor, MA 01270
      /42

      Est $139,140 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 777 Sq Ft

      52 Access 3b Rd, Windsor, MA 01270

      52 Access 3b Rd, Windsor, MA 01270

Showing Results 1 - 40, Page 1 of 18

Massachusetts Windsor

Real Estate & Homes

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 29 days on the market compared to the national average of 47 days. The average sale price for homes in Windsor, MA over the last 12 months is $374,950, down 23% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$424,950
Median Single Family Price
$424,950
Average Price Per Sq Ft
$246
Last 12 months Home Sales
4
Median List Price
$419,900
Median Discount From 1st List Price
-1%
Median Home Sale Price YoY Change
-19%
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