694

Windsor, MA Homes

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  • 49 Access Rd Unit 3b, Windsor, MA 01270
    49 Access Rd Unit 3b, Windsor, MA 01270
    49 Access Rd Unit 3b, Windsor, MA 01270
    /25

    $95,000

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    49 Access Rd Unit 3b, Windsor, MA 01270

    This charming and rustic seasonal lake cottage, rebuilt in 2011 with structural enhancements, replacement windows, and a large side deck, is a cozy retreat nestled on 1.24 wooded acres by Windsor Pond. The interiors are adorned with knotty pine, giving it a warm and inviting feel harkening to an era past. With two comfy bedrooms, a wood stove to keep you warm on chilly nights, a spacious screened

    Agent Photo

    Lisa Carroll

    Delap Real Estate LLC

    (413) 779-8496

    49 Access Rd Unit 3b, Windsor, MA 01270
  • 155 High St Hill Rd, Windsor, MA 01270
    155 High St Hill Rd, Windsor, MA 01270
    155 High St Hill Rd, Windsor, MA 01270
    /30

    $685,000 Sold Oct 30, 2025

    155 High St Hill Rd, Windsor, MA 01270

    • 3 Beds
    • 2.5 Baths
    • 2,572 Sq Ft
    • Built 2003

    Last Sold Summary

    • 1% Above List Price
    • $266/SF
    • 4 Days On Market

    Current Estimated Value $692,169

    Last Listing Agent Jesse Dimitropolis RE/MAX COMPASS

    155 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 $541,852 Not Listed For Sale

      140 Hill Cemetery Rd, Windsor, MA 01270

      • 4 Beds
      • 2.5 Baths
      • 2,260 Sq Ft
      • Built 2005
      140 Hill Cemetery Rd, Windsor, MA 01270

      Last Sold Summary

      • $239/SF
      • 50 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Michelle Picard NOCHER REALTY

  • 0 North St, Windsor, MA 01270
    0 North St, Windsor, MA 01270
    0 North St, Windsor, MA 01270
    /6

    $99,900

    • Land
    • 4 Acres
    • $24,975 per Acre

    0 North St, Windsor, MA 01270

    Discover the possibilities with this beautiful 4-acre wooded corner lot in Windsor, MA. Offering privacy and natural surroundings, the property features a small brook and direct frontage on a paved road for easy access. Across from state land, it's an ideal spot for a private retreat, vacation home, or year-round residence. Additional acreage is available for those seeking even more space to

    Amanda Kmetz ROBERTS & ASSOC. REALTY, INC

    0 North St, Windsor, MA 01270
  • 470 Peru Rd, Windsor, MA 01270
    470 Peru Rd, Windsor, MA 01270
    470 Peru Rd, Windsor, MA 01270
    /53

    $505,000 Sold Jun 27, 2025

    470 Peru Rd, Windsor, MA 01270

    • 3 Beds
    • 2.5 Baths
    • 1,562 Sq Ft
    • Built 1993

    Last Sold Summary

    • 12% Above List Price
    • $323/SF
    • 27 Days On Market

    Current Estimated Value $516,266

    Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

    470 Peru Rd, Windsor, MA 01270
    • 102 Monahan Rd, Windsor, MA 01270
      102 Monahan Rd, Windsor, MA 01270
      102 Monahan Rd, Windsor, MA 01270
      /56

      Est $454,518 Not Listed For Sale

      102 Monahan Rd, Windsor, MA 01270

      • 3 Beds
      • 2 Baths
      • 1,490 Sq Ft
      • Built 1992
      102 Monahan Rd, Windsor, MA 01270

      Last Sold Summary

      • 11% Above List Price
      • $275/SF
      • 1 Day On Market

      Last Sold Price $410,000

      Last Listing Agent Doug Collins LAMACCHIA REALTY, INC

  • 43 Access Road 4, Plainfield, MA 01070
    43 Access Road 4, Plainfield, MA 01070
    43 Access Road 4, Plainfield, MA 01070
    /10

    $114,999

    • 3 Beds
    • 1 Bath
    • 600 Sq Ft

    43 Access Road 4, Plainfield, MA 01070

    3 Bedroom camo with deeded lake rights at Windsor Pond. Ready for the new owner to make it their dreams into reality, needs well & septic, priced to sell

    Sean Taylor MORESI REAL ESTATE PARTNERS

    43 Access Road 4, Plainfield, MA 01070
  • 0 E Windsor Rd, Windsor, MA 01270
    0 E Windsor Rd, Windsor, MA 01270
    0 E Windsor Rd, Windsor, MA 01270
    /4

    $30,000 Sold Mar 31, 2026

    0 E Windsor Rd, Windsor, MA 01270

    • Land
    • 5.2 Acres
    • $5,769 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 393 Days On Market

    Last Listing Agent MARK MCILQUHAM REALTY STREET, LLC

    0 E Windsor Rd, 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

      Est $226,735 Not Listed For Sale

      1430 Old Route 9, Windsor, MA 01270

      • 2 Beds
      • 1 Bath
      • 975 Sq Ft
      • Built 1975
      1430 Old Route 9, Windsor, MA 01270

      Last Sold Summary

      • 8% Above List Price
      • $215/SF
      • 42 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Ann Jerebtsov LAMACCHIA REALTY, INC

  • 576 North St, Windsor, MA 01270
    576 North St, Windsor, MA 01270
    576 North St, Windsor, MA 01270
    /52

    $435,000 Sold Jul 10, 2025

    576 North St, Windsor, MA 01270

    • 4 Beds
    • 2 Baths
    • 2,444 Sq Ft
    • Built 1850

    Last Sold Summary

    • 3% Below List Price
    • $178/SF
    • 95 Days On Market

    Current Estimated Value $433,381

    Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

    576 North St, Windsor, MA 01270
    • 733 North St, Windsor, MA 01270
      733 North St, Windsor, MA 01270
      733 North St, Windsor, MA 01270
      /39

      Est $677,277 Not Listed For Sale

      733 North St, Windsor, MA 01270

      • 3 Beds
      • 2.5 Baths
      • 2,350 Sq Ft
      • Built 1988
      733 North St, Windsor, MA 01270

      Last Sold Summary

      • 3% Above List Price
      • $281/SF
      • 20 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Maggie Gavin William Pitt

  • 1952 Old Route 9, Windsor, MA 01270
    1952 Old Route 9, Windsor, MA 01270
    1952 Old Route 9, Windsor, MA 01270
    /19

    $135,000 Sold Jun 05, 2025

    1952 Old Route 9, Windsor, MA 01270

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1952

    Last Sold Summary

    • $112/SF
    • 25 Days On Market

    Current Estimated Value $140,420

    Last Listing Agent Kolleen Schmitt KELLER WILLIAMS REALTY

    1952 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 $553,622 Not Listed For Sale

      1496 North St, Windsor, MA 01270

      • 4 Beds
      • 2.5 Baths
      • 2,241 Sq Ft
      • Built 1986
      1496 North St, Windsor, MA 01270

      Last Sold Summary

      • 12% Above List Price
      • $221/SF
      • 5 Days On Market

      Last Sold Price $495,000

      Last Listing Agent Elle Strycharz Real Broker MA, LLC

  • 1621 Peru Rd, Windsor, MA 01270
    1621 Peru Rd, Windsor, MA 01270
    1621 Peru Rd, Windsor, MA 01270
    /28

    $225,000 Sold Sep 30, 2025

    1621 Peru Rd, Windsor, MA 01270

    • 2 Beds
    • 1 Bath
    • 1,158 Sq Ft
    • Built 2016

    Last Sold Summary

    • 32% Below List Price
    • $194/SF
    • 28 Days On Market

    Current Estimated Value $238,937

    Last Listing Agent Kim Dodge Kim Grant-Dodge

    1621 Peru Rd, 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

      Est $493,269 Not Listed For Sale

      130 High St Hill Rd, Windsor, MA 01270

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 2004
      130 High St Hill Rd, Windsor, MA 01270

      Last Sold Summary

      • 7% Above List Price
      • $205/SF
      • 3 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  • 1689 E Windsor Rd, Windsor, MA 01270
    1689 E Windsor Rd, Windsor, MA 01270
    1689 E Windsor Rd, Windsor, MA 01270
    /58

    $385,000 Sold Jan 09, 2026

    1689 E Windsor Rd, Windsor, MA 01270

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft
    • Built 1976

    Last Sold Summary

    • 34% Below List Price
    • $236/SF
    • 141 Days On Market

    Current Estimated Value $388,697

    Last Listing Agent Tanya LeRose THE KINDERHOOK GROUP

    1689 E Windsor 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 $519,844 Not Listed For Sale

      105 High St Hill Rd, Windsor, MA 01270

      • 3 Beds
      • 3 Baths
      • 2,500 Sq Ft
      • Built 1988
      105 High St Hill Rd, Windsor, MA 01270

      Last Sold Summary

      • 13% Above List Price
      • $184/SF
      • 129 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Tanya LeRose THE KINDERHOOK GROUP

  • 961 Peru Rd, Windsor, MA 01270
    961 Peru Rd, Windsor, MA 01270
    961 Peru Rd, Windsor, MA 01270
    /24

    $300,000 Sold Feb 03, 2026

    961 Peru Rd, Windsor, MA 01270

    • 1 Bed
    • 1 Bath
    • 1,082 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $277/SF
    • 75 Days On Market

    Last Listing Agent Carla Ness Delap Real Estate LLC

    961 Peru Rd, Windsor, MA 01270
    • 344 Worthington Rd, Windsor, MA 01270
      344 Worthington Rd, Windsor, MA 01270
      344 Worthington Rd, Windsor, MA 01270
      /107

      Est $480,025 Not Listed For Sale

      344 Worthington Rd, Windsor, MA 01270

      • 2 Beds
      • 1.5 Baths
      • 1,500 Sq Ft
      • Built 1989
      344 Worthington Rd, Windsor, MA 01270

      Last Sold Summary

      • 5% Below List Price
      • $337/SF
      • 4 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Cindy Carrigan LAMACCHIA REALTY, INC

  • 2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
    /51

    $288,400 Sold Oct 23, 2025

    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270

    • 2 Beds
    • 2 Baths
    • 2,080 Sq Ft
    • Built 2021

    Last Sold Summary

    • 18% Below List Price
    • $139/SF
    • 43 Days On Market

    Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
    • 1411 North St, Windsor, MA 01270
      1411 North St, Windsor, MA 01270
      1411 North St, Windsor, MA 01270
      /28

      Est $618,996 Not Listed For Sale

      1411 North St, Windsor, MA 01270

      • 3 Beds
      • 1.5 Baths
      • 2,160 Sq Ft
      • Built 1980
      1411 North St, Windsor, MA 01270

      Last Sold Summary

      • 8% Above List Price
      • $266/SF
      • 26 Days On Market

      Last Sold Price $575,000

      Last Listing Agent Kathleen Fisher NON-MEMBER / RECIPROCAL

  • 788 Flintstone Rd, Windsor, MA 01270
    788 Flintstone Rd, Windsor, MA 01270
    788 Flintstone Rd, Windsor, MA 01270
    /35

    $600,000 Sold Oct 16, 2025

    788 Flintstone Rd, Windsor, MA 01270

    • 4 Beds
    • 3 Baths
    • 1,914 Sq Ft
    • Built 2008

    Last Sold Summary

    • 9% Above List Price
    • $313/SF
    • 4 Days On Market

    Current Estimated Value $602,828

    Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

    788 Flintstone Rd, 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

      Not Listed For Sale

      143 Windsor Bush Rd, Cummington, MA 01026

      • 2 Beds
      • 1.5 Baths
      • 1,014 Sq Ft
      • Built 1965
      143 Windsor Bush Rd, Cummington, MA 01026

      Last Sold Summary

      • $286/SF
      • 4 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Altaluxre Group William Pitt Sotheby's International Realty

  • 915 High St Hill Rd, Windsor, MA 01270
    915 High St Hill Rd, Windsor, MA 01270
    915 High St Hill Rd, Windsor, MA 01270
    /60

    $397,000 Sold Oct 30, 2025

    915 High St Hill Rd, Windsor, MA 01270

    • 4 Beds
    • 2 Baths
    • 2,728 Sq Ft
    • Built 1987

    Last Sold Summary

    • 16% Below List Price
    • $146/SF
    • 14 Days On Market

    Current Estimated Value $412,910

    Last Listing Agent Jessica Rizzo LAMACCHIA REALTY, INC

    915 High St Hill Rd, Windsor, MA 01270
    • 1555 Bush Rd, Windsor, MA 01270
      1555 Bush Rd, Windsor, MA 01270
      1555 Bush Rd, Windsor, MA 01270
      /25

      Not Listed For Sale

      1555 Bush Rd, Windsor, MA 01270

      • 1 Bed
      • 350 Sq Ft
      • Built 1990
      1555 Bush Rd, Windsor, MA 01270

      Last Sold Summary

      • $231/SF
      • 3 Days On Market

      Last Sold Price $81,000

      Last Listing Agent Craig Kahn ALL SEASONS REALTY GROUP

  • 775 North St, Windsor, MA 01270
    775 North St, Windsor, MA 01270
    775 North St, Windsor, MA 01270
    /42

    $425,000 Sold May 23, 2025

    775 North St, Windsor, MA 01270

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Above List Price
    • $289/SF
    • 6 Days On Market

    Current Estimated Value $438,149

    Last Listing Agent Cindy Carrigan Lamacchia Realty, Inc.

    775 North St, Windsor, MA 01270
    • 696 River Rd, Windsor, MA 01270
      696 River Rd, Windsor, MA 01270
      696 River Rd, Windsor, MA 01270
      /42

      Est $637,994 Not Listed For Sale

      696 River Rd, Windsor, MA 01270

      • 2 Beds
      • 2 Baths
      • 1,596 Sq Ft
      • Built 1988
      696 River Rd, Windsor, MA 01270

      Last Sold Summary

      • 4% Above List Price
      • $383/SF
      • 18 Days On Market

      Last Sold Price $612,000

      Last Listing Agent Kolleen Schmitt KELLER WILLIAMS REALTY

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

    $397,500 Sold Jun 03, 2025

    1523 North St, Windsor, MA 01270

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft
    • Built 1982

    Last Sold Summary

    • 6% Below List Price
    • $159/SF
    • 342 Days On Market

    Current Estimated Value $420,832

    Last Listing Agent Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

    1523 North St, Windsor, MA 01270
    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /11

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 41 Days On Market

      Last Sold Price $44,900

      Last Listing Agent Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

    • 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

      Last Sold Summary

      • 3 Days On Market

      Last Sold Price $27,000

      Last Listing Agent Jeffrey Hiser Key Realty in Western MA

    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /7

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 8 Days On Market

      Last Sold Price $27,000

      Last Listing Agent Jeffrey Hiser KEY REALTY

    • 331 Shaw Rd, Windsor, MA 01270
      331 Shaw Rd, Windsor, MA 01270
      331 Shaw Rd, Windsor, MA 01270
      /18

      Not Listed For Sale

      331 Shaw Rd, Windsor, MA 01270

      331 Shaw Rd, Windsor, MA 01270

      Last Sold Summary

      • 7 Days On Market

      Last Sold Price $17,000

      Last Listing Agent Deb Trzcinski Steepleview Realty

    • Unlisted Address
      Unlisted Address
      Unlisted Address
      /3

      Not Listed For Sale

      Unlisted Address

      Unlisted Address

      Last Sold Summary

      • 126 Days On Market

      Last Sold Price $25,000

      Last Listing Agent Tanya LeRose THE KINDERHOOK GROUP

    • 877 Massachusetts 9, Windsor, MA 01270
      877 Massachusetts 9, Windsor, MA 01270
      877 Massachusetts 9, Windsor, MA 01270
      /38

      Not Listed For Sale

      877 Massachusetts 9, Windsor, MA 01270

      • 2 Beds
      • 1.5 Baths
      • 1,782 Sq Ft
      • Built 1952
      877 Massachusetts 9, Windsor, MA 01270

      Last Sold Summary

      • $247/SF
      • 5 Days On Market

      Last Sold Price $439,900

      Last Listing Agent Holly Berry Olde Towne Realty

    • 11 Windigo Rd, Windsor, MA 01070
      11 Windigo Rd, Windsor, MA 01070
      11 Windigo Rd, Windsor, MA 01070
      /6

      Not Listed For Sale

      11 Windigo Rd, Windsor, MA 01070

      • 5 Beds
      • 4 Baths
      • 3,266 Sq Ft
      • Built 1798
      11 Windigo Rd, Windsor, MA 01070

      Last Sold Summary

      • $148/SF
      • 238 Days On Market

      Last Sold Price $485,000

      Last Listing Agent Kolleen Schmitt Keller Williams Realty

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

      Est $571,499 Not Listed For Sale

      884 Cheshire Rd, Windsor, MA 01270

      • 2 Beds
      • 2 Baths
      • 2,042 Sq Ft
      • Built 1970
      884 Cheshire Rd, Windsor, MA 01270

      Last Sold Summary

      • 18% Above List Price
      • $238/SF
      • 106 Days On Market

      Last Sold Price $485,500

      Last Listing Agent Paul Harsch HARSCH ASSOCIATES

    • 1387 E Windsor Rd, Windsor, MA 01270
      1387 E Windsor Rd, Windsor, MA 01270
      1387 E Windsor Rd, Windsor, MA 01270
      /38

      Est $644,995 Not Listed For Sale

      1387 E Windsor Rd, Windsor, MA 01270

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 2004
      1387 E Windsor Rd, Windsor, MA 01270

      Last Sold Summary

      • 24% Above List Price
      • $236/SF
      • 87 Days On Market

      Last Sold Price $520,000

      Last Listing Agent Sherry Street REALTY STREET, LLC

    • 1742 E Windsor Rd, Windsor, MA 01270
      1742 E Windsor Rd, Windsor, MA 01270
      1742 E Windsor Rd, Windsor, MA 01270
      /29

      Est $416,269 Not Listed For Sale

      1742 E Windsor Rd, Windsor, MA 01270

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1994
      1742 E Windsor Rd, Windsor, MA 01270

      Last Sold Summary

      • 30% Above List Price
      • $168/SF
      • 34 Days On Market

      Last Sold Price $319,000

      Last Listing Agent Tim Hart HART REALTY

    • 1600 North St, Windsor, MA 01270
      1600 North St, Windsor, MA 01270
      1600 North St, Windsor, MA 01270
      /57

      Est $473,209 Not Listed For Sale

      1600 North St, Windsor, MA 01270

      • 3 Beds
      • 1 Bath
      • 1,680 Sq Ft
      • Built 1983
      1600 North St, Windsor, MA 01270

      Last Sold Summary

      • 14% Above List Price
      • $247/SF
      • 3 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Mariah Worth LAMACCHIA REALTY, INC

    • 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 $568,737 Not Listed For Sale

      235 High St Hill Rd, Windsor, MA 01270

      • 3 Beds
      • 2 Baths
      • 2,716 Sq Ft
      • Built 2001
      235 High St Hill Rd, Windsor, MA 01270

      Last Sold Summary

      • 27% Above List Price
      • $166/SF
      • 9 Days On Market

      Last Sold Price $449,500

      Last Listing Agent Jesse Dimitropolis RE/MAX

Showing Results 1 - 40, Page 1 of 18

Massachusetts Berkshire County Windsor

Real Estate & Homes

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 68 days on the market compared to the national average of 55 days. The median sale price for homes in Windsor, MA over the last 12 months is $397,500, down 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$397,500
Median Single Family Sale Price
$397,500
Average Price Per Sq Ft
$215
Number of Homes for Sale
1
Last 12 months Home Sales
16
Months of Supply
0.80
Median List Price
$425,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-10%
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