694

Windsor, MA Homes

Section Image Section Image
  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

  • /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
    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

    • /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

Home Trends in Windsor, MA

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%
How to Buy a Home How to Finance a Home How to Sell a Home