Windsor, MA Homes

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  /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
• Explore Windsor

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  /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

  Last Listing Agent Jesse Dimitropolis RE/MAX COMPASS

  155 High St Hill Rd, Windsor, MA 01270
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  /34

  Est $558,709 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
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  $33,200

  • Land
  • 5.2 Acres
  • $6,385 per Acre

  0 E Windsor Rd, Windsor, MA 01270

  Over 5 Acres of raw land located in the Berkshires that abuts a stream just waiting for the next chapter. The property does not have a current perk test and seller will not perform one prior. Seller will allow buyer to perform a perk test prior to purchase.

  MARK MCILQUHAM REALTY STREET, LLC

  0 E Windsor Rd, Windsor, MA 01270
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  $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 $516,487

  Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

  470 Peru Rd, Windsor, MA 01270
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  /56

  Est $450,523 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  102 Monahan Rd, Windsor, MA 01270

  102 Monahan Rd, Windsor, MA 01270
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  /24

  $325,000 Pending

  • 1 Bed
  • 1 Bath
  • 1,082 Sq Ft

  961 Peru Rd, Windsor, MA 01270

  Finish this super insulated house to your liking. Seller had to quit due to personal issues. High end kitchen cabinets are bought but not installed. Tub is installed. Sheet rock needs to be taped and spackled. Rough electric and plumbing are done. Super insulated tiny house for guests or separate home office has electricity but no plumbing. All work was permitted and inspected. Please see

  Carla Ness Delap Real Estate LLC

  961 Peru Rd, Windsor, MA 01270
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  /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 $433,277

  Last Listing Agent John Ciepiela BISHOP WEST REAL ESTATE

  576 North St, Windsor, MA 01270
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  /4

  Est $543,966 Not Listed For Sale

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

  884 Cheshire Rd, Windsor, MA 01270

  884 Cheshire Rd, Windsor, MA 01270
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  /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 $143,431

  Last Listing Agent Kolleen Schmitt BISHOP WEST REAL ESTATE

  1952 Old Route 9, Windsor, MA 01270
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  /24

  Est $235,702 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft

  1430 Old Route 9, Windsor, MA 01270

  1430 Old Route 9, Windsor, MA 01270
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  /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

  Last Listing Agent Kim Dodge Kim Grant-Dodge

  1621 Peru Rd, Windsor, MA 01270
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  /57

  Est $438,172 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  1600 North St, Windsor, MA 01270

  1600 North St, Windsor, MA 01270
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  /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

  Last Listing Agent Tanya LeRose THE KINDERHOOK GROUP

  1689 E Windsor Rd, Windsor, MA 01270
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  /39

  Est $680,032 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
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  $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
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  /42

  Est $591,848 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
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  /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 $593,196

  Last Listing Agent Laiken Rapisarda LAMACCHIA REALTY, INC

  788 Flintstone Rd, Windsor, MA 01270
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  /50

  Est $494,106 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  130 High St Hill Rd, Windsor, MA 01270

  130 High St Hill Rd, Windsor, MA 01270
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  $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

  Last Listing Agent Jessica Rizzo LAMACCHIA REALTY, INC

  915 High St Hill Rd, Windsor, MA 01270
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  /35

  Est $554,925 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
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  $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 $442,196

  Last Listing Agent Cindy Carrigan Lamacchia Realty, Inc.

  775 North St, Windsor, MA 01270
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  /21

  Est $572,730 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
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  $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 $418,310

  Last Listing Agent Pauline Green STEEPLEVIEW REALTY - ADAMS BRANCH

  1523 North St, Windsor, MA 01270
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  /107

  Est $515,677 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
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  /28

  Est $639,419 Not Listed For Sale

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

  1411 North St, Windsor, MA 01270

  1411 North St, Windsor, MA 01270
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  /29

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,014 Sq Ft

  143 Windsor Bush Rd, Cummington, MA 01026

  143 Windsor Bush Rd, Cummington, MA 01026
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  /25

  Not Listed For Sale

  • 1 Bed
  • 350 Sq Ft

  1555 Bush Rd, Windsor, MA 01270

  1555 Bush Rd, Windsor, MA 01270
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  /42

  Est $577,780 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,596 Sq Ft

  696 River Rd, Windsor, MA 01270

  696 River Rd, Windsor, MA 01270
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  /11

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /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
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  /7

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /18

  Not Listed For Sale

  331 Shaw Rd, Windsor, MA 01270

  331 Shaw Rd, Windsor, MA 01270
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  /42

  Est $140,894 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
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  /3

  Not Listed For Sale

  Unlisted Address

  Unlisted Address
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  /38

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,782 Sq Ft

  877 Massachusetts 9, Windsor, MA 01270

  877 Massachusetts 9, Windsor, MA 01270
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  /6

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,266 Sq Ft

  11 Windigo Rd, Windsor, MA 01070

  11 Windigo Rd, Windsor, MA 01070
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  /38

  Est $619,877 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
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  /29

  Est $402,381 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  1742 E Windsor Rd, Windsor, MA 01270

  1742 E Windsor Rd, Windsor, MA 01270
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  /36

  Est $380,353 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,202 Sq Ft

  449 High St Hill Rd, Windsor, MA 01270

  449 High St Hill Rd, Windsor, MA 01270

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