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Recently Sold Windsor, MA Homes

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  • /30

    $685,000 Sold Oct 30, 2025

    • 2,572 Sq Ft
    • $266/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    155 High St Hill Rd, Windsor, MA 01270

    Set on 10 private acres, this 3-bedroom, 2.5-bath Colonial offers comfort, privacy, and modern living. A welcoming entry, large windows, and an attached 3-car garage make a strong first impression. Inside, the open layout is perfect for entertaining or daily living. The kitchen features granite counters, stainless steel appliances, a center island, and plenty of storage, opening to the great room

    Jesse Dimitropolis RE/MAX COMPASS

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

    $397,000 Sold Oct 30, 2025

    • 2,728 Sq Ft
    • $146/SF
    • 14 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1987

    915 High St Hill Rd, Windsor, MA 01270

    This charming home is set on a peaceful county road surrounded by the natural beauty of the Berkshires. This inviting home features an open-concept layout with a seamless flow between the kitchen, dining, and living areas with a wood-burning fireplace. The first floor also includes a convenient bedroom and full bath. A three-season encllosed porch and a bright four-season sunroom provide

    Jessica Rizzo LAMACCHIA REALTY, INC

    915 High St Hill Rd, Windsor, MA 01270
  • /51

    $288,400 Sold Oct 23, 2025

    • 2,080 Sq Ft
    • $139/SF
    • 43 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2021

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

    The build started in 2021 and still in progress with passing Title V (2025) and Certificate of Occupancy (2023) in place. Relax and enjoy, this Cape style home is designed and built well, but the Owner is offering to you an opportunity to put your finishing touches on the property.The house boasts a steam shower with 2 tubs from Maxx Tubs, Loft and bonus rooms in basement. The Animal lover or

    John Ciepiela BISHOP WEST REAL ESTATE

    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
  • /35

    $600,000 Sold Oct 16, 2025

    • 1,914 Sq Ft
    • $313/SF
    • 4 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2008

    788 Flintstone Rd, Windsor, MA 01270

    Experience the ideal mix of comfort, privacy, and natural beauty on this beautifully maintained 19-acre property. Quietly tucked away, yet just minutes from the cultural and recreational attractions of the Berkshires, this move-in ready home offers serene country living with modern convenience.Built and cared for by the original owners, the home features 4 spacious bedrooms, 3 full bathrooms, and

    Laiken Rapisarda LAMACCHIA REALTY, INC

    788 Flintstone Rd, Windsor, MA 01270
  • /28

    $225,000 Sold Sep 30, 2025

    • 1,158 Sq Ft
    • $194/SF
    • 28 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 2016

    1621 Peru Rd, Windsor, MA 01270

    MOTIVATED SELLERS! 22 Private Acres in Windsor, MA The Perfect Off-The-Grid Escape! Ideal for the outdoor enthusiast. The unfinished home offers a solid start for a Hunting Cabin or Four Season Getaway. Surrounded by nature, the land is alive with Bear, Deer, Moose and more - Offering Prime Hunting or Snowmobiling as the trails are right there! Enjoy direct access to endless exploring and crisp

    Kim Dodge Kim Grant-Dodge

    1621 Peru Rd, Windsor, MA 01270
  • /52

    $435,000 Sold Jul 10, 2025

    • 2,444 Sq Ft
    • $178/SF
    • 95 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1850

    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
  • /53

    $505,000 Sold Jun 27, 2025

    • 1,562 Sq Ft
    • $323/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1993

    470 Peru Rd, Windsor, MA 01270

    Spacious 3-bedroom, 2.5-bath ranch offering over 1,500 sq. ft. of living space on 22+ peaceful acres. This well-maintained home features a finished basement with a cozy fireplace, perfect for relaxing or entertaining. The property includes a large two-bay barn, a charming sugar shack, and a network of scenic trails ideal for outdoor enjoyment. Whether you're looking for space to explore, hobby

    John Ciepiela BISHOP WEST REAL ESTATE

    470 Peru Rd, Windsor, MA 01270
  • /19

    $135,000 Sold Jun 05, 2025

    • 1,200 Sq Ft
    • $112/SF
    • 25 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1952

    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
  • /48

    $397,500 Sold Jun 03, 2025

    • 2,500 Sq Ft
    • $159/SF
    • 342 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1982

    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
  • /42

    $425,000 Sold May 23, 2025

    • 1,472 Sq Ft
    • $289/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    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
  • /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 the

    Laiken Rapisarda LAMACCHIA REALTY, INC

    130 High St Hill 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

Frequently Asked Questions

What is the average home price in Windsor, MA?
Homes for sale in Windsor, MA have an average home price of $434,646.
What is the average time to sell a house in Windsor, MA?
The houses for sale in Windsor, MA spend an average of 63 days on the market.
What is the number of active homes for sale in Windsor, MA?
There are 0 active homes for sale in Windsor, MA.
How many homes have sold over the last 12 months in Windsor, MA?
15 homes have sold in Windsor, MA over the last 12 months.

Home Trends in Windsor, MA

Housing Trends

Median Sale Price
$425,000
Median Single Family Sale Price
$425,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
0
Last 12 months Home Sales
15
Months of Supply
0.00
Median List Price
$439,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-15%
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