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Windsor, MA Homes for Sale

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  • 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
    /50

    $349,900 Open Sat 11AM - 12:30PM

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

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

    The build started in 2021 and still in progress this A frame 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 gardner will appreciate the natural spring on the property.

    Agent Photo

    John Ciepiela

    BISHOP WEST REAL ESTATE

    (413) 268-4615

    2652 Ma-9 (Berkshire Trail) Trail, Windsor, MA 01270
  • 49 Access Rd Unit 3b, Windsor, MA 01270
    49 Access Rd Unit 3b, Windsor, MA 01270
    49 Access Rd Unit 3b, Windsor, MA 01270
    /17

    $179,000

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft

    49 Access Rd Unit 3b, Windsor, MA 01270

    This charming 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) 741-2269

    49 Access Rd Unit 3b, Windsor, MA 01270
  • 1621 Peru Rd, Windsor, MA 01270
    1621 Peru Rd, Windsor, MA 01270
    1621 Peru Rd, Windsor, MA 01270
    /28

    $290,000

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

    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
  • 1828 Flintstone Rd, Windsor, MA 01270
    1828 Flintstone Rd, Windsor, MA 01270
    1828 Flintstone Rd, Windsor, MA 01270
    /69

    $1,195,000

    • 4 Beds
    • 3 Baths
    • 3,541 Sq Ft

    1828 Flintstone Rd, Windsor, MA 01270

    Welcome to Stone Hill - Your Private Oasis with Spectacular Views overlooking the Berkshire Hill Towns. Escape to a world of tranquility and luxury where nature's beauty meets exquisite living. Nestled on a 9.45 acre property, this spectacular estate offers the ultimate retreat for those seeking privacy and serenity. Immerse yourself in the beauty of the Chalet Wildlife Management Area

    Matt Carlino MACCARO REAL ESTATE

    1828 Flintstone Rd, Windsor, MA 01270
  • 961 Peru Rd, Windsor, MA 01270
    961 Peru Rd, Windsor, MA 01270
    961 Peru Rd, Windsor, MA 01270
    /24

    $325,000

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

    $435,000 Open Sun 10AM - 12PM

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

    1689 E Windsor Rd, Windsor, MA 01270

    A rare find: 3 Bedroom colonial home with a picturesque pond for endless enjoyment. Dining under the stars in your private backyard oasis and waking up to breathtaking views and gentle melodies of nature. Discover the magic where memories are waiting to be made. Anderson windows and doors. A brick chimney with a wood stove adds seasonal warmth to the living room. The back porch entices you to

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

    1689 E Windsor Rd, Windsor, MA 01270
Massachusetts Berkshire County Windsor

Real Estate & Homes for Sale in Windsor, MA

Why Live in Windsor

Windsor, Massachusetts, nestled in the tranquil Berkshires, offers residents a rural lifestyle surrounded by trees and natural beauty. Located 20 miles south of the Vermont border, Windsor is characterized by its quiet, slow-paced environment, ideal for those seeking a peaceful retreat. Home styles in Windsor range from off-grid cottages to expansive hillside retreats, with ranch-style homes, saltboxes, and farmhouses dotting the landscape. Outdoor recreation is abundant, with the Hoosac Range providing opportunities for hiking, snowshoeing, and snowmobiling. Tamarack Hollow Nature & Cultural Center offers guided hikes, while Wahconah Falls State Park features a dog-friendly trail leading to a stunning 40-foot waterfall. Windsor State Forest spans 1,800 acres, offering year-round activities such as hunting and hiking. Notchview, a Trustees of Reservations property, is popular for cross-country skiing and biking.

Residents are zoned for Central Berkshire Public Schools, which have high ratings and graduation rates between 94% and 97%. Windsor is a car-dependent area, with Berkshire Trail connecting it to other communities. Emergency care is available 30 minutes away at North Adams Regional Hospital, and Bradley International Airport is about an hour and 20 minutes south. Shopping and dining options are at least 20 minutes away, with local favorites like homemade samosas at Sanger General Store and groceries at Old Creamery Co-Op in Cummington. Dining in Dalton includes Shire Tavern, known for its farmhouse-style ambiance. Nearby Cummington hosts agricultural events and fairs, including the Hampshire County 4-H Fair and the Massachusetts Sheep and Woolcraft Fair, providing family-friendly entertainment.

Learn more about living in Windsor

Frequently Asked Questions

What is the average home price in Windsor, MA?
Homes for sale in Windsor, MA have an average home price of $411,175.
How many homes have sold over the last 12 months in Windsor, MA?
3 homes have sold in Windsor, MA over the last 12 months.
What are the most popular zip codes in Windsor, MA?
The most popular zip codes in Windsor, MA include 01270, 01256, 01235, 01225 and 01226.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $439,900. If you put a 20% down payment of $88,000 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $2,250 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $96K a year to afford the median home price in Windsor.
How are the schools in Windsor, MA?
Windsor, MA has highly rated public and private schools. Some of the best schools in Windsor based on Niche Grades are Wahconah Regional High School, Mohawk Trail Regional High School and Emma L. Miller Memorial Elementary School. Browse all the schools in Windsor, MA to learn more.

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 69 days on the market compared to the national average of 70 days. The median sale price for homes in Windsor, MA over the last 12 months is $439,900, up 443% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$439,900
Median Single Family Sale Price
$439,900
Average Price Per Sq Ft
$260
Number of Homes for Sale
1
Last 12 months Home Sales
3
Months of Supply
4.00
Median List Price
$439,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
443%
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