5

Windsor, MA Houses for Sale

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

    $549,000

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

    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
  • 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
    /35

    $485,000 Open Sat 10AM - 12PM

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

    1689 E Windsor Rd, Windsor, MA 01270

    Country colonial home which has never been on the market. Built by the sellers and their family of contractors. Situated on a picturesque corner lot with a spring & brook-fed pond. Step inside from the new deck to find a cherry wood floor, updated kitchen with granite countertops and a one of a kind island. The dining room and sunny living space boast hickory wood floors and Anderson windows. A

    Tanya LeRose THE KINDERHOOK GROUP - PITTSFIELD

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

Houses 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

Home Trends in Windsor, MA

On average, homes in Windsor, MA sell after 47 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%
How to Buy a Home How to Finance a Home How to Sell a Home

In Windsor, there are currently 5 houses for sale, offering an array of options for potential buyers. With houses priced between $179,000 to $1,195,000, there's a range to accomodate every budget. As of August, 2025 the median home price in Windsor is $439,900, while the average sale price is $439,900, offering insights into the local housing market. On average, houses spend 47 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Windsor, MA and find the perfect place to call home.

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