6

Windsor, MA Homes for Sale

Section Image
  • /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
  • /56

    $549,900

    • 3 Beds
    • 3 Baths
    • 2,142 Sq Ft

    1273 Old Route 9, Windsor, MA 01270

    Discover the charm and character of this 1980\text{s}-built home in Windsor, thoughtfully constructed on an original stone foundation. Set on approximately 2.5 acres, the property offers a blend of historic detail, comfortable living space, and a scenic setting.The home features three bedrooms and three full bathrooms, along with a fireplace that adds warmth and character to the living area.

    John Ciepiela BISHOP WEST REAL ESTATE

    1273 Old Route 9, Windsor, MA 01270
  • /38

    $395,000

    • 3 Beds
    • 1 Bath
    • 1,236 Sq Ft

    1760 Route 9, Windsor, MA 01270

    Idyllic Berkshire living on 3 open acres with views of Mt. Greylock and no close neighbors! This 3-bedroom ranch offers easy single-level living with hardwood floors, a spacious eat-in kitchen with new appliances, and a striking floor-to-ceiling stone fireplace that gives the home so much character. Outside, the property is made to be enjoyed, with a newer deck, raised garden beds, expansive

    THE KAHN TEAM BISHOP WEST REAL ESTATE

    1760 Route 9, Windsor, MA 01270
  • /36

    $724,900

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,744 Sq Ft

    255 High St Hill Rd, Windsor, MA 01270

    Tucked away on 3.24 wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across multiple finished levels. The main home features four bedrooms, 2.5 baths, spacious living, family and dining rooms, plus a third-floor great room and additional flex space. A separate in-law suite adds exceptional versatility with its own kitchen, living room, bedroom, full bath, deck

    Jesse Dimitropolis RE/MAX COMPASS

    255 High St Hill Rd, Windsor, MA 01270
  • /42

    $699,900

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft

    200 Peru Rd, Windsor, MA 01270

    Enjoy comfort, space, and privacy in this custom 8-room post and beam home set on 25.3 scenic acres. The property features 2½ bathrooms, Bruce hardwood floors, first-floor laundry, and a spacious living room with high ceilings and a pellet fireplace. The partially finished basement adds living space with a family room, wood-burning fireplace, and bar area. An oversized two-car garage provides

    Zahi Haddad Zee Haddad Realty

    200 Peru Rd, Windsor, MA 01270
  • /19

    $35,000

    • Land
    • 1.6 Acres
    • $21,875 per Acre

    Lot 134 Shaw Rd, Windsor, MA 01270

    Evamarie Best Wolcott Realty

    Lot 134 Shaw Rd, Windsor, MA 01270

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.

Windsor, MA Home Prices

Windsor, MA
Median Home Price
$472,450
Median Sale Price
$385,000
-11% YoY
Avg. Price per Square Foot
$226
Median Single Family Price
$396,000
Median Townhouse Price
$724,900
Total Active Listings
6 listings
Market Conditions
4 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Windsor, MA?
Homes for sale in Windsor, MA have an average home price of $483,733.
Are home prices dropping in Windsor?
Yes, home prices in Windsor are down 22% in the last 12 months.
How many homes have sold over the last 12 months in Windsor, MA?
13 homes have sold in Windsor, MA over the last 12 months.
What is the average household income in Windsor, MA?
The average household income in Windsor, MA is $134K.
What are the most popular zip codes in Windsor, MA?
The most popular zip codes in Windsor, MA include 01270, 01235, 01256, 01226 and 01225.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $472,450. If you put a 20% down payment of $94,500 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $2,500 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $107K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Windsor is $134K.
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 Emma L. Miller Memorial Elementary School, Wahconah Regional High School and Mohawk Trail Regional High School. Browse all the schools in Windsor, MA to learn more.
How to Buy a Home How to Finance a Home How to Sell a Home