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Windsor, MA Homes for Sale

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  • 0 North St, Windsor, MA 01270
    0 North St, Windsor, MA 01270
    0 North St, Windsor, MA 01270
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    $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
  • 255 High St Hill Rd, Windsor, MA 01270
    255 High St Hill Rd, Windsor, MA 01270
    255 High St Hill Rd, Windsor, MA 01270
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    $749,900

    • 5 Beds
    • 3.5 Baths
    • 3,744 Sq Ft

    255 High St Hill Rd, Windsor, MA 01270

    Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and a dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of

    Jesse Dimitropolis RE/MAX COMPASS

    255 High St Hill Rd, Windsor, MA 01270
  • 200 Peru Rd, Windsor, MA 01270
    200 Peru Rd, Windsor, MA 01270
    200 Peru 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 21⁄2 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
  • 43 Access Road 4, Plainfield, MA 01070
    43 Access Road 4, Plainfield, MA 01070
    43 Access Road 4, Plainfield, MA 01070
    /10

    $114,999

    • 3 Beds
    • 1 Bath
    • 600 Sq Ft

    43 Access Road 4, Plainfield, MA 01070

    3 Bedroom camp with deeded lake rights at Windsor Pond. Ready for the new owner to make it their dreams into reality, needs well & septic, priced to sell

    Sean Taylor MORESI REAL ESTATE PARTNERS

    43 Access Road 4, Plainfield, MA 01070
Massachusetts Berkshire County

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 $477,884.
Are home prices dropping in Windsor?
Yes, home prices in Windsor are down 17% in the last 12 months.
How many homes have sold over the last 12 months in Windsor, MA?
11 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, 01256, 01070, 01226 and 01235.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $470,000. If you put a 20% down payment of $94,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $2,330 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $100K 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.

Home Prices in Windsor, MA

The median home sale price in Windsor, MA is $385,000, down 9% year-over-year. Homes in Windsor sell in 39 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$385,000
Median Single Family Sale Price
$391,000
Median Townhouse Sale Price
$749,900
Median 2 Bedroom Sale Price
$225,000
Median 1 Bedroom Sale Price
$300,000
Average Price Per Sq Ft
$216
Number of Homes for Sale
2
Last 12 months Home Sales
11
Months of Supply
2.20
Median List Price
$470,000
Median Change From 1st List Price
16%
Median Home Sale Price YoY Change
-9%
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