$724,900
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 and upper-level flex room—ideal for extended living, guests or a variety of household needs. Soaring ceilings, exposed timber beams, hardwood floors and a dramatic center chimney add character throughout, complemented by multiple wood-burning fireplaces, a pellet stove and abundant natural light. Additional highlights include an owned 9.52 kW solar system, oversized attached garage, spacious decks and generous parking, all within a short drive of Berkshire attractions and Northampton.
Property Details
Price:
$724,900
MLS #:
73564933
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jul 6, 2026
Finished Sq Ft:
3,744
Total Sq Ft:
3,744
Lot Size:
141,134 sqft / 3.24 acres (approx)
Year Built:
1987
Schools
Interior
Above Grade Finished Area
3744
Appliances
Water Heater, Range, Refrigerator, Washer, Dryer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
None
Fireplaces Total
2
Flooring
Wood, Tile, Carpet, Laminate
Heating
Baseboard, Oil
Interior Features
High Speed Internet
Exterior
Architectural Style
Contemporary, Saltbox
Attached Garage YN
1
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Deck
Garage Spaces
2
Lot Features
Gentle Sloping
Open Parking Spaces
6
Parking Features
Under, Garage Door Opener, Off Street
Parking Spots
8
Parking Total
8
Patio And Porch Features
Deck
Roof
Shingle
Window Features
Insulated Windows
Financial
Tax Year
2025
Taxes
$5,263
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Windsor as of Sep 18, 2026
4
Single Family Listed
56
Avg DOM
230
Avg $ / SqFt
$543,700
Avg List Price
Community
- Address255 High St Hill Rd Windsor MA
- CityWindsor
- CountyBerkshire
- Zip Code01270
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Property Summary
- 255 High St Hill Rd Windsor MA is a Single Family for sale in Windsor, MA, 01270. It is listed for $724,900 and features 5 beds, 4 baths, and has approximately 3,744 square feet of living space, and was originally constructed in 1987. The current price per square foot is $194. The average price per square foot for Single Family listings in Windsor is $230. The average listing price for Single Family in Windsor is $543,700. To schedule a showing of MLS#73564933 at 255 High St Hill Rd in Windsor, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Berkshire Reciprocal. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
255 High St Hill Rd
Windsor, MA