Single Family for Sale: 255 High St Hill Rd, Windsor, MA 01270

5 beds
3 full, 1 half baths
3,744 sqft
$724,900
$724,900
255 High St Hill Rd, Windsor, MA 01270
5 beds
3 full, 1 half baths
3,744 sqft
$724,900
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Price:
$724,900
$25,000 - 08/27/2026

Type Single Family
Style Saltbox, Contemporary
Beds 5
Baths 3 full, 1 half baths
Square Feet 3,744 sqft
Garage Spaces 2
Lot Size 3.24 acres
Year Built 1987

City Windsor
County Berkshire

MLS 73564933
Status Active
DOM 96 days
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.

Lot & Building Features

Appliances Water Heater, Dryer, Washer, Refrigerator, Range
Construction Frame
Cooling None
Heating Oil, Baseboard
Sewer Private Sewer
Tax Year 2025
Taxes Paid $5,263
Water Private
Foundation Concrete Perimeter
Exterior Features Deck
Interior Features High Speed Internet
Roof Shingle
Full Baths 3
Half Baths 1
Parking Under, Garage Door Opener, Off Street
Total Rooms 9
Basement Feature Concrete, Full
Garage Spaces 2
Fireplaces 2

Price History of 255 High St Hill Rd, Windsor, MA

Date Name Price Difference
08/27/2026 Price Adjustment $724,900 3.33%
07/06/2026 Listing Price $749,900 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Map of 255 High St Hill Rd, Windsor, MA

Location Map Street View
Photo of Kathy Boot
Direct: 603-562-6677
Office
3 Executive Park Dr
Bedford, NH 03110
877-438-5986
Listed by Berkshire Reciprocal, Reciprocal Reciprocal
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255 High St Hill Rd (MLS #73564933) is a saltbox, contemporary single family home located in Windsor, MA. This single family home is 3,744 sqft and on a lot of 141,134 sqft (or 3.24 acres) with 5 bedrooms, 3.5 baths and is 39 years old. This property was listed on 08/18/2026 and has been priced for sale at $724,900.

Nearby zip codes are 01026, 01070, 01098 and 01235. This property neighbors other cities such as Cummington, Hinsdale, Peru, Plainfield and Worthington.

MLS PIN

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Listing information 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.