Single Family Residence at 255 High St Hill Rd, Windsor MA 01270
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$724,900

255 High St Hill Rd, Windsor MA 01270
Windsor, MA 01270
Listed by Reciprocal Reciprocal
Bedrooms
5
Bathrooms
3.5
Living area
3,744 sqft
Year built
1987

About this home

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.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73564933
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
109
On market date
July 6, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
2
Parking spaces
8
Lot size
3.24 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Emma L Miller Elementary School
5.99 mi away · Grades -1-6
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
51
Student:teacher ratio
10.2:1
District
Savoy
Middle
Nessacus Regional Middle School
7.17 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
322
Student:teacher ratio
13.4:1
District
Central Berkshire
High
Wahconah Regional High
7.18 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
513
Student:teacher ratio
11.9:1
District
Central Berkshire

Walkability

Blended score for Windsor's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

14
Very car-dependent
out of 100
EPA National Walkability Index
2.3 / 20 -- Least walkable
Google Places amenity density
17 / 100
Restaurants & cafes0
Grocery stores0
Parks2
Schools0
Transit stops2
Pharmacies0

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$4,515/mo
$144,980 down
$579,920 loan
Principal & interest$3,761
Property tax (est.)$604
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated September 16, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.