MaggieLi
Buy
Property SearchSearch all available MLS listingsSet AlertsGet notified about new listingsNeighborhood GuidesExplore local communities & data
Newton, MA
Cambridge, MA
Featured PropertiesBrowse our exclusive local listings
228 Wiswall Rd
5 Jarvis Circle
2 Saint Paul
View All Featured →
Sell
Home ValuationGet a free, instant estimateMy ListingsBrowse my active market properties
Insights
About
Meet the AgentMy background and experienceClient StoriesRead reviews from past clients
Contact Me
Buy
Property Search
Set Alerts
Neighborhood Guides
Newton, MA
Newton CentreWabanChestnut HillWest NewtonNewton CornerNewtonvilleNewton HighlandsAuburndaleNewton Upper FallsNewton Lower Falls
Cambridge, MA
Featured Properties
228 Wiswall Rd
5 Jarvis Circle
2 Saint Paul
View All Featured →
Sell
Home Valuation
My Listings
Insights
About
Meet the Agent
Client Stories
Contact Me

Maggie Li

I'm Maggie Li, a Newton, MA real estate agent serving first-time buyers, luxury clients and sellers across Greater Boston in English & Mandarin. Let's find your home.

Explore

  • Home
  • About
  • Home Search
  • Set Alerts
  • My Active Listings
  • Featured Listings
  • Home Valuation
  • Insights
  • Testimonials
  • Contact
  • Privacy Policy

Contact

  • 1229 Centre Street, Newton Centre, MA, USA
  • (774) 222-0952
  • lyx0402@gmail.com

Brokerage

William Raveis

© 2026 Maggie Li. All rights reserved.
Equal Housing Opportunity. Information deemed reliable but not guaranteed.

  1. Home
  2. Listings
  3. 255 High St Hill Rd, Windsor, MA 01270
Active
45 Days on market

$749,900

255 High St Hill Rd, Windsor, MA 01270

Windsor, MA 01270

Beds

5

Baths

3.5

SqFt

3,744

Style

Single Family

Built

1987

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 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 five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

Market Value Analysis

Not enough listings in Windsor for a city-only view.
This Property$200/sqft
Nearby Avg (5 mi)$234/sqft
15% BelowMarket Average

* Analysis is based on 2 actively listed and recently sold comparable properties within ~5 miles of this property.

Property Details

Financials

Original Price$749,900
Annual Taxes$5,263

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms9
Fireplaces2
FlooringWood, Tile, Carpet, Laminate
BasementFull, Concrete

Climate & Utilities

HeatingBaseboard, Oil
CoolingNone
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningR1

Property & Lot

Acres3.24
SqFt Lot141,134
Lot FeaturesGentle Sloping

Amenities & Appliances

Water Heater • Range • Refrigerator • Washer • Dryer

Geography

Population

1,036

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$116K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

3.9%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Berkshire County

144 housing units permitted in the last 12 months (+4% vs the prior 12 months) — 19 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,744 sq ft principal dwelling). Lot size: 141,134 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Windsor, MA market report ZIP 01270 market data
Listing Provided By

Listing Agent: Reciprocal Reciprocal

Listing Office: Berkshire Reciprocal

MLS® Number: 73564933

Browse More Homes in Windsor

Explore other active listings in the area.

  • 2241 Route 9
    $425,000
    2241 Route 9
    Windsor, MA
    4 bd3 ba2,720 sqft
  • 200 Peru Rd
    $699,900
    200 Peru Rd
Windsor, MA
4 bd3 ba2,248 sqft