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$749,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,744 Sq. Ft.
  • 3.24 Acres
  • 2 Car Garage
  • Updated 12 hours ago

Next open house:

Open House: 1:00 PM - 2:30 PM

Saturday 7/11 1:00 PM - 2:30 PM

255 High St Hill Rd,Windsor, MA 01270

255 High St Hill RdWindsorMA01270

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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 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.

Full Property Details for 255 High St Hill Rd

General

  • Price: $749,900
  • Taxes: $5,263 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 1109
  • MLS ID: 250133
  • Updated: 7/8/2026
  • Added to Site: Today

Interior

  • Number of Rooms: 9
  • Interior Features: Fireplace (s), Interior Balcony, Radon Mitigation System, Skylight(s)
  • Appliances: Dryer, Range, Refrigerator, Washer
  • Flooring: Carpet, Ceramic Tile, Laminate, Wood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Exterior

  • Exterior Features: Privacy, Deck, Landscaped

Parking

  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Garaged & Off-Street
  • Other Parking Type: Garaged & Off-Street
  • Garage Description: Attached, Auto Opener, Oversized

Location

  • Area: North Registry

Heating & Cooling

  • Heating Type: Oil, Hot Water

Utilities

  • Sewer: Private Sewer
  • Water: Well
  • Well: Yes
  • Utility Description: Fiber Optic Availabl

Structural Information

  • Architectural Style: Salt Box, Contemporary
  • Roof: Asphalt Shingles
  • Square Feet: 3,744
  • Year Built: 1987
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 3.24
  • Lot Size (Sq. Ft.): 141,134
  • Lot Dimensions: 228 x 697
  • Zoning: Residential

Green Features

  • Energy Generation: Solar, Solar Panels Owned

Financial Considerations

  • Tax Amount: $5,263
  • Tax Year: 2025

Disclosures and Reports

  • Property ID: M 14 L 115

Listed by Re/Max Compass, Jesse Dimitropolis

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Listing agent

— 255 High St Hill Rd —

  • Jesse Dimitropolis

    Re/Max Compass

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 255 High St Hill Rd

School District:Central Berkshire School District
NameGradesDistance
Craneville Elementary School
95 Park Avenue, Dalton, MA 01226
PK-59.2 mi
Nessacus Regional Middle School
35 Fox Road, Dalton, MA 01226
6-87.2 mi
Wahconah Regional High School
150 Windsor Rd, Dalton, MA 01226
9-127.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 255 High St Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/08/2026
Listed
$749,900
226.04%
MLS
10/15/1999
Sold
$230,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 255 High St Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,263
2%
$464,100
4%
2024
$5,138
4%
$445,200
18%
2023
$4,935
—
$376,400
—
2022
$4,940
2%
$375,700
2%
2021
$4,826
2%
$369,800
10%
2020
$4,718
—
$335,100
-5%
2019
$4,717
-18%
$354,400
-17%
2018
$5,764
10%
$428,200
11%
2017
$5,258
—
$387,200
-1%
2016
$5,254
-3%
$392,400
-4%
2015
$5,432
—
$408,100
-1%
2014
$5,406
—
$410,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Re/Max Compass, Jesse Dimitropolis

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255 High St Hill Rd, Windsor, MA 01270 (MLS# 250133) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 255 High St Hill Rd is currently listed for $749,900 and was received on July 08, 2026. Want to learn more about 255 High St Hill Rd? Do you have questions about finding other Single Family real estate for sale in Windsor? You can browse all Windsor real estate or contact a Coldwell Banker agent to request more information.

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