255 High St Hill Rd, Windsor, MA 01270 (MLS# 250133)

255 High St Hill Rd, Windsor, MA 01270

$749,900

Property Type: Residential Bedrooms: 5 Baths: 4 Square Footage: 3,744 Lot Size (sq. ft.): 141,134 Status: Active

Current Price: $749,900 List Date: 7/08/2026 Last Modified: 7/13/2026

Overview

Description

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.

Listing Details MLS# 250133

Location, Tax & Legal

Registry: North Registry
Street #: 255
Street Name: High St Hill
Street Ext: Rd
State/Province: MA
Postal Code: 01270
Map Ref: M 14 L 115
Elem School: Berkshire Trail
Middle School: Nessacus Regional
High School: Wahconah Regional
Taxes: 5263
Tax Year: 2025
Page: 1108

Contract Information

Start Showing Date: 2026-07-08
Accessory Dwelling Unit: Yes
Original List Price: 749900
Limited Service: No
Agent Interest: None

General Property Description

Realtor.COM Type: Residential - Single Family
Sq Ft Liv Apx: 3744
Sq Ft Source: Assessor
Total Rooms: 9
Total Bedrooms: 5
Total Full Baths: 3
Total Half Baths: Yes
Total Bathrooms: 4
Garage Stalls: 2
Parking Spaces Type: Garaged & Off-Street
Surveillance: Unk
Year Built Apx: 1987
Year Built Source: Assessor
Lot Size Dimensions: 228x697
Acres Apx: 3.24
Lot Size SqFt: 141134

Status Change Info

Status Change Date: 2026-07-08

Accessory Dwelling Unit Information

ADU Attached YN: Yes
ADU Bathrooms: Yes
ADU Bedrooms: Yes
ADU Building Type: Addition
ADU Gas Meter YN: No
ADU Heating YN: Yes
ADU Occupied YN: No
ADU Parking YN: Yes
ADU Rented YN: No
ADU Separate Address YN: No
ADU Water Meter YN: No
Number of ADUs: Yes
ADU Kitchen: Yes
ADU Living Room: Yes

Building Info

Exterior Color: Cedar Naturaltone

More Information

Restrict Covenants

No: Yes

Appliances Incl

Dryer: Yes
Range: Yes
Refrigerator: Yes
Washer: Yes

Basement

Concrete Floor: Yes
Full: Yes
Garage Access: Yes
Radon Remed Sys: Yes

Exterior Amenities

Deck: Yes
Landscaped: Yes
Privacy: Yes

Flood Hazard Area

No: Yes

Floor

Carpet: Yes
Ceramic Tile: Yes
Laminate: Yes
Wood: Yes

Fuel

Oil: Yes

Garage

Attached: Yes
Auto Opener: Yes
Oversized: Yes

Heat/Cool/Vent

Hot Water: Yes

Hot Water

Oil: Yes

Interior Amenities

Fireplace (s): Yes
Interior Balcony: Yes
Radon Mitigation System: Yes
Skylight(s): Yes

Internet Service

Fiber Optic Availabl: Yes

Lead Paint

N/A, built 1978 or later: Yes

Title V

Pass: Yes

Underground Oil Tank

Unk: Yes

Water

Well: Yes

Right to Farm Comm

Yes: Yes

Well Detail

Drilled: Yes

Sewer

Private: Yes

Easement

Unk: Yes

Survey

Unk: Yes

Right of Way

Unk: Yes

Accessibility

1st Fl Bdrm: Yes
1st Flr Full Bath: Yes

Electric Type

200 Amp: Yes
Circuit Breaker: Yes

Energy Features

Solar Panels Owned: Yes

Views

Hill/Mountain: Yes

Construction

Wood Frame: Yes

Roof

Asphalt Shingles: Yes

Stove Permit

Yes: Yes

Style

Contemporary: Yes
Salt Box: Yes

Zoning

Residential: Yes

Insulation

Mixed: Yes

Seller Disc

Yes: Yes

Green Energy Generation

Solar: Yes

Exterior Siding

Wood: Yes

Possession

Close Of Escrow: Yes

Property Features

Accessory Dwelling Unit Information: ADU Kitchen; ADU Living Room Restrict Covenants: No Title V: Pass Underground Oil Tank: Unk Water: Well Well Detail: Drilled Sewer: Private Easement: Unk Survey: Unk Right of Way: Unk Right to Farm Comm: Yes Flood Hazard Area: No Views: Hill/Mountain Stove Permit: Yes Electric Type: 200 Amp; Circuit Breaker Style: Contemporary; Salt Box Interior Amenities: Fireplace (s); Interior Balcony; Radon Mitigation System; Skylight(s) Internet Service: Fiber Optic Availabl Accessibility: 1st Fl Bdrm; 1st Flr Full Bath Exterior Amenities: Deck; Landscaped; Privacy Appliances Incl: Dryer; Range; Refrigerator; Washer Energy Features: Solar Panels Owned Green Energy Generation: Solar Construction: Wood Frame Exterior Siding: Wood Roof: Asphalt Shingles Basement: Concrete Floor; Full; Garage Access; Radon Remed Sys Floor: Carpet; Ceramic Tile; Laminate; Wood Garage: Attached; Auto Opener; Oversized Fuel: Oil Hot Water: Oil Insulation: Mixed Lead Paint: N/A, built 1978 or later Zoning: Residential Seller Disc: Yes Possession: Close Of Escrow

Room Information

Room Name	Level	Remarks
Foyer	First
Kitchen	First
Half Bathroom	First	With Laundry
Family Room	First
Living Room	First
Dining Room	First
Primary Bedroom	Second
Primary Bathroom	Second
Bedroom 2	Second
Bedroom 3	Second
Full Bathroom	Second
Great Room	Third
Kitchen	First	In-Law Suite
Living Room	First	In-Law Suite
Full Bathroom	First	In-Law Suite
Bedroom 4	First	In-Law Suite
Bedroom	Second	In-Law Suite

Documents

MA Home Inspection Disclosure ›

Seller Description of Property ›

Listing Office: RE/MAX COMPASS

Listing Agent: Jesse Dimitropolis

Last Updated: July - 13 - 2026

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