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


$724,900
255 High St Hill Rd
Windsor, MA 01270
MLS# 250133
Status: Pending
5 beds  |  4 baths  |  3744 sqft


Front of home
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Front of home Kitchen Kitchen Kitchen Sitting Room Living Room Dining Room Dining Room Half Bath First Floor Laundry in Half Bath Primary Bedroom Primary Bedroom Primary Bathroom Bedroom Two Bedroom Three Full Bath Second Floor Great Room Great room Great Room In-Law Kitchen In-Law Living Room In-Law Full Bath In-Law Bedroom First Floor In-Law Bedroom Second Floor Garage Front of home Wood storage area Front of home Front yard Side of home Side of home Deck Backyard Aerial View Aerial View Privacy!!!

Property Description
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.

Details
Maps
Documents
Contract Information
Current Price: $724,900
Status: Pending
Start Showing Date: 2026-07-08
List Date: 2026-07-06
Accessory Dwelling Unit: Yes
List Price: $724,900
Original List Price: 749900
Limited Service: No
Agent Interest: None
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
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: 1
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
Accessory Dwelling Unit Information
ADU Attached YN: Yes
ADU Bathrooms: 1
ADU Bedrooms: 1
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: 1
Building Info
Exterior Color: Cedar Naturaltone
Status Change Info
Status Change Date: 2026-10-12
Under Contract Date: 2026-10-09
Contingent: Yes
Contingent Remarks: Inspection/ Finance
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
Supplements
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.
Room Information
Room Name Level Remarks
FoyerFirst
KitchenFirst
Half BathroomFirstWith Laundry
Family RoomFirst
Living RoomFirst
Dining RoomFirst
Primary BedroomSecond
Primary BathroomSecond
Bedroom 2Second
Bedroom 3Second
Full BathroomSecond
Great RoomThird
KitchenFirstIn-Law Suite
Living RoomFirstIn-Law Suite
Full BathroomFirstIn-Law Suite
Bedroom 4FirstIn-Law Suite
BedroomSecondIn-Law Suite

Listing Office: RE/MAX COMPASS
Listing Agent: Jesse Dimitropolis

Last Updated: October - 12 - 2026

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