255 High St Hill Rd, Windsor, MA 01270 (MLS# 250133)
$724,900
Windsor, MA 01270
MLS# 250133
Status: Pending
5 beds | 4 baths | 3744 sqft
1 / 36
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
Start Showing Date: 2026-07-08
Accessory Dwelling Unit: Yes
Original List Price: 749900
Limited Service: No
Agent Interest: None
Current Price: $724,900
Status: Pending
List Date: 2026-07-06
List Price: $724,900
Location, Tax & Legal
Elem School: Berkshire Trail
Middle School: Nessacus Regional
High School: Wahconah Regional
Taxes: 5263
Tax Year: 2025
Page: 1108
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
Surveillance: Unk
Realtor.COM Type: Residential - Single Family
Total Bathrooms: 4
Parking Spaces Type: Garaged & Off-Street
Sq Ft Source: Assessor
Total Rooms: 9
Total Bedrooms: 5
Garage Stalls: 2
Year Built Source: Assessor
Lot Size Dimensions: 228x697
Lot Size SqFt: 141134
Sq Ft Liv Apx: 3744
Total Full Baths: 3
Total Half Baths: 1
Year Built Apx: 1987
Acres Apx: 3.24
Remarks & Misc
Directions: Route 9 to Old Route 9 to High Street Hill Road.
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 Kitchen: 1
ADU Living Room: 1
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
Restrict Covenants
No: 1
Appliances Incl
Dryer: 1
Range: 1
Refrigerator: 1
Washer: 1
Basement
Concrete Floor: 1
Full: 1
Garage Access: 1
Radon Remed Sys: 1
Exterior Amenities
Deck: 1
Landscaped: 1
Privacy: 1
Flood Hazard Area
No: 1
Floor
Carpet: 1
Ceramic Tile: 1
Laminate: 1
Wood: 1
Fuel
Oil: 1
Garage
Attached: 1
Auto Opener: 1
Oversized: 1
Heat/Cool/Vent
Hot Water: 1
Hot Water
Oil: 1
Interior Amenities
Fireplace (s): 1
Interior Balcony: 1
Radon Mitigation System: 1
Skylight(s): 1
Internet Service
Fiber Optic Availabl: 1
Lead Paint
N/A, built 1978 or later: 1
Title V
Pass: 1
Underground Oil Tank
Unk: 1
Water
Well: 1
Right to Farm Comm
Yes: 1
Well Detail
Drilled: 1
Sewer
Private: 1
Building Info
Exterior Color: Cedar Naturaltone
Easement
Unk: 1
Survey
Unk: 1
Right of Way
Unk: 1
Accessibility
1st Fl Bdrm: 1
1st Flr Full Bath: 1
Electric Type
200 Amp: 1
Circuit Breaker: 1
Energy Features
Solar Panels Owned: 1
Views
Hill/Mountain: 1
Construction
Wood Frame: 1
Roof
Asphalt Shingles: 1
Stove Permit
Yes: 1
Style
Contemporary: 1
Salt Box: 1
Zoning
Residential: 1
Insulation
Mixed: 1
Seller Disc
Yes: 1
Green Energy Generation
Solar: 1
Exterior Siding
Wood: 1
Possession
Close Of Escrow: 1
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 |
| 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 |
MA Home Inspection Disclosure 
Listing Office: RE/MAX COMPASS
Listing Agent: Jesse Dimitropolis
Last Updated: October - 12 - 2026
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