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255 High St Hill Rd, Windsor MA 01270
Windsor, MA 01270
$749,900
Est. $4,430/month
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About this home
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.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Aug 18, 2026
$749,900
Original listing
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/18/2026 | 🏠 Listed for Sale | $749,900 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $5,263 | $0 |
Financial Details
Annual Property Tax
$5,263
Tax Year 2025
Assessed Value
$0
Facts & Features
2 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1987
Living Area
3,744 sq ft
Lot Size
3.24 acres
Bedrooms
5
Full Baths
3
Half Baths
1
Total Rooms
9
Interior
Heating
Baseboard, Oil
Cooling
None
Flooring
Wood, Tile, Carpet, Laminate
Appliances
Water Heater, Range, Refrigerator, Washer, Dryer
Fireplace
None
Fireplaces
2
Basement
Full, Concrete
Laundry
None
Features
High Speed Internet
Exterior
Construction
Frame
Architecture
Contemporary, Saltbox
Roof
Shingle
Features
Deck
Pool
None
Spa
None
Fencing
None
Patio/Porch
Deck
Parking
Garage Spaces
2
Has Garage
Yes
Features
Under, Garage Door Opener, Off Street
Total Spaces
8
Utilities
Electric
200+ Amp Service
Water
Private
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$5,263
Assessed Value
0.00
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
None
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
Cedar
Sq Ft Source
Public Record
Documents
None
County
Berkshire
Total market time (incl. prior listings)
43 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1987
Bedrooms
5
Full Bathrooms
3
Half Bathrooms
1
Living Area
3,744 sq ft
Total Rooms
9
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,744 sq ft above grade
Display Options
Outdoor Areas
Patio & porchDeck
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Tile, Carpet, Laminate
Appliances:
Water Heater, Range, Refrigerator, Washer, Dryer
Interior Features:
High Speed Internet
Windows:
Insulated Windows
Basement:
Full, Concrete
Laundry:
Security:
Construction & Materials
Style:
Contemporary, Saltbox
Year Built:
1987
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Baseboard, Oil
Cooling:
None
Hot Water:
Water Source:
Private
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck
Patio & Porch:
Deck
Fencing:
Other Structures:
Lot Features:
Gentle Sloping
Road Frontage:
228.00 ft
Road Surface:
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
8
Parking Features:
Under, Garage Door Opener, Off Street
Special Features
Fireplaces:
2
Fireplace Type:
Community Amenities:
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$439
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
255 High St Hill Rd, Windsor MA 01270
Windsor, MA 01270
Listing Information
Listing Agent
Reciprocal Reciprocal
Listing Office
Berkshire Reciprocal
Office Phone
508-111-1111
Agent MLS ID
CN203095
Office MLS ID
AN0627
Listing Data Updated
Aug 18, 2026 10:38 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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