255 High St Hill Rd

3,744 Sq. Ft.
$200 / Sq. Ft.
3,744
Sq. Ft.
$200
per Sq. Ft.

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,...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.
  1. Listed by Jesse Dimitropolis • RE/MAX COMPASS

Property Details for 255 High St Hill Road

Architectural Style
Salt Box, Contemporary
View
Hill/Mountain
Parking Spaces Type
Garaged & Off-Street
Zoning Description
Residential

Open Houses

Saturday, Jul 11th1:00 PM - 2:30 PM
LISTING UPDATED: 07/08/2026 03:15 AM

Property Details for 255 High St Hill Road

StatusActive
MLS #250133
Days on Market1
Taxes$5,263 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1987
Lot Size3.24 AC / 141,134 SF
CountyBerkshire County

Location

Listing Courtesy of RE/MAX COMPASS, Jesse Dimitropolis
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Building Information for 255 High St Hill Road

Stories-Year Built1987Building Size-Lot Size3.24 AC / 141,134 SF

Payment Calculator

$4,175 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,737

Property Taxes

$439

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 255 High St Hill Road

Summary
Location and General Information
  • MLS Area Major: North Registry
  • Latitude: 42.48
  • Longitude: -73.00
  • MLS Area Minor: North Registry
  • Views HillMountain: Yes
Taxes and HOA
  • Tax Book Number: 992
  • Parcel Number: M 14 L 115
  • Association Fee: $.00
  • Tax Amount: $5,263.00
  • Tax Year: 2025
  • Book: 992
  • Page: 1108
School Information
  • Middle Or Junior School: Nessacus Regional
  • High School: Wahconah Regional
  • Elementary School: Berkshire Trail
  • Elementry School: Berkshire Trail
  • Middle School: Nessacus Regional
Parking
  • Garage Spaces: 2.00
  • Other Parking: Garaged & Off-Street
  • Attached Garage: Yes
  • Garage Stalls: 2.00
  • Garage Attached: Yes
  • Garage Auto Opener: Yes
  • Garage Oversized: Yes
Virtual Tour
  • Virtual Tours Count: 0
Property
Lot Information
  • Lot Size Area: 3.24
  • Lot Size Units: Acres
  • Lot Size Acres: 3.24
  • Lot Size Dimensions: 228x697
  • Lot Size Square Feet: 141134.0
  • Square Feet Source: Assessor
  • Living Area: 3744.0
  • Building Area Total: 3744.0
  • Property Type: Residential
  • Restrict Covenants No: Yes
Property and Assessments
  • Floor Plans Count: 5
  • Total Bathrooms Source: MLS
  • Photos Count: 34
  • Videos Count: 0
  • Documents Count: 5
  • Property Type: Residential
  • Easement Unknown: Yes
  • Survey Unknown: Yes
  • Year Built: 1987
  • Year Built Source: Assessor
  • Flood Hazard Area No: Yes
  • Title V Pass: Yes
Green Features
  • Green Energy Generation: Solar, Solar Panels Owned
  • Green Energy Generation Solar: Yes
  • Energy Features Solar Panels Owned: Yes
Utilities
  • Sewer: Private
  • Water Yes: Yes
  • Water Access Well: Yes
  • Drilled Well Detail: Yes
  • Sewer Private: Yes
  • Electric Type 200 Amp: Yes
  • Electric Type Circuit Breaker: Yes
  • Stove Permit Yes: Yes
  • Internet Service Fiber Optic Availabl: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Features: Privacy, Deck, Landscaped
  • Exterior Amenities Deck: Yes
  • Exterior Amenities Landscaped: Yes
  • Exterior Amenities Privacy: Yes
  • Exterior Siding Wood: Yes
  • Right of Way Unknown: Yes
  • Post Beam Wood Frame: Yes
  • Style Contemporary: Yes
  • Style Salt Box: Yes
Interior Features
  • Baths Half: 1
  • Baths Total: 4.00
  • Baths Full: 3
  • Total Bathrooms: 4
  • Bathrooms Total Decimal: 3.50
  • Bathrooms Total Notational: 3.10
  • Total Rooms: 9.00
  • Accessibility 1st Floor Full Bath: Yes
  • Heating: Oil, Hot Water
  • Kitchen Appliances: Dryer, Range, Refrigerator, Washer
  • Heating: Yes
  • Underground Oil Tank Unk: Yes
  • Building Information Exterior Color: Cedar Naturaltone
  • Interior Features: Fireplace (s), Interior Balcony, Radon Mitigation System, Skylight(s)
  • Interior Amenities Fireplaces: Yes
  • Interior Amenities Interior Balcony: Yes
  • Interior Amenities Skylight: Yes
  • Interior Amenities Radon Mitigation System: Yes
  • Basement Concrete Floor: Yes
  • Basement Full: Yes
  • Basement Garage Access: Yes
  • Basement Radon Remed System: Yes
  • Fuel Oil: Yes
  • Hot Water Oil: Yes
  • Insulation Mixed: Yes
  • Appliances Included Dryer: Yes
  • Appliances Included Refrigerator: Yes
  • Appliances Included Washer: Yes
  • Floor Carpet: Yes
  • Floor Laminate: Yes
  • Floor Wood: Yes
  • Heat/Cool/Vent Hot Water: Yes
  • Lead Paint NA built after 1978: Yes
Room Information
Room Details
  • Rooms Total: 9
  • Room Type: Foyer, Kitchen, Half Bathroom, Family Room, Living Room, Dining Room, Primary Bedroom, Primary Bathroom, Bedroom 2, Bedroom 3, Full Bathroom, Great Room, Bedroom 4, Bedroom
Room 1
  • Room Type: Foyer
  • Room Level: First
Room 2
  • Room Type: Kitchen
  • Room Level: First
Room 3
  • Room Type: Half Bathroom
  • Room Level: First
  • Room Description: With Laundry
Room 4
  • Room Type: Family Room
  • Room Level: First
Room 5
  • Room Type: Living Room
  • Room Level: First
Room 6
  • Room Type: Dining Room
  • Room Level: First
Room 7
  • Room Type: Primary Bedroom
  • Room Level: Second
Room 8
  • Room Type: Primary Bathroom
  • Room Level: Second
Room 9
  • Room Type: Bedroom 2
  • Room Level: Second
Room 10
  • Room Type: Bedroom 3
  • Room Level: Second
Room 11
  • Room Type: Full Bathroom
  • Room Level: Second
Room 12
  • Room Type: Great Room
  • Room Level: Third
Room 13
  • Room Type: Kitchen
  • Room Level: First
  • Room Description: In-Law Suite
Room 14
  • Room Type: Living Room
  • Room Level: First
  • Room Description: In-Law Suite
Room 15
  • Room Type: Full Bathroom
  • Room Level: First
  • Room Description: In-Law Suite
Room 16
  • Room Type: Bedroom 4
  • Room Level: First
  • Room Description: In-Law Suite
Room 17
  • Room Type: Bedroom
  • Room Level: Second
  • Room Description: In-Law Suite
Rental
Rental Information
  • Certified Occupancy Yes: Yes

Property History for 255 High St Hill Road

DateEvent & SourcePriceAppreciation
Jul 6, 2026

Listed (Active)

Berkshire County Board of REALTORS #250133

$749,900—
Oct 15, 1999

Sold (Public Record)

Public Record #88963376

$230,000—
Oct 15, 1999

Sold

Berkshire County Board of REALTORS #145314

$230,000—
DateEvent & SourcePrice
07/06/2026

Listed (Active)

Berkshire County Board of REALTORS #250133

$749,900
10/15/1999

Sold (Public Record)

Public Record #88963376

$230,000
10/15/1999

Sold

Berkshire County Board of REALTORS #145314

$230,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 255 High St Hill Road

Taxable ValueLand$31,300Additions$432,800Total$464,100
Tax Record2025$5,263 ($439 / month)
Home Facts
Baths3.5Total Finished SqFt3,744 SqFtAbove Grade Finished SqFt3,744 SqFtUnfinished Basement SqFt1,944 SqFtStories3Lot Size141,265 SqFtStyleDuplexYear Built1987ZoningR1CountyBERKSHIREAPNWIND M:014.0 B:0000 L:0115.0Fireplace TypeHas Fireplace

Schools near 255 High St Hill Road

This home is within Central Berkshire School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - K to 5
Rating
School
Distance
Kittredge Elementary School
PublicPK to 5

Nessacus Regional Middle School
Public6 to 8

Wahconah Regional High School
Public9 to 12

Craneville Elementary School
PublicK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

255 High St Hill Road is a single family home for sale in Windsor, MA 01270. This listing's school district is Central Berkshire School District. Nearby schools include Kittredge Elementary School, Nessacus Regional Middle School and Wahconah Regional High School. 255 High St Hill Road is a 5-bed, 4-bath, 3,744 sqft single family home built in 1987.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX COMPASS, Jesse Dimitropolis

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.