255 High St Hill Rd, Windsor, MA 01270

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5 Beds 3 Baths 1 Partial Bath 3,744 Sq Ft 3.24 Acres

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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.

255 High St Hill Rd | MLS# 250133

This single family home located at 255 High St Hill Rd, Windsor, MA 01270 is currently listed for sale with an asking price of $724,900. This property was built in 1987 and has 5 bedrooms and 3 full and 1 partial baths with 3744 sq. ft. Search Windsor real estate on www.coldwellbankerprime.com today.

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Property Features

Property Type: Residential - Single Family

Basement: Full, Garage Access, Concrete Floor, Radon Remed Sys

Fuel Type: Oil

Garage: 2 car attached

Garage: Attached, Oversized, Auto Opener

Home Style: Contemporary, Salt Box

Lot Size: 3.24 Acres

Roof Type: Asphalt Shingles

Taxes: $5,263

Year Built: 1987

Feature Descriptions

Accessibility: 1st Fl Bdrm,1st Flr Full Bath

Appliances: Dryer, Washer, Refrigerator, Range

Construction: Wood Frame

Days on Site: 129

Easment: Unk

Electric: 200 Amp, Circuit Breaker

Energy: Solar Panels Owned

Exterior: Wood

Exterior: Deck, Privacy, Landscaped

Flood Area: No

Flooring: Carpet, Laminate, Wood, Ceramic Tile

Heating/Cooling: Hot Water

Hot Water: Oil

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

Internet Service: Fiber Optic Availabl

Lead Paint: N/A, built 1978 or later

Lot Dimensions: 228x697

Parking Space Type: Garaged & Off-Street

Right of Way: Unk

Right to Farm: Yes

Sewer: Private

Special View Info: Hill/Mountain

Underground Oil Tank: Unk

Water: Well

Local Schools

High School: Wahconah Regional

Middle School: Nessacus Regional

Elementary School: Berkshire Trail

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Estimated Payment

$ 2,263.33 per month $1,613.31 Principal & Interest $438.58 Property Tax $211.43 Homeowner's Insurance

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Listed By / Shown By

Listing By

Agency Name: RE/MAX COMPASS
Agency Phone: (413) 394-4543

Shown By

Agency Title: Coldwell Banker Prime Properties
Agency Phone: 866-323-CBPP

255 High St Hill Rd, Windsor, MA 01270

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/14/2026. The listing information on this page last changed on 11/14/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 11/14/2026 12:04:59 AM EST) or Global MLS (last updated Fri 11/13/2026 11:52:45 PM EST) or New York State Alliance MLS (last updated Sat 11/14/2026 12:03:08 AM EST) or Hudson Valley Catskill Region MLS (last updated Sat 11/14/2026 12:01:10 AM EST) or Berkshire MLS (last updated Fri 11/13/2026 8:13:17 PM EST) or OneKey MLS (last updated Sat 11/14/2026 12:00:19 AM EST). Real estate listings held by brokerage firms other than Coldwell Banker Prime Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

C.B. Prime Properties, Inc. fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated.

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Coldwell Banker®. All rights reserved. The Coldwell Banker System is comprised of company owned offices which are owned by a subsidiary of Anywhere Advisors LLC and franchised offices. Coldwell Banker Real Estate LLC, fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with, or related to Coldwell Banker Real Estate LLC nor any of its affiliated companies.

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255 High St Hill Rd, Windsor, MA 01270

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Property Description

255 High St Hill Rd | MLS# 250133

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Property Features

Feature Descriptions

Local Schools

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255 High St Hill Rd, Windsor, MA 01270

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255 High St Hill Rd, Windsor, MA 01270

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