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139 High StreetWinchester, MA 01890

For Sale

$999,000

Smart Buyer Rebate $4,995

This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space. Additional highlights include a one-car garage under and a convenient layout with timeless appeal. Nestled beside conservation land, this home provides a peaceful, natural setting where you can enjoy watching birds and local wildlife right from the yard. Make this one yours for 2026!

Listed by Katie Tully

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Better Homes and Gardens Real Estate - The Shanahan Group

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617-877-6119

Last updated November 18, 2025

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Source: MLSPin #73453920

Listing Facts

  • TypeSingle-family
  • NeighborhoodWest Side
  • Bedrooms3
  • Bathrooms2
  • Days on Prevu7
  • Taxes$11,344/year
  • Size1,302 sqft
  • Price per sqft$767

Amenities

  • Dishwasher
  • Washer/Dryer
  • Parking

Location

Mortgage Calculator

Listing History

11/12/2025
Listed by Better Homes and Gardens Real Estate - The Shanahan Group
$999,000

Property Details for 139 High Street

Association

Amenities

  • Community Features: Public Transportation, Park, Walk/Jog Trails, Golf, Medical Facility, House Of Worship, Public School, T-Station

Exterior

Construction

  • Roof: Shingle
  • Year Built: 1949
  • Year Built Details: Approximate
  • Architectural Style: Cape
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters

Features

  • Road Frontage Type: Public

Measurements

  • Building Area Total: 1,302
  • Building Area Units: Square Feet
  • Lot Size Acres: 0.51
  • Lot Size Area: 0
  • Lot Size Square Feet: 22,120
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:024 B:0033 L:0,900743
  • Tax Annual Amount: $11,344.00
  • Tax Assessed Value: $1,022,900.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Electric Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Tile, Vinyl, Hardwood

Measurements

  • Living Area: 1,302
  • Living Area Source: Public Record

Rooms

  • Basement: Interior Entry, Garage Access
  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 3
  • Rooms Total: 6

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 1
  • Garage Spaces: 1
  • Garage: Yes
  • Open Parking: Yes
  • Parking Features: Attached, Under, Garage Door Opener, Paved Drive, Off Street, Paved
  • Parking Total: 2

Schools

Elementary School

  • Elementary School: Vinson Owen

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Heat Pump
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Heat Pump
  • Has Heating: Yes
  • Laundry Features: In Basement, Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Utilities: For Electric Range, For Electric Dryer, Washer Hookup
  • Water Source: Public

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.