$969,000
Price
3
Beds
1,302 Sq. Ft.
$744 / Sq. Ft.
1,302
Sq. Ft.
$744
per Sq. Ft.

Description

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,...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!
  1. Listed by Katie Tully • Better Homes and Gardens Real Estate - The Shanahan Group

Property Details for 139 High Street

Town
Winchester
Area
MA-Winchester
Architectural Style
Cape
Style
Cape
Garage Spaces
1
Parking Spaces
3.00
Parking Spaces Total
4
LISTING UPDATED: 12/07/2025 03:11 AM

Property Details for 139 High Street

StatusActive
MLS #73453920
Days on Market33
Taxes$11,344 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1949
CountyMiddlesex County

Location

Listing Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group, Katie Tully
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Building Information for 139 High Street

Stories-Year Built1949Building Size-Lot Size0.51 AC / 22,120 SF

Payment Calculator

$5,734 per month

30 year fixed, 6.28% Interest

Principal and Interest

$4,788

Property Taxes

$945

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 139 High Street

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Park, Walk/Jog Trails, Golf Course, Medical Facility, House of Worship, Public School, T-Station
  • Living Area: 1302.0
  • Color: White
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Location/School
  • Grade School: Vinson Owen
  • High School: Whs
  • Middle School: Mccall
Features
Interior Features
  • Appliances: Electric Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Basement Features: Interior Access, Garage Access
  • Num of Baths: 2.0
  • Num of Full Baths: 1
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 1.50
  • Bathrooms Total Integer: 2
  • FireplaceFeatures: Living Room
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: Tile, Vinyl, Hardwood
  • Laundry Features: In Basement, Electric Dryer Hookup, Washer Hookup
  • Primary Bath: No
  • SpaYN: No
Exterior Features
  • Construction: Frame
  • Exterior Features: Rain Gutters
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 1.00
  • Garage: Yes
  • Garage Parking: Attached, Under, Garage Door Opener, Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Under, Garage Door Opener, Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Off-Street, Paved Driveway
Utilities
  • Cooling: Heat Pump
  • Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Heat Pump
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Electric Range, for Electric Dryer, Washer Hookup
  • Water: Public
Room Information
Primary Bedroom
  • Room Primary Bedroom Area: 220.0
  • Room Primary Bedroom Features: Flooring - Hardwood,Lighting - Overhead
  • Room Primary Bedroom Length: 20.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 11.0
Bedroom 2
  • Bedroom2 Area: 108.0
  • Bedroom2 Features: Closet,Flooring - Hardwood,Lighting - Overhead
  • Bedroom2 Length: 12.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 9.0
Bedroom 3
  • Bedroom3 Area: 99.0
  • Bedroom3 Features: Closet,Flooring - Hardwood,Lighting - Overhead
  • Bedroom3 Length: 11.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 9.0
Bathroom 1
  • Bathroom1 Area: 24.0
  • Bathroom1 Features: Bathroom - Half,Flooring - Stone/Ceramic Tile
  • Bathroom1 Length: 6.0
  • Bathroom1 Level: First
  • Bathroom1 Width: 4.0
Bathroom 2
  • Bathroom2 Area: 35.0
  • Bathroom2 Features: Bathroom - Full,Bathroom - With Tub & Shower,Flooring - Stone/Ceramic Tile
  • Bathroom2 Length: 7.0
  • Bathroom2 Level: Second
  • Bathroom2 Width: 5.0
Dining Room
  • Dining Room Area: 132.0
  • Dining Room Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Lighting - Overhead
  • Dining Room Length: 12.0
  • Dining Room Level: First
  • Dining Room Width: 11.0
Kitchen
  • Kitchen Area: 130.0
  • Kitchen Features: Flooring - Vinyl,Pantry,Exterior Access,Remodeled,Lighting - Overhead
  • Kitchen Length: 13.0
  • Kitchen Level: First
  • Kitchen Width: 10.0
Living Room
  • Room Living Room Area: 242.0
  • Room Living Room Features: Flooring - Hardwood
  • Room Living Room Length: 22.0
  • Room Living Room Level: First
  • Room Living Room Width: 11.0
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
Tax Information
  • Tax ID: M:024 B:0033 L:0,900743
  • Assessments: $1,022,900
  • Book: 79232
  • Tax Year: 2025
  • Zoning: RDA
Building / Association Information
Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 6
  • Heat Zones: 6
Complex & Association Information
  • Adult Community: No

Property History for 139 High Street

DateEvent & SourcePriceAppreciation
Dec 3, 2025

Price Change

MLS PIN #73453920

$969,000—
Nov 12, 2025

Listed (Active)

MLS PIN #73453920

$999,000—
Nov 29, 2021

Sold

MLS PIN #72879748

$770,000—
Oct 14, 2021

Under Agreement

MLS PIN #72879748

—
Oct 14, 2021

Canceled

MLS PIN #72891612

$799,000—
Oct 14, 2021

Contingent

MLS PIN #72879748

—
Sep 8, 2021

Listed (Active)

MLS PIN #72891612

$979,000—
Aug 11, 2021

Listed (Active)

MLS PIN #72879748

$1,049,000—
Mar 1, 2012

Sold (Public Record)

Public Record #326657642

$1—
Mar 19, 2010

Sold (Public Record)

Public Record #326657259

$1—
DateEvent & SourcePrice
12/03/2025

Price Change

MLS PIN #73453920

$969,000
11/12/2025

Listed (Active)

MLS PIN #73453920

$999,000
11/29/2021

Sold

MLS PIN #72879748

$770,000
10/14/2021

Under Agreement

MLS PIN #72879748

—
10/14/2021

Canceled

MLS PIN #72891612

$799,000
10/14/2021

Contingent

MLS PIN #72879748

—
09/08/2021

Listed (Active)

MLS PIN #72891612

$979,000
08/11/2021

Listed (Active)

MLS PIN #72879748

$1,049,000
03/01/2012

Sold (Public Record)

Public Record #326657642

$1
03/19/2010

Sold (Public Record)

Public Record #326657259

$1

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

Public Records for 139 High Street

Taxable ValueLand$793,300Additions$229,600Total$1,022,900
Tax Record2025$11,344 ($945 / month)
Home Facts
Beds3Baths1.5Total Finished SqFt1,302 SqFtAbove Grade Finished SqFt1,302 SqFtUnfinished Basement SqFt874 SqFtStories2Lot Size22,120 SqFtStyleSingle Family ResidenceYear Built1949ZoningRDACountyMIDDLESEXAPNWINC M:024 B:0033 L:0Fireplace TypeHas Fireplace

Schools near 139 High Street

This home is within Winchester School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Rating
School
Distance
Vinson-Owen Elementary School
PublicPK to 5

McCall Middle School
Public6 to 8

Winchester High School
Public9 to 12

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.

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139 High Street is a single family home for sale in Winchester, MA 01890. This property was listed for sale on November 12, 2025 by Better Homes and Gardens Real Estate - The Shanahan Group, it's currently listed at $969,000. It has been on the market for a total of 33 days and was last sold on November 29, 2021. This listing's school district is Winchester School District. Nearby schools include Vinson-Owen Elementary School, McCall Middle School and Winchester High School. 139 High Street is a 3-bed, 2-bath, 1,302 sqft single family home built in 1949.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group, Katie Tully

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.