See Home Value
$850,000
● House - Off Market

65 High St

Winchester, MA 01890
bedrooms
6 Beds
bathrooms
3 Baths
square feet
2,843 Ft²
$1,428,185
RealtyHop Estimate
64.35%
Since Jan 1, 2017
MA-Boston
Primary Model

About This Property

Absolutely the BEST VALUE in Winchester in a desired neighborhood.  This expanded ranch has SIX true, substantial bedrooms and a location that enjoys exceptionally easy access to the sought-after AMBROSE School as well as downtown convenience for commuter rail, shops and restaurants. The sunny first floor flows nicely from room to room with hardwoods in the living areas and hallway that direct to the 3 original bedrooms ideal for office, guests or visiting in-laws (or a master-suite redesign!).  A screen porch and patio off the dining room beg for al fresco dining. The generous second floor renovation provides a full bath with double sinks, exclusive use laundry room, and 3 bedrooms each with three windows providing generous natural light and large, ideally designed closets. The back yard is private and level for grilling, gardening, and entertaining.  The huge basement is a blank slate ready for your creative design ideas for a playroom, gym, or man cave.
Unit Size
2,843 Ft²
Days on Market
-
Land Size
0.23 acres
Price per sqft
$306
Property Type
House
Property Taxes
$776
HOA Dues
-
Year Built
1949

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Last updated: 4 months ago (MLSPIN #72051212)

Price History

Date / Event Date Event Price
Jun 1, 2026 Sold
Sold
Apr 16, 2026 In contract -
In contract
Apr 9, 2026 Listed by K Stadium Realty INC $1,399,800
Listed by K Stadium Realty INC
Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level - ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester's most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.
Apr 6, 2026 Temporarily off market -
Temporarily off market
Mar 11, 2026 Listed by K Stadium Realty INC $1,499,999
Listed by K Stadium Realty INC
Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with double sinks, an exclusive-use laundry room, and 3 bedrooms, each with 3 windows for generous natural light. The backyard is private and level for grilling, gardening, and entertaining. The huge 1,165 sq ft basement is your creative space for a playroom, gym, and media room. Great school system (Ambros), and downtown convenience for commuter rail, shops, and restaurants. An amazingly beautiful backyard that's perfect for outdoor recreation. The seller will gift a pool and a ping-pong table to the new buyer in the playroom.
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Property Highlights

Garage
Parking Available
Air Conditioning
Fireplace

Building Info

Overview

    General

  • Year Built: 1949
  • Effective Year Built: 1949
  • Building Count: 1
  • Total Rooms: 9
  • Bedroom Count: 6
  • Bathroom Count: 3
  • Full Bathrooms: 3
  • Partial Bathrooms: 3
  • Building Condition: 3
  • Building Quality: 0
  • Construction Type: 6
  • Building Style: 5
  • Exterior Walls Type: 18
  • Interior Walls Type: 0
  • Roof Shape Type: 1
  • Roof Cover Type: 15
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 0
  • Basement Type: 7
  • Basement Area: 1,337
  • Garage Type: 0
  • Parking Space Count: 1
  • Patio Type: 0
  • Porch Type: 0
  • Pool Type: 0

    Dimensions

  • Lot Size Square Feet: 10,001
  • Total Building Area: 2,174
  • Gross Building Area: 3,931
  • Building Area: 2,174
  • Building Area Measurement: L

    Heating and Cooling

  • Fireplace Count: 1
  • Air Conditioning: 13
  • Heating: 10
  • Heated Square Feet: 2,174
  • Heating Fuel Type: 6

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Land Acres: 0000000230
  • Standard Land Use Code: 1001
  • County Land Use Code: 101

Neighborhood

  • School District Name: Winchester School District
  • School Tax School District: WINCHESTER SD
  • Census Tract: 338400

Zoning

  • Zoning: RDB

Geography

  • Parcel: WINC M:021 B:0082 L:0
  • Block: 82
  • Municipality: WINCHESTER
  • Latitude: 42.444
  • Longitude: -71.1598

    Address

  • Full Address: 65 High St
  • Address - House Number: 65
  • Address - Street Name: High
  • Address - Suffix Type: St
  • State: MA
  • City Name: Winchester
  • Carrier Code: C014
  • 4-Digit Zip Code: 3352
  • Zip Code: 01890

Valuation

    Tax

  • Tax Year: 2024
  • Tax Amount: $1,336,900

    Appraisal Valuation

  • Standard Deviation: 0.157
  • Valuation Date: Jan 17, 2024
  • Confidence Score: 80
  • Final Value: 1,372,543
  • High Value: 1,588,058
  • Low Value: 1,157,028

    Assessments Valuation

  • Assessed Year: 2024
  • Assessed Total Value: $1,180,000
  • Assessed Land Value: $726,000
  • Assessed Improvements Value: $454,000

    Sales

  • Current Sale Recording Date: Dec 30, 2016
  • Current Sale Price:
  • Current Sale Document Type: O
  • Current Sale Input Document Number: 236128
  • Previous Sale Recording Date: Apr 05, 1996
  • Previous Sale Amount: $228,000
  • Previous Sale Document Type: 27
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Winchester Town Center


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Frequently Asked Questions

When was property at 65 High Street built and last sold?
The property at 65 High Street was built in 1949 and last sold on Jan 1, 1970 for $850,000.
How much is this home worth?
The estimated value of the home located at 65 High Street is $1,366,364.
What are some comparable homes to 65 High Street?
There are currently no comparable homes to 65 High Street.