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85 High StreetWinchester, MA 01890

For Sale

$1,899,000

Smart Buyer Rebate $9,495

Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

Listed by Catherine Albiani

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Better Homes and Gardens Real Estate - The Shanahan Group

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7817996252

Listed by Carolyn Vernaglia

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Better Homes and Gardens Real Estate - The Shanahan Group

Last updated October 30, 2026

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Source: MLSPin #73596915

Listing Facts

  • TypeSingle-family
  • NeighborhoodWedgemere
  • Bedrooms4
  • Bathrooms3
  • Days on Prevu1
  • Taxes$15,671/year
  • Size3,757 sqft
  • Price per sqft$505

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

10/30/2026
Listed by Better Homes and Gardens Real Estate - The Shanahan Group
$1,899,000
  1. 10/30/2026$1,899,000
    Listed by Better Homes and Gardens Real Estate - The Shanahan Group

Property Details for 85 High Street

Association

Amenities

  • Community Features: Tennis Court(s), Park

Exterior

Construction

  • Roof: Shingle
  • Window Features: Screens
  • Year Built: 1931
  • Year Built Details: Approximate
  • Architectural Style: Colonial
  • Exterior Features: Rain Gutters

Features

  • Fencing: Fenced
  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 3,757
  • Building Area Units: Square Feet
  • Lot Features: Corner Lot, Level, Landscaped
  • Lot Size Acres: 0.29
  • Lot Size Area: 0
  • Lot Size Square Feet: 12,489
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:021 B:0086 L:0,900221
  • Tax Annual Amount: $15,671.00
  • Tax Assessed Value: $1,413,100.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Water Heater, Oven, Dishwasher, Disposal, Range, Refrigerator, Washer, Dryer
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Tile, Hardwood, Laminate
  • Interior Features: Entrance Foyer, Walk-In Closet(s)

Measurements

  • Living Area: 3,757
  • Living Area Source: Public Records

Rooms

  • Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Sump Pump, Concrete
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 4
  • Rooms Total: 12

Parking

Parking

  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Detached, Garage Door Opener, Heated Garage, Storage, Off Street, Paved
  • Parking Total: 6

Schools

Elementary School

  • Elementary School: Ambrose

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: Circuit Breakers, 200+ Amp Service
  • Heating: Natural Gas, Steam
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 3 bathrooms in this single-family home at 85 High Street.

What schools are nearby to 85 High Street?

Nearby schools include the Ambrose Elementary School, Mccall Middle School, and Whs High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 85 High Street.

What are the annual taxes for 85 High Street?

Annual taxes for this single-family home are estimated at $15,671.

How does 85 High Street compare to other single-family homes in Wedgemere?

This single-family home is listed 13% below the average price for single-family homes in Wedgemere and has been on the market for 61 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,757 sqft.

85 High Street is a 4-bedroom, 3-bath single-family home for sale in Winchester MA 01890. Listed on Prevu for 1 days at $1,899,000. This property features 3,757 square feet of living space, located in Wedgemere. The median listing price for single-family homes in this area is $1,974,000. Nearby schools include Ambrose Elementary School, Mccall Middle School, and Whs High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Explore more single-family home listings in Middlesex County.

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.