Contact Agent
Price
4,986 Sq. Ft.
/ Sq. Ft.
4,986
Sq. Ft.
per Sq. Ft.

Description

Welcome to 187 High St, Winchester – a rare opportunity. This private retreat is situated on just over 1 acre of serene, wooded land & manicured landscaping. From the moment you arrive, you're enveloped in unmatched privacy and a sense of escape. Inside, a vaulted-ceiling chef’s kitchen flows effortlessly into the grand living room, creating a show-stopping space. Whether you're hosting elegant dinner parties or casual get-togethers, this home is designed to impress. Upstairs, a spacious primary...Welcome to 187 High St, Winchester – a rare opportunity. This private retreat is situated on just over 1 acre of serene, wooded land & manicured landscaping. From the moment you arrive, you're enveloped in unmatched privacy and a sense of escape. Inside, a vaulted-ceiling chef’s kitchen flows effortlessly into the grand living room, creating a show-stopping space. Whether you're hosting elegant dinner parties or casual get-togethers, this home is designed to impress. Upstairs, a spacious primary suite is accompanied by two generously sized bedrooms & guest bathroom. The main level offers a private suite with its own kitchenette—perfect for overnight guests or a home office. A finished basement flexible living space, while both an attached and detached garage provide convenience and storage. The outdoor oasis features a spacious patio, in-ground pool, & expansive backyard—ideal for unforgettable summer celebrations. Truly an entertainer’s dream home for seeking privacy & convenience.

Listing Agents

  1. Dante Bruzzese

    Dante Bruzzese

    Alternative Listing Agent

    Compass

Property Details for High Street

Town
Winchester
Area
MA-Winchester
Parking Spaces Total
5

Amenities

  • Deck
  • Barbecue Area
  • Back Yard
  • Below Ground Pool
LISTING UPDATED: 03/04/2026 03:38 PM

Property Details for High Street

Status-
Days on Market-
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS Type-
Year Built1988
Lot Size-
CountyMiddlesex County
Buyer's Agent Compensation2%

Building Information for High Street

Stories-Year Built1988Building Size-Lot Size-

Property Information for High Street

Features
Interior Features
  • Num of Full Baths: 3
  • Num of Half Baths: 0
Building / Association Information
Living Characteristics
  • Beds Total: 3

Public Records for High Street

Taxable ValueLand$896,000Additions$924,400Total$1,820,400
Tax Record2025$20,188 ($1,682 / month)
Home Facts
Beds3Baths3Total Finished SqFt4,986 SqFtAbove Grade Finished SqFt4,986 SqFtUnfinished Basement SqFt798 SqFtStories2Lot Size45,268 SqFtStyleSingle Family ResidenceYear Built1988ZoningRDACountyMIDDLESEXFireplace TypeHas Fireplace

Schools near 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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High Street is a single family home for sale in Winchester, MA 01890. This listing's school district is Winchester School District. Nearby schools include Vinson-Owen Elementary School, McCall Middle School and Winchester High School. High Street is a 3-bed, 3-bath, 4,986 sqft single family home built in 1988.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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.

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.