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Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add’l BR’s, all generously sized. The expansive lower level features an inviting screened “Florida room” family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or for everyday living and entertaining. Must see this fabulous home~ The ultimate home for hosting!
Current real estate data for Single Family in Winchester as of Oct 07, 2025
62
Single Family Listed
64
Avg DOM
551
Avg $ / SqFt
$2,270,911
Avg List Price

Property Details

Price:
$3,499,000
MLS #:
73426449
Status:
Active
Beds:
5
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
West Side
Listed Date:
Sep 4, 2025
Finished Sq Ft:
7,101
Total Sq Ft:
7,101
Lot Size:
73,015 sqft / 1.68 acres (approx)
Year Built:
1994
WoodedWest SideVinson OwenMccall MiddleWinchester High

Schools

Elementary School:
Vinson Owen
Middle School:
Mccall Middle
High School:
Winchester High

Interior

Appliances
Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
Bathrooms
5 Full Bathrooms, 2 Half Bathrooms
Cooling
Central Air
Fireplaces Total
4
Flooring
Tile, Marble, Hardwood, Flooring – Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Wall to Wall Carpet
Heating
Forced Air, Natural Gas, Fireplace
Laundry Features
Flooring – Stone/Ceramic Tile, First Floor, Electric Dryer Hookup

Exterior

Architectural Style
Colonial, Contemporary
Community Features
Walk/Jog Trails, Public School
Construction Materials
Frame
Exterior Features
Porch, Porch – Enclosed, Deck, Patio, Patio – Enclosed, Balcony, Rain Gutters, Sprinkler System
Parking Features
Attached, Paved Drive, Paved
Parking Spots
7
Roof
Shingle
Security Features
Security System

Financial

Tax Year
2025
Taxes
$26,758

Map

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Community

Property Summary

    Located in the West Side subdivision, 257 High Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $3,499,000 and features 5 beds, 6 baths, and has approximately 7,101 square feet of living space, and was originally constructed in 1994. The current price per square foot is $493. The average price per square foot for Single Family listings in Winchester is $551. The average listing price for Single Family in Winchester is $2,270,911. To schedule a showing of MLS#73426449 at 257 High Street in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.

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CRP: Certified Relocation Professional
CRS: Certified Residential Specialist
GRI: Graduate of Realtors Institute
CBR: Certified Buyers Representative
BSBA: Bachelor of Science in Business Administration. Babson College 1979
MBA: Master of Business Administration. Babson College 2002

James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…

More About James
257 High Street
Winchester, MA