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!
Property Details
Price:
$3,299,000
MLS #:
73426449
Status:
Active
Beds:
5
Baths:
6
Address:
257 High Street
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
West Side
City:
Winchester
Listed Date:
Sep 4, 2025
State:
MA
Finished Sq Ft:
7,101
Total Sq Ft:
7,101
ZIP:
01890
Lot Size:
73,015 sqft / 1.68 acres (approx)
Year Built:
1994
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
9
Roof
Shingle
Security Features
Security System
Financial
Tax Year
2025
Taxes
$26,758
Map
Contact Us
Mortgage Calculator
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Courtesy of Compass. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
257 High Street
Winchester, MA
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