257 High Street Winchester MA 01890 MLS #73426449

257 High Street
Winchester, MA, 01890
$3,499,000
5 Beds
6 Baths
7,101 SqFt
1.68 Acres
$3,499,000
257 High Street
Winchester, MA, 01890
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:
$3,499,000
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 5, 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
7
Roof
Shingle
Security Features
Security System

Financial

Tax Year
2025
Taxes
$26,758
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Marie Andrews

Marie Andrews

Realtor®, Broker/Owner, GBREB, Notary Public

Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…

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257 High Street
Winchester, MA