$3,250,000
257 High Street
Winchester, MA, 01890
OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** 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 everyday living & entertaining. Must see this fabulous home~
Property Details
Price:
$3,250,000
MLS #:
73499287
Status:
Pending
Beds:
5
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
West Side
Listed Date:
Apr 9, 2026
Finished Sq Ft:
7,101
Total Sq Ft:
7,101
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
Above Grade Finished Area
7101
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
Interior Features
Breakfast Bar / Nook, Closet, Closet/Cabinets – Custom Built, Ceiling Fan(s), Dining Area, Countertops – Stone/Granite/Solid, Recessed Lighting, Slider, Study, Home Office, Kitchen, Living/Dining Rm Combo, Media Room, Central Vacuum, Sauna/Steam/Hot Tub, Wet Bar
Laundry Features
Flooring – Stone/Ceramic Tile, First Floor, Electric Dryer Hookup
Exterior
Architectural Style
Colonial, Contemporary
Attached Garage YN
1
Community Features
Walk/Jog Trails, Public School
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Porch, Porch – Enclosed, Deck, Patio, Patio – Enclosed, Balcony, Rain Gutters, Sprinkler System
Garage Spaces
2
Lot Features
Wooded
Open Parking Spaces
7
Open Parking YN
1
Parking Features
Attached, Paved Drive, Paved
Parking Spots
9
Parking Total
9
Patio And Porch Features
Porch, Porch – Enclosed, Deck, Patio, Enclosed
Roof
Shingle
Security Features
Security System
Window Features
Insulated Windows
Financial
Tax Year
2025
Taxes
$26,758
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…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Winchester as of May 04, 2026
71
Single Family Listed
48
Avg DOM
548
Avg $ / SqFt
$2,185,977
Avg List Price
Community
- Address257 High Street Winchester MA
- SubdivisionWest Side
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
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 $3,250,000 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 $458. The average price per square foot for Single Family listings in Winchester is $548. The average listing price for Single Family in Winchester is $2,185,977. To schedule a showing of MLS#73499287 at 257 High Street in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
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