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Properties

  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
  • 257 High Street, Winchester, Massachusetts, 5 Bedrooms Bedrooms, 16 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,High Street,73499287
Property Description

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!

Features
Heating System:
Forced Air, Natural Gas, Fireplace
Cooling System:
Central Air
Basement:
Full, Finished, Walk-out Access, Interior Entry
Fireplace:
Family Room, Master Bedroom
Security:
Security System
Parking:
Attached, Paved, Paved Drive
Appliances:
Disposal, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Freezer, Range Hood, Gas Water Heater, Oven, Other
Construction:
Frame
Exterior Unit Features:
Deck, Patio, Balcony, Porch, Patio - Enclosed, Sprinkler System, Porch - Enclosed, Rain Gutters
Flooring:
Tile, Hardwood, Marble, Flooring - Hardwood, Flooring - Wall To Wall Carpet, Flooring - Stone/ceramic Tile
Sewer:
Public Sewer
Style:
Colonial, Contemporary
Water:
Public
Disclosure
Electric Feature:
200+ Amp Service
Garage Parking:
2
Interior Features:
Central Vacuum, Sauna/steam/hot Tub, Closet/cabinets - Custom Built, Wet Bar, Recessed Lighting, Home Office, Media Room, Countertops - Stone/granite/solid, Closet, Slider, Kitchen, Study, Living/dining Rm Combo, Breakfast Bar / Nook, Ceiling Fan(s), Dining Area
Lead Paint:
Unknown
Laundry Features:
First Floor, Flooring - Stone/ceramic Tile, Electric Dryer Hookup
Road Type:
Paved
Additional Information
Grade School:
Vinson Owen
High School:
Winchester High
Middle School:
Mccall Middle
Parking Spaces:
9
Tax Year:
2025
Status:
Active
Price Per Sqft:
$458
Zoning:
res
Orig Price:
$3,250,000
Fireplaces:
4
Waterfront:
No
MlsStatus:
New
Address Map
City:
Winchester
State:
MA
County:
Middlesex
Postal Code:
01890
Longitude:
W72° 49' 15.5''
Latitude:
N42° 26' 38.2''
  • Google Map

Residential

257 High Street, Winchester, Massachusetts

5 Bedrooms
6 Total Bathrooms
7,101 Sqft
$3,250,000
Listing ID #73499287
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$3,250,000
Bedrooms :
5
Rooms :
16
Total Bathrooms :
6
Full Bathrooms :
5
Half Bathrooms :
2
Square Footage :
7,101 Sqft
Year Built :
1994
Lot Area :
1.68 Acre
Listing ID :
73499287
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Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

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.

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