257 High Street Winchester, MA 01890
Listing Courtesy of: MLS PIN / Compass / Kim Covino & Co. Team

  257 High Street Winchester, MA 01890

Active (3 Days)
$3,499,000
5
BED
5.2
BATH
7,101
SQFT

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!

MLS #:
73426449
Taxes
$26,758(2025)
Lot Size
1.68 acres
Type
Single-Family Home
Year Built
1994
Style
Colonial, Contemporary
County
Middlesex County
Community
West Side

Listed By

Kim Covino & Co. Team, Compass
Source
MLS PIN
Last checked Sep 7 2025 at 8:56 PM EDT
Bathroom Details
Interior Features
  • Central Vacuum
  • Sauna/Steam/Hot Tub
  • Range
  • Refrigerator
  • Dryer
  • Washer
  • Dishwasher
  • Slider
  • Microwave
  • Disposal
  • Freezer
  • Laundry: Electric Dryer Hookup
  • Laundry: First Floor
  • Windows: Insulated Windows
  • Gas Water Heater
  • Oven
  • Home Office
  • Laundry: Flooring - Stone/Ceramic Tile
  • Range Hood
  • Wet Bar
  • Closet
  • Recessed Lighting
  • Living/Dining Rm Combo
  • Ceiling Fan(s)
  • Study
  • Kitchen
  • Closet/Cabinets - Custom Built
  • Dining Area
  • Countertops - Stone/Granite/Solid
  • Media Room
  • Breakfast Bar / Nook
Kitchen
  • Flooring - Hardwood
  • Countertops - Stone/Granite/Solid
  • Exterior Access
  • Dining Area
  • Kitchen Island
  • Recessed Lighting
  • Stainless Steel Appliances
  • Pantry
  • Wine Chiller
  • Breakfast Bar / Nook
  • Gas Stove
  • Balcony - Exterior
  • Window(s) - Picture
  • French Doors
  • Wet Bar
  • Wainscoting
  • Lighting - Pendant
  • Crown Molding
  • Open Floorplan
Subdivision
  • West Side
Lot Information
  • Wooded
Property Features
  • Fireplace: 4
  • Fireplace: Master Bedroom
  • Fireplace: Family Room
  • Foundation: Concrete Perimeter
Heating and Cooling
  • Forced Air
  • Natural Gas
  • Fireplace
  • Central Air
Basement Information
  • Full
  • Finished
  • Walk-Out Access
  • Interior Entry
Flooring
  • Tile
  • Hardwood
  • Marble
  • Flooring - Hardwood
  • Flooring - Wall to Wall Carpet
  • Flooring - Stone/Ceramic Tile
Exterior Features
  • Roof: Shingle
Utility Information
  • Utilities: Water: Public, For Gas Range, For Electric Dryer, For Electric Range, For Electric Oven, For Gas Oven
  • Sewer: Public Sewer
School Information
  • Elementary School: Vinson Owen
  • Middle School: McCall Middle
  • High School: Winchester High
Garage
  • Attached Garage
Parking
  • Paved Drive
  • Paved
  • Attached
  • Total: 7
Living Area
  • 7,101 sqft
Location
   
Calculate drive times to this property
 
Powered by INRIX® Drive Time

Powered by Walk Score®

Estimated Monthly Mortgage Payment

*Based on Fixed Interest Rate withe a 30 year term, principal and interest only

Listing price
Down payment
%
Interest rate
%
Mortgage calculator estimates are provided by C21 Property Central and are intended for information use only. Your payments may be higher or lower and all loans are subject to credit approval.
Disclaimer: The property listing data and information, or the Images, set forth herein wereprovided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein. © 2025 MLS Property Information Network, Inc.. 9/7/25 13:56