257 High Street, Winchester MA 01890

Winchester, MA 01890 • West Side
$3,499,000
Est. $18,623/month
5
Beds
6
Baths
7,101
Sq Ft
$493
Price/Sq Ft
1.68
Acres
1994
Year Built
Single Family Residence
Type
21
Days on Market
Active Open House Listed Sep 26, 2025 • MLS# 73426449

About this home

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!

Open House Schedule

28
Sep
Sunday, September 28
1:00 PM - 3:00 PM EDT

Facts & Features

Property Overview

Property Type
Single Family Residence
Property Category
Residential
Year Built
1994
Bedrooms
5
Full Bathrooms
5
Half Bathrooms
2
Living Area
7,101 sq ft
Total Rooms
16

Interior Features

Flooring
Tile, Marble, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Heating
Forced Air, Natural Gas, Fireplace
Has Heating
Yes
Cooling
Central Air
Has Cooling
Yes
Fireplace Features
Family Room, Master Bedroom
Has Fireplace
Yes
Number of Fireplaces
4
Appliances
Gas Water Heater, Range, Oven, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer, Range Hood, Other
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
Basement Details
Full, Finished, Walk-Out Access, Interior Entry
Window Features
Insulated Windows
Door Features
Insulated Doors

Exterior & Structure

Construction Materials
Frame
Architectural Style
Colonial, Contemporary
Roof
Shingle
Foundation
Concrete Perimeter
Exterior Features
Porch, Porch - Enclosed, Deck, Patio, Patio - Enclosed, Balcony, Rain Gutters, Sprinkler System
Patio/Porch Features
Porch, Porch - Enclosed, Deck, Patio, Enclosed
Has Spa
No
Waterfront Property
No

Lot & Land

Lot Size
1.68 acres
Lot Size
73,015 sq ft
Lot Size Area
1.6800
Lot Features
Wooded
Road Surface Type
Paved
Road Frontage Type
Public

Parking & Garage

Garage Spaces
2
Has Garage
Yes
Attached Garage
Yes
Has Carport
No
Total Non-Garage Parking Spaces
7
Parking Features
Attached, Paved Drive, Paved
Covered Parking Spaces
2

Utilities & Systems

Utilities Available
for Gas Range, for Electric Range, for Gas Oven, for Electric Oven, for Electric Dryer
Water Source
Public
Sewer
Public Sewer
Electric
200+ Amp Service
Security Features
Security System

Community & HOA

Subdivision
West Side
Community Features
Walk/Jog Trails, Public School
HOA
No
Senior Community
No

Financial & Tax Information

Annual Tax Amount
$26,758
Tax Year
2025
Tax Assessed Value
$2,412,800
Parcel Number
M:027 B:0342 L:0,901606
Zoning
res

Additional Details

Year Built Source
Public Records
Year Built Details
Actual,Renovated Since
Attached Property
No
Disclosures
Rhino Shield* paint exterior, low maintenance* 2 driveways upper and lower~ Commercial grade ice maker included

Location

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Neighborhood

West Side

257 High Street, Winchester MA 01890

Winchester, MA 01890

Walkability

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Schools

Elementary School
Vinson Owen
Rating information coming soon
Middle School
Mccall Middle
Rating information coming soon
High School
Winchester High
Rating information coming soon

Monthly Payment Calculator

%
%
Estimated Monthly Payment $0

Payment Breakdown

Principal & Interest $0
Property Tax $2,230
Homeowners Insurance $200
PMI $0

Property History

Property Timeline

🏠
Listed for Sale
Sep 5, 2025
$3,499,000
Original listing
Agent: Kim Covino & Co. Team Office: Compass

Price & Status History

Date Event Price Change
Sep 5, 2025 New Listing Added $3,499,000

Market Statistics

Days on Market
21 days
Price per Sq Ft
$493

Tax History

Year Taxes Assessment
2025 $26,758 $2,412,800

Financial Details

Annual Property Tax
$26,758
Tax Year 2025
Assessed Value
$2,412,800

Listing Information

Listing Agent Kim Covino & Co. Team
Listing Office Compass
Agent MLS ID TM347383
Office MLS ID AN6433

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