257 High Street, Winchester, MA 01890 - Photo 1

1/1

$3,150,000

Sold
Closed
Single Family
5 Beds
5 Full Baths
2 Partial Baths
7,101 Sq. Ft.
1.68 Acres
2 Car Garage
Updated 4 hours ago

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Property Description

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~

Full Property Details

Full Property Details for 257 High St

General

Sold For: $3,150,000
Taxes: $26,758 (2025)
Status: Closed
Type: Single Family
MLS ID: 73499287
Added to Site: 50 day(s) ago

Rooms

Bathrooms

Total Bathrooms: 7
Full Bathrooms: 5
Half Bathrooms: 2
Bathroom 1: 8.00 x 5.00, First
Bathroom 2: 10.00 x 7.00, First
Bathroom 3: 16.00 x 12.00, Second

Bedrooms

Total Bedrooms: 5
Primary Bedroom: 31.00 x 23.00, Second
Bedroom 2: 14.00 x 13.00, Second
Bedroom 3: 15.00 x 15.00, Second
Bedroom 4: 17.00 x 14.00, Second

Other Rooms

Living Room: 20.00 x 14.00, First
Family Room: 26.00 x 16.00, First
Kitchen: 20.00 x 15.00, Main, First
Dining Room: 14.00 x 13.00, First
Office: 9.00 x 9.00, Second

Parking

Garage: Yes
Garage Spaces: 2
Parking Features: Attached, Paved Drive, Paved

Location

County: Middlesex

Structural Information

Architectural Style: Colonial, Contemporary
Basement: Yes
Square Feet: 7,101
Year Built: 1994

Lot Features

Lot Size (Acres): 1.68

Financial Considerations

Tax Amount: $26,758
Tax Year: 2025

Disclosures and Reports

Disclosures/Rstr.: Rhino Shield* paint exterior, low maintenance* 2 driveways upper and lower~ Commercial grade ice maker included. Furnishings and some paint colors are photo edited.
Property ID: M:027 B:0342 L:0, 901606

Listed by Compass, Kim Covino & Co. Team and Kim Covino
Sold by The Marino Group Collection, Anthony Marino

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Listing agents

— 257 High St —

Kim Covino & Co. Team

Compass
Kim Covino

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NMLS#: 1598647

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Schools

Schools serving 257 High St

School District:Winchester School District, Winchester, MA

Name	Grades	Distance
Vinson-Owen Elementary School 75 Johnson Road, Winchester, MA 01890	K-5	0.4 mi
Mccall Middle School 458 Main Street, Winchester, MA 01890	6-8	2.3 mi
Winchester High School 80 Skillings Road, Winchester, MA 01890	9-12	2.4 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 257 High St

Date

Details

Price

Change

Source

5/28/2026

Sold

$3,150,000

-3.08%

MLS

4/09/2026

Listed

$3,250,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Total Baths
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Active
Updated 1 day ago

3
Beds
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Total Baths
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Beds
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Total Baths
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Single Family
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Beds
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Total Baths
6,600
Sq. Ft.

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Beds
7
Total Baths
8,463
Sq. Ft.

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Beds
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Total Baths
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Beds
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Total Baths
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Sq. Ft.

257 High Street, Winchester, MA 01890 (MLS# 73499287) is a Single Family property that was sold at $3,150,000 on May 28, 2026. Want to learn more about 257 High Street? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

257 High St Winchester, MA 01890