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257 High Street, 
Winchester, MA 01890

$3,499,000

5

Beds

7

Baths

7,101

Sq Ft

Single Family

Active

Listed by

Kim Covino & Co. Team

Compass

7812190313

Last updated:

September 8, 2025, 10:29 AM

MLS#

73426449

Source:

MLSPIN

About This Home

257 High Street

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!

Home Facts

Single Family

7 Baths

5 Bedrooms

Built in 1994

Price Summary

3,499,000

$492 per Sq. Ft.

MLS #:

73426449

Last Updated:

September 8, 2025, 10:29 AM

Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

7

Full Bathrooms:

5

Interior

Living Area:

7,101 Sq. Ft.

Structure

Structure

Architectural Style:

Colonial, Contemporary

Building Area:

7,101 Sq. Ft.

Year Built:

1994

Lot

Lot Size (Sq. Ft):

73,015

Finances & Disclosures

Finances

Price:

$3,499,000

Price per Sq. Ft:

$492 per Sq. Ft.

Source:MLSPIN
The property listing data and information, or the Images, 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, and the Images, 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, or as to the accuracy of any of the Images, set forth herein.

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