257 High Street Winchester, MA ^$ 3,299,000

257 High Street

^$ 3,299,000

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257 High Street

Winchester, MA, 01890

^$ 3,299,000

Bedrooms5 Baths5.2 Sq 7,101

Monthly Estimate*

^$ 20,581

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Single Family Home for sale in Winchester, MA

for $3,299,000 with 5 bedrooms and 5 full baths, 2 half baths. This 7,101 square foot home was built in 1994 on a lot size of 1.68.

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!

Single Family Active

Price

^$ 3,299,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 26,758

Style

Colonial,Contemporary

Lot Size

1.68

Year Built

1994

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73426449

List By

Kim Covino & Co. Team

Listing Agent

Compass

Broker

Affordability Calculator

$22,811

Per Month

Monthly Principal & Interest: $20,581
Monthly Property Taxes: $2,230
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends

Single family listings in Winchester, MA

Average List Price ^$1,942,827

Percent of Sale Price 41%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

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Trends Information provided by ATTOM Data Solutions.

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Pricing History

Date	Price	Price Change	Description
10/14/2025	$3,299,000	-5.72%	Price Down
9/5/2025	$3,499,000		Listed Price

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257 High Street, Winchester, MA, 01890 is a Single Family Home for sale at $3,299,000 with 7,101 sqft and a lot size of 1.68. 257 High Street has 5 bedrooms, 5.2 baths, and was built in 1994. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 12/24/2025.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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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257 High Street

Single Family Home for sale in Winchester, MA

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