276 High Street Winchester, MA ^$ 2,299,000

276 High Street

^$ 2,299,000

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Open House 4/18 11am - 12:30pm

276 High Street

Winchester, MA, 01890

^$ 2,299,000

Bedrooms5 Baths3.1 Sq 5,006

Monthly Estimate*

^$ 14,155

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Single Family Home for sale in Winchester, MA

for $2,299,000 with 5 bedrooms and 3 full baths, 1 half bath. This 5,006 square foot home was built in 1992 on a lot size of 0.46.

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

Open House

4/18/2026 11:00 AM - 12:30 PM

276 High Street Winchester, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 2,299,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 23,217

Style

Colonial

Lot Size

0.46

Year Built

1992

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73496396

List By

Kim Covino & Co. Team

Listing Agent

Compass

Broker

Affordability Calculator

$16,090

Per Month

Monthly Principal & Interest: $14,155
Monthly Property Taxes: $1,935
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% 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 ^$2,466,866

Percent of Sale Price 7%

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.

Neighborhood & Schools

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Pricing History

Date	Price	Price Change	Description
4/6/2026	$2,299,000		Listed Price

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276 High Street, Winchester, MA, 01890 is a Single Family Home for sale at $2,299,000 with 5,006 sqft and a lot size of 0.46. 276 High Street has 5 bedrooms, 3.1 baths, and was built in 1992. 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 6.25% 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 4/16/2026.

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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276 High Street

Single Family Home for sale in Winchester, MA

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