65 High Street Winchester, MA ^$ 1,399,800

65 High Street

^$ 1,399,800

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65 High Street

Winchester, MA, 01890

^$ 1,399,800

Bedrooms6 Baths3.0 Sq 2,658

Monthly Estimate*

^$ 8,619

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Single Family Home for sale in Winchester, MA

for $1,399,800 with 6 bedrooms and 3 full baths. This 2,658 square foot home was built in 1949 on a lot size of 0.23.

Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level - ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester's most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.

Single Family Active

Price

^$ 1,399,800

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 13,499

Style

Colonial

Lot Size

0.23

Year Built

1949

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73498871

List By

Anna Jung

Listing Agent

K Stadium Realty Inc

Broker

Affordability Calculator

$9,744

Per Month

Monthly Principal & Interest: $8,619
Monthly Property Taxes: $1,125
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 ^$2,472,726

Percent of Sale Price 77%

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
4/9/2026	$1,399,800		Listed Price

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65 High Street, Winchester, MA, 01890 is a Single Family Home for sale at $1,399,800 with 2,658 sqft and a lot size of 0.23. 65 High Street has 6 bedrooms, 3.0 baths, and was built in 1949. 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 4/14/2026.

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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65 High Street

Single Family Home for sale in Winchester, MA

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