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65 High Street, 
Winchester, MA 01890

$1,399,800

6

Beds

3

Baths

2,658

Sq Ft

Single Family

Active

Listed by

Anna Jung

K Stadium Realty Inc

617-780-1675

Last updated:

April 24, 2026, 10:39 AM

MLS#

73498871

Source:

MLSPIN

About This Home

65 High Street

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.

Home Facts

Single Family

3 Baths

6 Bedrooms

Built in 1949

Price Summary

1,399,800

$526 per Sq. Ft.

MLS #:

73498871

Last Updated:

April 24, 2026, 10:39 AM

Rooms & Interior

Bedrooms

Total Bedrooms:

6

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

2,658 Sq. Ft.

Structure

Structure

Architectural Style:

Colonial

Building Area:

2,658 Sq. Ft.

Year Built:

1949

Lot

Lot Size (Sq. Ft):

10,001

Finances & Disclosures

Finances

Price:

$1,399,800

Price per Sq. Ft:

$526 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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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.