2 Canterbury Rd Winchester, MA ^$ 1,399,000

2 Canterbury Rd

^$ 1,399,000

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2 Canterbury Rd

Winchester, MA, 01890

^$ 1,399,000

Bedrooms3 Baths2.1 Sq 2,370

Monthly Estimate*

^$ 8,614

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Single Family Home for sale in Winchester, MA

for $1,399,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,370 square foot home was built in 1940 on a lot size of 0.29.

Classic New England charm defines this pristine 3-bedroom, 2.5-bath Colonial set on a generous, level corner lot with a beautiful stone wall in a sought-after neighborhood. Lovingly maintained by the same owners for over 50 years, the home is neat as a pin and filled with warmth and character. Hardwood floors, a traditional Colonial layout, and a fireplaced living room create comfortable living spaces, while a lovely sunroom brings in abundant natural light. Spacious bedrooms offer comfort, and the partially finished basement provides bonus space for work or play. An attached two-car garage adds everyday convenience. Ideally located just about .5 mile to the MBTA Wedgemere commuter rail station for easy Boston access, with quick connections to I-93 and nearby outdoor recreation at the Middlesex Fells Reservation. Move right in and enjoy, with the option to make thoughtful updates over time in a home that truly reflects pride of ownership.

Single Family Contingent

Price

^$ 1,399,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 15,398

Style

Colonial

Lot Size

0.29

Year Built

1940

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73475677

List By

Paula R. Sughrue

Listing Agent

Better Homes And Gardens Real Estate - The Shanahan Group

Broker

Affordability Calculator

$9,897

Per Month

Monthly Principal & Interest: $8,614
Monthly Property Taxes: $1,283
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 ^$2,313,395

Percent of Sale Price 65%

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
2/10/2026	$1,399,000		Listed Price

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2 Canterbury Rd, Winchester, MA, 01890 is a Single Family Home for sale at $1,399,000 with 2,370 sqft and a lot size of 0.29. 2 Canterbury Rd has 3 bedrooms, 2.1 baths, and was built in 1940. 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 2/20/2026.

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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2 Canterbury Rd

Single Family Home for sale in Winchester, MA

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