3 Chesterford Terrace Winchester, MA ^$ 1,300,000

3 Chesterford Terrace

^$ 1,300,000

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Open House 7/7 1:30pm - 2:30pm

3 Chesterford Terrace

Winchester, MA, 01890

^$ 1,300,000

Bedrooms3 Baths1.1 Sq 2,006

Monthly Estimate*

^$ 8,208

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Single Family Home for sale in Winchester, MA

for $1,300,000 with 3 bedrooms and 1 full bath, 1 half bath. This 2,006 square foot home was built in 1933 on a lot size of 0.3.

Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of Winchester's most desirable streets, the home offers endless potential for today's buyer. Enjoy the convenience of being a short stroll to Lynch Elementary School & moments from Winchester's scenic Three Ponds area, where walking trails & outdoor recreation await. Whether you're looking to restore & enhance an architectural gem or create your dream home in an unbeatable location, this property offers a truly special combination of history, charm, & opportunity. Rarely does a home with such pedigree, setting, & potential become available in Winchester. Estate Sale. Sold in as-is condition.

Open House

7/7/2026 1:30 PM - 2:30 PM

7/9/2026 5:30 PM - 7:00 PM

7/10/2026 11:00 AM - 12:30 PM

7/11/2026 1:00 PM - 2:30 PM

3 Chesterford Terrace 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

^$ 1,300,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 16,176

Style

Cape

Lot Size

0.3

Year Built

1933

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73545054

List By

The Fenway Group

Listing Agent

Compass

Broker

Affordability Calculator

$9,556

Per Month

Monthly Principal & Interest: $8,208
Monthly Property Taxes: $1,348
Monthly Home Insurance: --

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Yearly Home Insurance

Default based on a 30-year fixed rate of 6.49% 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 ^$2,090,830

Percent of Sale Price 61%

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
7/6/2026	$1,300,000		Listed Price

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3 Chesterford Terrace, Winchester, MA, 01890 is a Single Family Home for sale at $1,300,000 with 2,006 sqft and a lot size of 0.3. 3 Chesterford Terrace has 3 bedrooms, 1.1 baths, and was built in 1933. 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 6.49% 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 7/7/2026.

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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3 Chesterford Terrace

Single Family Home for sale in Winchester, MA

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