5 Squire Rd Winchester, MA ^$ 1,899,000

5 Squire Rd

^$ 1,899,000

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Open House 1/29 5:30pm - 6:30pm

5 Squire Rd

Winchester, MA, 01890

^$ 1,899,000

Bedrooms6 Baths3.1 Sq 4,696

Monthly Estimate*

^$ 11,692

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Single Family Home for sale in Winchester, MA

for $1,899,000 with 6 bedrooms and 3 full baths, 1 half bath. This 4,696 square foot home was built in 1958 on a lot size of 0.41.

Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable neighborhood, this fabulous 6-bedroom, 3.5 bath home offers luxury finishes at an exceptional value. The primary suite provides a private escape with a walk-in closet and dual vanity, complemented by three additional second-floor bedrooms—two with walk-in closets—a shared bath, and laundry. A large unfinished attic offers future expansion potential, while the finished lower level adds flexibility with full-size windows, a sixth bedroom, full bath, recreation space, and a mudroom with direct garage entry. Enjoy a landscaped, fenced yard with irrigation, close to top-rated schools.

Open House

1/29/2026 5:30 PM - 6:30 PM

1/31/2026 11:30 AM - 12:30 PM

2/1/2026 11:30 AM - 12:30 PM

5 Squire Rd 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

^$ 1,899,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 20,170

Style

Contemporary

Lot Size

0.41

Year Built

1958

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73471882

List By

Andersen Group Realty

Listing Agent

Keller Williams Realty Boston Northwest

Broker

Affordability Calculator

$13,373

Per Month

Monthly Principal & Interest: $11,692
Monthly Property Taxes: $1,681
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 ^$2,135,000

Percent of Sale Price 12%

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
1/27/2026	$1,899,000		Listed Price

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5 Squire Rd, Winchester, MA, 01890 is a Single Family Home for sale at $1,899,000 with 4,696 sqft and a lot size of 0.41. 5 Squire Rd has 6 bedrooms, 3.1 baths, and was built in 1958. 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 1/28/2026.

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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5 Squire Rd

Single Family Home for sale in Winchester, MA

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