9 Plymouth Rd Winchester, MA ^$ 2,500,000

9 Plymouth Rd

^$ 2,500,000

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Recently Listed

Open House 7/12 12pm - 2pm

9 Plymouth Rd

Winchester, MA, 01890

^$ 2,500,000

Bedrooms5 Baths3.0 Sq 4,071

Monthly Estimate*

^$ 15,785

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Single Family Home for sale in Winchester, MA

for $2,500,000 with 5 bedrooms and 3 full baths. This 4,071 square foot home was built in 1959 on a lot size of 0.52.

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

Open House

7/12/2026 12:00 PM - 2:00 PM

9 Plymouth 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

^$ 2,500,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 19,088

Style

Colonial

Lot Size

0.52

Year Built

1959

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73544924

List By

Steph Crawford Group

Listing Agent

Real Broker Ma, Llc

Broker

Affordability Calculator

$17,376

Per Month

Monthly Principal & Interest: $15,785
Monthly Property Taxes: $1,591
Monthly Home Insurance: --

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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 ^$2,176,776

Percent of Sale Price 13%

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	$2,500,000		Listed Price

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9 Plymouth Rd, Winchester, MA, 01890 is a Single Family Home for sale at $2,500,000 with 4,071 sqft and a lot size of 0.52. 9 Plymouth Rd has 5 bedrooms, 3.0 baths, and was built in 1959. 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 7/10/2026.

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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9 Plymouth Rd

Single Family Home for sale in Winchester, MA

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