5 Winchester Rd Medway, MA ^$ 874,900

5 Winchester Rd

^$ 874,900

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Recently Listed

Open House 6/18 4:30pm - 6pm

5 Winchester Rd

Medway, MA, 02053

^$ 874,900

Bedrooms4 Baths2.1 Sq 2,640

Monthly Estimate*

^$ 5,387

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Single Family Home for sale in Medway, MA

for $874,900 with 4 bedrooms and 2 full baths, 1 half bath. This 2,640 square foot home was built in 2003 on a lot size of 1.7.

Tucked away at the end of a long private drive, 5 Winchester Road offers the rare combination of timeless Colonial living & a truly exceptional setting. Nestled on 1.7 acres of beautifully manicured grounds surrounded by mature trees, this property provides a sense of privacy and tranquility that is increasingly hard to find. Hardwood floors run throughout the entire home, complementing the classic Colonial floorplan designed for both comfortable living & entertaining. The first floor features a custom fieldstone fireplace in the family room, formal sitting room, formal dining room, and an eat-in kitchen with sliders leading to a deck overlooking the peaceful backyard. Upstairs are four bedrooms, including a spacious primary suite w/ private bath. The finished lower level adds valuable living space with a wet bar, dedicated home office, and room for recreation or gatherings. Offering the perfect balance of privacy, space, and nature-this is a place you'll love coming home to.

Open House

6/18/2026 4:30 PM - 6:00 PM

6/20/2026 10:00 AM - 12:00 PM

5 Winchester Rd Medway, 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

^$ 874,900

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 10,232

Style

Colonial

Lot Size

1.7

Year Built

2003

Town/City

Medway

County/Region

Norfolk

MLS | Web ID

73536507

List By

Lisa Bailey

Listing Agent

Berkshire Hathaway Homeservices Evolution Properties

Broker

Affordability Calculator

$6,240

Per Month

Monthly Principal & Interest: $5,387
Monthly Property Taxes: $853
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 Medway, MA

Average List Price ^$785,852

Percent of Sale Price 10%

About Medway, MA

13,225 Population

6% Since 2002

^$115,431 Median Income

43.95 Median Age

39% 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
6/16/2026	$874,900		Listed Price

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5 Winchester Rd, Medway, MA, 02053 is a Single Family Home for sale at $874,900 with 2,640 sqft and a lot size of 1.7. 5 Winchester Rd has 4 bedrooms, 2.1 baths, and was built in 2003. The property's zip code is 02053 which is in Medway, 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 6/18/2026.

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 Winchester Rd

Single Family Home for sale in Medway, MA

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