5 Winchester Road

Off Market

5 Winchester Road

Medway MA 02053

2640 sq. ft.

73878 sq. ft.

Single-Family

Last sold for $930,000

Lisa Bailey, last sold this property on 31 July 2026 after 45 days on market.

Overview

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.

Features

4 bedrooms

3 bathrooms

8 carspaces

6 open car spaces

2 garage spaces

2640 sq. ft. floor area

73878 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Medway over the last 12 months, the estimated median property value of 5 Winchester Road is $895k.

Median value

$895k

Estimated value range

$530k - $1.43m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Medway. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 5 Winchester Road

2026

Sold

$930,000

31 Jul 2026 by Lisa Bailey, of Berkshire Hathaway HomeServices Evolution Properties

Happy sellers in Medway

We have insufficient information to provide an overview of customer satisfaction for Medway. Viewing the agent profiles, reviews and sales for Medway can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Medway

In the last 12 months, 52 four-bedroom single-family properties similar to 5 Winchester Road, have been sold.

This represents a 24% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Medway for a market analysis.

Michael Giovangelo

at Better Living Real Estate, LLC

(47 reviews)

Get a market analysis

William Driscoll

at ROVI Homes of Eastern Mass

(1 review)

Get a market analysis

Laina Kaplan

at Northeast Signature Properties, LLC

Get a market analysis

Maria Varrichione

at REMAX Executive Realty | Franklin

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Medway

Michael Giovangelo

Sellers who recommend Michael Giovangelo have praised them for being local expert, responsive, clear communication, honest, supportive, patient, and empathetic