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5 Winchester RdMedway, MA 02053

For Sale

$874,900

Smart Buyer Rebate $4,375

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.

Listed by Lisa Bailey

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Berkshire Hathaway HomeServices Evolution Properties

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774-210-0153

Last updated June 16, 2026

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Source: MLSPin #73536507

Listing Facts

  • TypeSingle-family
  • NeighborhoodMedway
  • Bedrooms4
  • Bathrooms3
  • Days on PrevuNew Today
  • Taxes$10,232/year
  • Size2,640 sqft
  • Price per sqft$331

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

06/16/2026
Listed by Berkshire Hathaway HomeServices Evolution Properties
$874,900

Property Details for 5 Winchester Rd

Association

Amenities

  • Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House Of Worship, Public School, T-Station

Exterior

Construction

  • Roof: Shingle
  • Window Features: Insulated Windows
  • Year Built: 2003
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage

Features

  • Patio And Porch Features: Porch, Deck, Deck - Wood, Patio
  • Road Frontage Type: Private Road, Dead End

Measurements

  • Building Area Total: 2,640
  • Building Area Units: Square Feet
  • Lot Size Acres: 1.70
  • Lot Size Area: 1
  • Lot Size Square Feet: 73,878
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:07 B:029,4419143
  • Tax Annual Amount: $10,232.00
  • Tax Assessed Value: $718,000.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker
  • Fireplace Features: Family Room
  • Fireplace: Yes
  • Fireplaces Total: 1
  • Flooring: Tile, Hardwood, Flooring - Wall To Wall Carpet, Flooring - Stone/Ceramic Tile
  • Interior Features: Recessed Lighting, Closet, Beadboard, Wet Bar, Cable Hookup, Office, Bonus Room, Den, Central Vacuum, Wet Bar

Measurements

  • Living Area: 2,640
  • Living Area Source: Measured

Rooms

  • Basement: Full, Partially Finished, Radon Remediation System
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 4
  • Rooms Total: 9

Other

Environmental

  • Green Energy Efficient: Thermostat

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 6
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Paved Drive, Off Street, Paved
  • Parking Total: 8

Schools

Elementary School

  • Elementary School: Burke/Memorial

High School

  • High School: Medway

Middle or Junior School

  • Middle Or Junior School: Medway

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: 200+ Amp Service, Generator Connection
  • Heating: Baseboard, Oil
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Sewer: Private Sewer
  • Utilities: For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
  • Water Source: Private

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 3 bathrooms in this single-family home at 5 Winchester Rd.

What schools are nearby to 5 Winchester Rd?

Nearby schools include the Burke/Memorial Elementary School, Medway Middle School, and Medway High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 5 Winchester Rd.

What are the annual taxes for 5 Winchester Rd?

Annual taxes for this single-family home are estimated at $10,232.

How does 5 Winchester Rd compare to other single-family homes in Medway?

This single-family home is listed 9% above the average price for single-family homes in Medway and has been on the market for 32 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,640 sqft.

5 Winchester Rd is a 4-bedroom, 3-bath single-family home for sale in Medway MA 02053. On Prevu for 0 days at $874,900. This residence features 2,640 square feet of living space, located in Medway. The median listing price for single-family homes in this area is $727,450. Nearby schools include Burke/Memorial Elementary School, Medway Middle School, and Medway High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and washer/dryer. Browse more single-family home listings in Norfolk County.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.