5 Winchester Rd

Medway, MA 02053

$874,900
Price
4
Beds
2,640 Sq. Ft.
$331 / Sq. Ft.
2,640
Sq. Ft.
$331
per Sq. Ft.
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Contingent
Contingent

Description

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...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.
  1. Listed by Lisa Bailey • Berkshire Hathaway HomeServices Evolution Properties

Property Details for 5 Winchester Road

Town
Medway
Area
MA-Medway
Architectural Style
Colonial
Style
Colonial
Garage Spaces
2
Open Parking Spaces
6.00
Parking Spaces Total
8
LISTING UPDATED: 06/22/2026 07:36 PM

Property Details for 5 Winchester Road

StatusContingent
MLS #73536507
Days on Market6
Taxes$10,232 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Detached
Year Built2003
CountyNorfolk County
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Location

Listing Courtesy of Berkshire Hathaway HomeServices Evolution Properties, Lisa Bailey
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Building Information for 5 Winchester Road

Stories-Year Built2003Building Size-Lot Size1.70 AC / 73,878 SF

Payment Calculator

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$5,212 per month

30 year fixed, 6.36% Interest

Principal and Interest

$4,360

Property Taxes

$853

HOA Dues

$0

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Property Information for 5 Winchester Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Tennis Court, Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
  • Living Area: 2640.0
  • Color: Beige
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Location/School
  • Grade School: Burke/Memorial
  • High School: Medway
  • Middle School: Medway
Features
Interior Features
  • Appliances: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker
  • Basement Features: Full, Partially Finished, Radon Remediation System
  • Num of Baths: 3.0
  • Num of Full Baths: 2
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 2.50
  • Bathrooms Total Integer: 3
  • DoorFeatures: Insulated Doors
  • FireplaceFeatures: Family Room
  • FireplaceYN: Yes
  • Fireplaces: 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, Wetbar
  • Interior Features: Central Vacuum, Wetbar
  • Laundry Features: Electric Dryer Hookup, Washer Hookup
  • Primary Bath: Yes
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage Shed
  • Exterior Features: Storage Shed, Porch, Deck, Deck - Wood, Patio
  • Patio And Porch Features: Porch, Deck, Deck - Wood, Patio
  • Roof Material: Shingle
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Garage Door Opener, Paved Drive, Off-Street, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Garage Door Opener, Paved Drive, Off-Street, Paved Driveway
  • Parking Features: Off-Street, Paved Driveway
Utilities
  • Cooling: Central Air
  • Cooling: Yes
  • Electric: 200+ Amp Service, Generator Connection
  • Green Energy Efficient: Thermostat
  • Heating: Baseboard, Oil
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
  • Water: Private
Room Information
Primary Bedroom
  • Room Primary Bedroom Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Cable Hookup,Crown Molding
  • Primary Bedroom Level: Second Floor
Bedroom 2
  • Bedroom2 Features: Closet,Flooring - Hardwood,Cable Hookup
  • Bedroom2 Level: Second
Bedroom 3
  • Bedroom3 Features: Closet,Flooring - Hardwood,Cable Hookup
  • Bedroom3 Level: Second
Bedroom 4
  • Bedroom4 Features: Closet,Flooring - Hardwood,Cable Hookup,Beadboard
  • Bedroom4 Level: Second
Bathroom 1
  • Bathroom1 Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Pedestal Sink
  • Bathroom1 Level: First
Bathroom 2
  • Bathroom2 Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid
  • Bathroom2 Level: Second
Bathroom 3
  • Bathroom3 Features: Bathroom - Full,Bathroom - With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid
  • Bathroom3 Level: Second
Dining Room
  • Dining Room Features: Flooring - Hardwood,Wainscoting,Lighting - Overhead,Crown Molding
  • Dining Room Level: First
Family Room
  • Family Room Features: Flooring - Hardwood,Cable Hookup,Recessed Lighting,Crown Molding
  • Family Room Level: Main,First
Kitchen
  • Kitchen Features: Flooring - Hardwood,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Deck - Exterior,Exterior Access,Recessed Lighting,Slider
  • Kitchen Level: First
Living Room
  • Room Living Room Features: Flooring - Hardwood,French Doors,Cable Hookup,Lighting - Overhead,Crown Molding
  • Room Living Room Level: Main,First
Other Room 1
  • Room Office Features: Flooring - Wall to Wall Carpet,Recessed Lighting
  • Room Office Level: Basement
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Private Road, Dead End
  • Road Responsibility: Private Maintained Road
  • Road Surface Type: Paved
  • Disclosures: Winchester is a private road,owned by 5 Wichester and 3 Winchester.
Tax Information
  • Listing Terms: Contract
  • Tax ID: M:07 B:029,4419143
  • Assessments: $718,000
  • Book: 20969
  • Tax Year: 2025
  • Zoning: AR-I
Building / Association Information
Living Characteristics
  • Beds Total: 4
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 1
  • Heat Zones: 4
Complex & Association Information
  • Adult Community: No

Property History for 5 Winchester Road

DateEvent & SourcePriceAppreciation
Jun 21, 2026

Contingent

MLS PIN #73536507

—
Jun 16, 2026

Listed (Active)

MLS PIN #73536507

$874,900—
May 5, 2004

Sold (Public Record)

Public Record #135967678

$499,900

+5469.8% / yr

DateEvent & SourcePrice
06/21/2026

Contingent

MLS PIN #73536507

—
06/16/2026

Listed (Active)

MLS PIN #73536507

$874,900
05/05/2004

Sold (Public Record)

Public Record #135967678

$499,900

+5469.8% / yr

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 5 Winchester Road

Taxable ValueLand$343,300Additions$374,700Total$718,000
Tax Record2025$10,232 ($853 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt2,016 SqFtAbove Grade Finished SqFt2,016 SqFtUnfinished Basement SqFt1,008 SqFtStories2Lot Size73,878 SqFtStyleSingle Family ResidenceYear Built2003ZoningAR-ICountyNORFOLKAPNMEDW M:07 B:029Fireplace TypeHas Fireplace

Schools near 5 Winchester Road

This home is within Medway School District.
Rating
School
Type
Grades
Distance
John D Mc Govern Elementary School
Public - PK to 1
Memorial Elementary School
Public - 2 to 4
Medway Middle School
Public - 5 to 8
Medway High School
Public - 9 to 12
Rating
School
Distance
John D Mc Govern Elementary School
PublicPK to 1

Memorial Elementary School
Public2 to 4

Medway Middle School
Public5 to 8

Medway High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Berkshire Hathaway HomeServices Evolution Properties, Lisa Bailey

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. 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., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS 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.