SOLD JUL 31, 2026

Sold on Jul 2026

$930,000

•

2,640

sq ft

5 Winchester Rd, Medway, MA 02053

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About this home

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.

Single-familyProperty Type

2003Year Built

1.7 acresLot Size

$352Price/Sq.Ft.

2 garage spacesParking

Listed by Lisa Bailey • Berkshire Hathaway HomeServices Evolution Properties

Listed by • Berkshire Hathaway HomeServices Evolution Properties

Bought with Team Rice • REMAX Executive Realty

Redfin checked: a minute ago

•Source:MLS PIN #73536507

Redfin Estimate

$892,975

$37K since sold in July 2026$4,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17% lower than the average sale price ($1.08M) of 6 comparable homes.

SOLD JUL 15, 2026
$1,060,000
A
4 beds2.5 baths2,714 sq ft
22 Diane Dr, Medway, MA 02053
SOLD AUG 13, 2026
$1,175,000
B
4 beds2.5 baths3,166 sq ft
3 Stable Way, Medway, MA 02053
SOLD JUN 30, 2026
$950,000
C
4 beds2.5 baths3,302 sq ft
133 Summer, Medway, MA 02053
SOLD AUG 18, 2026
$940,000
D
4 beds3 baths2,918 sq ft
13 Fairway Ln, Medway, MA 02053
SOLD JUL 31, 2026
$1,165,000
E
4 beds2.5 baths3,361 sq ft
16 Stable Way, Medway, MA 02053
SOLD APR 23, 2026
$1,164,000
F
4 beds2.5 baths2,600 sq ft
731 Norfolk St, Holliston, MA 01746

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Market trends in 02053, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.7%

+0.6% MoM

Median sale price

$746K

$56K MoM

Avg. days on market

18d

0 days MoM

Recently sold homes

10 MoM

New listings for sale

REDFIN OPEN SAT, 12PM TO 1:30PM
$970,000
4 beds2.5 baths2,870 sq ft
16 Jasmine Rd, Medway, MA 02053
OPEN SAT, 11AM TO 1PM
$499,000
2 beds1 bath1,089 sq ft
17 Cutler St, Medway, MA 02053
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Rental estimate

Est. $4,059 per month, based on comparable rentals

Sale and tax history for 5 Winchester Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$10,294 (+11.3%)

$312,800 + $333,000

$645,800

2022

$9,245 (+0.8%)

$232,200 + $313,900

$546,100

2021

$9,175 (+2.0%)

$216,900 + $308,600

$525,500

2020

$8,995 (+5.9%)

$216,900 + $297,100

$514,000

2019

$8,495 (−0.5%)

$208,200 + $292,400

$500,600

2018

$8,539 (+0.4%)

$199,500 + $284,000

$483,500

2017

$8,505 (+2.2%)

$195,200 + $279,400

$474,600

2016

$8,318 (+0.6%)

$179,900 + $279,400

$459,300

2015

$8,272 (+2.2%)

$177,700 + $275,800

$453,500

2014

$8,092 (+1.5%)

$181,200 + $248,300

$429,500

2013

$7,970 (+4.7%)

$181,200 + $248,200

$429,400

2012

$7,613 (−2.8%)

$181,200 + $254,300

$435,500

2011

$7,830 (+14.3%)

$138,800 + $319,100

$457,900

2010

$6,848 (+7.7%)

$144,700 + $275,700

$420,400

2009

$6,356

$144,700 + $275,700

$420,400

Public record

Public record
Permits

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

1.7 Acres

Year renovated

—

Sq. Ft.

2,016

Year built

2003

Style

Single Family Residential

County

Norfolk County

APN

4419143

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Open Parking Spaces: 6
Parking Spaces: 8
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Cable Hookup,Crown Molding

Bedroom #2 Information
Level: Second
Features: Closet,Flooring - Hardwood,Cable Hookup

Bedroom #3 Information
Level: Second
Features: Closet,Flooring - Hardwood,Cable Hookup

Bedroom #4 Information
Level: Second
Features: Closet,Flooring - Hardwood,Cable Hookup,Beadboard

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Pedestal Sink

Bathroom #2 Information
Level: Second
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Bathroom - With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid

Living Room Information
Level: Main,First
Features: Flooring - Hardwood,French Doors,Cable Hookup,Lighting - Overhead,Crown Molding

Family Room Information
Level: Main,First
Features: Flooring - Hardwood,Cable Hookup,Recessed Lighting,Crown Molding

Dining Room Information
Level: First
Features: Flooring - Hardwood,Wainscoting,Lighting - Overhead,Crown Molding

Kitchen Information
Level: First
Features: Flooring - Hardwood,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Deck - Exterior,Exterior Access,Recessed Lighting,Slider

Office Room Information
Level: Basement
Features: Flooring - Wall to Wall Carpet,Recessed Lighting

Basement Information
Basement: Full, Partially Finished, Radon Remediation System

Laundry Information
Laundry Features: Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Family Room

Appliances
Appliances: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker

Interior Features
# of Rooms (Total): 9
Door Features: Insulated Doors
Window Features: Insulated Windows
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

Exterior

Building Information
Building Area (Total): 2,640
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Beige

Exterior Features
Roof: Shingle
Patio And Porch Features: Porch, Deck, Deck - Wood, Patio
Exterior Features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage

Property Information
PropertySubType: Single Family Residence
Above Grade Finished Area: 2016
Below Grade Finished Area: 624
Green Energy Efficient : Thermostat
ADU: N

Lot Information
Lot Size (Acres): 1.7
Road Surface Type: Paved
Road Frontage Type: Private Road, Dead End
Road Responsibility: Private Maintained Road

Financial

Tax Information
Tax Annual Amount: $10,232
Tax Year: 2025

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
Sewer: Private Sewer
Water Source: Private
Electric: 200+ Amp Service, Generator Connection

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Oil
Cooling: Central Air

Location

School Information
Elementary School: Burke/Memorial
Middle Or Junior School: Medway
High School: Medway

Location Information
Directions: Winthrop St to Winchester. Winchester is a private road, 5 Winchester is at the end.
UnparsedAddress: 5 Winchester Rd, Medway MA 02053

Community Information
Senior CommunityYN: No
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

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,016
Stories: 2.0
Lot Size: 1.7 acres
Style: Single Family Residential
Year Built: 2003
Year Renovated: —
County: Norfolk County
APN: 4419143

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
StandardStatus: Closed

Around this home

Schools

John D Mc Govern Elementary School

Public PreK-1 • Assigned • 1.4mi

Medway Middle School

Public 5-8 • Assigned • 2.2mi

7/10

Medway High School

Public 9-12 • Assigned • 1.2mi

9/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

6/10 Wind Factor

53% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Medway, MA • 02053

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

96/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

5.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$849,000 – $1.03M

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Home values near 5 Winchester Rd

Data from public records.

Address	Redfin Estimate
1 Winchester Road, Medway, MA 4 Beds \| 2.5 Baths \| 2020 Sq. Ft.	$859,787
111 Winthrop Street, Medway, MA - Beds \| - Baths \| - Sq. Ft.	—

Address	Redfin Estimate
3 Winchester Road, Medway, MA 4 Beds \| 2.5 Baths \| 2793 Sq. Ft.	$924,636
105 Winthrop Street, Medway, MA 3 Beds \| 2.5 Baths \| 2362 Sq. Ft.	$655,780

Address	Redfin Estimate
2 Winchester Road, Medway, MA 4 Beds \| 2.5 Baths \| 2020 Sq. Ft.	$791,508
1 Diane Drive, Medway, MA 4 Beds \| 2.5 Baths \| 2179 Sq. Ft.	$864,279

Property information provided by MLS PIN when last listed in 2026. This data may not match . Learn more.

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