BMN Boston

Get our mobile app!

Download on the App Store

5 Winchester Rd, Medway MA 02053

Medway, MA 02053
$874,900
Est. $5,477/month
4
Beds
2.5
Baths
2,640
Sq Ft
$331
Price/Sq Ft
1.70
Acres
2003
Year Built
2
Garage Spaces
18
Days on Market
Pending Listed Jun 16, 2026 • MLS# 73536507 Copied! • Updated Jul 7, 2026

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.

View in the App

Save this property, schedule tours instantly, and get alerts when the price drops

Scan to download BMN Boston app Scan with phone
Get the full experience in the BMN Boston app

BMN Estimate

Get the number an algorithm can't give you

A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.

Recently Sold Nearby

Property History

Market Insights

Property Timeline

📋
Status: Active under contract
Jun 22, 2026
Active → Active Under Contract
Pending Sale
Jun 21, 2026
Offer accepted, sale pending
👁️
Showing Instructions Updated
Jun 16, 2026
New showing requirements
🏠
Listed for Sale
Jun 16, 2026
$874,900
Original listing
Agent: Lisa Bailey Office: Berkshire Hathaway HomeServices Evolution Properties

Tax History

Year Taxes Assessment
2025 $10,232 $718,000

Financial Details

Annual Property Tax
$10,232
Tax Year 2025
Assessed Value
$718,000

Facts & Features

2 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 2003
Living Area 2,640 sq ft
Lot Size 1.70 acres
Bedrooms 4
Full Baths 2
Half Baths 1
Total Rooms 9

Interior

Heating Baseboard, Oil
Cooling Central Air
Flooring Tile, Hardwood, Flooring - Wall To Wall Carpet, Flooring - Stone/ceramic Tile
Appliances Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker
Fireplace Family Room
Fireplaces 1
Basement Full, Partially Finished, Radon Remediation System
Laundry Electric Dryer Hookup, Washer Hookup
Features Recessed Lighting, Closet, Beadboard, Wet Bar, Cable Hookup, Office, Bonus Room, Den, Central Vacuum, Wet Bar

Exterior

Construction Frame
Architecture Colonial
Roof Shingle
Features Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage
Pool None
Spa None
Fencing None
Patio/Porch Porch, Deck, Deck - Wood, Patio
Garage Spaces 2
Has Garage Yes
Features Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Total Spaces 8
Electric 200+ Amp Service, Generator Connection
Water Private
Sewer Private Sewer
Gas None
Other For Electric Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
Annual Tax $10,232
Assessed Value $718,000
Fee Includes None
Amenities None
Optional Fee Includes None
Down Payment Resource Eligible
Seller Disclosures Winchester Is A Private Road, Owned By 5 Wichester And 3 Winchester.
Possession None
Accepted Financing Contract
Structure Type []
House Color Beige
Sq Ft Source Measured
Sq Ft Disclosures Buyer/Buyers Agent to confirm.
Documents None
County Norfolk
Total market time (incl. prior listings) 20 days

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2003
Bedrooms
4
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,640 sq ft
Total Rooms
9

Room Details

First Floor

Bathroom1
Bathroom - Half, Flooring - Stone/Ceramic Tile, Pedestal Sink
Dining Room
Flooring - Hardwood, Wainscoting, Lighting - Overhead, Crown Molding
Kitchen
Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Recessed Lighting, Slider

Second Floor

Bedroom4
Closet, Flooring - Hardwood, Cable Hookup, Beadboard
Bedroom3
Closet, Flooring - Hardwood, Cable Hookup
Bathroom2
Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
Bedroom2
Closet, Flooring - Hardwood, Cable Hookup
Bathroom3
Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
Master Bedroom
Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Cable Hookup, Crown Molding

Basement Floor

Office
Flooring - Wall to Wall Carpet, Recessed Lighting

Other Floor

Bedroom5
Master Bathroom
Yes

Main,First Floor

Living Room
Flooring - Hardwood, French Doors, Cable Hookup, Lighting - Overhead, Crown Molding
Family Room
Flooring - Hardwood, Cable Hookup, Recessed Lighting, Crown Molding

Interior Features

Flooring: Tile, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
Appliances: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker
Interior Features: Recessed Lighting, Closet, Beadboard, Wet bar, Cable Hookup, Office, Bonus Room, Den, Central Vacuum, Wet Bar
Windows: Insulated Windows
Basement: Full, Partially Finished, Radon Remediation System
Laundry: Electric Dryer Hookup, Washer Hookup
Security:

Construction & Materials

Style: Colonial
Year Built: 2003
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Baseboard, Oil
Heating Zones: 4
Cooling: Central Air
Cooling Zones: 1
Hot Water:
Water Source: Private
Sewer: Private Sewer
Energy Features: Thermostat

Exterior & Lot

Exterior Features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage
Patio & Porch: Porch, Deck, Deck - Wood, Patio
Fencing:
Other Structures:
Lot Features:
Road Surface: Paved

Parking & Garage

Garage Spaces: 2
Garage Type: Attached
Total Parking Spaces: 8
Parking Features: Attached, Garage Door Opener, Paved Drive, Off Street, Paved

Special Features

Fireplaces: 1
Fireplace Type: Family Room
Community Amenities: 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

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%

Monthly Payment Breakdown

Principal & Interest $0
Property Tax $853
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo

Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

Loading map...

Neighborhood

5 Winchester Rd, Medway MA 02053

Medway, MA 02053

Listing Information

Listing Agent Lisa Bailey
Listing Office Berkshire Hathaway HomeServices Evolution Properties
Office Phone 508-384-3435
Agent MLS ID CN233323
Office MLS ID AN5657
Listing Data Updated Jul 7, 2026 3:30 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

Contact Us

Steven Novak
Steven Novak
BMN Boston Real Estate
Ask about this property — free, no obligation.

Similar Homes for Sale

Comparable Properties

Customize Comparable Search

Finding comparable properties...

Market Analytics for Medway, MA

Real-time market trends and pricing data for this area

5 Winchester Rd, Medway MA 02053 - Photo 1 5 Winchester Rd, Medway MA 02053 - Photo 2 5 Winchester Rd, Medway MA 02053 - Photo 3 5 Winchester Rd, Medway MA 02053 - Photo 4 5 Winchester Rd, Medway MA 02053 - Photo 5 5 Winchester Rd, Medway MA 02053 - Photo 6 5 Winchester Rd, Medway MA 02053 - Photo 7 5 Winchester Rd, Medway MA 02053 - Photo 8 5 Winchester Rd, Medway MA 02053 - Photo 9 5 Winchester Rd, Medway MA 02053 - Photo 10 5 Winchester Rd, Medway MA 02053 - Photo 11 5 Winchester Rd, Medway MA 02053 - Photo 12 5 Winchester Rd, Medway MA 02053 - Photo 13 5 Winchester Rd, Medway MA 02053 - Photo 14 5 Winchester Rd, Medway MA 02053 - Photo 15 5 Winchester Rd, Medway MA 02053 - Photo 16 5 Winchester Rd, Medway MA 02053 - Photo 17 5 Winchester Rd, Medway MA 02053 - Photo 18 5 Winchester Rd, Medway MA 02053 - Photo 19 5 Winchester Rd, Medway MA 02053 - Photo 20 5 Winchester Rd, Medway MA 02053 - Photo 21 5 Winchester Rd, Medway MA 02053 - Photo 22 5 Winchester Rd, Medway MA 02053 - Photo 23 5 Winchester Rd, Medway MA 02053 - Photo 24 5 Winchester Rd, Medway MA 02053 - Photo 25 5 Winchester Rd, Medway MA 02053 - Photo 26 5 Winchester Rd, Medway MA 02053 - Photo 27 5 Winchester Rd, Medway MA 02053 - Photo 28 5 Winchester Rd, Medway MA 02053 - Photo 29 5 Winchester Rd, Medway MA 02053 - Photo 30 5 Winchester Rd, Medway MA 02053 - Photo 31 5 Winchester Rd, Medway MA 02053 - Photo 32 5 Winchester Rd, Medway MA 02053 - Photo 33 5 Winchester Rd, Medway MA 02053 - Photo 34 5 Winchester Rd, Medway MA 02053 - Photo 35 5 Winchester Rd, Medway MA 02053 - Photo 36 5 Winchester Rd, Medway MA 02053 - Photo 37 5 Winchester Rd, Medway MA 02053 - Photo 38 5 Winchester Rd, Medway MA 02053 - Photo 39 5 Winchester Rd, Medway MA 02053 - Photo 40 5 Winchester Rd, Medway MA 02053 - Photo 41 5 Winchester Rd, Medway MA 02053 - Photo 42
Steven Novak

Steven Novak

BMN Boston Real Estate

Your message will be sent to Steven Novak.

Schedule a Tour