FeaturesCloset, Flooring - Hardwood, Cable Hookup, Beadboard
LevelSecond
5 Winchester Rd, Medway MA 02053
Medway, MA 02053
$874,900
Est. $5,477/month
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.
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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
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 06/22/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 06/21/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 06/16/2026 | 👁️ Showing Instructions Updated | - | - | - | New showing requirements |
| 06/16/2026 | 🏠 Listed for Sale | $874,900 | - | - | Original listing |
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
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Total Spaces
8
Utilities
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
Financial
Annual Tax
$10,232
Assessed Value
$718,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Down Payment Resource
Eligible
MA Disclosures
Seller Disclosures
Winchester Is A Private Road, Owned By 5 Wichester And 3 Winchester.
Additional Details
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
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,016 sq ft above grade
624 sq ft below grade
FeaturesCloset, Flooring - Hardwood, Cable Hookup
LevelSecond
FeaturesBathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
LevelSecond
FeaturesCloset, Flooring - Hardwood, Cable Hookup
LevelSecond
FeaturesBathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
LevelSecond
FeaturesBathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Cable Hookup, Crown Molding
LevelSecond
FeaturesBathroom - Half, Flooring - Stone/Ceramic Tile, Pedestal Sink
LevelFirst
FeaturesFlooring - Hardwood, Wainscoting, Lighting - Overhead, Crown Molding
LevelFirst
FeaturesFlooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Recessed Lighting, Slider
LevelFirst
FeaturesFlooring - Hardwood, French Doors, Cable Hookup, Lighting - Overhead, Crown Molding
LevelMain,First
FeaturesFlooring - Hardwood, Cable Hookup, Recessed Lighting, Crown Molding
LevelMain,First
FeaturesFlooring - Wall to Wall Carpet, Recessed Lighting
LevelBasement
FeaturesYes
Display Options
Outdoor Areas
Patio & porchPorch, Deck, Deck - Wood, Patio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
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
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
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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.
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