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.
Under contract
$874,900
5 Winchester Rd, Medway, MA 02053
4beds
2,640sqft
Single Family Residence
Built in 2003
1.7 Acres Lot
$905,800 Zestimate®
$331/sqft
$-- HOA
What's special
Formal dining roomLong private driveDedicated home officeSurrounded by mature treesFormal sitting roomWet bar
- 15 days |
- 905 |
- 69 |
Zillow last checked:
Listing updated:
Listed by:
Lisa Bailey 774-210-0153,
Berkshire Hathaway HomeServices Evolution Properties 508-384-3435
Source: MLS PIN,MLS#: 73536507
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Cable Hookup, Crown Molding
- Level: Second
Bedroom 2
- Features: Closet, Flooring - Hardwood, Cable Hookup
- Level: Second
Bedroom 3
- Features: Closet, Flooring - Hardwood, Cable Hookup
- Level: Second
Bedroom 4
- Features: Closet, Flooring - Hardwood, Cable Hookup, Beadboard
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Flooring - Stone/Ceramic Tile, Pedestal Sink
- Level: First
Bathroom 2
- Features: Bathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
- Level: Second
Bathroom 3
- Features: Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid
- Level: Second
Dining room
- Features: Flooring - Hardwood, Wainscoting, Lighting - Overhead, Crown Molding
- Level: First
Family room
- Features: Flooring - Hardwood, Cable Hookup, Recessed Lighting, Crown Molding
- Level: Main,First
Kitchen
- Features: Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Deck - Exterior, Exterior Access, Recessed Lighting, Slider
- Level: First
Living room
- Features: Flooring - Hardwood, French Doors, Cable Hookup, Lighting - Overhead, Crown Molding
- Level: Main,First
Office
- Features: Flooring - Wall to Wall Carpet, Recessed Lighting
- Level: Basement
Heating
- Baseboard, Oil
Cooling
- Central Air
Appliances
- Included: Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Water Softener, Plumbed For Ice Maker
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Recessed Lighting, Closet, Beadboard, Wet bar, Cable Hookup, Office, Bonus Room, Den, Central Vacuum, Wet Bar
- Flooring: Tile, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Stone/Ceramic Tile
- Doors: Insulated Doors
- Windows: Insulated Windows
- Basement: Full,Partially Finished,Radon Remediation System
- Number of fireplaces: 1
- Fireplace features: Family Room
Interior area
- Total structure area: 2,640
- Total interior livable area: 2,640 sqft
- Finished area above ground: 2,016
- Finished area below ground: 624
Property
Parking
- Total spaces: 8
- Parking features: Attached, Garage Door Opener, Paved Drive, Off Street, Paved
- Attached garage spaces: 2
- Uncovered spaces: 6
Features
- Patio & porch: Porch, Deck, Deck - Wood, Patio
- Exterior features: Porch, Deck, Deck - Wood, Patio, Rain Gutters, Storage
Lot
- Size: 1.7 Acres
Details
- Parcel number: M:07 B:029,4419143
- Zoning: AR-I
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 2003
Utilities & green energy
- Electric: 200+ Amp Service, Generator Connection
- Sewer: Private Sewer
- Water: Private
- Utilities for property: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
Green energy
- Energy efficient items: Thermostat
Community & HOA
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
HOA
- Has HOA: No
Location
- Region: Medway
Financial & listing details
- Price per square foot: $331/sqft
- Tax assessed value: $718,000
- Annual tax amount: $10,232
- Date on market: 6/16/2026
- Listing terms: Contract
- Road surface type: Paved
Estimated market value
$905,800
$861,000 - $951,000
$5,004/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/22/2026 | Contingent | $874,900$331/sqft |
Source: MLS PIN #73536507 Report a problem | ||
| 6/16/2026 | Listed for sale | $874,900+75%$331/sqft |
Source: MLS PIN #73536507 Report a problem | ||
| 5/5/2004 | Sold | $499,900$189/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,232 -1% | $718,000 |
| 2024 | $10,339 +0.4% | $718,000 +11.2% |
| 2023 | $10,294 +11.3% | $645,800 +18.3% |
| 2022 | $9,245 +0.8% | $546,100 +3.9% |
| 2021 | $9,175 +2% | $525,500 +2.2% |
| 2020 | $8,995 +5.9% | $514,000 +2.7% |
| 2019 | $8,495 -0.5% | $500,600 +3.5% |
| 2018 | $8,539 +0.4% | $483,500 +1.9% |
| 2017 | $8,505 +2.2% | $474,600 +3.3% |
| 2016 | $8,318 +0.6% | $459,300 +1.3% |
| 2015 | $8,272 +2.2% | $453,500 +5.6% |
| 2014 | $8,092 +1.5% | $429,500 +0% |
| 2013 | $7,970 +4.7% | $429,400 -1.4% |
| 2012 | $7,613 -2.8% | $435,500 -4.9% |
| 2011 | $7,830 +14.3% | $457,900 +8.9% |
| 2010 | $6,848 +7.7% | $420,400 |
| 2009 | $6,356 +3.1% | $420,400 -4.1% |
| 2008 | $6,164 -0.5% | $438,400 -5.8% |
| 2007 | $6,196 +2.2% | $465,200 -0.6% |
| 2006 | $6,063 +21.5% | $468,200 +33.5% |
| 2005 | $4,992 +132.5% | $350,800 +128.1% |
| 2004 | $2,147 | $153,800 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 02053
Nearby schools
GreatSchools rating
- NAJohn D Mc Govern Elementary SchoolGrades: PK-1Distance: 1.4 mi
- 6/10Medway Middle SchoolGrades: 5-8Distance: 2.2 mi
- 9/10Medway High SchoolGrades: 9-12Distance: 1.2 mi
Schools provided by the listing agent
- Elementary: Burke/Memorial
- Middle: Medway
- High: Medway
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Massachusetts
- Norfolk County
- Medway
- 02053
- 5 Winchester Rd
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