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.
Sold for $930,000
$930,000
5 Winchester Rd, Medway, MA 02053
4beds
2,640sqft
Single Family Residence
Built in 2003
1.7 Acres Lot
$929,400 Zestimate®
$352/sqft
$4,640 Estimated rent
Home value
$929,400
$874,000 - $985,000
$4,640/mo
Zestimate® history
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List your homeWhat's special
Formal dining roomLong private driveDedicated home officeSurrounded by mature treesFormal sitting roomWet bar
Zillow last checked:
Listing updated:
Listed by:
Lisa Bailey 774-210-0153,
Berkshire Hathaway HomeServices Evolution Properties 508-384-3435
Bought with:
Team Rice
REMAX Executive Realty
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: $352/sqft
- Tax assessed value: $718,000
- Annual tax amount: $10,232
- Date on market: 7/11/2026
- Listing terms: Contract
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 7/31/2026 | Sold | $930,000+6.3%$352/sqft |
Source: MLS PIN #73536507 Report a problem | ||
| 7/6/2026 | Pending sale | $874,900$331/sqft |
Source: MLS PIN #73536507 Report a problem | ||
| 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
Neighborhood: 02053
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Nearby schools
GreatSchools rating
- NAJohn D Mc Govern Elementary SchoolGrades: PK-1Distance: 1.4 mi
- 7/10Medway 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.
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Estimated market value
$929,400
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Estimated market value
$929,400
- Massachusetts
- Norfolk County
- Medway
- 02053
- 5 Winchester Rd
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