1 Plymouth Rd.
Winchester, MA, 01890
$3,299,000
Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester’s best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you’ll find a huge butler’s pantry, a must-have feature in today’s homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today’s buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.
Current real estate data for Single Family in Winchester as of Oct 17, 2026
65
Single Family Listed
61
Avg DOM
564
Avg $ / SqFt
$2,108,182
Avg List Price
Property Details
Price:
$3,299,000
MLS #:
73585058
Status:
Active
Beds:
7
Baths:
7.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 1, 2026
Finished Sq Ft:
7,226
Total Sq Ft:
7,226
Lot Size:
18,730 sqft / 0.43 acres (approx)
Year Built:
2025
Schools
Elementary School:
Vo
Middle School:
Mccall
High School:
Whs
Interior
Above Grade Finished Area
5075
Appliances
Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Range Hood
Bathrooms
7 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
2151
Cooling
Central Air
Fireplaces Total
2
Flooring
Wood, Flooring – Hardwood, Flooring – Stone/Ceramic Tile, Flooring – Engineered Hardwood
Heating
Central
Interior Features
Bedroom, Inlaw Apt., Mud Room, Media Room, Wet Bar
Laundry Features
Second Floor
Exterior
Architectural Style
Colonial
Attached Garage YN
1
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, House of Worship, Private School, Public School
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Porch, Deck – Composite, Rain Gutters, Professional Landscaping, Sprinkler System
Garage Spaces
2
Green Energy Efficient
Thermostat
Lot Features
Corner Lot, Wooded
Open Parking Spaces
4
Open Parking YN
1
Parking Features
Attached, Under, Paved Drive, Off Street
Parking Spots
6
Parking Total
6
Patio And Porch Features
Porch, Deck – Composite
Roof
Shingle
Window Features
Insulated Windows
Financial
Tax Year
2026
Map
Contact Us
Mortgage Calculator
Community
- Address1 Plymouth Rd. Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 1 Plymouth Rd. Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $3,299,000 and features 7 beds, 8 baths, and has approximately 7,226 square feet of living space, and was originally constructed in 2025. The current price per square foot is $457. The average price per square foot for Single Family listings in Winchester is $564. The average listing price for Single Family in Winchester is $2,108,182. To schedule a showing of MLS#73585058 at 1 Plymouth Rd. in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
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CRP: Certified Relocation Professional CRS: Certified Residential Specialist GRI: Graduate of Realtors Institute CBR: Certified Buyers Representative BSBA: Bachelor of Science in Business Administration. Babson College 1979 MBA: Master of Business Administration. Babson College 2002 James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…
More About JamesCourtesy of Leading Edge Real Estate. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
1 Plymouth Rd.
Winchester, MA



