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About this home
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.
Single-familyProperty Type
2025Year Built
0.43 acresLot Size
$457Price/Sq.Ft.
2 garage spacesParking
Listed by The Pallotta Group• Gibson Sotheby's International Realty
Listed by Nancy Pallotta• Gibson Sotheby's International Realty
West Side, located between the Aberjona River and the Middlesex Fells Reservation, is a residential and commuter-friendly Winchester neighborhood with leafy side streets and trail-forward green space. The neighborhood’s character concentrates around the Winchester Center area at Main Street and Church Street, where independent cafes, small shops, and the commuter rhythm of the station set the pace. Community pillars include the Winchester Community Music School, the Winchester Unitarian Society’s historic campus, and the Jenks Center. Housing reads as classic New England—Colonial Revivals, Victorians, and well-kept mid-century homes—on walkable blocks with stone walls and mature trees. The Fells’ trailheads and reservoirs shape daily routines, while the river corridor adds a quieter, tucked-away geography. A short ride to the station keeps Boston-bound schedules in view without turning the streetscape into a thoroughfare.
Provided by Walk Score and Local Logic
Market insights
1 Plymouth Rd · $3,299,000
DAYS ON MARKET
1 days
The average home goes pending in 22 days.
SALE-TO-LIST
101.2%
Most homes are selling 1% above list price.
LIST PRICE
$3,299,000
Median sale price in this area is $919,982. (72% lower than this home)
PRICE DROP
0 price drops
18% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
15 total rooms
In-law apartment
Mud room
Home office
Media room
Wet bar
Insulated doors
Insulated windows
Bedrooms
Master bedroom on second floor with full bath, walk-in closet, and hardwood flooring
Bedrooms 2–4 on second floor, each with full bath; Bedrooms 3 and 4 have hardwood flooring; Bedroom 2 has walk-in closet
Bedroom 5 on first floor with full bath and hardwood flooring
Bathrooms
Seven full bathrooms
One half bathroom
Master bathroom present
Kitchen
Hardwood flooring
Dining area
Stone/granite/solid countertops
Kitchen island
Wet bar
Pot filler faucet
Gas stove
Laundry & utility
Laundry located on second floor
Gas water heater
Flooring
Wood and hardwood flooring
Engineered hardwood
Heating & cooling
Central heating
Central air conditioning
Thermostat (energy efficient feature)
Exterior features
Porch
Composite deck
Rain gutters
Professional landscaping
Sprinkler system
Corner lot
Wooded lot
Public road frontage
Porch and deck outdoor spaces
Home design
Single family residence
Above-grade and below-grade finished living areas
Parking
Attached garage (under)
2 garage spaces
2 covered spaces
4 open parking spaces
Paved drive and off-street parking
Total of 6 parking spaces
Construction
Frame construction
Concrete perimeter foundation
Shingle roof
Built by builder (year built: actual)
Utilities
Public water
Public sewer
Gas available for range
HOA & community
Community offers access to public transportation, shopping, pool, tennis courts, parks, walk/jog trails, golf, medical facility, bike path, conservation area, house of worship, private and public schools
Not a senior community
Other
Basement is full
Above-grade finished area and finished below-grade area present
Electricity and solar
View estimated energy costs and solar savings for this home
This wonderful home is spacious and sunny and priced below assessment! Four large bedrooms including a master suite. Enclosed porch overlooks private wooded yard. Lower level has above ground family room. This is an exceptional value for a desirable Vinson Owen neighborhood.Ready for your personal touch.
Year
Property tax
Land + Additions
Assessment*
2026
$19,022 (+3.5%)
$1,165,800 + $551,000
$1,716,800
2025
$18,385 (+13.7%)
$1,125,800 + $532,000
$1,657,800
2023
$16,166 (−0.9%)
$1,045,800 + $494,500
$1,540,300
2022
$16,318 (+11.1%)
$845,300 + $459,100
$1,304,400
2021
$14,683 (+7.3%)
$685,300 + $459,100
$1,144,400
2020
$13,684 (+11.2%)
$645,300 + $459,100
$1,104,400
2019
$12,310 (+2.7%)
$605,300 + $411,200
$1,016,500
2018
$11,990 (+8.6%)
$583,300 + $400,300
$983,600
2017
$11,038 (+6.4%)
$520,300 + $378,600
$898,900
2016
$10,373 (+8.1%)
$520,300 + $367,800
$888,100
2015
$9,592 (+0.2%)
$435,300 + $354,800
$790,100
2014
$9,573 (+6.0%)
$435,300 + $320,900
$756,200
2013
$9,035 (+1.8%)
$395,300 + $312,200
$707,500
2012
$8,879 (+2.8%)
$395,300 + $312,200
$707,500
2011
$8,635 (+5.6%)
$395,300 + $318,300
$713,600
2010
$8,180 (+2.1%)
$423,300 + $287,400
$710,700
2009
$8,010
$423,300 + $287,400
$710,700
Public record
Beds
4
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.67 Acres
Year renovated
—
Finished Sq. Ft.
2,685
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,685
Year built
1959
Style
Single Family Residential
County
Middlesex County
APN
3400381S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 16, 2026.
Climate risks
9/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 98° expected this year, 15 days in 30 years
6/10 Wind Factor
54% chance of strong winds in next 30 years
3/10 Air Factor
2 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Winchester, MA • 01890
Average low and high temperatures (°F)
34
20
36
21
51
32
60
40
69
51
80
61
84
66
80
60
75
56
64
46
53
36
39
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
84/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.3 hrs
4.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 1 Plymouth Rd
$3,295,860
$3,140 under list price of $3.30M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $2.0M to $3.5M.