Active
3 Days on market
1 Plymouth Rd. Winchester — Photo 1 of 28

1 Plymouth Rd. Winchester — Photo 1 of 28

$3,299,000

1 Plymouth Rd., Winchester, MA 01890

Winchester, MA 01890

Beds

7

Baths

7.5

SqFt

7,226

Style

Single Family

Built

2025

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.

Key facts

It was listed on October 1, 2026. It sits on a 0.43-acre (18,730 sq ft) lot.

Open Houses

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$457/sqft
Local Avg (Winchester)$584/sqft
22% BelowMarket Average

* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.

Property Details

Financials

Original Price$3,299,000
Annual Taxes--

Parking

Garage2
Off-Street6

Interior Specifications

Total Rooms15
Fireplaces2
FlooringWood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Engineered Hardwood
BasementFull

Climate & Utilities

HeatingCentral
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
Zoningrda

Property & Lot

Acres0.43
SqFt Lot18,730
Lot FeaturesCorner Lot, Wooded

Amenities & Appliances

Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Range Hood

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomBedroom 5Bathroom 1
Living Room
Lvl First

23 x 24

Cathedral Ceiling(s), Flooring - Hardwood

Dining Room
Lvl First

16 x 10

Flooring - Hardwood

Kitchen
Lvl First

18 x 15

Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Wet Bar, Pot Filler Faucet, Gas Stove

Family Room
Lvl First

27 x 16

Flooring - Hardwood

Primary Bedroom
Lvl Second

14 x 16

Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood

Bedroom 2
Lvl Second

11 x 16

Bedroom 3
Lvl Second

16 x 11

Bathroom - Full, Flooring - Hardwood

Bedroom 4
Lvl Second

16 x 11

Bathroom - Full, Flooring - Hardwood

Bedroom 5
Lvl First

19 x 10

Bathroom - Full, Flooring - Hardwood

Bathroom 1
Lvl First

17 x 11

Bathroom 2
Lvl Second
Bathroom 3
Lvl Second

Property History

Listed
$3,299,000

Oct 1, 2026

MLS® 73585058

Expired
$3,299,000

Sep 15, 2026

MLS® 73498293

Listed
$3,299,000

Apr 8, 2026

MLS® 73498293

Questions about this home

When was 1 Plymouth Rd., Winchester listed?

1 Plymouth Rd., Winchester was listed on October 1, 2026.

Has the price of 1 Plymouth Rd., Winchester changed?

The price hasn't changed since it was listed at $3,299,000.

How big is the lot at 1 Plymouth Rd., Winchester?

1 Plymouth Rd., Winchester sits on a 0.43-acre (18,730 sq ft) lot.

What is the status of 1 Plymouth Rd., Winchester?

1 Plymouth Rd., Winchester is actively listed for sale.

Population

23,406

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$230K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

18.3%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Middlesex County

2,698 housing units permitted in the last 12 months (+3% vs the prior 12 months) — 1,713 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jul '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 7,226 sq ft principal dwelling). Lot size: 18,730 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Listing Provided By

Listing Agent: The Pallotta Group

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73585058