Active
65 Days on market
9 Plymouth Rd Winchester — Photo 1 of 37

9 Plymouth Rd Winchester — Photo 1 of 37

Recent Drop: $100,000

$2,500,000
$2,400,000

$2,400,000

9 Plymouth Rd, Winchester, MA 01890

Winchester, MA 01890 — Winchester Highlands

Beds

5

Baths

3

SqFt

4,071

Style

Single Family

Built

1959

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$590/sqft
Local Avg (Winchester)$532/sqft
11% AboveMarket Average

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

Property Details

Financials

Original Price$2,500,000
Annual Taxes$19,088

Parking

Garage2
Off-Street4

Interior Specifications

Total Rooms11
Fireplaces1
FlooringWood
BasementPartial

Climate & Utilities

HeatingBaseboard, Oil
CoolingCentral Air, None
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRDA

Property & Lot

Acres0.52
SqFt Lot22,599
Lot Features--

Amenities & Appliances

Water Heater • Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Freezer • Washer • Dryer

Neighborhood

Park • Walk/Jog Trails • Golf • Bike Path • Conservation Area • Highway Access

Geography

Property History

Price Drop
$2,400,000

Was $2,500,000

Sep 8, 2026

MLS® 73544924

Listed
$2,500,000

Jul 6, 2026

MLS® 73544924

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

2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '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 4,071 sq ft principal dwelling). Lot size: 22,599 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: Steph Crawford Group

Listing Office: Real Broker MA, LLC

MLS® Number: 73544924

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