9 Plymouth Rd Winchester — Photo 1 of 37
Recent Drop: $150,000
$2,250,000
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.
Key facts
It was listed on July 6, 2026. The price has come down from an original $2,500,000 to $2,250,000 across 2 changes, most recently on September 24, 2026. The annual property taxes are $19,088 (2025 tax year). It sits on a 0.52-acre (22,599 sq ft) lot.
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
$2,250,000
Was $2,400,000
Sep 24, 2026
MLS® 73544924
$2,400,000
Was $2,500,000
Sep 8, 2026
MLS® 73544924
$2,500,000
Jul 6, 2026
MLS® 73544924
Questions about this home
When was 9 Plymouth Rd, Winchester listed?
9 Plymouth Rd, Winchester was listed on July 6, 2026.
Has the price of 9 Plymouth Rd, Winchester changed?
The price has come down from an original $2,500,000 to $2,250,000 across 2 changes, most recently on September 24, 2026.
What are the property taxes for 9 Plymouth Rd, Winchester?
The annual property taxes for 9 Plymouth Rd, Winchester are $19,088 (2025 tax year).
How big is the lot at 9 Plymouth Rd, Winchester?
9 Plymouth Rd, Winchester sits on a 0.52-acre (22,599 sq ft) lot.
What is the status of 9 Plymouth Rd, Winchester?
9 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 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 Agent: Steph Crawford Group
Listing Office: Real Broker MA, LLC
MLS® Number: 73544924
