9 Plymouth Rd Winchester — Photo 1 of 37
Recent Drop: $100,000
$2,400,000
Investment Analysis — 9 Plymouth Rd
Winchester, MA 01890 — Winchester Highlands
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 01890 carries an estimated $4,120/mo in gross rent — about a 0.77% cap rate and $18,486/yr in estimated NOI at the $2,400,000 list price. Adjust every assumption in the calculator below.
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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
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
$2,400,000
Was $2,500,000
Sep 8, 2026
MLS® 73544924
$2,500,000
Jul 6, 2026
MLS® 73544924
Listing Agent: Steph Crawford Group
Listing Office: Real Broker MA, LLC
MLS® Number: 73544924