38 Upwey Rd Wellesley — Photo 1 of 42
Recent Drop: $54,000
$2,295,000
Investment Analysis — 38 Upwey Rd
Wellesley, MA 02481
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 02481 carries an estimated $5,340/mo in gross rent — about a 1.29% cap rate and $29,508/yr in estimated NOI at the $2,295,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
3.5
SqFt
3,776
Style
Single Family
Built
1993
Welcome to 38 Upwey Road, offering generous living space, a flexible floor plan and an unbeatable Wellesley location. Built in 1993, this 4-bedroom, 3.5 bath home offers three finished levels, an oversized 2-car garage and a bright, open-concept floor plan. Newly refreshed, the kitchen features brand-new countertops and appliances, while recent roof and system updates offer added peace of mind. A dedicated home office provides the perfect work-from-home space. The walk-out lower level adds tremendous versatility with a spacious recreation area, full bath and wine storage room. Enjoy a private backyard while being just moments from Linden Square, Wellesley’s commuter rail, schools and major commuting routes. A wonderful opportunity to enjoy space, convenience and a prime Wellesley 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 3,776 sq ft principal dwelling). Lot size: 13,408 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
Neighborhood
Public Transportation • Shopping • Highway Access • Public School
Geography
Property History
$2,295,000
Was $2,349,000
Jul 21, 2026
MLS® 73546333
$2,349,000
Jul 8, 2026
MLS® 73546333
Listing Agent: Erica Lockberg
Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate
MLS® Number: 73546333
