
355 High St Westwood — Photo 1 of 8
$1,195,000
Investment Analysis — 355 High St
Westwood, MA 02090
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02090 carries an estimated $4,250/mo in gross rent — about a 2.21% cap rate and $26,455/yr in estimated NOI at the $1,195,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
2.5
SqFt
2,907
Style
Single Family
Built
1929
Exceptional two-acre property offers the perfect balance of privacy and convenience, with easy access to the town center, major commuter routes in premier MetroWest community of Westwood. Built in 1929, this classic Colonial showcases timeless architectural character, featuring high ceilings, oversized windows and french doors providing an abundance of natural light, and hardwood floors throughout. Rich in charm and original detail, this home presents a rare opportunity to restore and reimagine a property with enduring appeal. The expansive grounds are a true highlight—an exceptional, rolling yard surrounded by a serene, natural setting that offers both tranquility and space for outdoor living, entertaining, or future enhancements. Located in highly sought-after Westwood—known for its top-rated schools, strong community feel —this property represents a unique opportunity for buyers looking to customize and create their ideal home in a prime location. No open houses.
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 2,907 sq ft principal dwelling). Lot size: 87,045 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
Range • Dishwasher • Refrigerator • Freezer • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First29 x 14
Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access
Dining Room
Lvl First20 x 15
Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access
Kitchen
Lvl First20 x 12
Dining Area, Dryer Hookup - Electric, Washer Hookup
Primary Bedroom
Lvl Second20 x 15
Bathroom - Full, Closet, Flooring - Hardwood
Bedroom 2
Lvl Second20 x 12
Bedroom 3
Lvl Second14 x 13
Closet, Flooring - Hardwood
Bedroom 4
Lvl Second13 x 11
Closet, Flooring - Hardwood
Bedroom 5
Lvl Second13 x 12
Closet
Bathroom 1
Lvl SecondBathroom 2
Lvl SecondBathroom 3
Lvl SecondProperty History
$1,195,000
Aug 4, 2026
MLS® 73558725
$1,195,000
Jun 30, 2026
MLS® 73528538
$1,195,000
Jun 2, 2026
MLS® 73528538
Listing Agent: Jane Wemyss
Listing Office: Compass
MLS® Number: 73558725