Active
40 Days on market
355 High St Westwood — Photo 1 of 8

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.

View Standard Listing

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

Original Price$1,195,000
Annual Taxes$12,305

Parking

Garage2
Off-Street12

Interior Specifications

Total Rooms9
Fireplaces3
FlooringWood, Tile, Vinyl
BasementFull, Interior Entry, Sump Pump, Concrete, Unfinished

Climate & Utilities

HeatingSteam, Oil
CoolingWindow Unit(s)
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationBlock
ZoningRC

Property & Lot

Acres2
SqFt Lot87,045
Lot FeaturesGentle Sloping

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

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 1Bathroom 2Bathroom 3
First
Dining RoomKitchen
Main,First
Living Room
Living Room
Lvl Main,First

29 x 14

Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access

Dining Room
Lvl First

20 x 15

Flooring - Hardwood, French Doors, Deck - Exterior, Exterior Access

Kitchen
Lvl First

20 x 12

Dining Area, Dryer Hookup - Electric, Washer Hookup

Primary Bedroom
Lvl Second

20 x 15

Bathroom - Full, Closet, Flooring - Hardwood

Bedroom 2
Lvl Second

20 x 12

Bedroom 3
Lvl Second

14 x 13

Closet, Flooring - Hardwood

Bedroom 4
Lvl Second

13 x 11

Closet, Flooring - Hardwood

Bedroom 5
Lvl Second

13 x 12

Closet

Bathroom 1
Lvl Second
Bathroom 2
Lvl Second
Bathroom 3
Lvl Second

Property History

Listed
$1,195,000

Aug 4, 2026

MLS® 73558725

Expired
$1,195,000

Jun 30, 2026

MLS® 73528538

Listed
$1,195,000

Jun 2, 2026

MLS® 73528538

Listing Provided By

Listing Agent: Jane Wemyss

Listing Office: Compass

MLS® Number: 73558725