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Active

355 High St

Westwood, MA 02090

Offered at$1,195,000

Residential · Active · MLS #73558725
Listing Courtesy of Compass | Jane Wemyss

5Bedrooms
3Bathrooms
2,907Square feet
1929Year built

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MLS PIN data

About this home

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.

Property information

Details at a glance

Interior

Rooms
9
Heating
Steam, Oil
Cooling
Window Unit(s)
Flooring
Wood, Tile, Vinyl
Fireplaces
3

Building

Style
Single Family Residence
Year built
1929
Garage
2
Parking
12
Foundation
Block
Roof
Shingle

Land & utilities

Lot size
2 acres
Water
Public
Sewer
Public Sewer
Zoning
RC

Financial

Annual taxes
$12,305
Assessment year
2026

Listing history

Price and status timeline

  1. Exp

    $1,195,000 · Jun 2, 2026

Property value estimate

An informed starting point

Estimated value$1,238,450

Estimated range $1,180,349$1,296,551

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Automated estimates are not appraisals or guarantees of market value.

Comparable sales

Recent properties for context

Recent comparable sales are not available for this property.

Photo insights

Condition signals

Overall presentationbelow average

Generated from listing photography; not a substitute for an inspection.

Local market context

How this home compares in Westwood

MetricThis propertyWestwood
List price$1,195,000$2,365,00049% below local
Price / sq ft$411$56427% below local
Days on market307459% below local
Explore homes in Westwood

Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.

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Common questions

About 355 High St

Can I schedule a private showing?

Yes. Request a tour of 355 High St and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.