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Bean Group
Offered at $1,050,000Pending
beds
5
baths
3
sq ft
2,907
Built
1929

355 High St

Westwood, MA 02090

About this home

NEW PRICE! Exceptional opportunity to live in Westwood on a two-acre property which offers the perfect balance of privacy and convenience, easy access to the town center, major commuter routes in premier MetroWest community. 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.

Listing last checked: Listing updated:

Listed by Jane Wemyss · Compass · MLS #73558725

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Details at a glance

Interior6 property facts
Rooms
9
Heating
Steam, Oil
Cooling
Window Unit(s)
Flooring
Wood, Tile, Vinyl
Basement
Yes · Full, Interior Entry, Sump Pump, Concrete, Unfinished
Fireplaces
3
Building6 property facts
Style
Single Family Residence
Year built
1929
Garage
2
Parking
12
Foundation
Block
Roof
Shingle
Land & utilities5 property facts
Lot size
2 acres
Water
Public
Sewer
Public Sewer
Pool
Not reported
Zoning
RC
Financial2 property facts
Annual taxes
$12,305
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $1,050,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$6,335 / monthAdjust
Principal & interest
$5,309
Property tax
$1,025
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $12,305. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Price and status timeline

  1. Exp

    $1,195,000 · Jun 2, 2026

More property insights

Automated value estimate $1,238,450

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

Automated estimates are not appraisals or guarantees of market value.

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Photo-based condition insights

Overall presentation: below average

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About 355 High St

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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.