Active
5 beds2,907 sqft

355 High St, Westwood, MA 02090

Single FamilyProperty Type
2.00 acresLot Size
1929Year Built
$361/sq ftPrice per sq ft
12 carsParking Spaces
2.5% CompensationBuyer's Agent

Description

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...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 Agents
  1. Jane Wemyss

    Jane Wemyss

    Listing Agent

    Compass

    P: (617) 803-5149

    M: (617) 803-5149

  2. Taryn Connor

    Taryn Connor

    Alternative Listing Agent

    Compass

    P: (617) 504-7621

    M: (617) 504-7621

66 days on Market
Last updated: 10/09/2026 03:08 AM • Source: MLS PIN, MLS#: 73558725

Location

Add your commute
Payment Calculator

$6,631 per month

30 year fixed, 7.03% Interest

Principal and Interest

$5,605

Property Taxes

$1,025

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.
Know your buying power with a preapproval and custom rate in minutes
Rocket Mortgage1

Property Information for 355 High Street

Property Details

  • Taxes: $12,305 / year
  • MLS Type: Single Family / Detached
  • Buyer's Agent Compensation: 2.5%
  • Compensation Remarks: 0
  • Town: Westwood
  • Area: MA-Westwood
  • Architectural Style: Colonial
  • Style: Colonial
  • Garage Spaces: 2
  • Open Parking Spaces: 10.00
  • Parking Spaces Total: 12

Building Information

  • Year Built: 1929
  • Lot Size: 2.00 AC / 87,045 SF

General Details

Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Swimming Pool, Tennis Court, Park, Walk/Jog Trails, Conservation Area, Highway Access, House of Worship, Public School, T-Station, Sidewalks
  • Living Area: 2907.0
  • Color: white
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records

Features

Interior Features
  • Appliances: Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer
  • Basement Features: Full, Interior Access, Sump Pump, Concrete Floor, Unfinished Basement
  • Num of Baths: 3.0
  • Num of Full Baths: 2
  • Num of Half Baths: 1
  • Bathrooms Total Decimal: 2.50
  • Bathrooms Total Integer: 3
  • DoorFeatures: French Doors
  • FireplaceFeatures: Dining Room, Living Room, Master Bedroom
  • FireplaceYN: Yes
  • Fireplaces: 3
  • Flooring: Wood, Tile, Vinyl
  • Interior Features: French Doors, Window AC
  • Laundry Features: First Floor, Electric Dryer Hookup, Washer Hookup
  • Primary Bath: Yes
  • SpaYN: No
Exterior Features
  • Construction: Frame
  • Exterior Features: Porch - Screened, Stone Wall
  • Exterior Features: Stone Wall, Porch - Screened
  • Lot Description: Gentle Sloping
  • Patio And Porch Features: Screened
  • Roof Material: Shingle
  • View: Scenic View(s)
  • View: Yes
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Off-Street, Stone/Gravel, Unpaved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Off-Street, Stone/Gravel, Unpaved Driveway
  • Parking Features: Off-Street, Stone/Gravel, Unpaved Driveway
Utilities
  • Cooling: Window AC
  • Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Steam, Oil
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup
  • Water: Public

Room Information

Primary Bedroom
  • Room Primary Bedroom Area: 300.0
  • Room Primary Bedroom Features: Bathroom - Full,Closet,Flooring - Hardwood
  • Room Primary Bedroom Length: 20.0
  • Primary Bedroom Level: Second Floor
  • Room Primary Bedroom Width: 15.0
Bedroom 2
  • Bedroom2 Area: 240.0
  • Bedroom2 Features: Bathroom - Half,Closet,Flooring - Hardwood
  • Bedroom2 Length: 20.0
  • Bedroom2 Level: Second
  • Bedroom2 Width: 12.0
Bedroom 3
  • Bedroom3 Area: 182.0
  • Bedroom3 Features: Closet,Flooring - Hardwood
  • Bedroom3 Length: 14.0
  • Bedroom3 Level: Second
  • Bedroom3 Width: 13.0
Bedroom 4
  • Bedroom4 Area: 156.0
  • Bedroom4 Features: Closet,Flooring - Hardwood
  • Bedroom4 Length: 13.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 12.0
Bedroom 5
  • Bedroom5 Area: 154.0
  • Bedroom5 Features: Closet
  • Bedroom5 Length: 11.0
  • Bedroom5 Level: Second
  • Bedroom5 Width: 14.0
Bathroom 1
  • Bathroom1 Level: Second
Bathroom 2
  • Bathroom2 Level: Second
Bathroom 3
  • Bathroom3 Level: Second
Dining Room
  • Dining Room Area: 300.0
  • Dining Room Features: Flooring - Hardwood,French Doors,Deck - Exterior,Exterior Access
  • Dining Room Length: 20.0
  • Dining Room Level: First
  • Dining Room Width: 15.0
Kitchen
  • Kitchen Area: 240.0
  • Kitchen Features: Dining Area,Dryer Hookup - Electric,Washer Hookup
  • Kitchen Length: 20.0
  • Kitchen Level: First
  • Kitchen Width: 12.0
Living Room
  • Room Living Room Area: 406.0
  • Room Living Room Features: Flooring - Hardwood,French Doors,Deck - Exterior,Exterior Access
  • Room Living Room Length: 29.0
  • Room Living Room Level: Main,First
  • Room Living Room Width: 14.0

Property Information

Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Road Responsibility: Public Maintained Road
  • Road Surface Type: Paved
  • Disclosures: Furnace replaced 12/2017; Electrical has been upgraded; water line from street was replaced; roof 2010.
Tax Information
  • Tax ID: M:009 B:000 L:202,299715
  • Assessments: $956,100
  • Book: 00
  • Tax Year: 2026
  • Zoning: RC

Building / Association Information

Living Characteristics
  • Beds Total: 5
Other Building Characteristics
  • Foundation: Block
  • Cooling Zones: 1
  • Heat Zones: 1
Complex & Association Information
  • Adult Community: No

Property History for 355 High Street

DateEvent & SourcePriceAppreciation
Oct 5, 2026

Price Change

MLS PIN #73558725

$1,050,000—
Sep 29, 2026

Canceled

MLS PIN #73583334

$1,195,000—
Sep 28, 2026

Listed (Active)

MLS PIN #73583334

$1,195,000—
DateEvent & SourcePrice
10/05/2026

Price Change

MLS PIN #73558725

$1,050,000
09/29/2026

Canceled

MLS PIN #73583334

$1,195,000
09/28/2026

Listed (Active)

MLS PIN #73583334

$1,195,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public records

355 High Street

Beds

5

Baths

2.5

Total Finished SqFt

2,907 SqFt

Above Grade Finished SqFt

2,907 SqFt

Unfinished Basement SqFt

1,342 SqFt

Stories

2

Schools near 355 High Street

This home is within Westwood School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Public - PK to 5
Rating
School
Distance
Deerfield School
PublicK to 5

E W Thurston Middle School
Public6 to 8

Westwood High School
Public9 to 12

Pine Hill Elementary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 02090

$849,900 | 290 East Street, Westwood, MA 02090
1/20
Open: 10/11 12:00PM - 01:30PMNew

$849,900

5
Bedrooms
1,419
Square Feet
0.50
Acres
$624,995 | 130 University Avenue, Unit 1210, Westwood, MA 02090
1/21
Open: 10/10 11:00AM - 12:30PM

$624,995

1
Bedrooms
1,036
Square Feet
$1,700,000 | 115 Cobleigh Street, Westwood, MA 02090
1/4

$1,700,000

5
Bedrooms
3,293
Square Feet
0.22
Acres
$2,800,000 | 74 Ridge Road, Westwood, MA 02090
1/35
Listed By Coldwell Banker Realty

$2,800,000

4
Bedrooms
6,847
Square Feet
1.47
Acres
$1,299,000 | 138 Forbes Road, Westwood, MA 02090
1/40
Contingent

$1,299,000

4
Bedrooms
2,632
Square Feet
0.47
Acres
$850,000 | 130 University Avenue, Unit 1201, Westwood, MA 02090
1/42

$850,000

2
Bedrooms
1,480
Square Feet
$949,000 | 857 Gay Street, Westwood, MA 02090
1/42
Listed By Coldwell Banker RealtyVirtual Tour

$949,000

4
Bedrooms
1,840
Square Feet
0.32
Acres
front view of a house with a yard
1/35
Listed By Coldwell Banker Realty

$1,390,000

4
Bedrooms
3,076
Square Feet
1.84
Acres
$1,275,000 | 444 Clapboardtree Street, Westwood, MA 02090
1/34
Listed By Coldwell Banker Realty

$1,275,000

4
Bedrooms
3,336
Square Feet
1.84
Acres

355 High Street is a single family home for sale in Westwood, MA 02090. This property was listed for sale on August 4, 2026 by Compass, it's currently listed at $1,050,000. This listing's school district is Westwood School District. Nearby schools include Deerfield School, E W Thurston Middle School and Westwood High School. 355 High Street is a 5-bed, 3-bath, 2,907 sqft single family home built in 1929.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.