355 High St

2,907 Sq. Ft.
$411 / Sq. Ft.
2,907
Sq. Ft.
$411
per Sq. Ft.

Description

One of Boston MetroWest premier communities, Westwood. This exceptional two-acre property offers the perfect balance of privacy and convenience, with easy access to the town center, major commuter routes, and everyday amenities. Built in 1929, this classic Colonial showcases timeless architectural character, featuring high ceilings, oversized windows with an abundance of natural light, and beautiful hardwood floors throughout. Rich in charm and original detail, this home presents a rare opportunity...One of Boston MetroWest premier communities, Westwood. This exceptional two-acre property offers the perfect balance of privacy and convenience, with easy access to the town center, major commuter routes, and everyday amenities. Built in 1929, this classic Colonial showcases timeless architectural character, featuring high ceilings, oversized windows with an abundance of natural light, and beautiful 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.

Listing Agents

  1. Jane Wemyss

    Jane Wemyss

    Listing Agent

    Compass

    P: (617)-803-5149

  2. Taryn Connor

    Taryn Connor

    Alternative Listing Agent

    Compass

    P: (617)-504-7621

Property Details for 355 High Street

Town
Westwood
Area
MA-Westwood
Architectural Style
Colonial
Style
Colonial
Garage Spaces
2
Open Parking Spaces
10.00
Parking Spaces Total
12
LISTING UPDATED: 06/02/2026 04:13 PM

Property Details for 355 High Street

StatusNew
MLS #73528538
Days on Market1
Taxes$11,999 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1929
CountyNorfolk County
Buyer's Agent Compensation2.5%
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Building Information for 355 High Street

Stories-Year Built1929Building Size-Lot Size2.00 AC / 87,045 SF

Payment Calculator

$6,955 per month

30 year fixed, 6.36% Interest

Principal and Interest

$5,955

Property Taxes

$1,000

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 355 High Street

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, 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
  • 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, Unpaved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Off-Street, Unpaved Driveway
  • Parking Features: Off-Street, Unpaved Driveway
Utilities
  • Cooling: Window AC
  • Cooling: Yes
  • Heating: Baseboard, Oil
  • Heating: Yes
  • Sewer: City/Town Sewer
  • Utility Connections: for Electric Range, 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: 143.0
  • Bedroom4 Features: Closet,Flooring - Hardwood
  • Bedroom4 Length: 13.0
  • Bedroom4 Level: Second
  • Bedroom4 Width: 11.0
Bedroom 5
  • Bedroom5 Area: 156.0
  • Bedroom5 Features: Closet
  • Bedroom5 Length: 13.0
  • Bedroom5 Level: Second
  • Bedroom5 Width: 12.0
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
Tax Information
  • Listing Terms: Contract
  • Tax ID: M:009 B:000 L:202,299715
  • Assessments: $937,400
  • Book: 00
  • Tax Year: 2025
  • Zoning: RC
Building / Association Information
Living Characteristics
  • Beds Total: 5
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Cooling Zones: 1
  • Heat Zones: 1
Complex & Association Information
  • Adult Community: No

Property History for 355 High Street

DateEvent & SourcePriceAppreciation
Jun 2, 2026

Listed (Active)

MLS PIN #73528538

$1,195,000
DateEvent & SourcePrice
06/02/2026

Listed (Active)

MLS PIN #73528538

$1,195,000

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

Public Records for 355 High Street

Taxable ValueLand$450,400Additions$487,000Total$937,400
Tax Record2025$11,999 ($1,000 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt2,907 SqFtAbove Grade Finished SqFt2,907 SqFtStories2Lot Size87,045 SqFtStyleSingle Family ResidenceYear Built1929ZoningRCCountyNORFOLKAPNWWOO M:009 B:000 L:202Fireplace TypeHas Fireplace

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.

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355 High Street is a single family home for sale in Westwood, MA 02090. This property was listed for sale on June 2, 2026 by Compass, it's currently listed at $1,195,000. 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 descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. 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.