Skip to main content

41 Trolley Road

Westbrook, Connecticut 06498

ACTIVE - NEW$275,000
Beds
2
Baths
1
SqFt
573
Acres
0.29
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt

About This Home

Tucked along Trolley Road in downtown Westbrook, CT, this year-round cottage offers shoreline living with walk-to-town convenience and access to the town beach. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, shops, restaurants, and the Westbrook train station, you can enjoy coffee, dining, and outings close to home. South of Route 1 and within walking distance of Westbrook's sandy beaches, the location puts the best of this coastal town within easy reach. The home needs love and is ready for a new owner's vision, updates, and care. Set on a generous, level lot, this property offers an opportunity to refresh the existing single-family cottage or explore new construction, subject to applicable approvals. A small section of wetlands at the very back creates a natural buffer, with the majority of the land open and usable. A great-size lot in downtown Westbrook is a standout asset, offering space to envision gardens, outdoor entertaining, and a private shoreline retreat. Whether you are looking for a year-round home, coastal getaway, or your next renovation project, this property combines beach access, downtown convenience, and room to imagine what's next. Bring your ideas, see potential, and discover how much this walkable Westbrook location has to offer. A chance to create something special in a setting you'll love.

Key Facts

City/Town
Westbrook
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
1900
Days on Market
0 days
Beds
2
Baths
1 full
Living Area
573 sq ft
Lot Size
0.29 acres
Garage / Parking
4 total
Property Taxes
$5,253 / Annually

Market Snapshot

The Westbrook Market

Single Family · trailing 12 months

Median Days on Market

37

22 active listings

Median $ / Sq Ft

$266

22 active listings

Sale-to-List Ratio

100.0%

81 sales

How this home compares

List Price

$275,000

vs $559,450 median

50.8% below median

Price / Sq Ft

$480

vs $266 median

80.5% above median

Days on Market

0 days

vs 37 days median

37 days fresher than median

Based on 22 active and 81 closed sales (trailing 12 mo) of single family in Westbrook. Source: SmartMLS · As of October 14, 2026.

Location

41 Trolley Road, Westbrook, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,053

per month

  • Principal & Interest$1,523
  • Property Taxes$438
  • Insurance$92
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Westbrook
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Cape Cod
Year Built
1900
New Construction
No/Resale
Living Area
573 sq ft

Schools

Elementary
Daisy Ingraham
High
Westbrook

Interior

Heating
Hot Water
Heat Fuel
Electric
Cooling
None
Laundry
Main Level
Appliances
Oven/RangeRefrigerator
Basement
Crawl Space
In-Law Apartment
No

Exterior & Lot

Lot Size
0.29 acres
Zoning
HDR
Garage / Parking
4 total parking spacesPavedDrivewayAsphalt
Waterfront Details
Access
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
white
Roof
Asphalt Shingle
Foundation
Block
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$5,253 / Annually
Days on Market
0
MLS #
24214471
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jennifer Gurnell

(860) 227-1212

William Raveis Real Estate

(203) 453-0391

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/14/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 10/14/2026 at 11:25 PM UTC.