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41 Trolley Road

Westbrook, Connecticut 06498

ACTIVE$275,000

Reduced from $375,000

Beds
2
Baths
1
SqFt
573
Acres
0.29
Year Built
1900
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Price Reduced

About This Home

Tucked along Trolley Road in Westbrook, this year-round cottage offers a rare opportunity in one of the shoreline's most sought-after locations. The home itself is ready for a new owner's vision and care, but it's the walk-to-town lifestyle that makes this property truly special. Just steps from Christie's, Julie's Cup of Joe, The Turtle Cafe, and the Westbrook train station, you'll enjoy the ease of downtown living while still being south of Route 1 and within walking distance to Westbrook's sandy beaches. Set on a generous, level lot, with test holes already completed, the property offers incredible potential well beyond its current footprint. A small section of wetlands rests quietly at the very back, creating natural privacy while preserving the majority of the land as open and usable. Whether you envision refreshing the existing single-family home or building new construction, this property provides a prime canvas for your ideas. An ideal choice for buyers seeking both lifestyle and location, this home can also be purchased together with MLS #24124260, offering an even larger opportunity in the heart of Westbrook's shoreline community.

Key Facts

City/Town
Westbrook
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
1900
Days on Market
306 days
Beds
2
Baths
1 full
Living Area
573 sq ft
Lot Size
0.29 acres
Property Taxes
$5,084 / Annually

Market Snapshot

The Westbrook Market

Single Family · trailing 12 months

Median Days on Market

37

19 active listings

Median $ / Sq Ft

$291

19 active listings

Sale-to-List Ratio

99.2%

71 sales

How this home compares

List Price

$275,000

vs $500,000 median

45.0% below median

Price / Sq Ft

$480

vs $291 median

64.9% above median

Days on Market

306 days

vs 37 days median

269 days longer than median

Based on 19 active and 71 closed sales (trailing 12 mo) of single family in Westbrook. Source: SmartMLS · As of July 29, 2026.

Location

41 Trolley Road, Westbrook, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$1,918

per month

  • Principal & Interest$1,402
  • Property Taxes$424
  • 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
Baseboard
Heat Fuel
OilPropane
Cooling
None
Appliances
None
Basement
Crawl Space

Exterior & Lot

Lot Size
0.29 acres
Zoning
HDR
Waterfront Details
Walk to Water
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Vinyl Siding
Color
White
Roof
Gable
Foundation
Wood
Lot Description
Level LotOpen Lot

Listing & Financials

Property Taxes
$5,084 / Annually
Days on Market
306
MLS #
24129413
MLS Status
Active
Financing
FHA,VA,CHFA

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 7/29/2026. 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 7/29/2026 at 10:55 AM UTC.