41 Trolley Road
Westbrook, Connecticut 06498
Reduced from $375,000
- Beds
- 2
- Baths
- 1
- SqFt
- 573
- Acres
- 0.29
- Year Built
- 1900
- Property Type
- Single Family

Matt Caiola
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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
Active Listings
19
20 under contract
Median List Price
$500,000
19 active listings
Median Closed Price
$625,000
71 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.