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

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
22
15 under contract
Median List Price
$559,450
22 active listings
Median Closed Price
$625,000
81 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per 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
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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 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.