38 South Main Street
Westbrook, Connecticut 06498
- Beds
- 3
- Baths
- 2
- SqFt
- 2,514
- Acres
- 0.48
- Year Built
- 1760
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Step into timeless New England charm with this enchanting antique home, circa 1760, ideally set in the heart of the beloved shoreline community of Westbrook. Rich in character and history, this beautifully maintained residence blends classic period details with modern comforts for effortless coastal living. Featuring six inviting fireplaces, the home's warmth, ambiance and thoughtfully preserved architectural details celebrate this home's true heritage. An in-ground, heated pool creates a private backyard retreat while the "walk-to-everything" location makes this home a perfect escape from a hustle and bustle daily life. Just moments from the beach, charming town center, dining and community events, this home also features a two-story barn creating extra valuable storage or flexible space for hobbies, game room, beach gear or workshop space. Located in a desirable beach community, this special property also boasts a proven and successful rental history with excellent income potential or a seamless blend of personal use and investment opportunity. A rare chance to own a piece of history in a prime shoreline setting where coastal lifestyle, character and convenience come together beautifully.
Key Facts
- City/Town
- Westbrook
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1760
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,514 sq ft
- Lot Size
- 0.48 acres
- Property Taxes
- $6,648 / Annually
Market Snapshot
The Westbrook Market
Single Family · trailing 12 months
Active Listings
26
13 under contract
Median List Price
$542,000
26 active listings
Median Closed Price
$625,000
79 sales
Median Days on Market
33
26 active listings
Median $ / Sq Ft
$267
26 active listings
Sale-to-List Ratio
100.0%
79 sales
How this home compares
List Price
$605,000
vs $542,000 median
11.6% above median
Price / Sq Ft
$241
vs $267 median
9.7% below median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 26 active and 79 closed sales (trailing 12 mo) of single family in Westbrook. Source: SmartMLS · As of September 23, 2026.
Location
38 South Main Street, Westbrook, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$3,204
- Property Taxes$554
- Insurance$202
- 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
- Colonial,Antique
- Year Built
- 1760
- New Construction
- No/Resale
- Living Area
- 2,514 sq ft
Schools
- Elementary
- Daisy Ingraham
- High
- Westbrook
Interior
- Heating
- Steam
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Fireplaces
- 6
- Laundry
- Main Level
- Laundry Location
- Laundry Room near kitchen
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedFull With Hatchway
- In-Law Apartment
- PossibleDetached
- Additional Rooms
- Laundry Room
Exterior & Lot
- Lot Size
- 0.48 acres
- Zoning
- MDR
- Waterfront Details
- Walk to Water
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedIn Ground Pool
- Construction
- Shingle
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- PorchBarn
- Lot Description
- Corner LotLightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $6,648 / Annually
- Days on Market
- 0
- MLS #
- 24206967
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Robin Linares
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/23/2026. 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 9/23/2026 at 12:50 AM UTC.