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38 South Main Street

Westbrook, Connecticut 06498

ACTIVE - NEW$605,000
Beds
3
Baths
2
SqFt
2,514
Acres
0.48
Year Built
1760
Matt Caiola

Matt Caiola

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Pool6 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,960

per 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.

Listed By

Bonnie Foster

(860) 575-5099

William Pitt Sotheby's Int'l

(860) 767-7488

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.