54 Captains Dr, Westbrook, CT 06498
Property image
Property image
OFF MARKET

$3,334,200

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 6,546 sqft (on 0.59 acres)

54 Captains Dr, Westbrook, CT 06498

Westbrook Center
Refinance Your Home
Currently Off Market - Sold Oct 21, 2009 for $1,925,000

Home Value

Trulia Estimate
$3.33M
Since last month
Increased$48K (+1.4%)
Since last year
Increased$110K (+3.4%)
Since last sale
Increased$1M (+73.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +138% in the last 10 years
MonthEstimated value
2026
August 2026$3.33M
August 2026$3.33M
July 2026$3.29M
June 2026$3.31M
May 2026$3.3M
April 2026$3.19M
March 2026$3.28M
February 2026$3.13M
January 2026$3.12M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
42 Bluff Street, Westbrook, CT
0.60
Single-Family Home
$1,800,000
10/15/25
4
4
4,236
184 Grove Beach Rd S, Westbrook, CT
0.76
Single-Family Home
$3,000,000
12/22/25
3
4
4,000
40 Hammock Road South, Westbrook, CT
0.38
Single-Family Home
$1,100,000
03/17/26
4
3
1,512
273 Seaside Avenue, Westbrook, CT
0.77
Single-Family Home
$1,730,000
07/23/26
4
2.5
2,622
76 Osprey Circle, Westbrook, CT
0.58
Single-Family Home
$700,000
09/12/25
2
2
1,981
201 Old Mail Trl, Westbrook, CT
0.15
Single-Family Home
$1,650,000
11/21/25
4
4
3,000
47 Old Mail Trail, Westbrook, CT
0.42
Single-Family Home
$2,450,000
08/04/26
3
2
1,800
123 Old Mail Trail, Westbrook, CT
0.29
Single-Family Home
$1,300,000
06/23/26
5
1
1,976
68 Groveway, Clinton, CT
0.85
Single-Family Home
$1,000,000
06/24/26
3
1.5
1,729
3 Mohican Road, Westbrook, CT
0.51
Single-Family Home
$960,000
08/14/26
3
2
1,787

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
54 Captains Dr....pilots Point, Westbrook, CT 06498
0.01
$2,890,000
4
6.5
5,010
Off Market
67 Captains Drive, Westbrook, CT 06498
0.03
$1,393,100
3
3
2,448
Off Market
83 Captains Drive, Westbrook, CT 06498
0.05
$1,198,600
5
3
2,640
Off Market
7 Captains Drive, Westbrook, CT 06498
0.09
$1,360,500
3
3
1,793
Off Market
165 Captains Drive, Westbrook, CT 06498
0.15
$1,676,100
2
3
2,104
Off Market
6 Leeway Drive, Westbrook, CT 06498
0.16
$1,275,000
3
3
2,475
For Sale
157 Old Mail Trail, Westbrook, CT 06498
0.23
$1,424,200
4
1.5
1,664
Off Market
155 Old Mail Trail, Westbrook, CT 06498
0.24
$1,617,000
4
3
2,098
Off Market
151 Old Mail Trail, Westbrook, CT 06498
0.24
$2,459,100
4
3.5
2,513
Off Market
123 Old Mail Trail, Westbrook, CT 06498
0.29
$1,300,000
5
1
1,976
Recently Sold
98 Old Mail Trail, Westbrook, CT 06498
0.33
$890,600
3
2
1,216
Off Market
518 Seaside Avenue, Westbrook, CT 06498
0.32
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 54 Captains Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2012
0.59 acre lot
6,546 sqft
$509/sqft
Garage

About this House

Come escape to your very own private retreat. Direct waterfront property offering panoramic water views from nearly every angle. This premiere 4 bedroom, 4.5 bathroom, custom built contemporary residence is situated in the Pilot's Point Beach Community. The home has an expansive, open floor plan with a formal dining space surrounded by windows facing the water. The master bedroom boasts its own private deck and water views galore, even from its second floor loft. The custom master closet has all the storage you need and the master bathroom is ready for you to de-stress with the ambiance of a fireplace next to your soaking tub and separate shower. Boaters take note of the private 180 foot dock with electric and water provided, only seconds from Long Island Sound. Some of the well appointed features include: Interior/exterior professional audio system, professional theater room, bedroom level laundry room with double washer & dryer, sauna, exercise room with water views leading up to a private office space with a widows walk featuring 360 degree views. On the exterior you will find your own exclusive private beach, 4,500+ square feet of Ipe decking, in-ground pool, hot tub, outdoor pizza oven and fireplace. Conveniently located halfway between NYC and Boston.
54 Captains Dr, Westbrook, CT 06498 is a 4 bedroom, 5 bathroom, 6,546 sqft single-family home in Westbrook Center, built in 2012. It last sold for $1,925,000 on Oct 21, 2009. More recently, it was listed as a rental in April 2020 with an asking price of $30,000 per month. That rental listing was removed on April 17, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,334,200, with a rent estimate of $6,740/month.

Home Details for 54 Captains Dr

Interior Features

Heating & Cooling
Heating: Radiant, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Concrete
Interior Details
Number of Rooms: 10Types of Rooms: Laundry RoomCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Stone, VinylPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.59 acres

Building

Fitness & Sports
Basketball CourtTennis Court
Pool
Sauna

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Apr 17, 2020
Source: Agent Provided
ListingRemoved
$30,000
Apr 5, 2020
Source: Agent Provided
Listed For Rent
$30,000
Oct 21, 2009
Source: N/A
Sold
$1,925,000
Sep 14, 1999
Source: N/A
Sold
$785,000

Market trends in Westbrook

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
24
6MoM

Around this home

Neighborhood Overview

Westbrook Center
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Westbrook Center

At least 2 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say streets are well-lit

  • 100 % Say kids play outside

  • 100 % Say neighbors are friendly

  • 100 % Say they plan to stay for at least 5 years

  • 100 % Say there's holiday spirit

  • 100 % Say yards are well-kept

  • 100 % Say it's quiet

  • 100 % Say there's wildlife

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say people would walk alone at night

  • 75 % Say there are sidewalks

  • 67 % Say there are community events

  • 50 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Annie Picardi
    "Beautiful area ,public transit is excellent,Resturant’s, shopping close by, Catholic Church is a bit far from our area, other houses of worship are close by,neighbors are friendly"
    0
    Flag
  • Annie Picardi
    "Great neighbors , awesome restaurants, amazing beach, easy accessibility to I 95 , walking distance to buses and shore line east train, under a mile and half to Amtrak station, nice churches, convient to three grocery stores, "
    0
    Flag
  • Annie Picardi
    "Great neighborhood nice friendly neighbors Cute dogs in the area easy to get to grocery stores retail stores and houses of worship "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 54 Captains Dr

  • What is 54 Captains Dr estimated to be worth?
    Trulia's estimated value for 54 Captains Dr in Westbrook, CT is $3,334,200.
  • What is the price history for 54 Captains Dr?
    54 Captains Dr in Westbrook, CT last sold for $1,925,000 in October 2009.
  • Is Westbrook a buyer's or seller's market?
    Westbrook is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 54 Captains Dr?
    The closest schools to 54 Captains Dr in Westbrook, CT are Daisy Ingraham School (Pre-K/Elementary, rated 7/10), Westbrook High School (rated 7/10), Westbrook Middle School (rated 8/10).
  • Does 54 Captains Dr have air conditioning?
    Yes, 54 Captains Dr in Westbrook, CT has air conditioning.
  • Does 54 Captains Dr have a pool?
    Yes, 54 Captains Dr in Westbrook, CT has a pool.

Explore by feature - Air Conditioning

11 rentals with air conditioning in Westbrook, CT

Explore by feature - Washer/dryer

12 rentals with a washer/dryer in Westbrook, CT

Apartments for Rent

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Off Market Homes Near 54 Captains Dr

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