165 Captains Drive, Westbrook, CT 06498
OFF MARKET

$1,701,600

Trulia Estimate
  • 2 Beds
  • 3 Baths
  • 2,104 sqft

165 Captains Drive, Westbrook, CT 06498

Westbrook Center
Est. Refi. Payment $11,871/mo*
Refinance Your Home
Currently Off Market - Sold May 9, 2025 for $1,540,000

Home Value

Trulia Estimate
$1.7M
Since last month
Increased$25K (+1.5%)
Since last year
Increased$137K (+8.8%)
Since last sale
Increased$161K (+10.4%)
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 +123% in the last 10 years
MonthEstimated value
2026
September 2026$1.7M
August 2026$1.68M
July 2026$1.69M
June 2026$1.65M
May 2026$1.63M
April 2026$1.65M
March 2026$1.66M
February 2026$1.64M
January 2026$1.61M
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
201 Old Mail Trail, Westbrook, CT
0.29
Single-Family Home
$1,650,000
11/21/25
4
3.5
1,824
40 Hammock Road South, Westbrook, CT
0.39
Single-Family Home
$1,100,000
03/17/26
4
3
1,512
273 Seaside Avenue, Westbrook, CT
0.66
Single-Family Home
$1,730,000
07/23/26
4
2.5
2,622
10 Lynne Avenue, Westbrook, CT
0.64
Single-Family Home
$843,000
08/19/26
2
2
1,748
6 Indian Trail, Westbrook, CT
0.57
Single-Family Home
$825,000
10/20/25
2
2
1,086
3 Mohican Road, Westbrook, CT
0.66
Single-Family Home
$960,000
08/14/26
3
2
1,787
47 Old Mail Trail, Westbrook, CT
0.58
Single-Family Home
$2,450,000
08/04/26
3
2
1,800
123 Old Mail Trail, Westbrook, CT
0.44
Single-Family Home
$1,300,000
06/23/26
5
1
1,976
51 Sunrise Road, Westbrook, CT
0.70
Single-Family Home
$1,100,000
10/24/25
3
2
1,353

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
7 Captains Drive, Westbrook, CT 06498
0.07
$1,348,100
3
3
1,793
Off Market
83 Captains Drive, Westbrook, CT 06498
0.12
$1,198,600
5
3
2,640
Off Market
67 Captains Drive, Westbrook, CT 06498
0.14
$1,386,400
3
3
2,448
Off Market
54 Captains Dr....pilots Point, Westbrook, CT 06498
0.14
$2,908,500
4
6.5
5,010
Off Market
518 Seaside Avenue, Westbrook, CT 06498
0.21
-
-
-
-
Off Market
201 Old Mail Trail, Westbrook, CT 06498
0.29
$1,776,100
4
3.5
1,824
Off Market
7 Dolphin Avenue, Westbrook, CT 06498
0.31
$587,500
1
1
848
Off Market
442 Seaside Avenue, Westbrook, CT 06498
0.34
$2,010,200
3
4
2,499
Off Market
8 Tarpon Avenue, Westbrook, CT 06498
0.35
$716,100
2
1
849
Off Market
40 Hammock Road South, Westbrook, CT 06498
0.39
$1,100,000
4
3
1,512
Recently Sold
157 Old Mail Trail, Westbrook, CT 06498
0.38
$1,429,600
4
1.5
1,664
Off Market

Local Information

  • Map ViewExplore the area around 165 Captains Drive.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
2,104 sqft
$809/sqft
2 Car Garage
HOA $33/mo

About this House

Coastal Retreat with Water Views in a Vibrant Beach Community Experience the ultimate in seaside living with this beautifully remodeled 2-bedroom, 3-bathroom home, perfectly situated in a lively beachside neighborhood. Enjoy stunning water views and a spacious open floor plan that seamlessly connects the living, dining, and kitchen areas-ideal for both relaxation and entertaining. Bathrooms: 3 fully renovated bathrooms featuring modern fixtures and finishes. Kitchen: A state-of-the-art kitchen with high-end appliances, sleek countertops, and ample storage. Living Area: An open-concept living space with large windows that flood the area with natural light and provide picturesque water views. Outdoor Space: A large deck perfect for entertaining guests, dining al fresco, or simply enjoying the coastal breeze. Community: Located in a friendly beach community with easy access to local amenities, dining, and recreational activities. This move-in-ready home combines modern elegance with the charm of coastal living. Don't miss the opportunity to own a slice of paradise.
165 Captains Drive, Westbrook, CT 06498 is a 2 bedroom, 3 bathroom, 2,104 sqft single-family home in Westbrook Center, built in 1996. It last sold for the $1,540,000 asking price on May 9, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,701,600, with a rent estimate of $3,398/month.
Last check for updates: about 20 hours ago
Listed by Robin Morrell, (203) 245-6700
William Pitt Sotheby's Int'l, (203) 245-6700
Bought with: Jules G Etes, (203) 687-6997, William Pitt Sotheby's Int'l, (203) 453-2533
Source: Smart MLS, MLS#24085835

Home Details for 165 Captains Drive

Interior Features

Interior Details
Basement: NoneNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2104 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Electric,OilHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,DuctlessHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: Thermopane Windows
View
Has a ViewView: Water
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: DeckExterior: Stone Wall, Underground SprinklerFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Driveway,Garage Door Opener,Paved
Frontage
Waterfront: Walk to Water, Beach Access, Water CommunityNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 2104 Square Feet

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1041467

Price & Status

Price
List Price: $1,540,000
Status Change & Dates
Off Market Date: Fri Apr 11 2025Possession Timing: Immed

Active Status

MLS Status: Closed

Location

Direction & Address
City: WestbrookCommunity: Pilot's Point
School Information
Elementary School: Daisy IngrahamHigh School: Westbrook

Building

Building Area
Building Area: 2104 Square Feet

HOA

Has an HOAHOA Fee: $400/Annually

Lot Information

Lot Area: 6098.4 sqft

Energy

Energy Efficiency Features: Windows

Miscellaneous

Mls Number: 24085835Attic: NoneWater ViewWater View: WaterAbove Grade Unfinished Area: 2104

Additional Information

HOA Amenities: Lake/Beach Access

Price and Tax history

DateEventPrice
May 9, 2025
Source: Smart MLS #24085835
Sold
$1,540,000
Apr 11, 2025
Source: Smart MLS #24085835
Pending
$1,540,000
Jun 21, 2021
Source: N/A
Sold
$825,000
Sep 13, 1994
Source: N/A
Sold
$93,500

Market trends in Westbrook

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
3MoM

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

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 165 Captains Drive

  • What is 165 Captains Drive estimated to be worth?
    Trulia's estimated value for 165 Captains Drive in Westbrook, CT is $1,701,600.
  • What is the price history for 165 Captains Drive?
    165 Captains Drive in Westbrook, CT last sold for $1,540,000 in May 2025.
  • 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 165 Captains Drive?
    The closest schools to 165 Captains Drive 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 165 Captains Drive have air conditioning?
    Yes, 165 Captains Drive in Westbrook, CT has air conditioning.
  • Does 165 Captains Drive have laundry facilities?
    Yes, 165 Captains Drive in Westbrook, CT has in-unit laundry.

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