165 Captains Drive, Westbrook, CT 06498
OFF MARKET

165 Captains Drive
Westbrook, CT 06498

Westbrook Center
  • 2 Beds
  • 3 Baths
  • 2,104 sqft

$1,689,400

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $11,408/mo*
Refinance Your Home

$1,689,400

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $11,408/mo*
Refinance Your Home
2 Beds
3 Baths
2,104 sqft

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

Property Type
Single-Family Home
Year Built
1996
Living Area
2,104 sqft
Price/Sqft
$803
Parking
2 Car Garage
HOA
$33/Monthly

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. It is currently off market. The Trulia Estimate is $1,689,400, with a rent estimate of $3,099/month.

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
Last check for updates: about 7 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

Price History for 165 Captains Drive

DatePriceEventSource
05/09/2025$1,540,000Sold
Smart MLS #24085835
04/11/2025$1,540,000PendingSmart MLS #24085835
06/21/2021$825,000Sold
N/A
09/13/1994$93,500Sold
N/A

Market trends in Westbrook

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
3MoM
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Property Tax and Assessment

Year2025
Tax$13,319
Assessment$591,970
Home facts updated by county records

Comparable Sales for 165 Captains Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
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
6 Indian Trail, Westbrook, CT
0.57
Single-Family Home
$825,000
10/20/25
2
2
1,086
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
76 Osprey Circle, Westbrook, CT
0.69
Single-Family Home
$700,000
09/12/25
2
2
1,981
42 Bluff Street, Westbrook, CT
0.76
Single-Family Home
$1,800,000
10/15/25
4
4
4,236

Nearby homes

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Assigned Schools

These are the assigned schools for 165 Captains Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

Apartments for Rent

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Explore by feature - Air Conditioning

6 rentals with air conditioning in Westbrook, CT

Homes for sale near 165 Captains Drive

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Off Market Homes Near 165 Captains Drive

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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.