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

66 Captains Dr
Westbrook, CT 06498

Westbrook Center
  • 3 Beds
  • 4 Baths
  • 2,460 sqft

$2,259,200

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $15,231/mo*
Refinance Your Home

$2,259,200

Trulia Estimate
as of Aug 4, 2026
Est. Refi. Payment $15,231/mo*
Refinance Your Home
3 Beds
4 Baths
2,460 sqft

Local Information

  • Map ViewExplore the area around 66 Captains Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1989
Living Area
2,460 sqft
Price/Sqft
$918
Parking
Garage

About this House

DIRECT WATERFRONT WITH PRIVATE BEACH RIGHTS! Located on Long Island Sound in the quaint New England town of Westbrook, this very spacious home with wrap around deck and 85' of water frontage offers spectacular, panoramic views! Boating enthusiast? Pilot's Point Marina, world renown, is steps away. Golf courses, casinos, theaters, antique shops, outlet malls and numerous restaurants will occupy your free time. Excellent schools with low enrollment. Open floor plan designed to capture the water views from every window, offers several living spaces, a fireplace, kitchen, and a separate dining room. Upstairs, the master bedroom, facing the water with it's private deck, has a gas fireplace, walk-in closet and numerous built-in cabinets for storage.The master bath has great space, double sinks, Jacuzzi tub, separate shower and more closet storage. Two more bedrooms, plus another star gazing deck, and full bath complete this level. Working from home? The finished basement has ample office space, another family room and bedroom, plus a full bath. Westbrook is conveniently located two hours from NYC and Boston, with easy access to ACELA & Amtrak rail service.
66 Captains Dr, Westbrook, CT 06498 is a 3 bedroom, 4 bathroom, 2,460 sqft single-family home in Westbrook Center, built in 1989. It last sold for $1,325,000 on Oct 19, 2020. It is currently off market. The Trulia Estimate is $2,259,200, with a rent estimate of $3,508/month.

Home Details for 66 Captains Dr

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: Forced Air, Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
DeckExterior: OtherPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Price History for 66 Captains Dr

DatePriceEventSource
10/19/2020$1,325,000Sold
Smart MLS #170263081
03/18/2020$1,395,000Listed For SaleAgent Provided
12/18/2019$1,395,000ListingRemovedAgent Provided
10/23/2019$1,395,000PriceChange
Agent Provided
09/15/2019$1,495,000PriceChange
Agent Provided
07/05/2019$1,595,000Listed For SaleAgent Provided
09/23/1997$685,000Sold
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$22,913
Assessment$1,018,370
Home facts updated by county records

Comparable Sales for 66 Captains Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40 Hammock Road South, Westbrook, CT
0.42
Single-Family Home
$1,100,000
03/17/26
4
3
1,512
123 Old Mail Trail, Westbrook, CT
0.28
Single-Family Home
$1,300,000
06/23/26
5
1
1,976
273 Seaside Avenue, Westbrook, CT
0.80
Single-Family Home
$1,730,000
07/23/26
4
2.5
2,622
201 Old Mail Trl, Westbrook, CT
0.13
Single-Family Home
$1,650,000
11/21/25
4
4
3,000
51 Sunrise Road, Westbrook, CT
0.55
Single-Family Home
$1,100,000
10/24/25
3
2
1,353
42 Bluff Street, Westbrook, CT
0.60
Single-Family Home
$1,800,000
10/15/25
4
4
4,236
440 Seaside Ave, Westbrook, CT
0.49
Single-Family Home
$910,000
03/11/26
3
2
1,004
6 Indian Trail, Westbrook, CT
0.46
Single-Family Home
$825,000
10/20/25
2
2
1,086
184 Grove Beach Rd S, Westbrook, CT
0.76
Single-Family Home
$3,000,000
12/22/25
3
4
4,000
76 Osprey Circle, Westbrook, CT
0.60
Single-Family Home
$700,000
09/12/25
2
2
1,981

Nearby homes

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Assigned Schools

These are the assigned schools for 66 Captains Dr.
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
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  • 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

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Apartments for Rent

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Explore by feature - Air Conditioning

6 rentals with air conditioning in Westbrook, CT

Homes for sale near 66 Captains Dr

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Off Market Homes Near 66 Captains Dr

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