164 Captains Dr, Westbrook, CT 06498
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OFF MARKET

164 Captains Dr
Westbrook, CT 06498

Westbrook Center
  • 4 Beds
  • 3 Baths
  • 3,014 sqft

$2,265,200

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $15,009/mo*
Refinance Your Home

$2,265,200

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $15,009/mo*
Refinance Your Home
4 Beds
3 Baths
3,014 sqft

Local Information

  • Map ViewExplore the area around 164 Captains Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Located in the Shoreline's prestigious waterfront community and private association, Pilot's Point. Truly a once in a lifetime opportunity to acquire a front row position on Long Island Sound with Panoramic views. This custom built shingle-style home is ideally positioned to capture the spectacular and dramatic views of Menunketesuck Island and Long Island Sound. Sunlight streams through every window of this waterside home. Bright spacious kitchen with sliders to an expansive terrace offering unmatched outdoor living space. Stunning interior design compliments 3000 sq ft of living space with this 4 bedroom, 4 bath home. Kitchen, breakfast room, dining room, and family room combination. Living room with beach stone fireplace. Screened porch off the Master Bedroom. Third floor provides office, playroom, exercise room and additional storage. Ample parking as you entertain. Marina located a golf cart ride away for easily docking your boat. Just 2 hours to New York or Boston with easy access by highway or train. Convenient location close to Route 1 with shopping, restaurants, parks and schools nearby. Enjoy 60 feet of private beach with this breathtaking year round home.
164 Captains Dr, Westbrook, CT 06498 is a 4 bedroom, 3 bathroom, 3,014 sqft single-family home in Westbrook Center, built in 2004. It last sold for $605,000 on Mar 1, 2002. It is currently off market. The Trulia Estimate is $2,265,200, with a rent estimate of $4,074/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 164 Captains Dr

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticNumber of Rooms: 8
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
DeckExterior: WoodFoundation Type: SlabPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 6098 sqft

Price History for 164 Captains Dr

DatePriceEventSource
03/01/2002$605,000Sold
Smart MLS #M9064112

Market trends in Westbrook

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
4MoM
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Property Tax and Assessment

Year2025
Tax$24,093
Assessment$1,070,820
Home facts updated by county records

Comparable Sales for 164 Captains Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40 Hammock Road South, Westbrook, CT
0.40
Single-Family Home
$1,100,000
03/17/26
4
3
1,512
442 Seaside Avenue, Westbrook, CT
0.33
Single-Family Home
$1,835,000
07/30/25
3
4
2,499
440 Seaside Ave, Westbrook, CT
0.34
Single-Family Home
$910,000
03/11/26
3
2
1,004
12 Bellstone Avenue, Westbrook, CT
0.82
Single-Family Home
$1,050,000
07/14/25
4
3
2,292
6 Indian Trail, Westbrook, CT
0.59
Single-Family Home
$825,000
10/20/25
2
2
1,086
123 Old Mail Trail, Westbrook, CT
0.46
Single-Family Home
$1,300,000
06/23/26
5
1
1,976
51 Sunrise Road, Westbrook, CT
0.72
Single-Family Home
$1,100,000
10/24/25
3
2
1,353
42 Bluff Street, Westbrook, CT
0.78
Single-Family Home
$1,800,000
10/15/25
4
4
4,236
201 Old Mail Trl, Westbrook, CT
0.31
Single-Family Home
$1,650,000
11/21/25
4
4
3,000
49 Seaside Avenue, Westbrook, CT
0.96
Single-Family Home
$550,000
12/17/25
3
2
2,052

Nearby homes

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Assigned Schools

These are the assigned schools for 164 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

8 rentals with air conditioning in Westbrook, CT

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8 rentals with a washer/dryer in Westbrook, CT

Homes for sale near 164 Captains Dr

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Off Market Homes Near 164 Captains Dr

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