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

$2,056,900

Trulia Estimate
as of Sep 19, 2026
  • 3 Beds
  • 2 Baths
  • 1,998 sqft

158 Captains Dr, Westbrook, CT 06498

Westbrook Center

Home Highlights

Single-Family Home
1,998 sqft
$1,029/sqft

Local Information

  • Map ViewExplore the area around 158 Captains Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Sister Sands is our Waterfront Boho Beach House nestled in sunny Westbrook, CT on the Long Island Sound & close to Mohegan Sun, Foxwoods & CT Wineries. There is a two-week minimum stay requirement.

On Season: (2 week min)
June approximately $600 per night
July & Aug approximately $850 per night
Sept approximately $600 per night

Off Season: (1 month min - 6 month max)
November 1 to April 30 @ $4,750 per month.

Sister Sands is newly renovated, furnished, and cozy! There are three bedrooms, a queen sleeper sofa in living room, two full bathrooms, great room (family room & dining room combined) and a large coastal backyard space with patio, beach sand, & sand bars

Interior:
Three Bedrooms with Tuft & Needle mattresses!
One full Bathroom & one 3/4 Bathroom!
Fully equipped newly renovated Kitchen with all appliances, including microwave!
Family Room with queen sleeper sofa and fireplace and Samsung Frame TV with artwork on display!
Great Room with 360 degree view of the Long Island Sound and cozy lounging area (3 Love Sac sofas) and 10-seat dining table overlooking the shoreline!
Washer & Dryer included!
Central Air!

Exterior:
A large coastal backyard space with large patio, beach sand, & sand bars!
Outdoor patio dining room set, living room set, & 3 lounge chairs!
Outdoor grille + utensils and Bluetooth speaker for outdoor music!
5 parking spots available on driveway!
Equipped with beach chairs, umbrellas, blankets, toys & games, and 2 adult bikes with 2 helmets provided!

Off season rental available from Nov 1 - April 30th

Utilities Included - Heat, Hot Water, Electricity, Water, Sewer, Refuse, & Cable! (House cleaning fee not included)
158 Captains Dr, Westbrook, CT 06498 is a 3 bedroom, 2 bathroom, 1,998 sqft single-family home in Westbrook Center. It last sold for $1,315,000 on Dec 1, 2021 (27,584% above the $4,750 asking price). More recently, it was listed as a rental in August 2026 with an asking price of $5,000 per month. That rental listing was removed on September 7, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,056,900, with a rent estimate of $2,978/month.

Home Details for 158 Captains Dr

Interior Features

Heating & Cooling
Heating: Baseboard, CentralAir ConditioningCooling System: Air Conditioner, Central AirHeating Fuel: Baseboard
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 MonthAvailable: Nov 1st

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 158 Captains Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
440 Seaside Ave, Westbrook, CT
0.35
Single-Family Home
$910,000
03/11/26
3
2
1,004 sqft
201 Old Mail Trail, Westbrook, CT
0.30
Single-Family Home
$1,650,000
11/21/25
4
3.5
1,824 sqft
40 Hammock Road South, Westbrook, CT
0.41
Single-Family Home
$1,100,000
03/17/26
4
3
1,512 sqft
47 Old Mail Trail, Westbrook, CT
0.59
Single-Family Home
$2,450,000
08/04/26
3
2
1,800 sqft
3 Mohican Road, Westbrook, CT
0.68
Single-Family Home
$960,000
08/14/26
3
2
1,787 sqft
123 Old Mail Trail, Westbrook, CT
0.45
Single-Family Home
$1,300,000
06/23/26
5
1
1,976 sqft
51 Sunrise Road, Westbrook, CT
0.71
Single-Family Home
$1,100,000
10/24/25
3
2
1,353 sqft
10 Lynne Avenue, Westbrook, CT
0.65
Single-Family Home
$843,000
08/19/26
2
2
1,748 sqft
6 Indian Trail, Westbrook, CT
0.58
Single-Family Home
$825,000
10/20/25
2
2
1,086 sqft
273 Seaside Avenue, Westbrook, CT
0.66
Single-Family Home
$1,730,000
07/23/26
4
2.5
2,622 sqft

Nearby homes

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Rental Market Trends in Westbrook Center

Last updated Sep 2026
Trulia Rent Estimate$2,978/mo
Average rent
$2K
$500MoM
Available listings
9
View rental market trends in Westbrook, CT

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

Price and Tax history

DateEventPrice
Sep 7, 2026
Source: Zillow Rentals
ListingRemoved
$4,750
Aug 18, 2026
Source: Zillow Rentals
PriceChange
$4,750
Price decreased by 5%
Aug 7, 2026
Source: Zillow Rentals
Listed For Rent
$5,000
Oct 20, 2025
Source: Zillow Rentals
ListingRemoved
$3,900
Oct 12, 2025
Source: Zillow Rentals
PriceChange
$3,900
Price increased by 26%

Frequently asked questions about 158 Captains Dr

  • What is 158 Captains Dr estimated to be worth?
    Trulia's estimated value for 158 Captains Dr in Westbrook, CT is $2,056,900.
  • What is the price history for 158 Captains Dr?
    158 Captains Dr in Westbrook, CT last sold for $1,315,000 in December 2021.
  • 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 158 Captains Dr?
    The closest schools to 158 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 158 Captains Dr have air conditioning?
    Yes, 158 Captains Dr in Westbrook, CT has air conditioning.
  • Does 158 Captains Dr have laundry facilities?
    Yes, 158 Captains Dr in Westbrook, CT has in-unit laundry.

Homes for rent near 158 Captains Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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