158 Captains Drive - Westbrook, CT

$4,025

Beds

2.00

Baths

1,998

SqFt

0.16

Acres

Pricing Insight: Originally listed for $4,025, the price has remained unchanged for approximately 208 days. This property has been on the market for approximately 208 days.

158 Captains Drive, Westbrook, CT is a 3-bed, 2-bath, 1,998 square foot home built in 1962 , featuring ranch architecture. This home is part of a homeowners association. The HOA fee includes: lake/beach access, road maintenance, and insurance.

This home is within the Westbrook school district. Local, with nearby schools including Per Board of Ed.

MLS #: 24122596

Offered Price: $4,025

Residence Type: Residential Rental

Architectural Style: Ranch

Living Area: 1,998 Sq. Ft.

Lot Size: 0.16 Acres

Neighborhood: Pilot's Point

County: Middlesex

Year Built: 1962

Design & Construction: N/A

Heating: Hot Air

Cooling: Central Air

Garage Spaces: 0

Price per Sq Ft as listed: $2

Estimated Tax: $0

Days on Market: 208

$2,300

3 Beds · 2 Baths · 1,200 Sq Ft

14 Leeway Drive, Westbrook

$3,999

3 Beds · 3 Baths · 2,475 Sq Ft

6 Leeway Drive, Westbrook

Home Automation: Not specified

Energy Features: Not specified

Solar Contract: Not specified

Heating Fuel: Oil

Fuel Type: Hot Air

Fuel Tank Location: Above Ground

Cooling System: Central Air

Hot Water System: Tank Size Unknown

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $2 / Sq. Ft.

Tax assessed value: $0

Estimated Tax: $0

Architectural Style: Ranch

Design & Construction: N/A

Residence Type: Residential Rental

Year Constructed: 1962

Living Area: 1,998 Sq. Ft.

Lot Size: 0.16 Acres

Fuel: Oil

Loading automated valuation...

AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

Request CMA Schedule Tour

Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Westbrook
Statistical modeling algorithms

Local Market Context

Active Listings: 18

Average Price: $187,535

Average DOM: 208 days

Complimentary CMAs, no obligation

Experience coastal living at its finest in this gorgeous furnished rental located directly on the waterfront, overlooking the serene beauty of Long Island Sound. Available for monthly or academic rental, this newly renovated beachfront home invites you to relax and unwind while enjoying breathtaking sunrises and sunsets. Nestled in the highly sought-after Pilots Point Community, the heart of the home is the stunning great room, featuring walls of glass that offer panoramic water views, a vaulted ceiling, exposed beams and hardwood flooring. This spacious area seamlessly blends a dining space with a comfortable family room, perfect for entertaining or quiet conversation. The remodeled kitchen boasts quartz countertops, bar-top seating, and stainless steel appliances, while the living room offers a cozy fireplace and a queen-size pull-out couch. With three spacious bedrooms-including one with bunk beds (full size bed with twin on top) and queen size beds in both the primary and middle bedrooms along with two beautifully updated bathrooms and a full laundry room, this home is designed for comfort and convenience. Additional features include central air conditioning, a private sandy beach, and a private driveway that accommodates approximately five cars. Whether you're seeking a peaceful retreat or a vibrant coastal lifestyle, this exceptional rental delivers it all.

Continue reading ▾

Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 0.2 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

18

Homes For Sale

$187,535

Average List Price

Mechanicals & Utilities: Hot Air • Oil • Central Air • Public Water Connected water • 1 fireplaces

Exterior Features

Exterior Construction: Aluminum

Patio/Deck: Patio

Utilities: Water: Public Water Connected

Only motif connects you to a certified
"Local Market Expert"

Steve Simos

Real Estate Advisor

Westbrook • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0003

george@appzentric.com

Good evening Steve, I'm interested in
158 Captains Drive, Westbrook, Connecticut

By proceeding, you consent to receive calls and texts at the number you provided, and artificial voice, and email, from motif about your inquiry and similar properties. Your personal information will never be sold or given to a 3rd party.

motif, the motif logo, and other various trademarks, logos, designs, and slogans are the registered and unregistered trademarks of motif, LLC. dba Motif Luxe International Realty in the U.S. and/or other countries. Corporate Responsibility, Privacy & Legal Notices: motif is a licensed real estate broker, licensed to do business as Motif LLC. No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property conditions), such should be independently verified, and Motif expressly disclaims any liability in connection therewith. No financial or legal advice provided. Equal Housing Opportunity.

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. MLS

. Designed by Appzentric for motif

Good evening. Welcome to 158 Captains Drive, Westbrook, CT