Date
Details
Price
Change
Source
8/29/2025
Listed
$4,025
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/37
$4,025
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Property Description
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.
Full Property Details
Full Property Details for 158 Captains Dr
General
- Rent: $4,025
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24122596
- Updated: 11/26/2025
- Added to Site: 139 day(s) ago
Rental Information
- Rental Type: Month-to-Month Furnished, Short Term Furnished, Acad
- Lease Terms: Per Month
- Short Term: Yes
Interior
- Number of Rooms: 6
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Electric Dryer
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom, Main
- Bedroom 1: Bedroom, Main
- Bedroom 2: Bedroom, Main
Other Rooms
- Great Room: Great Room, Main
- Kitchen: Kitchen, Main
- Dining Room: Dining Room, Main
- Laundry: Main Level
Exterior
- Exterior Features: Patio
Parking
- Parking: None
Location
- County: Middlesex
- Neighborhood: Pilot&Apos;S Point
- Driving Directions: Route 1 to Seaside Ave into Pilot's Point to 158 Captains Drive
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Community
- Community Name: Pilot&Apos;S Point
- Home Owners Assn.: 1
- Assoc. Fees Include: Lake/Beach Access, Road Maintenance, Insurance
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Tank Size Unknown
Utilities
- Sewer: Septic
- Water: Public Water Connected
Structural Information
- Architectural Style: Ranch
- Construction Status: No/Resale
- Exterior Const.: Aluminum
- Basement Desc.: None
- Attic: Yes
- Square Feet: 1,998
- Above Ground: 1,998 Sq. Ft.
- Year Built: 1962
Lot Features
- Lot Size (Acres): 0.16
- Zoning: HDR2
- Lot Description: Level Lot, Water View
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: L. I. Sound Frontage
Financial Considerations
- Tenant Pays: Snow Removal
Disclosures and Reports
- Property ID: 1040634
Buyer's Brokerage Compensation: 50%
Not binding unless confirmed by separate agreement among applicable parties.
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Schools
Schools serving 158 Captains Dr
School District:Westbrook School District
| Name | Grades | Distance |
|---|---|---|
Daisy Ingraham School 105 Goodspeed Drive, Westbrook, CT 06498 | PK-4 | 1.7 mi |
Westbrook Middle School 154 McVeagh Road, Westbrook, CT 06498 | 5-8 | 2 mi |
Westbrook High School 156 McVeagh Road, Westbrook, CT 06498 | 9-12 | 2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 158 Captains Dr
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- Apartment
- Active
- Updated 3 days ago
- 1Bed
- 1Total Bath
- 500Sq. Ft.
- Single Family
- Active
- Updated 12 hours ago
- 3Beds
- 1Total Bath
- 980Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 2,741Sq. Ft.
Listed by Sue Clifford (203) 215-7261
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- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 3Total Baths
- 2,741Sq. Ft.
Listed by Sue Clifford (203) 215-7261
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 5,228Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,568Sq. Ft.
- Apartment
- Active
- Updated 5 days ago
- 3Beds
- 2Total Baths
- 1,350Sq. Ft.
Listed by Amy Lapierre (203) 903-1950
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- Single Family
- Closed
- 3Beds
- 2Total Baths
- 1,306Sq. Ft.
Listed and Sold by Samantha Celentano
158 Captains Drive, Westbrook, CT 06498 (MLS# 24122596) is a Single Family property with 3 bedrooms and 2 full bathrooms. 158 Captains Drive is currently listed for rent at $4,025 and was received on August 29, 2025. This property is listed by Buddy Degennaro from our Woodbridge Office.Want to learn more about 158 Captains Drive? Do you have questions about finding other real estate for sale or rent in Westbrook? You can browse all Westbrook rentals or contact a Coldwell Banker agent to request more information.