Date
Details
Price
Change
Source
6/01/2026
Listed
$3,200
—
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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Property Description
Enjoy all the amenities of Port Jefferson without the responsibilities of homeownership. This well-maintained residence features beautiful new hardwood floors and an updated kitchen with white shaker-style cabinetry. Residents enjoy access to Port Jefferson Village amenities, including private beaches, private parking, and country club privileges. Conveniently located near the train station, St. Charles Hospital, Mather Hospital, Stony Brook University Hospital, as well as local shopping, dining, and waterfront attractions. A wonderful opportunity to enjoy the Port Jefferson lifestyle in a prime location-this is a must-see!
Full Property Details
Full Property Details for 253 Windward Dr
General
- Rent: $3,200
- Status: Active
- Type: Condo
- Source: Long_Island
- MLS ID: 1007518
- Updated: 6/1/2026
- Added to Site: 9 day(s) ago
Interior
- Number of Rooms: 6
- Interior Features: Eat-in Kitchen
- Appliances: Dishwasher, Microwave, Refrigerator, Washer, Gas Water Heater
- Laundry Facilities: Yes
- Furnishings: Unfurnished
- Flooring: Hardwood, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 1
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: In Basement
Additional Information
- Amenities: Clubhouse, Fitness Center, Playground, Pool, Tennis Court(s)
- Shared Amenities: Park
Exterior
- Exterior Features: Balcony
- Porch/Patio/Deck: Deck, Patio
Parking
- Garage: Yes
- Garage Spaces: 1
- Parking Features: Attached, Driveway, Garage
Location
- County: Suffolk County
- Subdivision: The Highlands
- Cross Streets: Highlands Blvd
- Driving Directions: Highland Blvd to Windward Drive
School Information
- High School District: Brookhaven-Comsewogue
- Elementary School: Terryville Road School
- Middle School: John F Kennedy Middle School - Suffolk
- High School: Comsewogue High School
Community
- Association: Yes
- Assoc. Fees Include: Sewer, Snow Removal
Heating & Cooling
- Central air: Yes
- Cooling Type: Central Air
- Heating Type: Forced Air, Natural Gas
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable Available
Structural Information
- Architectural Style: Other
- Detached/Attached: Attached
- Construction: Frame
- Basement: Yes
- Basement Desc.: Partially Finished
- Unfinished Attic: Yes
- Common Walls: 2+ Common Walls
- Entry Floor Number: 1
- Stories/Levels: 3
- Stories in Building: 3
- Sq. Ft. Source: Public Records
- Year Built: 1993
Lot Features
- Lot Size (Sq. Ft.): 1,097
- Lot Features: Near Public Transit
Water Features
- Water Front View: Beach Access
Financial Considerations
- Security Deposit: $3,200
Disclosures and Reports
- Special Conditions: None
- Property ID: 0206-022-00-04-00-253-000
- Block: 4
- Lot Number: 253
Listed by Douglas Elliman Real Estate
Schools
Schools serving 253 Windward Dr
School District:Brookhaven-Comsewogue Union Free School District
| Name | Grades | Distance |
|---|---|---|
John F Kennedy Middle School, Port Jefferson Station, NY 200 Jayne Boulevard, Port Jefferson Station, NY 11776 | 6-8 | 1.3 mi |
Terryville Road School 401 Terryville Road, Port Jefferson Station, NY 11776 | 3-5 | 1.8 mi |
Clinton Avenue School, Port Jefferson Station, NY 140 Clinton Avenue, Port Jefferson Station, NY 11776 | PK-2 | 2.1 mi |
Comsewogue High School 565 North Bicycle Path, Port Jefferson Station, NY 11776 | 9-12 | 1.9 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 253 Windward Dr
253 Windward Drive, Port Jefferson, NY 11777 (MLS# 1007518) is a Condo property with 2 bedrooms, 1 full bathroom and 1 partial bathroom. 253 Windward Drive is currently listed for rent at $3,200 and was received on June 01, 2026. Want to learn more about 253 Windward Drive? Do you have questions about finding other real estate for sale or rent in Port Jefferson? You can browse all Port Jefferson rentals or contact a Coldwell Banker agent to request more information.