Updated 5+ Days Ago
Location
253 Windward Dr, Port Jefferson, NY 11777, USA|Port Jefferson
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Amenities for 253 Windward Dr, Port Jefferson
Features
| Central Air | Hardwood Floor |
| Natural Gas | Three Floors |
Appliances
| Dishwasher | In-Unit Laundry |
Community
| Basement | Exterior Type: Frame |
Grounds
| Garage Parking |
Other
| Six Rooms |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
Contact Property
REQUIRED FEES
Security Deposit
One-time. Refundable.
Contact Property
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About 253 Windward Dr
Property Status: Active 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! Office Phone: (631) 576-5380 Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 253 Windward Dr compares to other nearby properties.
Positives
- More space
- The 2-bedroom is 173 sqft larger than other listings nearby
- Images Available
- There are at least 10 photos of this address
Considerations
- Greater distance from high schools
- The nearest high school is farther than 1 mile away
- Greater distance from middle schools
- The nearest middle school is farther than 1 mile away
Address details
| Neighborhood | Port Jefferson |
|---|---|
| Zip code | 11777 |
| Type | Condo for rent |
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Rent trends in Port Jefferson
2-bedroom apartments at 253 Windward Dr cost about the same as the average rent price for 2-bedroom apartments in Port Jefferson.
Median rents as of Jul 18 2026.
Port Jefferson
Port Jefferson
| Month | Median Rent |
|---|---|
| October 2024 | $2,850 |
| November 2024 | $3,662 |
| December 2024 | $4,000 |
| January 2025 | $4,400 |
| February 2025 | $3,834 |
| March 2025 | $3,990 |
| April 2025 | $3,950 |
| May 2025 | $4,200 |
| June 2025 | $4,400 |
| July 2025 | $3,980 |
| August 2025 | $3,500 |
| April 2026 | $3,400 |
| May 2026 | $3,175 |
| June 2026 | $3,162 |
| July 2026 | $3,241 |
| Month | Median Rent |
|---|---|
| November 2024 | $4,400 |
| December 2024 | $4,000 |
| January 2025 | $4,400 |
| February 2025 | $3,834 |
| March 2025 | $3,990 |
| April 2025 | $3,950 |
| May 2025 | $4,200 |
| June 2025 | $4,400 |
| July 2025 | $4,100 |
| May 2026 | $3,191 |
| June 2026 | $3,162 |
| July 2026 | $3,200 |
Affordability calculator
Can I afford to live at 253 Windward Dr?
Bedrooms
2 bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$128,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $128,000 annually to afford this 2-bedrooms monthly rent price of $3,200.
For more information on rent affordability, visit our rent calculator.
Schools near 253 Windward Dr
Terryville Road School
401 terryville rd
port jefferson sta, NY, 11776
3-5Public
C+
Clinton Avenue School
140 clinton ave
port jefferson sta, NY, 11776
K-2Public
A-
Eastern Suffolk BOCES
201 sunrise hwy
patchogue, NY, 11772
K-12Public
Little Flower School
2460 n wading river rd
wading river, NY, 11792
3-12Public
William Floyd Learning Center
111 lexington rd
shirley, NY, 11967
K-5Public
C+
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Internet available near 253 Windward Dr
Neighborhood
Port Jefferson | Port Jefferson, NY
Getting around Port Jefferson near 253 Windward Dr
Walking
5/10
Some shops and stores are within a few minutes.
Driving
7/10
This area is close to freeways and has adequate parking options.
Cycling
4/10
More spots are within biking distance and some roads are cyclist-friendly.
Transit
6/10
Popular public transit options are just a short walk from this location.
Points of interest for 253 Windward Dr, Port Jefferson
Groceries
7/10
At least one supermarket within a 15-minute walk
Shopping
5/10
Several shops within walking distance
Cafes
4/10
Some cafés within walking distance
Restaurants
5/10
Some restaurants within a few minutes’ walk
Primary schools
3/10
At least one elementary school within a 30-minute walk
High schools
1/10
Closest high school further than a 30-minute walk
Nightlife
2/10
Few or no bars within walking distance
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