Updated 5+ Days Ago
Highlights
- Spa like bathroom
- Outdoor kitchen and bar
- Lagoon style pool
Location
355 Windjammer Dr, Southold, NY 11971, USA
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Amenities for 355 Windjammer Dr
Features
| Baseboard | Central Air |
| Hardwood Floor |
Community
| Basement | Exterior Type: Frame |
Grounds
| Outdoor Space | Swimming Pool |
Other
| Architecture Style: Cape Cod | Oil |
| Seven 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.
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REQUIRED FEES
Security Deposit
One-time. Refundable.
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About 355 Windjammer Dr
Property Status: Active This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer place... you will not want to leave! Permit #1002, Additional information: Appearance:Mint Office Phone: (631) 848-7730 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 355 Windjammer Dr compares to other nearby properties.
Positives
- Images Available
- There are at least 10 photos of this address
Considerations
- Greater distance from grade schools
- The nearest elementary school is farther than 2 miles away
- Greater distance from high schools
- The nearest high school is farther than 2 miles away
Address details
| Zip code | 11971 |
|---|---|
| Type | House for rent |
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Rent trends in Southold
3-bedroom apartments at 355 Windjammer Dr cost about 307% more than the average rent price for 3-bedroom apartments in Southold.
Median rents as of Sep 19 2026.
Southold
| Month | Median Rent |
|---|---|
| October 2024 | $17,250 |
| November 2024 | $12,600 |
| December 2024 | $9,000 |
| January 2025 | $14,000 |
| February 2025 | $11,500 |
| March 2025 | $13,700 |
| April 2025 | $11,062 |
| May 2025 | $8,800 |
| June 2025 | $11,275 |
| July 2025 | $12,700 |
| August 2025 | $13,500 |
| September 2025 | $10,500 |
| October 2025 | $8,928 |
| November 2025 | $8,400 |
| December 2025 | $7,437 |
| January 2026 | $4,339 |
| February 2026 | $5,375 |
| March 2026 | $6,687 |
| April 2026 | $7,812 |
| May 2026 | $9,700 |
| June 2026 | $10,476 |
| July 2026 | $14,937 |
| August 2026 | $14,750 |
| September 2026 | $14,750 |
Affordability calculator
Can I afford to live at 355 Windjammer Dr?
Bedrooms
3 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
$2,400,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $2,400,000 annually to afford this 3-bedrooms monthly rent price of $60,000.
For more information on rent affordability, visit our rent calculator.
Rent history
The increase or decrease in monthly rent compared to the previous listing price.| 1 year ago | $70,000 |
Schools near 355 Windjammer Dr
Southold Elementary School
420 oaklawn ave
southold, NY, 11971
K-6Public
B-
Oysterponds Elementary School
23405 main rd
orient, NY, 11957
PK, K-6Public
B
Tuckahoe School
468 magee st
southampton, NY, 11968
PK, K-8Public
B-
Wainscott School
47 main st
wainscott, NY, 11975
K-3Public
Springs School
48 school st
east hampton, NY, 11937
PK, K-8Public
B
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Internet available near 355 Windjammer Dr
Neighborhood
Getting around Southold near 355 Windjammer Dr
Walking
1/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Driving
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Cycling
4/10
This is semi-bikeable, but you’ll need another way of getting around.
Transit
0/10
FYI, there are little to no public transit options within walking distance.
Points of interest for 355 Windjammer Dr, Southold
Groceries
0/10
No grocery stores within walking distance
Shopping
2/10
Few or no shops within walking distance
Cafes
1/10
Few or no cafés within walking distance
Restaurants
2/10
Few or no restaurants within walking distance
Primary schools
0/10
No elementary schools within a 30-minute walk
High schools
0/10
No high schools within a 30-minute walk
Nightlife
0/10
Few or no bars within walking distance
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