• Primary Photo - 355 Windjammer Dr
  • Building Photo - 355 Windjammer Dr
    Building Photo - 355 Windjammer Dr
  • Building Photo - 355 Windjammer Dr
    Building Photo - 355 Windjammer Dr
$60,000 / Month

355 Windjammer Dr

,

Southold, NY 11971

Share Listing
Favorites
631-848-7730

  • Bedrooms

    3

  • Bathrooms

    2

  • Square Feet

    --

  • Available

    Available Now

Highlights

  • Beach Access
  • Private Pool
  • Cape Cod Architecture
  • Wood Flooring
  • Main Floor Bedroom
  • 1 Fireplace
355 Windjammer Dr
Share Listing
Favorites

About This Home

Available Now

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 MLS ID KEYL3513704 Based on information submitted to the MLS GRID as of [see last changed date above]. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Prices displayed on all Sold listings are the Last Known Listing Price and may not be the actual selling price.

355 Windjammer Dr is a house located in Suffolk County and the 11971 ZIP Code. This area is served by the Southold Union Free School District attendance zone.

* Price shown is base rent. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.

Home Details

Home Type

Single Family Detached Home

Basement

Basement Fills Entire Space Under The House

Bedrooms and Bathrooms

Main Floor Bedroom 2 Full Bathrooms 3 Bedrooms

Home Design

Cape Cod Architecture Frame Construction

Interior Spaces

Wood Flooring 1 Fireplace

Kitchen

Eat-In Kitchen

Listing and Financial Details

Legal Lot and Block 40 / 4 Assessor Parcel Number 1000-079-00-04-00-040-000 Rent includes grounds care, water

Lot Details

22,651 Sq Ft Lot

Outdoor Features

Beach Access

Parking

Driveway

Pool

Private Pool

Schools

Southold Junior-Senior High Middle School Southold Junior-Senior High School

Utilities

Central Air Baseboard Heating Oil Water Heater Heating System Uses Oil Cesspool

Community Details

Pet Policy

Call for details about the types of pets allowed

Contact

  • Listed by Sheri Winter Parker | Corcoran
  • Phone Number
  • Contact
  • Source
    OneKey® MLS
Information Copyright 2026, OneKey® MLS. All Rights Reserved. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.
Location Get Directions
| Edit
Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
City - Southold

Southold, New York sits near the tip of Long Island's North Fork, where vineyards line the back roads and the Long Island Sound is never far from view. This town has a distinct identity shaped by agriculture, maritime heritage, and a slower pace of life that sets it apart from the bustle of metro New York, roughly 80 miles to the west. Unlike the Hamptons to the south, Southold has held onto a grounded character that draws people looking for a more sedate, rooted location.

The town stretches across several hamlets, including Cutchogue, Peconic, and Mattituck, each with its own personality but all connected by a strong sense of place. North Fork wineries and farm stands have brought steady attention to the area, helping fuel a modest but consistent local economy. Stony Brook Southampton and other East End institutions add an educational presence to the broader region.

Rentals here lean toward single-family homes, cottages, and smaller apartment communities tucked within the hamlets.

Learn more about living in Southold 
Amenities
  • Air Conditioning
  • Smoke Free
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 43 min 23.4 mi
Connecticut College
Drive: 124 min 35.6 mi
University of Connecticut
Drive: 132 min 39.4 mi
Yale University, Main Campus
Drive: 173 min 75.7 mi
355 Windjammer Dr is within 43 minutes or 23.4 miles from SUNY Suffolk Co., Eastern. It is also near Connecticut College and University of Connecticut.
Schools
Southold Elementary School
Public Elementary School
Grades K-5
305 Students
Attendance Zone
Shelter Island School
Public Elementary, Middle & High School
Grades PK-12
183 Students
Nearby
Southold Junior Senior High School
Public Middle & High School
Grades 6-12
334 Students
Attendance Zone
The Hayground School
Private Elementary & Middle School
Grades PK-8
87 Students
Nearby
Our Lady Of Mercy Regional School
Private Elementary School
Grades PK-5
92 Students
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

355 Windjammer Dr is near Tweed/New Haven, located 78.9 miles or 179 minutes away.

Commuter Rail Distance
Commuter Rail Distance
Southold Station
Drive: 6 min 2.7 mi
Greenport Station
Drive: 15 min 7.2 mi
Mattituck Station
Drive: 16 min 9.6 mi
Southampton Station
Drive: 58 min 37.2 mi
Bridgehampton Station
Drive: 69 min 42.5 mi
Airports Distance
Airports Distance
Tweed/New Haven
 Drive: 179 min 78.9 mi
Getting Around
Not Walkable
Walkability
10 / 100
Minimal Public Transit
Transit
0 / 100
Exceptionally Drivable
Drivability
100 / 100
Fairly Bikeable
Bikeability
40 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
-
Soundscore™
- / 100

Traffic

-

Airport

-

Businesses

-

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 355 Windjammer Dr.

Shopping Centers Distance
Shopping Centers Distance
Lighthouse Center
Drive: 7 min 2.8 mi
Southold Square
Drive: 8 min 3.4 mi
Village Of Southold
Drive: 8 min 3.4 mi
355 Windjammer Dr has 3 shopping centers within 3.4 miles, which is about a 8-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Custer Institute Observatory
 Drive: 5 min 2.1 mi
Red House Nature Center
 Drive: 13 min 6.8 mi
East End Seaport Maritime Museum
 Drive: 15 min 7.2 mi
Elizabeth A. Morton National Wildlife Refuge
 Drive: 67 min 19.0 mi
South Fork Natural History Museum & Nature Center
 Drive: 69 min 19.9 mi
355 Windjammer Dr has 5 parks within 19.9 miles, including Custer Institute Observatory, Red House Nature Center, and East End Seaport Maritime Museum.
Hospitals Distance
Hospitals Distance
Stony Brook Eastern Long Island Hospital
Drive: 16 min 8.2 mi
355 Windjammer Dr is 8.2 miles and a 16 minute drive from Stony Brook Eastern Long Island Hospital.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 124 min 35.2 mi
New London Naval Sub Base
Drive: 132 min 39.1 mi
Naval & Marine Reserve Center
Drive: 189 min 81.3 mi
355 Windjammer Dr has 3 military bases within 81.3 miles, the nearest is Fort Trumbell US Navy which is 35.2 miles away and a 124 minute drive.

You May Also Like

Similar Rentals Nearby

Report an Issue Print Get Directions