• Primary Photo - 53 Windward Way
  • Building Photo - 53 Windward Way
    Building Photo - 53 Windward Way
  • Building Photo - 53 Windward Way
    Building Photo - 53 Windward Way
$25,000 / Month

53 Windward Way

,

Southampton, NY 11968

2 Weeks Ago
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Under 30 minutes

Commute Time is calculated at rush hour.
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Beds Baths Average SF
3 Bedrooms 3 Bedrooms 3 Br 4 Baths 4 Baths 4 Ba —

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.

Details

Lease Options

  • 12 Months

About This Property

Welcome to this exquisitely renovated 1,200 SF home in the picturesque Village of Southampton. This charming residence, updated in 2022, offers 3 bedrooms and 3.5 baths, including a newly added powder room in 2024. Upon entry, you're greeted by a spacious living room that seamlessly integrates with the kitchen and dining area, creating an open-concept living space. Elegant white oak flooring runs throughout, while the living room features a cozy fireplace and a chic mini bar that opens to the outdoor deck. The kitchen is a culinary enthusiast's dream, boasting marble countertops and modern appliances. The dining area is perfect for family meals and gatherings. Step outside to enjoy a host of outdoor amenities, including a newly added saltwater heated pool in 2024, an outdoor shower, a breakfast nook, a relaxing chill-out area, and a grill for al fresco dining. This single-story home also includes a finished basement, updated in 2025, with an egress window and walk-out access to the backyard, providing additional living space and convenience. The property is equipped with an alarm system and smoke detectors for enhanced security. Located close to parks, shopping, Main Street, and a variety of renowned restaurants such as T-Bar Southampton, 75 Main, Shippy's, and El Verano, this home offers easy access to local amenities. The newly reopened Southampton Imax Theatre adds to the entertainment options and the beach is just a 10-minute drive away. Experience the perfect blend of comfort and style in this thoughtfully designed Southampton home, offering an unparalleled lifestyle in a prime location.

53 Windward Way is a house located in Suffolk County and the 11968 ZIP Code. This area is served by the Southampton Union Free School District attendance zone.

House Features

  • Air Conditioning
  • Package Service
  • Laundry Facilities
  • Controlled Access
Location
53 Windward Way, Southampton,
NY 11968
Get Directions
City - Southampton

Southampton, NY sits at the edge of the Atlantic on Long Island's South Fork, where salt air and crashing waves define this storied Hamptons village that has drawn New Yorkers east for generations. Founded in 1640 by settlers from Lynn, Massachusetts—making it one of New York State's oldest English settlements—Southampton balances lively Main Street lined with art galleries, boutique shops, and coffeehouses with stretches of open shoreline and quieter residential neighborhoods. While beaches draw summer crowds, the village maintains an intentional, relaxed pace year-round, with preserved architecture reflecting its deep community roots. The rental market favors cottage-style homes and smaller apartment communities over high-rises, preserving the town's low-density character. Whether seeking a studio or multi-bedroom rental, options move quickly given Southampton's enduring appeal as a place where downtown energy meets coastal tranquility.

Learn more about living in Southampton 

Below are rent ranges for similar nearby apartments

Beds Average Size Lowest Typical Premium
1 Bed 1 Bed 1 Bed 800 Sq Ft $1,175 $1,185 $1,195
Amenities
  • Air Conditioning
  • Package Service
  • Laundry Facilities
  • Controlled Access
Education
Colleges & Universities Distance
Colleges & Universities Distance
SUNY Suffolk Co., Eastern
Drive: 34 min 20.3 mi
St Joseph's Coll., Long Island
Drive: 53 min 36.0 mi
SUNY Suffolk Co., Ammerman
Drive: 59 min 39.5 mi
University of Connecticut
Drive: 177 min 69.1 mi
53 Windward Way is within 34 minutes or 20.3 miles from SUNY Suffolk Co., Eastern. It is also near St Joseph's Coll., Long Island and SUNY Suffolk Co., Ammerman.
Schools
Southampton Intermediate School
Public Elementary & Middle School
Grades K-8
Attendance Zone
Southampton Elementary School
Public Elementary School
Grades PK-5
Attendance Zone
Southampton High School
Public High School
Grades 9-12
Attendance Zone
Our Lady Of The Hamptons Regional Catholic School
Private Elementary & Middle School
Grades PK-8
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
Commuter Rail Distance
Commuter Rail Distance
Southampton Station
Walk: 16 min 0.8 mi
Bridgehampton Station
Drive: 14 min 6.8 mi
Hampton Bays Station
Drive: 16 min 8.0 mi
East Hampton Station
Drive: 29 min 13.4 mi
Mattituck Station
Drive: 41 min 23.9 mi

Walkability Near 53 Windward Way Southampton, NY 11968

Getting Around
Fairly Walkable
Walkability
40 / 100
Limited Public Transit
Transit
30 / 100
Exceptionally Drivable
Drivability
90 / 100
Fairly Bikeable
Bikeability
50 / 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 53 Windward Way.

Shopping Centers Distance
Shopping Centers Distance
Village East Shopping Center
Drive: 5 min 2.1 mi
Otb Center
Drive: 5 min 2.1 mi
Water Mill Village
Drive: 5 min 2.2 mi
53 Windward Way has 3 shopping centers within 2.2 miles, which is about a 5-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Shinnecock East County Park
 Drive: 19 min 6.3 mi
Meschutt Beach County Park
 Drive: 16 min 6.7 mi
South Fork Natural History Museum & Nature Center
 Drive: 17 min 8.0 mi
Elizabeth A. Morton National Wildlife Refuge
 Drive: 18 min 8.8 mi
Sears Bellows County Park
 Drive: 16 min 10.1 mi
53 Windward Way has 5 parks within 10.1 miles, including Shinnecock East County Park, Meschutt Beach County Park, and South Fork Natural History Museum & Nature Center.
Military Bases Distance
Military Bases Distance
Fort Trumbell US Navy
Drive: 169 min 64.9 mi
New London Naval Sub Base
Drive: 177 min 68.9 mi
53 Windward Way is 64.9 miles from Fort Trumbell US Navy, and is convenient to other military bases, including New London Naval Sub Base.

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