Escape to your own private waterfront retreat on Long Island Sound. Located at the end of private Windward Road, this beautiful four-bedroom home offers breathtaking water views, direct beach access, and a peaceful setting unlike anywhere else on the North Fork.

What truly sets this property apart is its extraordinary setting on 200 acres of private land, offering a rare sense of seclusion and tranquility. You will usually enjoy the beach almost entirely to yourselves, creating a unique private waterfront experience that is increasingly difficult to find.

The home features four spacious bedrooms, including a king master suite with a private bathroom and balcony overlooking the water. Three additional bedrooms, one of which has a private bathroom, offer comfortable accommodations, desks for remote work, queen size beds, and balconies. A skylit bathroom serves the additional guest rooms.

The main level includes two elegant living rooms, one warm and sophisticated with modern furnishings, and another bright sun-filled room that welcomes the morning light. Between them is a large dining room and a fully equipped kitchen featuring granite countertops, a gas range, and everything needed for preparing meals at home. Large glass doors open to a waterfront terrace where guests can dine, relax, and enjoy uninterrupted views of Long Island Sound.

The home also offers a barbecue grill, washer and dryer, and plenty of indoor and outdoor space for families and groups to gather comfortably.

Guests have access to four kayaks, a beach hut, umbrellas, and lounge chairs for relaxing by the shore. The calm waters and expansive beachfront provide excellent opportunities for swimming, kayaking, fishing, birdwatching, beachcombing, and exploring the natural beauty of the area.

As the sun sets, the house and beach transform into a peaceful retreat. Relax under a canopy of stars, listen to the gentle waves along the shoreline, enjoy a beach fire, or simply unwind in the quiet beauty of the waterfront. The evenings here are every bit as memorable as the days.

The property is just a short drive from Greenport Village, local wineries, farm stands, restaurants, beaches, ferries, and many of the attractions that make the North Fork one of New York’s most desirable vacation destinations.

Your host brings many years of experience in hospitality and vacation rentals and takes pride in helping guests enjoy a memorable stay. From local recommendations and area insights to ensuring the home is comfortable and welcoming, every effort is made to help families and visitors experience the very best of the North Fork.

Guests have access to the entire main floor and second floor of the home. The basement and garage are not included in the rental and are reserved for occasional owner use.

Whether you’re seeking a family vacation, a peaceful retreat, or a memorable waterfront getaway, this exceptional home offers luxury, privacy, personal hospitality, and unforgettable views in one of Long Island’s most beautiful locations. We comply with 14 minimum stay Suffolk County regulation.