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Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Sunset Cottage

This spacious newly renovated home‘s 120 feet of waterfront overlooks the Ashamomuck pond, the largest inlet of Shelter Bay. With 180 degree views from the wall of South west facing windows and wide wrap around deck, enjoy the tranquil panorama and awesome sunsets from living rooms, gardens or master bedroom suite. Designed for the extended family, from children to great grand parents, and even the family dog, it is handicapped accessible with extra wide doorways and ramps to the outside.

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase. A new baby gate has been installed at the top of the stairs. Village of Greenport Short Term Rental Permit #R26-021.

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Harbor Heights

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 2nd floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

Waterfront Escape | Private Beach, Pool & Views

Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.

Renovated Townhouse, Walk to All

Discover the North Fork from our stylishly renovated 100-year-old townhouse! Perfectly located, you can walk to town, beaches, and a local brewery. This bright, airy home features a new kitchen, central AC, and a private patio with a grill. Comfortably sleeping up to 8 guests, it's the ideal base for families or groups exploring Long Island's wine country. Park your car and enjoy a walkable getaway!

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!