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HomeAway Inc.

Shelter Island Waterfront Home!

#386080 · Vacation rental in , ,

5 Bedrooms
10 guests
4 Full Bathrooms
Vacation rental

Property Description

A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, pool and other areas of the home; this house is your vacation paradise. It has four bedrooms (comfortably sleeping 8), as well as four dedicated full bathrooms. With is also a den with a queen size fold out couch that can accommodate 2 additional people allowing the house to accommodate up to 10 people. Located on Shelter Island, only a three hour drive from Manhattan, and a short ferry ride from the east end of Long Island.

This unique waterfront home features over 500 feet of private beach with stunning sunset views. Privately it is located at the end of a dead end street on the ocean/sound with a small adjacent boat ramp. During the day your private beach is perfect for beach fishing, minnow netting, kayaking, sailing, shell collecting or just relaxing with a book and watching the boats go by. The ocean/sound is tranquil and safe for children, with easy launching of kayaks or boats. Access to the beach is simply steps down from the pool/deck area onto the sand and ocean below.

At night the home is the perfect place to watch a sunset, stargaze or enjoy the lights of the boats that go silently by in the ocean/sound. Shelter Island is far enough from the city and light pollution that you can even see the Milky Way.

Your family can enjoy the large yard between the house and the entrance road providing ample space for recreation. It is suitable for pickup football, soccer and yard games such as bocce or croquet. The island itself lends itself perfectly for those who enjoy biking as there are many roads throughout that provide the ability to ride through tree covered roads, stop at a beach or go into town for a bite to eat or drink.

A large patio overlooking the sound from the main living room is a large patio. Lounge chairs for sunbathing line this outdoor living area including table, chairs, couch for reading and outdoor grill. It’s a great place to sit with a cup of coffee in the morning watching the wildlife, or to enjoy the stunning sunsets with a glass of wine in the evening.

Entering the house through the entry vestibule, you walk into the main living room or into the main dining area with a table that seats 8; each with glorious views of the ocean. From the dining room you can enter into the kitchen that also has a small breakfast bar for relaxing. A washer, dryer, and dishwasher are provided here which make cleanup easy. Through the kitchen is either a formal den, complete with fold out couch and bathroom or alternatively going through a small hall, enter into the main TV room. It includes a flat screen TV that comes with a DVD player, stereo and the modem (WIFI included).

The bedroom wing of the house has a homey charm. It was built in 1958 when the grandparents of the family made it their summer retreat. Two of the bedrooms have king-sized beds (one is comprised of two twins put together as a King and the other a full King), and one has two twin beds. The room with the King size bed and the 2 twin beds have a Jack and Jill bathroom; while the bedroom with a King bed has an ensuite bath with an ocean view. Another bedroom, off the kitchen is separately private with a private bath.

The house is located about five minutes from the North Ferry from which it is another fifteen minutes to Greenport on North Shore of Long Island. Do some window shopping, grab a bite to eat, see a movie, and enjoy this delightful North Fork town, a historic center of 19th century whaling. To the South is Historic Sag Harbor, 25 minutes away by ferry, Easthampton’s boutiques 40 minutes away, and ocean beaches to catch some bigger waves are 40 minutes to 1 hour away. You can go to Montauk Point in an hour as well to hike around the park or do chartered fishing from either Greenport or the South Shore. The wineries, only some 20 minutes away, on both the North and South forks are also a great escape during the week that provide the fun of wine tasting along their routes lined with fresh farm/markets that sell fresh vegetables, pies, jams, corn and many other items.

On the island itself, you are fifteen minutes away from Shelter Island Heights with its many restaurants, charming coffee shops, and quaint stores. On the way you can stop at the organic farm and education center at Sylvester Manor, the original 17th century manor house of the island.

You’re also a ten minute drive from two of the best restaurants in the region (18 Bay and Vine Street Cafe) and a ten minute drive from a reasonably priced 2,500 yard public golf course. For the kids, it’s a scenic bike ride (or ten minute drive) to mini golf or one of two ice cream shops. Or for those young at heart, try the eclectic Sunset Beach renowned for its European flair and beach side location.

If you like hiking, then Shelter Island is the place for you. One third of the island is a preserve known as Mashomack Preserve. Owned by the Nature Conservancy, the 2,100 acres shelter a large population of breeding ospreys as well as nesting populations of the endangered piping plover and least tern, as well as a number of rare plants.

All of these delights and more await you in your stunning vacation rental. We’ll be waiting for you on the beach!

Property Type • House • 3006 sq. ft. Accommodation Type • Vacation Rental Meals • Guests Provide Their Own Meals Onsite Services • Housekeeper Optional Suitability • Minimum Age Limit For Renters: 25

• Children Welcome • Non Smoking Only • Wheelchair Inaccessible Bedrooms: 4 Bedrooms, Sleeps 10, Beds for 10 • Bedroom 1: 1 King • Bedroom 2: 2 twins • Bedroom 3: 1 King (made up of 2 twin beds) • Bedroom 4: 2 twins • Bedroom 5: 1 queen pull out couch Bathrooms: 4 Bathrooms • Bathroom 1: toilet, combination tub/shower • Bathroom 2: toilet, combination tub/shower

• Bathroom 3: toilet, combination tub/shower

• Bathroom 4: toilet, shower

Owner info:

Year Purchased: 1958

About the owner: My grandparents bought this house in 1958 and it has been a beloved part of our family ever since. My siblings and I grew up spending every summer at this house, and as we grew up and had families the trend continued on a larger scale.

Why the Owner Chose (Shelter Island Heights, NY, USA):

Who wouldn't want a large private beach and huge yard? In 1958 it was a chance for my grandparents to buy a house that let them escape the busy city life they led. This property, between being in a quiet part of the island, and being waterfront, has the benefit of being simultaneously removed from everything, and extremely close to it. It has the dual benefit of being both private, so you can enjoy time to truly unwind, and also very close to shopping, restaurants, and public beaches so you can enjoy your vacation with family and friends.

The Unique Benefits at this House:

A large private beach to fish, minnow net, boat, kayak, and generally relax on. Beautiful ocean views with a large deck so you can enjoy breakfast (lunch, dinner, and after dinner drinks) outside looking at the gorgeous water views. Huge yard for recreation (or laying on a blanket outside). Very private location but also no more than ten minutes away from anything.

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House Rules

Check In Time: 16:00
Check Out Time: 11:00
Max occupancy: 10 guests

Sleeping Arrangements

Common Space
Bed types not specified
Bedroom 1
1 King Bed
Bedroom 2
2 Twins
Bedroom 3
1 King Bed
Bedroom 4
2 Twins
Bedroom 5
1 Queen Bed


Rate Name Nightly Weekend Weekly Monthly
Default Rate
7 Nights Minimum
$644 CAD - - -
02/16/18 - 02/16/21
7 Nights Minimum
$1012 CAD - - -



Internet Access
Stereo System
Cable / Satellite TV
DVD Player


Heated Pool
Air Conditioned


Dishes / Utensils
Small Appliances


BBQ / Grill
Parking Available
Deck / Patio
Sandy Beach
Tennis Court


Maid Service
Spa Services
Restaurant On Site
Guided Fishing Tours
Gym / Fitness Centre

Availability Calendar


  • Unavailable
  • Check In Available
  • Check Out Available
Availability last updated Mar 14, 2018
Overall Rating

Owner Information