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.
Our prices include all fees. No hidden fees.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Shelter Island Heights
Located on the beach, this vacation home is in Silver Beach, a neighborhood in Shelter Island Heights. Havens House and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions include Shelter Island Whale's Tail and Greenport Carousel. Railroad Museum of Long Island and Norman E. Klipp Marine Park are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking and cycling.
Shelter Island Country Club - 3 min drive - 2.8 km
Shell Beach - 4 min drive - 3.9 km
Havens House - 6 min drive - 5.6 km
Getting around
Greenport Station - 25 min drive
East Hampton, NY (HTO) - 44 min drive
Restaurants
Shelter Island Craft Brewery - 5 min drive
Eddie’s - 28 min drive
North Fork Table & Inn - 32 min drive
Léon 1909 - 3 min drive
Vine Street Cafe - 7 min drive
Frequently asked questions
Does Shelter Island Waterfront Home! have a pool?
Yes, this property has a pool.
How much does it cost to stay at Shelter Island Waterfront Home!?
As of May 14, 2026, prices found for a 1-night stay for 2 adults at Shelter Island Waterfront Home! on Jun 2, 2026 start from $803, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Shelter Island Waterfront Home! pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Shelter Island Waterfront Home!?
Check-in begins at 4:00 PM.
What time is check-out at Shelter Island Waterfront Home!?
Check-out is at 11:00 AM.
Where is Shelter Island Waterfront Home! located?
Nestled on the beach, this Silver Beach vacation home is within 2 mi (3 km) of Crescent Beach, Sunset Beach, and Shelter Island Country Club. Shell Beach is 2.1 mi (3.3 km) away.
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
A great stay in this lovely house. The U shape of the house around the pool was great with young kids. Very helpful and responsive host. Solid wifi and appliances. Really nothing to suggest in terms of improvements. Hope to be back next next year.
We all enjoyed the home very much. The owner was very responsive (replaced our A/C in bedroom immediately). The home is a bit vintage so forget marble/latest appliances or 300 thread count linens, but if you come to Shelter Island to enjoy the outdoors and the general uniqueness of the island, then this home is ideal.
This home is perfect for those looking for a family vacation spot. Beautiful setting, private and spacious. This home is designed for comfottable family gatherings with a huge living room, good size kitchen and grill for meal prep.(well stocked) It has a large media room with a smaller den for get away reading and napping. The bedroom area is great with comfortable beds and newly remodeled bathrooms. The pool and water view provided us all with entertainment. Watching all the boats and most exciting the ospreys feed. The beach area was great for quiet walks collecting shells, fishing and kayaking. Very peaceful. Many happy memories!
This was the third year that we rented this property its location is tremendously beautiful my grandchildren and my children and I have created incredible memories here
Second stay at this Shelter Island waterfront home!
My family recently enjoyed our second stay at this property. The location is spectacular. The private beach is such a rare find. Most days we were the only people on the entire stretch of beachfront. The evenings on the beach were gorgeous. There is a nice breeze that always seems to exist on this side of the island.
This family-friendly house has plenty of space and multiple bathrooms. The kids have plenty of space to run around - huge lawn, private beach and a pool with tons of toys provided by the owner. If you are looking for a good place for tweens and older kids, this one is it. It may not be a great house for toddlers or small children that can’t swim as the pool is located directly outside all the doors on the backside of the house.
The host was very responsive.
Laura M.
Verified
10/10 Excellent
Phyllis F.
Aug 26, 2018
Amazing
We had a wonderful week on Shelter Island. The house was spacious, the view and sunsets were great, and the pool and beach. It exceeded our expectation ,it was spacious and very comfortable for our family . The owner was very easy to work with and we can’t wait to go back.
Phyllis F.
Stayed 7 nights in Aug 2018
Verified
10/10 Excellent
Joan P.
Aug 7, 2018
This lovely home is a classic beach house! Fantastic views of the water!
This home was perfect for our family vacation! Plenty of space for gathering together, sharing meals, and catching up! Private sleeping areas with water views- very peaceful. Room for everyone! The pool was a real bonus! We loved the short walk to the shore enjoying the shelling and kayaking and sea air! Our granddaughter had fun observing the local wildlife including rabbits, chipmunks, and of course the ospreys fishing. Wonderful two weeks!
Joan P.
Stayed 14 nights in Jul 2018
Archival
10/10 Excellent
Daniel W.
Sep 3, 2017
Perfect Location for a Week of Relaxation
Terrific place for a family vacation. We spent a week - the house is very comfortable. Its location right on the bay, with beach access, is fantastic. Nice pool, grill on the deck, lots of rooms. All around awesome place. And Kurt, the owner, is down-to-earth, responsive, and easy to work with. Highly recommended!
Daniel W.
Stayed 7 nights in Aug 2017
Archival
10/10 Excellent
Carol D.
Aug 31, 2017
Beautiful home with lots of space inside and outside! The pool is delightful.
The house is spacious and lovely. Eating dinner outside with the sunset as our natural TV cannot be beat! We loved it. The pool is wonderful all times of day. The beach is perfect for relaxing on a beach chair and for enjoying a walk, and swimming was really enjoyable too.
The owner is responsive and easy to communicate with.
We had fun too exploring the Island.
We had a most wonderful time!!
Carol D.
Stayed 7 nights in Aug 2017
About the host
Hosted by Kurt Schrader
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 they chose this property
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.
What makes this property unique
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 only minutes away from anything.