Take the singular Shelter Island drive over Ram Island’s renowned causeways to this meticulously renovated and expanded 1933 charming, waterview home of stone and cedar on the most sought after Big Ram Island block. 5 bedrooms, 6 bathrooms and large living spaces flow seamlessly with the outdoors, thanks to the expansive covered porches off the living room and large patio connecting the pool and hot tub with the kitchen and family room. Every detail was considered in the home in terms of beauty, function and experience. It’s owner, a veteran in the home decor industry, designed all fabrics and wallpapers and spec’ed every detail. The house sits on 1.4 acres of land, with a large lawn, wraparound porches to take in the views and space for everyone to enjoy, lounge, play or explore.
Bask in the sparkling sunshine on Coecles Harbor, take in the sunset from the two hanging porch-beds, or waterview-dine on the covered veranda. Swim in the heated pool, relax in the grotto-like hot tub or infrared sauna, or paddleboard, sail, fish or kayak just out your front door off the small beach that’s shared by the neighbors. Paddleboards stay parked here, and morning dips are mandatory in this idyllic spot. Off the beach, 37 Tuthill has a boat mooring, useable by renters. A short walk to the end of Tuthill Drive brings you to Reel Point, a sand peninsula lined with osprey nest platforms and blankets of seashells.
Coecles Harbor is a protected deep-water harbor that faces Mashomack Preserve, with over 2000 acres of interlacing tidal creeks, woodlands and freshwater marshes, easily accessible by paddleboard off our beach. The harbor is prized by sailors, swimmers and fishermen for its pristine, protected waters. The island enjoys a similar sense of peace and tranquility.
Perfect for everything from a relaxing couples getaway to a fun-filled family or friends gathering, this is fantastically special home designed for making cherished memories, in a magical corner of the world.
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Events allowed: family gatherings and birthday parties
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Pets
No pets allowed
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Smoking
Smoking is not permitted
Important information
You need to know
Property Registration Number 2024-L-0018
Property # 2408229vb
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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 30
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Shelter Island
Located in Shelter Island, this holiday home is on the waterfront. The area's natural beauty can be seen at The Hamptons Beaches and East Hampton Main Beach. Consider The Clubhouse Hamptons for a night out or Shelter Island Whale's Tail if you're travelling with kids. Discover the area's water adventures with kayaking, waterskiing and windsurfing nearby, or enjoy the great outdoors with cycling.
Gardiner's Bay Country Club - 6 min drive - 6.4 km
Shelter Island Whale's Tail - 7 min drive - 7.4 km
Shelter Island Historical Society - 9 min drive - 8.8 km
Mashomack Preserve - 10 min drive - 10.2 km
Getting around
Greenport Station - 31 min drive
East Hampton, NY (HTO) - 47 min drive
Restaurants
Claudio’s Waterfront - 30 min drive
Lucharitos - 30 min drive
Noah's - 29 min drive
La Capricciosa - 29 min drive
Billys By The Bay Tiki Bar - 33 min drive
Frequently asked questions
Does NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT have a pool?
Yes, this property has an outdoor pool. Pool types include heated pools.
How much does it cost to stay at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?
As of 21 Aug, 2026, prices found for a 1-night stay for 2 adults at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT on 20 Nov, 2026 start from S$35,970, 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 NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT pet-friendly?
No, pets are not allowed at this property.
How much is parking at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?
On-site parking is available at the property.
What time is check-in at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?
Check-in begins at 4:00 PM.
What time is check-out at NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT?
Checkout is at 11:00 AM.
Where is NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT located?
This family-friendly Shelter Island holiday home is located on the waterfront, 1.7 mi (2.7 km) from Menhadden Lane Beach, and within 6 mi (10 km) of Shelter Island Whale's Tail and East End Seaport Maritime Museum. Greenport Carousel and Railroad Museum of Long Island are also within 6 miles (10 km).
About the host
Hosted by Serena Dugan
I co-founded the home decor brand Serena & Lily (serenaandlily.com) 20 years ago, and oversaw design for the brand as their CCO for 14 years. I now have my own textile collection under the name Serena Dugan Studio (Serena Dugan.com) and am a painter. This house was my ultimate form of creative expression, and I used all my own fabrics and wallpapers, aside from a few fabrics I’ve collected from far off places. I plan on using this house as a creative retreat, as well as a showcase for what I make. I live on the West Coast and want to share this beautiful spot when I am not able to use it with those who will appreciate it.
Why they chose this property
Shelter Island, and particularly Ram Island, is a magical spot, and this house is my most peaceful place. I envision years of memories being made here, and others sharing the beauty and peace of this spot with those who appreciate it as I do.
What makes this property unique
This house has been considered to the nines, both in terms of beauty, comfort and overall experience. Decorating a home that feels wonderful to be in includes all three. I have gone to great lengths to create something wonderful there on Shelter. It’s my happiest spot, and I know visitors will feel and appreciate this as well.