Tucked behind a canopy of mature trees on six private acres, this Shelter Island estate is the kind of property that rarely comes available — a true compound, not just a large house. The main house and a fully separate guest cottage sit together on sweeping, secluded grounds with a heated pool, slate terrace, outdoor dining, and the quiet that the East End promises but doesn’t always deliver. Sleeps 10 in exceptional comfort. Bootleggers Alley beach is a short walk away.
Key Features
☀ Sleeps 10
☀ 5 bedrooms, 5 bathrooms, 6 beds
☀ Heated pool, outdoor shower, stone patio, grill, loungers, benches, and outdoor dining
☀ Separate guest cottage for added privacy and flexibility
☀ Chef’s kitchen with high-end appliances
☀ Fireplace, family room, library, screened porch, formal dining room, and office
☀ Set on a secluded private estate with expansive lawn and multiple parking spaces
☀ Pet-friendly with high-speed internet
☀ Walk to Bootleggers Alley and close to Crescent Beach, the Pridwin, Sunset Beach, and Leon 1909
☆☆ BEDROOMS ☆☆
With room for up to 10 guests, the sleeping setup feels especially well suited for refined family stays or elevated group getaways. The main-level primary suite features a king bed and ensuite bath, creating a peaceful private retreat. Upstairs in the main house, you’ll find a queen bedroom and a twin bedroom with two twin beds, each with access to a full bath. The separate guest cottage adds wonderful privacy with two upper-level queen bedrooms and shared bathroom access, making it ideal for another couple, grandparents, or friends traveling together.
☆☆ BATHROOMS ☆☆
The home offers 5 bathrooms total, including 3 full baths and 2 half baths, giving your group the convenience and flexibility needed for easy mornings and relaxed evenings. The primary bedroom enjoys an ensuite bath, while the remaining baths are thoughtfully positioned for comfortable shared access. Guests will appreciate the upscale feel throughout, with attractive tile work, glass shower doors, and a polished, luxurious finish. All bathrooms are stocked with body wash, shampoo, conditioner, and the essentials you need for a seamless stay.
☆☆ KITCHEN & RELAXING AREAS ☆☆
This is a home designed for gathering beautifully. The gorgeous white kitchen is equipped with high-end appliances and a gourmet feel, making everything from morning coffee to full group dinners feel effortless. Beyond the kitchen, the main house offers a rich collection of living spaces including a family room, library, screened porch, formal dining room, and a primary suite office. Zillow’s description also notes original architectural details, period furnishings, a piano room, and French doors opening to a charming stone terrace. The guest cottage adds even more flexibility with its own kitchen, living area, office, and laundry.
☆☆ OUTSIDE SPACE ☆☆
The outdoor setting is what makes this estate unforgettable. Surrounded by mature trees and sweeping lawn, the property offers a true sense of privacy and calm. Spend sunny afternoons by the heated natural-style pool, unwind on the stone patio, rinse off in the outdoor shower, or gather for al fresco meals with the grill and outdoor dining table. Loungers, benches, and additional seating make it easy to settle in for long, relaxed days outside. With a wide drive, garage access, and space for approximately 6 to 8 vehicles, arrivals are easy for larger groups. The location is equally special, with Bootleggers Alley a short walk away and Crescent Beach, the Pridwin, Sunset Beach, and Leon 1909 all just minutes from the home.
★☆ Book Today & Let Us Take Care Of You ☆★
Whether you’re planning a polished summer escape, a memorable family gathering, or a stylish stay with friends, this Shelter Island estate offers the privacy, comfort, and elevated atmosphere that make a trip feel truly special. Reserve your dates now and enjoy one of the island’s most serene and sought-after settings.
The entire property is yours for the duration of your stay — both dwellings, the pool, all outdoor spaces, the garage, and the grounds. We ask only that you’re mindful of the neighbors and treat the estate with the same care you’d want in your own home.
The Suite Serenity Properties team as well as Tide & Tyme, a local Shelter Island concierge service, will be sure to take care of you and are always available should you need anything during your stay. We give our guests space to fully enjoy the property while remaining just a phone call away. A direct contact person and phone number will be provided upon booking confirmation.
You can expect a prompt response to any inquiry. Our standard is simple — a five-star experience at every property, every stay.
The property sits within Green Lawns, Shelter Island’s original estate enclave established in the late 1800s and one of the island’s most historic and private residential corridors.
Bootleggers Alley beach is a short walk away. Crescent Beach, the Pridwin, Sunset Beach, and Leon 1909 are all under five minutes by car. Mashomack Preserve, 2,100 acres of trails and coastline occupying a full third of the island, is ten minutes away.
Shelter Island is accessible only by ferry. The South Ferry from North Haven runs approximately five minutes and is the most convenient route if you’re coming from the city or the Hamptons. The North Ferry from Greenport takes about eight minutes and connects from the North Fork. Both ferries run frequently throughout the day and no reservations are needed. Just drive on.
Once on the island, a car is the easiest way to get around. The property has a pebbled drive with parking for six to eight vehicles, and most beaches, restaurants, and attractions are within ten minutes.
Bikes are a favorite way to explore. Piccozzi’s Bike Shop is five minutes away and rents by the day or week. For guests arriving without a car, Shelter Island Go-Fors provides local car service across the island.
This home is professionally managed by Suite Serenity Properties — a boutique short-term rental company dedicated to exceptional stays across the Northeast, and Tide & Tyme, a local Shelter Island property management and concierge service company.
This home is privately owned. By booking, all guests acknowledge they have read and agreed to the posted house rules and surveillance conditions. Suite Serenity Properties reserves the right to cancel reservations or enforce fees in the event rules are not followed.
Please note that the owners and management assume no responsibility for accidents, injuries, illness, or loss of personal belongings occurring on or around the property. By booking, guests accept personal responsibility for themselves and all members of their party.
Please remember that you’re staying in a house, not a hotel. Please treat the space with respect. If any problems arise, we will do our best to take action asap.
Please respect the property.
We strongly recommend purchasing travel insurance prior to your stay. Our cancellation policy is strictly enforced, and travel insurance ensures you are fully protected in the event of any unexpected changes to your plans.
We look forward to welcoming you to Shelter Island.
– Seth & Tasha
Suite Serenity Properties
