Shelter Island, New York · Summer 2026
4 bedrooms. Heated pool. Community beach access. Cathedral ceilings. Stone fireplace. Dogs welcome. Available June–September 2026.
Glynn Gardens is available for weekly and monthly rentals June through September 2026. August books earliest — inquire now to secure peak-season availability. Listed exclusively through Douglas Elliman Real Estate.
Glynn Gardens sits in Shelter Island Heights — the island's historic summer community — on a lushly wooded lot with the privacy and scale that make a long summer stay actually work.
Private heated outdoor pool on the main deck. Operational from late May through September.
Included with the rental. Access Shelter Island's pristine coastline for swimming, kayaking, and paddleboarding on Peconic Bay.
2,620 sq ft of living space with soaring ceilings, floor-to-ceiling windows, and natural light throughout.
Wood-burning stone fireplace in the main living room — essential for cool June evenings and early September nights.
Large private grounds and deck, dog-friendly community beaches nearby, and direct access to Mashomack Preserve trails.
Fully updated HVAC and water heater installed 2026. Comfortable in any summer conditions.
Fully renovated primary bathroom with Carrara marble finishes. Three full baths across the property.
Lush, mature landscaping provides natural shade and privacy — rare for a property this close to the beach community.
Shelter Island has no traffic lights, no chain stores, and one-third of its land permanently protected as Mashomack Preserve. Everything you need for a summer — beaches, restaurants, hiking, wine country day trips — is either on the island or a short ferry ride away.
Greenport (North Fork) to Shelter Island. 8 min crossing, runs 5am–1am daily.
northferry.com →North Haven/Sag Harbor (South Fork) to Shelter Island. 8 min, runs 365 days/year.
southferry.com →The island's essential gourmet market. Rotisserie chickens, organic produce, espresso, 5 min from the house.
Read our guide →André Balazs's legendary waterfront hotel and restaurant — the social heart of the island's summer season.
Read our guide →2,350 acres of trails, tidal creeks, and 11 miles of undeveloped coastline. One-third of the entire island.
Read our guide →The island's most popular swimming beaches. Permits via Pavemint app; Wade's Beach is dog-friendly.
Read our guide →37 wineries, 30 minutes away via ferry. Wölffer Estate, Paumanok, White Oak Wine Garden.
Read our guide →Official visitor information, events calendar, and island business directory.
shelterislandchamber.org →100,000+ maps, deeds, and documents. The island's full story from the Manhanset to today.
Read our history →Shelter Island sits between the North and South Forks of Long Island — accessible only by ferry, which is precisely what keeps it the way it is. No Route 27 traffic. No strip malls. No Starbucks. The ferry crossing takes eight minutes and functions as a filter: only people who actually want to be here make the crossing. The result is a summer community that is quieter, more local, and more genuinely focused on the place itself than anything the Hamptons can currently offer.
Comparable luxury rentals in East Hampton command $200,000 or more per season. Glynn Gardens offers a four-bedroom, pool, beach-access property at a fraction of that — with the kind of privacy and natural character that overbuilt Hamptons corridors have largely lost. Read the full comparison →
Contact the listing agent directly for current availability and rates. Booking direct saves 12–15% in platform fees.
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