Shelter Island, New York · 4 Glynn Drive
Glynn Gardens
4 bedrooms. Heated pool. Stone fireplace. Cathedral ceilings. Community beach access. Shelter Island's most distinctive summer rental.
4 bedrooms. Heated pool. Stone fireplace. Cathedral ceilings. Community beach access. Shelter Island's most distinctive summer rental.
Glynn Gardens is a 4-bedroom, 3-bathroom retreat at 4 Glynn Drive, Shelter Island, NY — a property defined by the kind of architectural details that stop you at the door and hold you inside. The great room soars to cathedral ceilings lined with skylights, flooding the space with shifting light throughout the day. A stone wood-burning fireplace anchors the room at one end; floor-to-ceiling windows and sliding glass doors to the deck open it at the other.
The floors throughout the main level are checkerboard Carrara marble — dramatic, cool underfoot, and unmistakably considered. The kitchen continues the palette with white cabinetry and open shelving. The primary bathroom was fully renovated with floor-to-ceiling dark green subway tile, unlacquered brass fixtures, and a hexagon marble mosaic shower floor — a spa-level renovation that photographs as well as it lives. The second primary suite features a boucle upholstered bed, hand-knotted Moroccan rug, and paired brass pendant sconces.
The property includes a heated pool and wrap-around deck — a private outdoor retreat ideal for summer mornings and long evenings. Mechanically, the property is sound: both HVAC and water heater were replaced in 2026. Community beach access is included. Dogs are welcome on the grounds. 2,620 square feet total across four bedrooms and three full baths. Listed exclusively through Douglas Elliman Real Estate at $80,000/month for the summer season.
Shelter Island sits between the North and South Forks of Long Island, accessible only by ferry — which is precisely the point. The 8-minute crossing from Greenport or Sag Harbor is the natural filter that keeps the island quiet, unhurried, and genuinely residential.
Known as "the un-Hamptons," Shelter Island offers the same East End beauty — pristine beaches, farm stands, sailing, kayaking — without the traffic or the scene. Nearly one-third of the island is protected as Mashomack Nature Preserve. The dining and marina at Shelter Island Heights are minutes from Glynn Gardens.
From Manhattan: 2 hours by car to the North Ferry in Greenport. From the Hamptons: 20 minutes to the South Ferry in Sag Harbor.
Glynn Gardens is listed exclusively through Douglas Elliman Real Estate. Fill out the form or contact the listing agent directly — all inquiries receive a same-day response.