On an island where history is measured not only in years but in craftsmanship and stewardship, a rare collection of historic residences has quietly come to market. From a Revolutionary War era homestead to a Victorian with deepwater dock, these properties reflect Shelter Island’s evolving architectural narrative—thoughtfully preserved, gently modernized, and never far from the water’s edge.
“These homes aren’t just historic by date—they each represent a continuity of vision,” said Penelope Moore, Licensed Associate Real Estate Broker with Saunders & Associates. “They’ve been shaped by architects, historians, designers, and artists who respected their past while making space for contemporary life.”
6 Ward Road | Greatfields, 1788
Built in 1788 by Samuel Havens, “Greatfields” stands among the oldest private residences on Shelter Island and remains remarkably faithful to its origins. Featured in the Wall Street Journal and several design volumes, the home was described by a previous owner—an architectural historian—as a rare example of “folk wren vernacular architecture.” Wide plank floors, exposed beams, and high ceilings evoke early American restraint, while a luminous kitchen, Gunite pool, and meditation garden add a gentle modernity. “This home was never over-restored,” noted Moore. “It was cultivated with patience and reverence.”
8 Gardiner Way & 15A Shore Road | Victorian with Dock, 1887
Tucked into the manicured lanes of Dering Harbor Village, this 1887 Victorian estate offers 1.44± acres, a Gunite pool, harbor views, and a deepwater dock. A gracious wraparound porch, butler’s pantry, claw-foot tub, vintage stained glass and screen porches speak to its Gilded Age roots, while thoughtful upgrades—central air, a 2021 chef’s kitchen, and pool—support modern living. “It’s one of those rare properties where the elegance of the past still frames the daily rhythm of the present,” Moore said.
45 West Neck Road | Shingle-Style Farmhouse, Circa 1870
Built circa 1870 and moved from Shelter Island Heights to its current location near the resort section along Crescent Beach, this clapboard farmhouse has a literary and cultural lineage. Once home to Margaret Walters, daughter of prominent Shelter Island figure Squire Chase, and later to Nathan Cuffee, co-author of Lords of the Soil, the home features 6-over-6 windows, exposed beams, three finished levels of living space and views of Goat Hill. “It’s a house that’s been lived in with great affection,” Moore said. “You see it in the floorboards and feel it in the light.”
5 Washington Street | Shelter Island Heights Traditional, 1874
In the heart of the Heights near the Chequit Hotel, Rainbow Park and the North Ferry, this classic 1874 home sits just above the road, with winding garden paths and twin porches—one open, one lattice-covered—offering distinct places for reflection or gathering. “The house retains its soul: tall ceilings, original woodwork, and a layout that embraces summer living,” Moore explained. With five bedrooms and sensitive updates, it remains faithful to its origins as a seasonal escape.
For those seeking not just a home but a heritage, these properties offer the rare opportunity to live within the story of Shelter Island’s architectural past.
PENELOPE A. MOORE
Licensed Associate Real Estate Broker
[email protected]
Cell: (917) 208-5519
