Timeless Shelter Island Estates Blend Historic Integrity with Enduring Design

Rarely available homes from 1788 to the Gilded Age come to market on storied East End enclave

SHELTER ISLAND, NY, NY, UNITED STATES, June 26, 2025 /EINPresswire.com/ -- 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 deep water 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 three levels of living space, 1.44± park-like acres, a Gunite pool, sunset harbor views, and a deep water 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 19th century 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 and views of Shelter Island Country Club, affectionately known as "Goat Hill". “It’s a house that’s been lived in with great affection,” Moore said. “You see it in the original beams and 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, Union Chapel, 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, wide plank floors which were recently sanded and finished, milk glass lighting, 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 slice of Eastern Long Island heritage, these properties offer the rare opportunity to live within the story of Shelter Island’s architectural past.

Penelope A Moore
Saunders & Associates
+1 917-208-5519
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