Developing Long Island: Legacy on the creek:
A century of Shelter Island summers

A century ago, summer seekers drifted east toward the Hamptons, the North Fork, and Shelter Island — drawn to the same quiet magic that still lingers today. Some came for a season. Others never left.

Evolving from Antique Shop to Arboretum: A Landscape Cultivated with Care

Herman and Marguerite Chiaramonte were among those who stayed. After an earthquake in Sicily, Herman arrived in New York to begin again. He became a lawyer and accountant, and together with Marguerite, opened an antique shop on Shelter Island. In the late 1920s, they purchased nearly five acres along the Menantic Creek, an idyllic setting of calm water, tall grasses, and salty breeze, and built a simple two-bedroom summer cottage.

Over time, the land became the anchor of family life. There are photos: the couple with their four daughters standing in front of the original white house, another in front of the antique shop near the firehouse, and one of them gardening, hands deep in the soil, smiling like they owned the summer.

By the 1940s, the waterfront had become the family’s playground. Generations of memories were made here, clamming in the shallows, crabbing from a small boat, racing to the dock with the day’s catch. The gardens fed the family all summer, while the arboretum-like setting evolved with each generation. Rare specimen trees were planted and nurtured: a monkey puzzle, a thriving southern magnolia nestled near the pond, Copper Beech, Osage Orange, White Birch, and more.

When Herman passed in 1975, the land was divided between his daughter and her sister. In the late 1970s, Camille, their granddaughter, and her husband, Michael, were deeded two waterfront acres to build their own home. Decades later, Camille inherited the remaining parcel, bringing the land full circle, back under the care of a single branch of the original family.

Sheltered Turnkey Boating Access in Shelter Island’s Storied “Hurricane Hole”

By the 1990s, Camille and Michael had added two substantial moorings, and in 2010, they built a deep-water dock—transforming the waterfront into a boater’s dream. Known as “Hurricane Hole” for the protection its embankments offer during storms, this stretch of Menantic Creek is cherished by the local boating community. It provides direct access to both the North and South Forks, and a quick run to Montauk. In the 1980s, the home also received the rare designation of a legal two-family dwelling, expanding its flexibility for future generations or discerning investors.

A Waterfront Property with Boundless Potential

Today, for the first time in over a century, this historic, generational estate is being offered for sale as a whole. The property includes three separate, buildable parcels totaling 4.9 acres, each with distinct character, yet forming one harmonious, waterfront compound.

What sets this offering apart is not just its scale or location, but its soul. The grounds feel more like a private arboretum than a residential plot, with carefully tended trees and gardens that speak to decades of love and stewardship. Wildlife flourishes here, egrets wading through lilies, frogs tuning up at dusk, and yet it remains fully accessible and turnkey for modern living.

Boaters will have a 100-ft. stationary dock with a wide walkway and bench, a floating dock with anchor pilings, and two moorings (available pending reapplication). The possibilities for future development are extensive: a substantial primary residence, pool and pool house, tennis court, boathouse, or multiple garages, all subject to town regulations.

Located on Shelter Island, ferry-accessed, unhurried, and richly storied, this property offers a rare combination of history, nature, privacy, and possibility. Just minutes from Mashomack Preserve, the island’s famed farm stands, beaches, marinas, and understated dining scene, the estate sits at the heart of what makes Shelter Island so beloved.

This is more than a property; it’s a legacy. A once-in-a-lifetime opportunity to write the next chapter in a story nearly 100 years in the making.

“The best part of living on Shelter Island is its tranquil, secluded lifestyle and strong sense of community, which offer a peaceful escape from busy city life. Accessible only by ferry, the island provides a quiet, rural atmosphere focused on nature, rich history, and low-key recreation,” said Paula Quesnel-Jerman, listing agent, Sotheby’s International Realty.

Exclusively listed by Paula Quesnel-Jerman, Associate Real Estate Broker with Daniel Gale Sotheby’s International Realty, this property at 15A/15 & 13 South Menantic Road in Shelter Island Heights (MLS# 842673) offers a unique commercial and residential opportunity. For more information or to arrange a private tour, please contact Paula at the Daniel Gale Sotheby’s Westhampton Beach office - 100 Main St., by calling 631-288-1050 or 917-690-4622, or by email at [email protected].