Shelter Island 1865 Historic Lester House

Named “Lester House” after its original owners who built it around 1865, this charming Shelter Island home is perched on a slight hill on one acre in “Eeltown,” one of the island’s earliest established areas. Owned by multi-generations of the Lester family through 1916, this well-maintained traditional home is described in archives as a “five bay, center entrance house with six over six windows located at the turn in the road.” The Shelter Island Reporter highlighted its unique feature: “the only circular staircase on Shelter Island.” This distinctive mahogany staircase is a true work of art, with intricate needlework depicting island life in the late 1800s. In 1972, a former owner remarked that he “fell in love with it and bought [the house] in 15 minutes.” The home’s open and airy layout allows sunlight to brighten nearly every corner throughout the day. The living room, just off the entry foyer, features a welcoming fireplace framed by windows. The southerly facing, 300sf sunroom (not included in the total square footage) serves as a natural gathering spot with a dining area on one end and lounges on the other, creating a cheerful setting for both plants and people. On the opposite side of the entry foyer, a guest room currently used as a library offers easy access to the first-floor full bath with washer/dryer. The kitchen is a quintessential country kitchen, with an efficient layout, windows on three sides, and handsome cabinetry. The second floor includes two bedrooms on the west side, a full bathroom along the hallway, and a larger bedroom on the east side, each with its own unique charm. The grounds feature meandering paths leading to various highlights, including a 798 sf patio with a barbecue area, an elaborate outdoor shower, a shady spot for hammocking or meditation, and a carriage house with 370 sf dependent residence and full bath. Historical records note that the “foundation and cellar walls are fieldstone laid up with lime and cow hair mortar. The house is wood construction throughout, except for the stucco covering of outside walls, added in 1905.” Located near Coecles Harbor, this enchanting home has been lovingly cared for, with many recent upgrades including a new wood shingle roof. The total square footage includes the carriage house residence. This historic and charming home is ready to be yours to have and to hold.

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