66 N Midway Rd #A, Shelter Island, NY 11964

Set on the gentle slope of a spring-fed pond, this Shelter Island residence, similar in ways to a duplex, reveals itself not all at once, but as you explore the home. One enters by way of a circular drive that curves around an old maple and up a short path to the front entrance. The home design understands the value of sunlight, privacy, and practicality. Inside, the main floor offers a living room where light from the west falls generously across books, armchairs, and a raised stone fireplace. A modest kitchen, thoughtfully arranged, adjoins a small breakfast area, a fine place for morning coffee and a quiet view. Down the hall, the primary bedroom includes its own bath, set apart in a way that grants quiet. At the rear of the house, a library lined with built-ins opens to a deck overlooking the water, where the pond's surface shifts with wind and the passage of sunlight. Below, the lower level is wholly its own space - 832 sf of additional finished living space-not merely an extension of the upstairs, but a dwelling with purpose. A living room, dining room, second fireplace, full kitchen (one of two legally established in the house), bedroom, and bath occupy this floor, with sliding doors that open to a hidden stretch of land and a view that belongs almost entirely to ducks, frogs, turtles, and the birds that stop in from nearby Sachem's Woods. The pond has its own rhythm; Spring-fed and self-sustaining, it hums with life. And while the property is not far from the ferry, from shops, or from the beach, it feels content to exist slightly apart, offering its new owner not just a house, but a setting in which to think, observe, and live quietly among living things. Property taxes per annum as of 2025 are $4,866.