Perched high atop a bluff overlooking Port Jefferson Harbor, this charming expanded cottage delivers an unmatched North Shore waterfront lifestyle in the Village of Poquott. The unobstructed views, stretching from Belle Terre and Pirates Cove to the harbor inlet and Long Island Sound, are simply mesmerizing. A private staircase leads to your own stretch of shoreline and a vintage boathouse of yesteryear—a rare find—complete with running water, electricity, and multiple doors that welcome in the sea breeze. It's the perfect setting for carefree summer days harborside - think kayaking, paddleboarding, swimming, fishing - and evenings of vibrant sunsets and the lapping of waves. Exclusive mooring rights and a village dock just a few hundred feet away make this a truly special opportunity for boaters. Whether you're seeking out a weekend or seasonal getaway, looking to construct your waterfront dream home, or simply want to retain the home as the charmer that it is, 31 Chestnut Avenue is teeming with possibility. Inside, living room windows frame the stunning and ever-changing view, while an original wood-burning fireplace adds warmth. An eat-in coastal kitchen is quaint and inviting. Two comfortably sized bedrooms and a bathroom, updated in 2018, round out the main level. Step out to the rear wraparound covered patio - an extension of the indoor living space - to enjoy al fresco lounging and dining, while taking in the sights and sounds of the harbor. Bonus spaces include an unfinished basement with an outside entrance, attic storage, a one-car garage, and very generous driveway space. Recent improvements, from upgraded bamboo flooring and a 2013 roof, to new appliances and multiple updated windows, make Chestnut a move-in ready home. The Incorporated Village of Poquott is a gem of a community, affording residents exclusive access to three private beaches on Port Jefferson & Setauket Harbors, a village dock, boat ramp, acres of parkland, a tennis court, kayak racks, multiple playgrounds, and private security/code enforcement. An active association sponsors a fantastic social calendar of events and activities held throughout the year. California Park, with many of the aforementioned amenities, is just a stone's throw down the block from 31 Chestnut. Port Jefferson Village, just 4 minutes to the east by car, is a maritime locale offering restaurants, boutiques, multiple marinas, tons of events and activities, a ferry line that makes travel to New England a breeze, and more. Stony Brook University and Hospital, world renowned institutions, lie just 8 minutes to the west - and the idyllic waterfront business district of Stony Brook Village is just beyond. Poquott is zoned for attendance at Setauket Elementary, Gelinas Junior High, and Ward Melville High School, with the Three Village School District. Residents are also afforded access to all Town of Brookhaven amenities. © 2025 OneKey™ MLS, LLC