100 W Shore Drive

Set in the highly sought-after Reydon Shores community, 100 W Shore Dr, Southold is a rare dog-friendly North Fork waterfront seasonal rental with your own private, sandy beach and sweeping bay views to Shelter Island. This renovated classic offers three levels of living with a great room and sunroom, 6 bedrooms, 3.5 baths, two wood-burning fireplaces, and a huge Trex deck built for sunset dinners and effortless entertaining. The walk-out lower level opens directly to the backyard and shoreline, featuring a waterfront family room plus an entertainment/bonus room with a bar and fireplace. For true North Fork ease, you can moor your boat right off the private beach, with an additional private marina option for effortless boating days; arrive, depart, and live on the water all season long. Monthly Pricing May: $8,000 June: $10,000 July: $25,000 August: $30,000 September: $10,000 October–April: $6,000 / month