Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for enjoying the island setting. The home features three bedrooms, 2.5 baths, a chef’s kitchen, formal dining room, living room, parlor, office, full basement, and detached one-car garage—providing flexible space for everyday living, entertaining, work, or guests. Landscaped outdoor areas create a peaceful backdrop for dining, gardening, recreation, or quiet relaxation. Conveniently located near Bridge Street, local shops, restaurants, Shelter Island Yacht Club, and other Heights destinations, the home also includes access to Heights Association parks and the Beach Club, with nearby clay tennis courts. A rare opportunity to enjoy historic character, modern comfort, water views, and the sought-after Shelter Island Heights lifestyle.

An exceptional opportunity to embrace the North Fork lifestyle awaits at 65 Oak Drive in Baiting Hollow. Set on approximately 0.70 acres, this four-bedroom, two-bath ranch pairs expansive living spaces with generous grounds. An impressive great room creates a welcoming centerpiece for gathering and entertaining, complemented by hardwood floors and an eat-in kitchen. A main-level primary bedroom, full basement, attached one-car garage, and private driveway complete the home’s versatile layout.

Outside, the spacious property invites you to create your own outdoor dining, gardening, or unwinding space. Beyond the home, discover what makes the North Fork so appealing—from local vineyards and coastal beaches to restaurants and shopping. Whether hosting a lively gathering or enjoying a quiet evening, 65 Oak Drive offers an exciting opportunity to bring your vision to life in Baiting Hollow.

Handy Man special sold as is in Plainedge School District. 25'x33' dormer & basement entrance