Step into timeless elegance with this iconic single-family residence with an option for an owner-occupied 5-bedroom bed & breakfast (B&B) license. Originally constructed in 1902 and beautifully reimagined to meet modern standards. Nestled in the serene Shelter Island Heights, 7 Stearns Point Road offers an exquisite blend of historic charm and contemporary luxury. This expansive property sits on a 0.70- acre parcel, equipped with 5, 838 +/- sq. ft. of living space, plus a spacious basement level adding 2, 588 +/- sq. ft. The property features 7 ensuite bedrooms complemented by 2 large living rooms and a well-appointed kitchen. Recent renovations have expanded the living space to include an extension with 2 additional bedrooms, a stunning double-height Great Room, as well as a state-of-the-art gym/yoga studio. Enjoy the beautiful backyard with a heated 40x18 in-ground Gunite pool, perfect for relaxing after a day exploring the nearby Crescent Beach and Sunset Beach which is moments away. The property also includes a full liquor license, which enhances its appeal as a premier vacation destination. The spacious basement areas provide ample storage and laundry facilities, ensuring convenience. A wonderful investment opportunity for an owner-occupied 5-bedroom bed and breakfast. The property also includes 2 driveways. Key Features: - Historic property built in 1902, fully renovated - 9 bedrooms and 9 bathrooms, including recent additions - Option for an owner-occupied 5 Bedroom bed and breakfast - Two driveways - Heated 40x18 in-ground Gunite pool - State-of-the-art gym/yoga studio - Full-height basements for storage and laundry - Walking distance to Crescent Beach & Sunset Beach - Full liquor license