Southold, NY 11935

The estate of the late legendary New York art dealer Barbara Gladstone, this meticulously restored Gilded Age shingle-style home offers a rare opportunity to own one of the few remaining large, turn-of-the-century North Fork summer estates. Set on 140 feet of pristine bayfront with a private sandy beach, the primary residence spans over 10,000 sq. ft. and seamlessly blends period architecture with modern luxury. Every element, from the doorknobs to the custom hardware, has been carefully curated, resulting in a warm, classic home defined by craftsmanship and elegance. Well suited for both grand entertaining and intimate gatherings, expansive living spaces feature soaring ceilings, multiple fireplaces, and thoughtfully designed moments throughout. Highlights on the first floor include a large waterside living room and dining room with charming fireplace alcoves, a sprawling chef's kitchen with breakfast room and handsome butler's pantry, a dedicated flower-cutting room with custom marble sink, and an enormous screened-in outdoor sitting porch complete with an outdoor dining room and kitchen. The second floor houses the large primary suite with an ensuite bath, extensive walk-in closets, a dressing room, and a cozy sitting room with an oversized fireplace. The balance of the second and third floors includes five additional waterside bedrooms, a library, an office, multiple wet bars, a laundry room, and five baths with steam showers and soaking tubs. Outside, lush, professionally designed perennial gardens and hedged lawns surround the property. A beautiful, private gunite pool sits on the waterside, offering a serene oasis overlooking the bay. Just beyond, a sweeping lawn with panoramic water views leads to a sandy path framed by sea grasses and wildflowers, guiding you down to the private bayfront beach. A charming carriage house adds further versatility, featuring a great room, home theater, and gym. The estate also includes a historic icehouse, preserving its rich legacy. Whether sitting by the bay, hosting holidays, or enjoying movie nights in the theater, this extraordinary property promises a lifestyle of laid-back elegance and tranquility.