105 Waterview Drive, Southold, NY

About 105 Waterview Drive

Set on 6.5 ultra private waterfront acres, this gated estate offers two single and separate waterfront lots being sold together. The property features a recently updated colonial farmhouse-style residence (Zone X with raised mechanicals off the garage) showcasing panoramic water views from nearly every room, along with a new waterside Gunite pool, 2,100 square feet deck and private dock—perfect for boating, indoor and outdoor entertaining, and relaxed coastal living. The home offers four bedrooms, a large home office, an oversized den, and three full baths. Designed with flexibility in mind, the property provides substantial opportunities to expand within the existing structure. There’s bonus space above the three-car garage with rough plumbing, an enormous attic (future 3rd floor) with 8.5+ foot ceilings, and a walk-out basement with 9+ foot ceilings, two egresses, and additional plumbing already in place. Outdoor amenities elevate the estate’s appeal, featuring a new 16 x 32 heated saltwater gunite pool with an electric cover, high end luxurious 6-person hot tub, outdoor shower, and an expansive 2,100 SF deck overlooking the water. A wide, clear path leads to a fire pit area and private dock previously docking a 23-foot Grady-White—with direct access to the bay. The chef’s kitchen, wood-burning fireplace, and high ceilings (9 feet on the 1st floor, 8 feet on the 2nd) enhance the home’s warm yet sophisticated character. Radiant heated floors in eat-in kitchen, all bathrooms and more. Recent updates include: Gunite pool, hot tub, new circular driveway, freshly painted Hardie board siding, all-new interior paint, door hardware, and lighting fixtures. This remarkable property blends space, style, and waterfront luxury—an ideal retreat for year-round living or a spectacular summer getaway.

Listing Map