105 Waterview Drive Southold, NY 11971

About this home

Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential. The enormous attic, featuring 8.5+ ft ceilings, offers the possibility of a third-floor buildout. The walk-out basement, with 9+ ft ceilings, two egresses, and plumbing in place, adds even more room for customization. Resort-style amenities continue across the grounds: a 16' x 32' heated saltwater gunite pool with electric cover is set into a 2,100 SF deck, a high-end 6-person hot tub and an outdoor shower. A wide path leads to a fire pit area and the private dock, which previously accommodated a 23' Grady-White and provides direct access to the bay. Inside, a chef’s kitchen, wood-burning fireplace, and generous ceiling heights enhance the home’s warm yet refined ambience. Radiant heat warms the eat-in kitchen, all bathrooms, and additional spaces throughout. Recent upgrades include the new pool and hot tub, a newly constructed circular driveway, freshly painted Hardie board siding, all-new interior paint, updated lighting, and modern hardware. A truly exceptional offering of space, serenity, and waterfront luxury—ideal as a full-time residence or a memorable seasonal escape.

Description supplied by the listing broker.

Features

• First Floor Bedroom
• First Floor Full Bath
• Built-in Features
• Cathedral Ceiling(s)
• Ceiling Fan(s)
• Central Vacuum
• Chandelier
• Chefs Kitchen
• Crown Molding
• Eat-in Kitchen
• Entrance Foyer
• Formal Dining
• Granite Counters
• High Ceilings

This listing

1. October 25, 2025 Listed at $3,695,000 295 days ago

Location

105 Waterview Drive, Southold, NY 11971