105 Waterview Drive • Southold, NY 11971

$3,850,000 Beds: 6 • Baths: 4 full • Sq. Feet: 4663 • MLS ID: 928708 • Subdivision:School Dist: Southold
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. View this listing at: http://moishestern.laffey.com/mls=928708

Property Features

  • Garage: 3
  • Taxes: $17,588
  • Basement: Yes
  • Formal Dining: Yes
  • Swimming Pool: Yes
  • Sauna: Yes
  • Exterior: Advanced Framing Technique,Batts Insulation,Frame,
  • Special View Info: Water
  • Lot Size: 6.50 Acres
  • Heating: Forced Air,Oil,Radiant,Radiant Floor
  • Cooling: Central Air
  • Year Built: 2006
  • Fireplaces: 1
  • Water: Public
  • Sewer: Septic Tank
  • On Market Date: 2025-10-30
  • Appliances: Cooktop,Dishwasher,Dryer,Electric Cooktop,Electric Oven,Freezer,Microwave,Oven,Refrigerator,Washer
  • Basement: Full,Unfinished,Walk-Out Access
  • Building Area Total: 6616
  • Fireplace Features: Living Room,Masonry,Wood Burning
  • Fireplace Y/N: Yes
  • Flooring: Hardwood,Tile
  • Frontage: 490
  • GarageY/N: Yes
  • Interior 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,His and Hers Closets,Marble Counters,Pantry,Primary Bathroom,Recessed Lighting,Sauna,Soaking Tub,Stone Counters,Storage,Walk-In Closet(s),Washer/Dryer Hookup
  • Laundry: Laundry Room
  • Attic: Full,Pull Stairs,Unfinished
  • Number Of Kitchens: 1
  • Parcel Number: 1000-078-00-07-00-009-000
  • Parking Features: Driveway,Garage,Garage Door Opener,Off Street,Private
  • Pool Features: Outdoor Pool,Pool Cover,Salt Water
  • Rental Term: Monthly
  • Rooms Total: 10
  • Spa Y/N: Yes
  • Utilities: Electricity Connected,Water Connected
  • Waterfront Features: Bayfront,Waterfront

School Information

  • High School: Southold Junior-Senior High School
  • Middle School: Southold Junior-Senior High School
  • Elementary School: Southold Elementary School
  • School District: Southold
Printed June 04, 2026


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