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105 Waterview Drive, Southold, NY, 11971 $3,850,000

Single Family For Sale 4 Beds , 3 Full Bath , 4103 SqFt 

Property Picture
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Aerial View Waterfront Front of Structure Front of Structure Front of Structure Back of Structure Aerial View View Waterfront Pool Pool Pool Deck Other Sitting Room Primary Bathroom Dock Dock Dock Dock Back of Structure Yard Back of Structure Aerial View Aerial View Bathroom Laundry Back of Structure Pool Pool Deck Other View Back of Structure Waterfront Yard Dock Dock Aerial View Aerial View Dock Back of Structure
 

Details ML#: 928708  

  • Style: Colonial
  • Year Built: 2006
  • Taxes: $17,588
  • Status:Active

Upcoming Open House:

Date:  11/29/2025 - 11/29/2025 11:00 AM - 01:00 PM
Address:  105 Waterview Drive, Southold, NY, 11971

Open House Note: 

Description

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 4-bedroom, 3-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 versatile 700+ bonus area has rough plumbing, while 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.

More Property Details

Room Information

Bedroom: 4   Full Bath: 3   Other: 3  

Property Features

Lot Size: 6.5   Lot Sq Ft: 283140   Approx. Int. Sq. Ft.: 4103.00   Garage: Yes   Garage: 3.0   Parking Spaces: Yes   Parking Facilities: Driveway, Garage, Garage Door Opener, Off Street, Private   Existing Structures: Yes    Waterfront: Yes   Waterfront Desc: Bayfront, Waterfront  

Appliances & Utilities

Heat: Forced Air, Oil, Radiant, Radiant Floor   A/C: Central Air   Water: Public   Sewer: Septic Tank  

Financial

Taxes: $17,588  

Local Area Information

School District: Southold Elementary School  

Listing Information provided courtesy of Compass Greater NY LLC  917-626-1381
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