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105 Waterview Drive, 
Southold, NY 11971

$3,850,000


4

Beds


3

Baths


4,103

Sq Ft


Single Family

Active

Listed by

Roric Tobin

Justin R. Concannon

Compass Greater Ny LLC.

Last updated:

November 5, 2025, 09:40 PM

MLS#

928708

Source:

OneKey MLS

About This Home

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.

Home Facts

Single Family

3 Baths

4 Bedrooms

Built in 2006

Price Summary

3,850,000

$938 per Sq. Ft.

MLS #:

928708

Last Updated:

November 5, 2025, 09:40 PM

Added:

13 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

4,103 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

6,616 Sq. Ft.

Year Built:

2006


Lot

Lot Size (Sq. Ft):

283,140


Finances & Disclosures

Finances

Price:

$3,850,000

Price per Sq. Ft:

$938 per Sq. Ft.

Source:OneKey MLS
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