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6 Beds
4 Baths
4,663 sqft

$3,695,000

105 Waterview Drive, Southold NY, 11971

Price per sqft$792.41
Built in2006
Property size4,663 sqft
Property typeResidential
Courtesy of Compass Greater NY LLC, Roric Tobin Listing Contact: 917-626-1381

Overview

Active

Listed Oct 30, 2025

Updated 4 weeks ago

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.

$24,583/mo

Est. mortgage payment based on a $3,695,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
928708

Interior Features

Bedrooms
6
Bathrooms
4
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
6.5 Acres

Other Property Details

Taxes
$17,588
Tax Frequency
Annually
Garage
Yes
View
Yes
Pool
Yes
Waterfront
Yes
55+/Senior Community
No

Listings courtesy of OneKey MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Lauryn Koke shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS.

Based on information submitted to the MLS GRID as of 3:38 AM UTC on 8/22/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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