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105 Waterview Drive, Southold, NY 11971

Southold
Local realty services provided by:CENTURY 21 AllPoints Realty
105 Waterview Drive,Southold, NY 11971
$3,850,000
  • 6 Beds
  • 4 Baths
  • 4,663 sq. ft.
  • Single family
  • Active
Listed by: roric tobin, justin r. concannon
Office: compass greater ny llc.
MLS#:928708
Source:OneKey MLS

Price summary

  • Price:$3,850,000
  • Price per sq. ft.:$581.92

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...

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Home facts

  • Year built:2006
  • Listing ID #:928708
  • Added:202 day(s) ago
  • Updated:May 20, 2026 at 10:40 AM

Rooms and interior

  • Bedrooms:6
  • Total bathrooms:4
  • Full bathrooms:4
  • Rooms Total:10
  • Flooring:Hardwood
  • Dining Description:Eat-In Kitchen, Formal Dining
  • Bathrooms Description:Soaking Tub
  • Kitchen Description:Chefs Kitchen, Cooktop, Dishwasher, Eat-in Kitchen, Freezer, Microwave, Oven, Pantry, Refrigerator
  • Bedroom Description:First Floor Bedroom
  • Basement:Yes
  • Basement Description:Full, Unfinished, Walk-Out Access
  • Living area:4,663 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Forced Air, Oil, Radiant
  • Central air:Yes

Structure and exterior

  • Year built:2006
  • Building area:4,663 sq. ft.
  • Lot area:6.5 Acres
  • Architectural Style:Colonial
  • Construction Materials:Advanced Framing Technique, Batts Insulation, Frame, HardiPlank Type
  • Levels:3 Story

Schools

  • High school:Southold Junior-Senior High School
  • Middle school:Southold Junior-Senior High School
  • Elementary school:Southold Elementary School

Utilities

  • Water:Public
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$3,850,000
  • Price per sq. ft.:$581.92
  • Tax amount:$17,588 (2025)

Features and amenities

  • Appliances:Cooktop, Dishwasher, Dryer, Freezer, Microwave, Oven, Refrigerator, Washer
  • Laundry features:Dryer, Washer, Washer/Dryer Hookup
  • Amenities:Cathedral Ceiling(s), Entrance Foyer, Granite Counters, High Ceilings, Marble Counters, Storage, Walk-In Closet(s)
  • Pool features:Outdoor Pool

Parking

  • Parking description:Driveway, Garage, Off Street, Private
  • Garage:Yes
  • Garage spaces:3
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