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

Southold, NY, 11971
$ 3,850,000
Bedrooms4 Baths3.0 Sq 4,103

Monthly Estimate*

$ 24,019

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Single Family Home for sale in Southold, NY

for $3,850,000 with 4 bedrooms and 3 full baths. This 4,103 square foot home was built in 2006 on a lot size of 6.5.

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.

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Single Family Active

Price

$ 3,850,000

Bedrooms

4

Full Bath

3

Property Type

Single Family

Taxes

$ 17,588

Style

Colonial

Lot Size

6.5

Year Built

2006

Town/City

Southold

County/Region

Suffolk

MLS | Web ID

928708

Features
Interior
Interior Amenities 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 Grani
Basement Full Unfinished Walk-Out Access
Flooring Hardwood Tile
Total Fireplaces 1
Fireplace Features Living Room Masonry Wood Burning
Basement Features Full Unfinished Walk-Out Access
Basement (Y/N) Y
Fireplace Y/N Y
Half Baths 0
Total Bedrooms 4
Total Baths 3
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General
Sewer Septic Tank
Heating Forced Air Oil Radiant Radiant Floor
Cooling Central Air
Utilities Electricity Connected Water Connected
Appliances Cooktop Dishwasher Dryer Electric Cooktop Electric Oven Freezer Microwave Oven Refrigerator Washer
Garage Spaces 3
Architectural Style Colonial
Pool Features Outdoor Pool Pool Cover Salt Water
Construction Materials Advanced Framing Technique Batts Insulation Frame HardiPlank Type
Year Built 2006
View Water
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 1000-078-00-07-00-009-000
Waterfront Features Bayfront Waterfront
County Suffolk County
Property Type Residential
HOA N
Garage Y/N Y
Total Rooms 10
Full Baths 3
High School Southold Junior-Senior High School
City Southold
Senior Community Y/N N
High School District Southold
Carport Y/N N
Spa Features Bath
Elementary School Southold Elementary School
Property Attached Y/N N
Tax Annual Amount 17588.04
Middle/Junior High School Southold Junior-Senior High School
Property Condition Updated/Remodeled
Additional Parcels Y/N Y
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Southold
Elementary School District Southold
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Exterior
Parking Features Driveway Garage Garage Door Opener Off Street Private Driveway Garage Garage Door Opener Off Street Private
Water Source Public
Foundation Details Concrete Perimeter
Spa Y
Building Area Total 6616
Frontage Length 490
Waterfront Y/N Y
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Internal Only
Street Number 1 105
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* Excluded Features
List By
Roric Tobin

Listing Agent

Compass Greater Ny Llc

Broker

917-626-1381

Contact

Affordability Calculator

$25,485
Per Month
94%
6%
0%
Monthly Principal & Interest
$24,019
Monthly Property Taxes
$1,466
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4100176 Elementary School
4099535 Middle School
Southold Junior-Senior High School High School
Pricing History
DatePricePrice ChangeDescription
10/29/2025$3,850,000 Listed Price

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105 Waterview Drive, Southold, NY, 11971 is a Single Family Home for sale at $3,850,000 with 4,103 sqft and a lot size of 6.5. 105 Waterview Drive has 4 bedrooms, 3.0 baths, and was built in 2006. The property's zip code is 11971 which is in Southold, NY