Pending
Sale Pending at 105 Waterview Dr, Southold, NY 11971 | MLS# 928708 | Listing updated on 2026-09-29
Photo 1 of Sale Pending at 105 Waterview Dr, Southold, NY 11971 | MLS# 928708 | Listing updated on 2026-09-29
Photo 2 of Sale Pending at 105 Waterview Dr, Southold, NY 11971 | MLS# 928708 | Listing updated on 2026-09-29
Photo 3 of Sale Pending at 105 Waterview Dr, Southold, NY 11971 | MLS# 928708 | Listing updated on 2026-09-29
Photo 4 of Sale Pending at 105 Waterview Dr, Southold, NY 11971 | MLS# 928708 | Listing updated on 2026-09-29
38+
Beds Icon

Street View

$3,695,000

Monthly Est:$18,391

  • Beds Icon6 Beds
  • Beds Icon
    4 Baths
  • Beds Icon4,663sqft

105 Waterview Dr, Southold, NY 11971

$18,391/moEst:

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  • Single Family Residence

  • Built in 2006

  • $-- HOA

  • 6.5 acres lot

  • $792/sq.ft

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 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.

  • Houzeo last checked: 3 hours ago
  • Listing updated: September 29, 2026 at 7:01 am
  • Listing Provided by: Roric Tobin (917) 626-1381 , Justin R. Concannon | Compass Greater NY LLC (631) 251-8644
  • Source: OneKey MLS-NY | MLS#: 928708 OneKey MLS-NY

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Suffolk County

  • City

    Southold

  • Neighborhood

    --

  • Year Built

    2006

  • HOA Fees

    -

  • Finished Area

    4,663 sqft

  • Lot Size

    6.5 acres lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    928708

  • MLS Status

    Pending

  • Days on Market

    344

  • Cumulative Days on Market

    332

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 4

  • Living Room

    Level: First

  • Dining Room

    Level: First

  • Den

    Level: First

  • Kitchen

    Level: First

  • Office

    Level: First

  • Bathroom 1

    Level: First

  • Primary Bedroom

    Level: Second

  • Primary Bathroom

    Level: Second

  • Sauna

    Level: Second

  • Bedroom 2

    Level: Second

  • Bedroom 3

    Level: Second

  • Bathroom 2

    Level: Second

  • Laundry

    Level: Second

  • Auxiliary Room

    Level: First

  • Basement

    Level: Lower

Interior

  • Sewer

    Septic Tank

  • Interior Features

    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, Granite Counters, High Ceilings, His And Hers Closets, Marble Counters, Pantry, Primary Bathroom, Recessed Lighting, Sauna, Soaking Tub, Stone Counters, Storage, Walk In Closet(s), Washer/dryer Hookup

  • Appliances

    Cooktop, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Freezer, Microwave, Oven, Refrigerator, Washer

  • Flooring

    Hardwood, Tile

  • Cooling

    Central Air

  • Heating

    Forced Air, Oil, Radiant, Radiant Floor

Construction

  • Year Built

    Year Built: 2006

  • Home type

    Single Family Residence

  • Property Condition

    Updated/remodeled

  • Foundation Details

    Concrete Perimeter

  • Architectural Style

    Colonial

  • Construction Materials

    Advanced Framing Technique, Batts Insulation, Frame, Hardi Plank Type

Utilities & Energy

  • Water Source

    Public

  • Laundry Features

    Laundry Room

  • Fireplace Features

    Living Room, Masonry, Wood Burning

  • Utilities

    Electricity Connected, Water Connected

  • Basement

    Full, Unfinished, Walk Out Access

  • Parking Features

    Driveway, Garage, Garage Door Opener, Off Street, Private

  • Pool Features

    Outdoor Pool, Pool Cover, Salt Water

Price History

DateEventPrice

09/28/2026

Source: mls_logoOneKey MLS-NY #KEY928708

Pending

$3,695,000 -4.03%

$792/sqft

10/30/2025

Source: mls_logoOneKey MLS-NY #KEY928708

Listed for Sale

$3,850,000

$826/sqft

10/30/2025

Source: mls_logoOneKey MLS-NY #KEY928708

Off Market

$3,850,000 +4.19%

$826/sqft

10/30/2025

Source: mls_logoOneKey MLS-NY #KEY928708

Price Decreased

$3,695,000 -4.03%

$792/sqft

10/29/2025

Source: mls_logoOneKey MLS-NY #KEY928708

Coming Soon

$3,850,000 +79.07%

$826/sqft

Show more

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Based on information from OneKey MLS, through Oct 09, 2026, 02:32PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group