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 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.
For sale
$3,695,000
105 Waterview Dr, Southold, NY 11971
6beds
4,663sqft
Single Family Residence
Built in 2006
6.5 Acres Lot
$3,571,400 Zestimate®
$792/sqft
$-- HOA
What's special
Waterfront propertyModern hardwareAll-new interior paintWarm yet refined ambienceWood-burning fireplaceUpdated lightingOutdoor shower
- 239 days
- 878
- 36
Zillow last checked:
Listed by:
Compass 631-537-7700,
Roric Tobin - Real Estate Sales Person 917-626-1381
Source: Out East,MLS#: 392886
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 4
- Full bathrooms: 4
Rooms
- Room types: Family Room, Laundry
Cooling
- Central Air
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 4,663
- Total interior livable area: 4,663 sqft
Video & virtual tour
Property
Parking
- Parking features: GarageDetached
- Has garage: Yes
Features
- Stories: 3
- Has private pool: Yes
- Pool features: Heated
- Has spa: Yes
- Spa features: Heated
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront
- Frontage type: Waterfront
Lot
- Size: 6.5 Acres
Details
- Parcel number: 1000078000700009000
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 2006
Community & HOA
Community
- Features: Room for a Tennis Court
Location
- Region: Southold
Financial & listing details
- Price per square foot: $792/sqft
- Tax assessed value: $2,109,091
- Date on market: 1/15/2026
- Lease term: Contact For Details
Estimated market value
$3,571,400
$3.39M - $3.75M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/15/2026 | Price change | $3,695,000-4%$792/sqft |
Source: | ||
| 10/30/2025 | Listed for sale | $3,850,000+79.1%$826/sqft |
Source: | ||
| 12/31/2020 | Sold | $2,150,000+13.2%$461/sqft |
Source: | ||
| 11/21/2020 | Pending sale | $1,899,500$407/sqft |
Source: Daniel Gale Sothebys Int'l #3220414 Report a problem | ||
| 9/28/2020 | Price change | $1,899,500-5%$407/sqft |
Source: Daniel Gale Sothebys Int'l #3220414 Report a problem | ||
| 8/18/2020 | Price change | $1,999,000-13.1%$429/sqft |
Source: Daniel Gale Sothebys Int'l #3220414 Report a problem | ||
| 6/8/2020 | Listed for sale | $2,299,900+15%$493/sqft |
Source: Daniel Gale Sothebys Int'l #3220414 Report a problem | ||
| 11/1/2019 | Listing removed | $1,999,999$429/sqft |
Source: Daniel Gale Sotheby's International Realty #345159 Report a problem | ||
| 6/26/2019 | Price change | $1,999,999-9%$429/sqft |
Source: Daniel Gale Sotheby's International Realty #345159 Report a problem | ||
| 5/25/2019 | Price change | $2,199,0000%$472/sqft |
Source: Daniel Gale Sothebys Int'l #3132130 Report a problem | ||
| 5/29/2018 | Price change | $2,199,999-8.3%$472/sqft |
Source: Daniel Gale Sothebys Int'l #3014333 Report a problem | ||
| 3/23/2018 | Listed for sale | $2,399,999-4%$515/sqft |
Source: Daniel Gale Sothebys Int'l #3014333 Report a problem | ||
| 10/1/2017 | Listing removed | $2,499,999$536/sqft |
Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem | ||
| 5/5/2017 | Price change | $2,499,999-16.5%$536/sqft |
Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem | ||
| 3/6/2017 | Listed for sale | $2,995,000+866.1%$642/sqft |
Source: Daniel Gale Sotheby's International Realty #p1277374 Report a problem | ||
| 4/1/2004 | Sold | $310,000+63.2%$66/sqft |
Source: Public Record Report a problem | ||
| 1/2/1998 | Sold | $190,000$41/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $11,600 |
| 2024 | -- | $11,600 |
| 2023 | -- | $11,600 |
| 2022 | -- | $11,600 |
| 2021 | -- | $11,600 +19.6% |
| 2020 | -- | $9,700 |
| 2019 | -- | $9,700 |
| 2018 | -- | $9,700 -7.6% |
| 2017 | $12,434 | $10,500 |
| 2016 | -- | $10,500 |
| 2015 | -- | $10,500 -16% |
| 2014 | -- | $12,500 |
| 2013 | -- | $12,500 |
| 2012 | -- | $12,500 |
| 2011 | -- | $12,500 |
| 2010 | -- | $12,500 |
| 2009 | -- | $12,500 |
| 2008 | -- | $12,500 |
| 2007 | $11,997 +613.4% | $12,500 +525% |
| 2005 | $1,682 +4.5% | $2,000 |
| 2004 | $1,608 +3.6% | $2,000 |
| 2003 | $1,552 +4.7% | $2,000 |
| 2002 | $1,483 | $2,000 |
| 2001 | -- | $2,000 |
| 2000 | $1,279 | $2,000 |
Find assessor info on the county website





