
The Hamptons
Southold
Living in Southold
40.9246° N 72.3548° W
Southold is a historic town located on the North Fork of Long Island, stretching from Long Island Sound to the Peconic Bay and encompassing a collection of hamlets, waterfront areas, farmland, and village centers. The town is known for its agricultural heritage, maritime setting, and preserved open spaces that shape its overall character. Southold offers a mix of residential neighborhoods, working farms, vineyards, marinas, and small commercial areas, creating a balanced environment that supports both year-round and seasonal living. Access to nearby villages such as Greenport, as well as regional transportation routes, provides connections to dining, shopping, cultural attractions, and ferry service. Southold’s geography allows for varied coastal experiences, with beaches along the Sound and protected bayfront areas offering boating and water access. The town’s planning emphasizes preservation, community scale, and continuity with its historic roots, making it a distinct part of the North Fork while remaining connected to the broader East End of Long Island.
The market today
51
Homes for sale
50
Rentals
$1,600,000
Median sale asking price
Available homes by listing type
- Sale51
- Lease50
Homes for sale in Southold

Single Family | Southold
600 Highwood Road
$1,295,000
- 2 Beds
- 2 Baths
- 1,925 Sq Ft

Single Family | Southold
1725 N Sea Drive
$4,595,000
- 4 Beds
- 4 Baths
- 2,500 Sq Ft

Single Family | Southold
275 Main Bayview Road
$799,000
- 3 Beds
- 2 Baths
- 1,270 Sq Ft

Single Family | Southold
4595 S Harbor Road
$829,000
- 5 Beds
- 2 Baths
- 2,300 Sq Ft

Single Family | Southold
2220 Akerly Pond Lane
$999,000
- 5 Beds
- 2 Baths
Curious what life in Southold is like?
Our concierge knows the buildings, the blocks and the recent sales here, and it can tell you what your budget buys in Southold today.

