Southold

Southold

Southold has long been a vibrant community which continues to evolve with each passing year. The hamlet of Southold features miles of both bay and sound front beaches, sprawling vineyards, boutique wineries, farm stands, museums, an observatory, and unlimited recreational activities. There are a number of quaint home décor shops in Southold’s downtown, as well as a good number of casual eateries and coffee shops. Most of Southold Town's government buildings are also located in the hamlet of Southold.


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Real Estate Statistics

Average Price $955K
Lowest Price $25
Highest Price $7.5M
Total Listings 140
Avg. Days On Market 290
Avg. Price/SQFT $387

Property Types (active listings)

Southold

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1750 Hobart Road, Southold

$7,450,000

↓ $750,000

1750 Hobart Road, Southold

5 Beds 5 Baths 4,627 SqFt Residential MLS® # 946886

Daniel Gale Sothebys Intl Rlty Status: Active

920 Cedar Point Drive E, Southold

$6,550,000

920 Cedar Point Drive E, Southold

5 Beds 5 Baths 3,500 SqFt Residential MLS® # 999173

Daniel Gale Sothebys Intl Rlty Status: Active

11535 N Bayview Road, Southold

$4,300,000

11535 N Bayview Road, Southold

0 Beds 0 Baths 0 SqFt Land MLS® # L3514107

Daniel Gale Sothebys Intl Rlty Status: Pending

1480 Old Wood Path, Southold

$4,000,000

1480 Old Wood Path, Southold

3 Beds 4 Baths 3,496 SqFt Residential MLS® # 997738

Compass Greater NY LLC Status: Active

46975 Main Road, Southold

$3,899,000

46975 Main Road, Southold

0 Beds 0 Baths 0 SqFt Land MLS® # 992332

Douglas Elliman Real Estate Status: Active

150 Deer Run, Southold

$3,695,000

↓ $104,999

150 Deer Run, Southold

5 Beds 6 Baths 5,285 SqFt Residential MLS® # 937270

Corcoran Status: Active

Open House
105 Waterview Drive, Southold

$3,695,000

105 Waterview Drive, Southold

6 Beds 4 Baths 4,663 SqFt Residential
Sat, Jul 18th, 2026 @ 12pm - 2pm
MLS® # 928708

Compass Greater NY LLC Status: Active

790 N Sea Drive, Southold

$3,450,000

790 N Sea Drive, Southold

5 Beds 4 Baths 4,500 SqFt Residential MLS® # 995842

Douglas Elliman Real Estate Status: Active

80 Deer Run, Southold

$3,295,000

80 Deer Run, Southold

4 Beds 6 Baths 7,341 SqFt Residential MLS® # 906322

Corcoran Status: Active

405 Williamsburgh Drive, Southold

$2,899,000

405 Williamsburgh Drive, Southold

4 Beds 3 Baths 2,351 SqFt Residential MLS® # 1005049

BERKSHIRE HATHAWAY Status: Active

1135 Wildberry Lane, Southold

$2,895,000

1135 Wildberry Lane, Southold

5 Beds 6 Baths 3,240 SqFt Residential MLS® # 990263

Douglas Elliman Real Estate Status: Active

1350 Hortons Lane, Southold

$2,799,000

↓ $200,000

1350 Hortons Lane, Southold

8 Beds 7 Baths 5,600 SqFt Residential MLS® # 859020

Thomas J McCarthy Real Estate Status: Active

1475 Laurel Avenue, Southold

$2,795,000

1475 Laurel Avenue, Southold

4 Beds 5 Baths 4,327 SqFt Residential MLS® # 999394

Douglas Elliman Real Estate Status: Active

Open House
3470 N Bayview Road, Southold

$2,500,000

↑ $300,000

3470 N Bayview Road, Southold

5 Beds 5 Baths 3,800 SqFt Residential
Sat, Jul 18th, 2026 @ 10am - 12pm
MLS® # 903844

Douglas Elliman Real Estate Status: Active

1455 Cedar Point Drive, Southold

$2,495,000

1455 Cedar Point Drive, Southold

3 Beds 2 Baths 1,250 SqFt Residential MLS® # 932327

Daniel Gale Sothebys Intl Rlty Status: Active

Open House
470 Goose Creek Lane, Southold

$2,399,000

470 Goose Creek Lane, Southold

3 Beds 2 Baths 2,000 SqFt Residential
Sat, Jul 18th, 2026 @ 12pm - 2pm
MLS® # 943087

Thomas J McCarthy Real Estate Status: Active

 


  


Nowhere in Southold Town is there a more rich history than in its namesake hamlet of Southold.

Southold was the first English settlement in the future New York State, founded by Puritans from New Haven, Connecticut, in the summer of 1640, on land purchased from the Corchaug Indians. The Indian name for the land that would become Southold was Yenicott. Southold remained under the jurisdiction of Connecticut until 1674.

The name Southold is believed by some to be a misspelling of Southwold, which is a coastal town in the corresponding English county of Suffolk. This claim is debatable, but John Youngs, one of the town’s founding fathers, was born and raised in Southwold.

A portion of this historic hamlet is a federally recognized historic district and there are many homes and structures dating back to the 17th Century.

Southold students attend the elementary, middle and senior high school centrally located on a single sprawling campus on Oaklawn Avenue.