Southold Real Estate & Homes for Sale

Explore homes for sale with Thomas J. McCarthy Real Estate, a locally owned brokerage based in the heart of the North Fork. Browse current listings and learn more about Southold's neighborhoods, waterfront properties, history, and local real estate market.

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 $1.8M
Lowest Price $895K
Highest Price $3M
Total Listings 8
Avg. Days On Market 203
Avg. Price/SQFT $732

Property Types (active listings)

Southold

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Listings Per Page:
Open House
37 Second Neck Lane, Quogue

$19,800,000

37 Second Neck Lane, Quogue

8 Beds 13 Baths 10,451 SqFt Residential MLS® # 998122

Douglas Elliman Real Estate Status: Active

Open House
1245 Veeder Drive, Hewlett Bay Park

$15,000,000

1245 Veeder Drive, Hewlett Bay Park

5 Beds 8 Baths 11,031 SqFt Residential
Fri, Oct 9th, 2026 @ 4pm - 7pm
MLS® # 991350

Nest Seekers LLC Status: Active

Open House
15 Old Point Road, Quogue

$11,888,000

15 Old Point Road, Quogue

7 Beds 8 Baths 8,000 SqFt Residential
Sat, Oct 10th, 2026 @
MLS® # 984952

Douglas Elliman Real Estate Status: Active

1140 Park Avenue, Mattituck

$11,500,000

1140 Park Avenue, Mattituck

5 Beds 5 Baths 5,000 SqFt Residential MLS® # 1036287

Compass Greater NY LLC Status: Active

10 Hicks Lane, Port Washington

$10,800,000

10 Hicks Lane, Port Washington

7 Beds 8 Baths 8,761 SqFt Residential MLS® # 1036588

Signature Premier Properties Status: Active

Open House
158 Cobb Road, Water Mill

$9,975,000

158 Cobb Road, Water Mill

7 Beds 9 Baths 9,600 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 937172

Corcoran Status: Active

225 Route 22, Pawling

$9,750,000

225 Route 22, Pawling

0 Beds 0 Baths 4,800 SqFt Commercial Sale MLS® # H6215756

Houlihan Lawrence Inc. Status: Active

225 Route 22, Pawling

$9,750,000

225 Route 22, Pawling

0 Beds 0 Baths 0 SqFt Land MLS® # H6215066

Houlihan Lawrence Inc. Status: Active

New Open House
311 Main Street, Sag Harbor

$9,600,000

311 Main Street, Sag Harbor

4 Beds 6 Baths 2,670 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 2pm
MLS® # 1058964

Douglas Elliman Real Estate Status: Active

142 N 11th Street, Brooklyn

$9,499,000

142 N 11th Street, Brooklyn

0 Beds 0 Baths 6,500 SqFt Residential Income MLS® # 1051318

Capri Jet Realty Corp Status: Pending

New
291 Muttontown Eastwoods Road, Muttontown

$8,250,000

291 Muttontown Eastwoods Road, Muttontown

6 Beds 9 Baths 8,000 SqFt Residential MLS® # 1059808

Vision Homes Real Estate LLC Status: Active

New Open House
25 Old Wheatley Road, Brookville

$8,250,000

25 Old Wheatley Road, Brookville

6 Beds 10 Baths 7,396 SqFt Residential MLS® # 1058948

Daniel Gale Sothebys Intl Rlty Status: Active

276 N Main Street, Southampton

$8,195,000

276 N Main Street, Southampton

7 Beds 10 Baths 6,500 SqFt Residential MLS® # 852599

Brown Harris Stevens Hamptons Status: Active

New
422 Mt Holly Road, Katonah

$7,900,000

422 Mt Holly Road, Katonah

6 Beds 4 Baths 3,285 SqFt Residential MLS® # 1058707

Houlihan Lawrence Inc. Status: Active

717 E 5th Street, New York (Manhattan)

$7,500,000

717 E 5th Street, New York (Manhattan)

0 Beds 0 Baths 9,345 SqFt Commercial Sale MLS® # 1024507

All Island Estates Realty Corp Status: Active

New
563 Johnson Avenue, Brooklyn

$7,000,000

563 Johnson Avenue, Brooklyn

0 Beds 0 Baths 18,859 SqFt Commercial Sale MLS® # 1060471

Chase Global Realty Corp Status: Active

 


  


Nowhere in Southold Town is there a richer 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.