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3 beds New construction With a pool

37 listings

Luxury Homes in Southold, NY

Luxury Homes in Southold, NY

24 of 37 Listings

Luxury Homes in Southold, NY

24 of 37 Listings

11

Active

$3,295,000

4 bd · 5 ba · 5,100 sqft

390 Wildberry Lane, Southold, NY

Shaun McQuilkin · Migrate Realty LLC

$2,200,000

3 bd · 3 ba · 2,600 sqft

225 Lakeside Drive S, Southold, NY

Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

$1,277,000

4 bd · 4 ba · 3,000 sqft

1025 Seawood Drive, Southold, NY

Clorinda F. Tagios · Douglas Elliman Real Estate

$2,695,000

3 bd · 2 ba · 2,050 sqft

2850 Main Bayview Road, Southold, NY

Bridget Elkin · Compass Greater NY LLC

$2,795,000

4 bd · 5 ba · 4,327 sqft

1475 Laurel Avenue, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

$2,895,000

5 bd · 6 ba · 3,240 sqft

1135 Wildberry Lane, Southold, NY

Melissa Principi · Douglas Elliman Real Estate

$2,895,000

3 bd · 2 ba · 1,840 sqft

21515 Soundview Avenue, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

$3,675,000

5 bd · 6 ba · 5,285 sqft

150 Deer Run, Southold, NY

Jeffrey R. Mead · Corcoran

$2,695,000

5 bd · 4 ba · 3,500 sqft

605 Cedar Drive, Southold, NY

Bridget Elkin · Compass Greater NY LLC

$2,650,000

4 bd · 4 ba · 2,600 sqft

195 Williamsburg Drive, Southold, NY

Sheri Winter Parker · Corcoran

$1,375,000

3 bd · 2 ba · 1,841 sqft

1050 Bayview Avenue, Southold, NY

Eric P. Elkin · Compass Greater NY LLC

Price Reduced44Active

$1,999,999

3 bd · 3 ba · 2,367 sqft

2245 Little Peconic Bay Lane, Southold, NY

Andrea Parks · Douglas Elliman Real Estate

Price Reduced43Active

$1,395,000

4 bd · 4 ba · 2,600 sqft

425 Maple Lane, Southold, NY

Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

Price Reduced36Active

$1,299,000

4 bd · 3 ba · 2,200 sqft

4408 Old North Road, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

$1,299,000

4 bd · 3 ba · 2,240 sqft

1075 Ships Drive, Southold, NY

Joshua Whalley · Douglas Elliman Real Estate

Price Reduced38Active

$1,599,000

4 bd · 4 ba · 2,668 sqft

1700 Smith Drive S, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

Price Reduced43Active

$1,849,000

4 bd · 4 ba · 2,850 sqft

2100 Glenn Road, Southold, NY

Alexis Meadows · Compass Greater NY LLC

$2,899,000

4 bd · 3 ba · 2,351 sqft

405 Williamsburgh Drive, Southold, NY

Laura M. Cochran · BERKSHIRE HATHAWAY

Price Reduced9Active

$3,695,000

3 bd · 4 ba · 3,496 sqft

1480 Old Wood Path, Southold, NY

Bridget Elkin · Compass Greater NY LLC

$1,150,000

2 bd · 1 ba · 1,500 sqft

380 Clark Road, Southold, NY

Susan M. Orioli · Engel & Volkers North Fork

Price Reduced33Active

$1,445,000

4 bd · 3 ba · 2,900 sqft

2015 Kenneys Road, Southold, NY

Alexis Meadows · Compass Greater NY LLC

Price Reduced39Active

$5,995,000

5 bd · 5 ba · 3,500 sqft

920 Cedar Point Drive E, Southold, NY

William C. McIntosh · Daniel Gale Sothebys Intl Rlty

Price Reduced25Active

$1,549,999

4 bd · 4 ba · 2,200 sqft

3715 Hortons Lane, Southold, NY

Arelis Olivieri · RIN

$3,450,000

5 bd · 4 ba · 4,500 sqft

790 N Sea Drive, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

1 2

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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New construction
With a pool

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' 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 deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Southold, NY community profile

Area: 15.2 sq. mi.

Source: HJN community data

Southold housing market

July 2026 · This period is still settling

Homes on the market · MLS, as of Jul 21, 2026

Median list price: $1,499,000
Homes for sale: 51

Luxury Homes in Southold, NY