Waterfront Homes in Southold, NY

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24 of 43 Listings

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24 of 43 Listings

Open house Sat, Oct 3 · 1:30 PM49

43 listings

Waterfront Homes in Southold, NY

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24 of 43 Listings

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Waterfront Homes in Southold, NY

24 of 43 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Open house Sat, Oct 3 · 1:30 PM49

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Active

$6,200,000

7 bd · 5 ba · 4,628 sqft

3645 and 3651 Soundview Avenue, Southold, NY

Nicholas S. Liappas · Compass Greater NY LLC

Open house Sat, Oct 3 · 1:00 PM22Active

$835,000

1 bd · 2 ba · 886 sqft

2820 Shipyard Lane 2C1, Southold, NY

Denice L. Lara SFR CBR · Daniel Gale Sothebys Intl Rlty

42Active

$4,299,000

4 bd · 3 ba · 3,500 sqft

3525 Paradise Point Road, Southold, NY

Nicholas J. Planamento · William Raveis New York LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

3Active

$1,495,000

4 bd · 4 ba · 4,300 sqft

3995 Wells Avenue, Southold, NY

James Bissett · Hedgestone Commercial Rlty LLC

24Active

$2,950,000

4 bd · 4 ba · 4,241 sqft

9305 Soundview Avenue, Southold, NY

Thomas J. McCarthy C2EX · Thomas J McCarthy Real Estate

Open house Sat, Oct 3 · 12:00 PM27Active

$1,995,000

4 bd · 2 ba · 1,950 sqft

795 Glen Court, Southold, NY

Roric Tobin · Compass Greater NY LLC

Price ReducedOpen house Sat, Oct 3 · 11:30 AM50Active

$1,549,000

4 bd · 3 ba · 2,500 sqft

1541 Stillwater Avenue, Southold, NY

Christine L. Peddy · Engel & Volkers North Fork

34Active

$3,100,000

3 bd · 2 ba · 1,600 sqft

3651 Soundview Avenue, Southold, NY

Nicholas S. Liappas · Compass Greater NY LLC

27Active

$1,200,000

2 bd · 2 ba · 1,100 sqft

1405 Bay Avenue, Southold, NY

Jasmeet Kaur-Soni · Signature Premier Properties

28Active

$2,200,000

3 bd · 3 ba · 2,600 sqft

225 Lakeside Drive S, Southold, NY

Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

37Active

$3,250,000

3 bd · 2 ba · 2,254 sqft

380 The Strand, Southold, NY

Sheri Winter Parker · Corcoran

Price ReducedOpen house Sun, Oct 4 · 1:00 PM35Active

$779,000

2 bd · 2 ba · 1,100 sqft

2820 Shipyard Lane 1B2, Southold, NY

Paul Loeb CBR · Douglas Elliman Real Estate

50Active

$11,500,000

5 bd · 5 ba · 5,000 sqft

1140 Park Avenue, Southold, NY

Alexis Meadows · Compass Greater NY LLC

6Active

$4,500,000

2 bd · 2 ba · 1,500 sqft

Address withheld · Southold, NY

Sheri Winter Parker · Corcoran

34Active

$8,400,000

6 bd · 7 ba · 5,700 sqft

1600 King Street, Southold, NY

Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

Price ReducedOpen house Sat, Oct 3 · 12:00 PM48Active

$2,595,000

3 bd · 2 ba · 1,840 sqft

21515 Soundview Avenue, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

36Active

$5,700,000

4 bd · 3 ba · 3,200 sqft

Address withheld · Southold, NY

Sheila M. Izzo CBR · Century 21 Albertson Realty

30Active

$1,499,000

3 bd · 2 ba · 1,013 sqft

80 Rabbit Lane, Southold, NY

Patrick J. Carpenter · Signature Premier Properties

27Active

$2,650,000

4 bd · 4 ba · 2,600 sqft

195 Williamsburg Drive, Southold, NY

Sheri Winter Parker · Corcoran

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 ReducedOpen house Sat, Oct 3 · 12:00 PM28Active

$1,199,000

4 bd · 2 ba · 1,378 sqft

8440 Main Road, Southold, NY

Peggy VanGorden CBR SFR · Daniel Gale Sothebys Intl Rlty

49Active

$6,450,000

6 bd · 8 ba · 7,340 sqft

1775 Point Pleasant Road, Southold, NY

William J. Walters CBR · Daniel Gale Sothebys Intl Rlty

49Active

$16,800,000

10 bd · 11 ba · 11,000 sqft

1350 W Cove Road, Southold, NY

Sheri Winter Parker · Corcoran

30Active

$5,695,000

4 bd · 5 ba · 4,500 sqft

160 Sound Drive, Southold, NY

Alexis Meadows · Compass Greater NY LLC

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 housing market

August 2026 · This period is still settling

Homes on the market · MLS, as of Aug 24, 2026

Median list price: $1,599,000
Homes for sale: 55

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Median home size: 1,634 sq. ft.

Southold, NY community profile

Area: 15.2 sq. mi.

Source: HJN community data

Explore Southold homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

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

August 2026 · This period is still settling

Homes on the market · MLS, as of Aug 24, 2026

Median list price: $1,599,000
Homes for sale: 55

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Median home size: 1,634 sq. ft.

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Southold housing market

Homes on the market · MLS, as of Aug 24, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Southold, NY community profile

Explore Southold homes

Your local brokerage

Listing data & MLS disclosures

Southold, NY community profile

Southold housing market

Homes on the market · MLS, as of Aug 24, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026