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Homes with a Pool in Southold, NY
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67 listings
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3 bedsWith a pool

Homes with a Pool in Southold, NY

Homes with a Pool in Southold, NY

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24 of 67 Listings
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Homes with a Pool in Southold, NY

24 of 67 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 825 Munn Lane — photoOpen house Sat, Oct 31 · 11:00 AM22Active

    $1,800,000

    6 bd · 5 ba · 3,000 sqft

    825 Munn Lane, Southold, NY

    Gerald J. Cibulski CBR E-PRO CRS G · Century 21 Albertson Realty

  2. 1635 Ships Drive — photo19Active

    $869,000

    3 bd · 2 ba · 1,567 sqft

    1635 Ships Drive, Southold, NY

    Erin R. Kaelin CBR · Signature Premier Properties

  3. 2785 Sigsbee Road — photo23Active

    $1,200,000

    3 bd · 2 ba · 1,200 sqft

    2785 Sigsbee Road, Southold, NY

    Erica S. McKenzie · Andrew Stype Realty Inc

  4. 205 Grange Road — photoOpen house Sat, Oct 31 · 12:00 PM39Active

    $2,195,000

    4 bd · 4 ba · 3,900 sqft

    205 Grange Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  5. 1165 Shipyard Lane — photo39Active

    $1,990,000

    4 bd · 5 ba · 3,050 sqft

    1165 Shipyard Lane, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  6. 39595 Main Road — photoOpen house Sat, Oct 31 · 1:30 PM16Active

    $1,350,000

    4 bd · 3 ba · 2,400 sqft

    39595 Main Road, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  7. 1000 Sound Drive — photo38Active

    $5,350,000

    5 bd · 5 ba · 3,700 sqft

    1000 Sound Drive, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  8. 845 Orchard Street — photoOpen house Sat, Oct 31 · 11:00 AM23Active

    $1,890,000

    3 bd · 3 ba · 1,690 sqft

    845 Orchard Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  9. Main Bayview Main Bayview — photo49Active

    $999,000

    4 bd · 4 ba · 3,000 sqft

    Main Bayview Main Bayview, Southold, NY

    Jared Eisenberg · Corcoran SRG Residential

  10. 1050 Tasker Lane — photo44Active

    $2,795,000

    7 bd · 7 ba · 4,562 sqft

    1050 Tasker Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  11. 1355 Little Peconic Bay Road — photo32Active

    $3,200,000

    6 bd · 7 ba · 4,760 sqft

    1355 Little Peconic Bay Road, Southold, NY

    Alex Giannikas · Corcoran

  12. 3825 Stars Road — photo18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  13. 1430 Bay Haven Lane — photoPrice ReducedOpen house Sun, Nov 1 · 11:00 AM36Active

    $2,548,000

    4 bd · 4 ba · 3,035 sqft

    1430 Bay Haven Lane, Southold, NY

    Basil Boziotis · Compass Greater NY LLC

  14. 860 Hillcrest Drive — photo24Active

    $2,350,000

    3 bd · 4 ba · 2,700 sqft

    860 Hillcrest Drive, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  15. 225 Marion Lane — photoPrice Reduced50Active

    $1,675,000

    3 bd · 4 ba · 3,457 sqft

    225 Marion Lane, Southold, NY

    Laura Wanamaker · Howard Hanna Coach

  16. 5750 Aldrich Lane — photo23Active

    $1,565,000

    4 bd · 3 ba · 2,577 sqft

    5750 Aldrich Lane, Southold, NY

    Bryce Levy CBR · Daniel Gale Sothebys Intl Rlty

  17. 775 Mulford Court — photoPrice Reduced43Active

    $1,595,000

    4 bd · 4 ba · 2,930 sqft

    775 Mulford Court, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  18. 985 Silver Colt Road — photo31Active

    $950,000

    3 bd · 2 ba · 1,321 sqft

    985 Silver Colt Road, Southold, NY

    Deborah A. Dooley CBR · Signature Premier Properties

  19. 3360 Wunneweta Road — photo27Active

    $4,750,000

    6 bd · 9 ba · 8,500 sqft

    3360 Wunneweta Road, Southold, NY

    Marco L. Maida · Compass Greater NY LLC

  20. 3995 Wells Avenue — photo3Active

    $1,495,000

    4 bd · 4 ba · 4,300 sqft

    3995 Wells Avenue, Southold, NY

    James Bissett · Hedgestone Commercial Rlty LLC

  21. 2737 Rocky Point Road — photo34Active

    $1,675,000

    4 bd · 3 ba · 2,117 sqft

    2737 Rocky Point Road, Southold, NY

    Amy L. Kirincic · The Agency Northshore NY

  22. 2080 Elijahs Lane — photoPrice Reduced26Active

    $1,195,000

    4 bd · 3 ba · 2,578 sqft

    2080 Elijahs Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  23. 2105 Pequash Avenue — photo22Active

    $3,300,000

    5 bd · 6 ba · 4,195 sqft

    2105 Pequash Avenue, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  24. 1200 Indian Neck Lane — photoPrice Reduced43Active

    $2,950,000

    5 bd · 5 ba · 4,460 sqft

    1200 Indian Neck Lane, Southold, NY

    Esteban Gomez · Compass Greater NY LLC

123

About Homes with a Pool in Southold, NY

Homes with a Pool in Southold, NY: 67 active listings as of October 30, 2026, 15:58 UTC.

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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
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Southold, NY community profile

    Area
    15.2 sq. mi.

    Source: HJN community data

    Southold housing market

    September 2026 · This period is still settling

    Homes on the market · MLS, as of Sep 27, 2026

    Median list price
    $1,849,000
    Homes for sale
    45

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 9, 2026

    Median home size
    1,634 sq. ft.