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Homes with a Pool in Southold, NY
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68 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 68 Listings
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Homes with a Pool in Southold, NY

24 of 68 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 1000 Sound Drive — photo31Active

    $5,350,000

    5 bd · 5 ba · 3,700 sqft

    1000 Sound Drive, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  2. 845 Orchard Street — photoOpen house Sat, Oct 17 · 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

  3. 1050 Tasker Lane — photoOpen house Sun, Oct 18 · 11:00 AM3Active

    $2,795,000

    7 bd · 7 ba · 4,562 sqft

    1050 Tasker Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  4. Main Bayview Main Bayview — photoOpen house Sat, Oct 17 · 11:00 AM49Active

    $999,000

    4 bd · 4 ba · 3,000 sqft

    Main Bayview Main Bayview, Southold, NY

    Jared Eisenberg · Corcoran SRG Residential

  5. 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

  6. 3825 Stars Road — photo18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  7. 1430 Bay Haven Lane — photoOpen house Sun, Oct 18 · 12:00 PM34Active

    $2,698,000

    4 bd · 4 ba · 3,035 sqft

    1430 Bay Haven Lane, Southold, NY

    Basil Boziotis · Compass Greater NY LLC

  8. 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

  9. 225 Marion Lane — photo50Active

    $1,850,000

    3 bd · 4 ba · 3,457 sqft

    225 Marion Lane, Southold, NY

    Laura Wanamaker · Howard Hanna Coach

  10. 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

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 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

  18. 405 Birch Lane — photo27Active

    $1,425,000

    3 bd · 3 ba · 2,679 sqft

    405 Birch Lane, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  19. 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

  20. 9305 Soundview Avenue — photo24Active

    $2,950,000

    4 bd · 4 ba · 4,241 sqft

    9305 Soundview Avenue, Southold, NY

    Thomas J. McCarthy C2EX · Thomas J McCarthy Real Estate

  21. 390 Wildberry Lane — photoPrice ReducedOpen house Sat, Oct 17 · 10:30 AM48Active

    $2,895,000

    4 bd · 5 ba · 5,100 sqft

    390 Wildberry Lane, Southold, NY

    Shaun McQuilkin · Migrate Realty LLC

  22. 225 Lakeside Drive S — photo28Active

    $2,200,000

    3 bd · 3 ba · 2,600 sqft

    225 Lakeside Drive S, Southold, NY

    Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

  23. 130 Tasker Lane — photo25Active

    $1,175,000

    4 bd · 3 ba · 2,400 sqft

    130 Tasker Lane, Southold, NY

    Kristen E. Rishe CBR · Signature Premier Properties

  24. 2850 Main Bayview Road — photo44Active

    $2,695,000

    3 bd · 2 ba · 1,650 sqft

    2850 Main Bayview Road, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

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About Homes with a Pool in Southold, NY

Homes with a Pool in Southold, NY: 68 active listings as of October 15, 2026, 08:12 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

    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.