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Homes with a Pool in Southold, NY — Page 2
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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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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 225 Lakeside Drive S — photo29Active

    $2,200,000

    3 bd · 3 ba · 2,600 sqft

    225 Lakeside Drive S, Southold, NY

    Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

  2. 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

  3. 2820 Shipyard Lane Unit 1B2 — photoPrice Reduced35Active

    $779,000

    2 bd · 2 ba · 1,100 sqft

    2820 Shipyard Lane Unit 1B2, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  4. 1140 Park Avenue — photo49Active

    $11,500,000

    5 bd · 5 ba · 5,000 sqft

    1140 Park Avenue, Southold, NY

    Alexis Meadows · Compass Greater NY LLC

  5. 1135 Wildberry Lane — photoPrice Reduced45Active

    $2,795,000

    5 bd · 6 ba · 4,750 sqft

    1135 Wildberry Lane, Southold, NY

    Melissa Principi · Douglas Elliman Real Estate

  6. 1600 King Street — photo34Active

    $8,400,000

    6 bd · 7 ba · 5,700 sqft

    1600 King Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  7. 1850 Highland Road — photoPrice Reduced30Active

    $1,375,000

    4 bd · 3 ba · 2,096 sqft

    1850 Highland Road, Southold, NY

    Phyllis L. Caldwell ABR SFR · Daniel Gale Sothebys Intl Rlty

  8. 705 Gus Drive — photo24Active

    $2,249,000

    4 bd · 4 ba · 3,800 sqft

    705 Gus Drive, Southold, NY

    Donna J. Fakiris · Modern Age Realty Group LLC

  9. 150 Deer Run — photo45Active

    $3,675,000

    5 bd · 6 ba · 5,285 sqft

    150 Deer Run, Southold, NY

    Jeffrey R. Mead · Corcoran

  10. 605 Cedar Drive — photoPrice Reduced38Active

    $2,395,000

    5 bd · 4 ba · 3,500 sqft

    605 Cedar Drive, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  11. 2340 Fairway Drive — photo42Active

    $1,590,000

    5 bd · 4 ba · 3,200 sqft

    2340 Fairway Drive, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  12. 4725 Orchard Street — photo47Active

    $6,000,000

    3 bd · 3 ba · 2,500 sqft

    4725 Orchard Street, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  13. 8440 Main Road — photoPrice Reduced28Active

    $1,199,000

    4 bd · 2 ba · 1,378 sqft

    8440 Main Road, Southold, NY

    Peggy VanGorden CBR SFR · Daniel Gale Sothebys Intl Rlty

  14. 205 Kats Court — photo25Active

    $2,795,000

    5 bd · 5 ba · 4,250 sqft

    205 Kats Court, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  15. 47100 Route 25 — photo42Active

    $2,650,000

    6 bd · 6 ba · 5,111 sqft

    47100 Route 25, Southold, NY

    Edmond Zenuni · Saunders & Associates

  16. 1775 Point Pleasant Road — photo49Active

    $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

  17. 12950 Oregon Road — photoPrice Reduced30Active

    $2,795,000

    4 bd · 4 ba · 4,100 sqft

    12950 Oregon Road, Southold, NY

    Sheri Winter Parker · Corcoran

  18. 1350 W Cove Road — photo49Active

    $16,800,000

    10 bd · 11 ba · 11,000 sqft

    1350 W Cove Road, Southold, NY

    Sheri Winter Parker · Corcoran

  19. 160 Sound Drive — photo30Active

    $5,695,000

    4 bd · 5 ba · 4,500 sqft

    160 Sound Drive, Southold, NY

    Alexis Meadows · Compass Greater NY LLC

  20. 1760 McCann Lane — photo1Active

    $2,399,000

    4 bd · 4 ba · 2,250 sqft

    1760 McCann Lane, Southold, NY

    John Quinn · John Quinn Inc

  21. 820 Gabriella Court — photoPrice Reduced27Active

    $1,249,000

    3 bd · 2 ba · 1,800 sqft

    820 Gabriella Court, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  22. 1895 Pequash Avenue — photoPrice Reduced29Active

    $2,500,000

    4 bd · 5 ba · 3,400 sqft

    1895 Pequash Avenue, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  23. 790 N Sea Drive — photo44Active

    $3,450,000

    5 bd · 4 ba · 4,500 sqft

    790 N Sea Drive, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  24. 435 Old Saddle Lane — photoPrice Reduced18Active

    $1,095,000

    3 bd · 2 ba · 1,500 sqft

    435 Old Saddle Lane, Southold, NY

    Scott Bortzner CBR · Compass Greater NY LLC

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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
    • Homes with a Pool
    • Waterfront Homes

    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.