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Southold, NY Homes for Sale — Page 5 | Realty.com
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Homes for Sale in Southold, NY

Homes for Sale in Southold, NY

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24 of 175 Listings
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Homes for Sale in Southold, NY

24 of 175 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 47100 Route 25 — photoOpen house Sun, Oct 18 · 1:00 PM42Active

    $2,650,000

    6 bd · 6 ba · 5,111 sqft

    47100 Route 25, Southold, NY

    Edmond Zenuni · Saunders & Associates

  2. 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

  3. 12950 Oregon Road — photoPrice Reduced30Active

    $2,795,000

    4 bd · 4 ba · 4,100 sqft

    12950 Oregon Road, Southold, NY

    Sheri Winter Parker · Corcoran

  4. 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

  5. 1075 Ships Drive — photo42Active

    $1,299,000

    4 bd · 3 ba · 2,240 sqft

    1075 Ships Drive, Southold, NY

    Joshua Whalley · Douglas Elliman Real Estate

  6. 605 Halyoake Avenue — photoPrice Reduced23Active

    $1,999,999

    7 bd · 3 ba · 4,376 sqft

    605 Halyoake Avenue, Southold, NY

    Sarah Doud · Saunders West LLC

  7. 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

  8. 300 Terry Path — photoPrice Reduced20Active

    $3,850,000

    6 bd · 4 ba · 3,000 sqft

    300 Terry Path, Southold, NY

    William J. Walters CBR · Daniel Gale Sothebys Intl Rlty

  9. 136 Bayview Avenue — photoPrice Reduced14Active

    $999,000

    2 bd · 1 ba · 800 sqft

    136 Bayview Avenue, Southold, NY

    Joseph Nina · Douglas Elliman Real Estate

  10. 725 Peconic Lane — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM17Active

    $789,900

    3 bd · 1 ba · 0 sqft

    725 Peconic Lane, Southold, NY

    Savita Ramphal · Island Group Realty Inc

  11. 1700 Smith Drive S — photoPrice Reduced38Active

    $1,599,000

    4 bd · 4 ba · 2,668 sqft

    1700 Smith Drive S, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  12. 865 Track Avenue — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM19Active

    $895,000

    2 bd · 1 ba · 1,300 sqft

    865 Track Avenue, Southold, NY

    Sheri Winter Parker · Corcoran

  13. 4210 Ole Jule Lane — photoPrice Reduced38Active

    $1,850,000

    2 bd · 3 ba · 2,200 sqft

    4210 Ole Jule Lane, Southold, NY

    William J. Walters CBR · Daniel Gale Sothebys Intl Rlty

  14. 420 Sigsbee Road — photoPrice Reduced25Active

    $759,000

    2 bd · 1 ba · 1,014 sqft

    420 Sigsbee Road, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  15. 1100 (Aka 702 Linnett) 7th Street — photoPrice Reduced28Active

    $899,000

    1 bd · 1 ba · 580 sqft

    1100 (Aka 702 Linnett) 7th Street, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  16. 1640 Grandview Drive — photo50Active

    $4,250,000

    4 bd · 5 ba · 5,200 sqft

    1640 Grandview Drive, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  17. 315 Wicks Road — photoPrice ReducedOpen house Sun, Oct 11 · 11:00 AM27Active

    $825,000

    3 bd · 2 ba · 1,141 sqft

    315 Wicks Road, Southold, NY

    William J. Walters CBR · Daniel Gale Sothebys Intl Rlty

  18. 405 Williamsburgh Drive — photo48Active

    $2,899,000

    4 bd · 3 ba · 2,351 sqft

    405 Williamsburgh Drive, Southold, NY

    Laura M. Cochran · BERKSHIRE HATHAWAY

  19. 1760 McCann Lane — photo1Active

    $2,399,000

    4 bd · 4 ba · 2,250 sqft

    1760 McCann Lane, Southold, NY

    John Quinn · John Quinn Inc

  20. 8579 New Suffolk Avenue — photoPrice Reduced20Active

    $1,450,000

    4 bd · 4 ba · 2,950 sqft

    8579 New Suffolk Avenue, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  21. 430 Grove Road — photo15Active

    $699,000

    3 bd · 1 ba · 0 sqft

    430 Grove Road, Southold, NY

    Karyn Flores GRI SFR · Compass Greater NY LLC

  22. 6200 New Suffolk Avenue — photoPrice Reduced32Active

    $715,000

    3 bd · 2 ba · 1,200 sqft

    6200 New Suffolk Avenue, Southold, NY

    Paula Nolan · Alexander Madison Realty Inc

  23. 1480 Old Wood Path — photoPrice Reduced9Active

    $3,695,000

    3 bd · 4 ba · 3,496 sqft

    1480 Old Wood Path, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  24. 380 Clark Road — photoOpen house Sat, Oct 10 · 1:00 PM21Active

    $1,150,000

    2 bd · 1 ba · 1,500 sqft

    380 Clark Road, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

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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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    Thomas O'Leary

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    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.

    Nearby areas

    ZIP codes

    • 11937 (113)
    • 11968 (110)
    • 11946 (101)
    • 11901 (99)
    • 11978 (61)
    • 11949 (52)
    • 11933 (51)
    • 11963 (51)

    Cities

    • Southampton (476)
    • Riverhead (181)
    • East Hampton (142)
    • Brookhaven (140)
    • Shelter Island (40)
    • Hampton Bays (14)
    • Sag Harbor (14)
    • Water Mill (9)