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4 Bedroom Homes in Southold, NY
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65 listings
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3 bedsWith a pool

4 Bedroom Homes in Southold, NY

4 Bedroom Homes in Southold, NY

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24 of 65 Listings
Map

4 Bedroom Homes in Southold, NY

24 of 65 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 3735 Deep Hole Drive — photo19Active

    $1,250,000

    4 bd · 3 ba · 1,747 sqft

    3735 Deep Hole Drive, Southold, NY

    Thomas J. McCarthy C2EX · Thomas J McCarthy Real Estate

  2. 2605 Grand Avenue — photo1Active

    $799,999

    4 bd · 3 ba · 2,500 sqft

    2605 Grand Avenue, Southold, NY

    Nancy Davila Campo · Four Seasons Realty Team

  3. 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

  4. 1430 Bay Haven Lane — photo34Active

    $2,698,000

    4 bd · 4 ba · 3,035 sqft

    1430 Bay Haven Lane, Southold, NY

    Basil Boziotis · Compass Greater NY LLC

  5. 9680 N Bayview Road — photo39Active

    $2,999,000

    4 bd · 6 ba · 7,000 sqft

    9680 N Bayview Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  6. 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

  7. 25105 Main Road N — photo31Active

    $1,189,000

    4 bd · 4 ba · 3,000 sqft

    25105 Main Road N, Southold, NY

    Suzette Reiss CBR · Douglas Elliman Real Estate

  8. 1000 Haywaters Road — photo49Active

    $1,595,000

    4 bd · 2 ba · 1,885 sqft

    1000 Haywaters Road, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  9. 795 Bayview Avenue — photo49Active

    $2,395,000

    4 bd · 5 ba · 3,000 sqft

    795 Bayview Avenue, Southold, NY

    Donielle Cardinale McKinnon CBR · Daniel Gale Sothebys Intl Rlty

  10. 3525 Paradise Point Road — photo42Active

    $4,299,000

    4 bd · 3 ba · 3,500 sqft

    3525 Paradise Point Road, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  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. 61341 Route 25 — photo36Active

    $1,100,000

    4 bd · 3 ba · 2,000 sqft

    61341 Route 25, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  13. 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

  14. 185 Maiden Lane — photo19Active

    $1,100,000

    4 bd · 3 ba · 2,050 sqft

    185 Maiden Lane, Southold, NY

    Bridget Elkin · Compass Greater NY 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. 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

  17. 3980 Vanston Road — photoPrice Reduced50Active

    $2,295,000

    4 bd · 4 ba · 4,000 sqft

    3980 Vanston Road, Southold, NY

    Andrea Parks · Douglas Elliman Real Estate

  18. 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

  19. 795 Glen Court — photo27Active

    $1,995,000

    4 bd · 2 ba · 1,950 sqft

    795 Glen Court, Southold, NY

    Roric Tobin · Compass Greater NY LLC

  20. 1541 Stillwater Avenue — photoPrice Reduced50Active

    $1,549,000

    4 bd · 3 ba · 2,500 sqft

    1541 Stillwater Avenue, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  21. 3645 Soundview Avenue — photo40Active

    $3,300,000

    4 bd · 3 ba · 3,028 sqft

    3645 Soundview Avenue, Southold, NY

    Nicholas S. Liappas · Compass Greater NY LLC

  22. 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

  23. 40495 Main Road — photo26Active

    $1,699,999

    4 bd · 3 ba · 2,081 sqft

    40495 Main Road, Southold, NY

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

  24. 1025 Seawood Drive — photo33Active

    $1,277,000

    4 bd · 4 ba · 3,000 sqft

    1025 Seawood Drive, Southold, NY

    Clorinda F. Tagios · Douglas Elliman Real Estate

123

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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.