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5 Bedroom Homes in Southold, NY
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18 listings
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3 bedsWith a pool

5 Bedroom Homes in Southold, NY

5 Bedroom Homes in Southold, NY

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18 Listings
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5 Bedroom Homes in Southold, NY

18 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 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

  2. 1200 Indian Neck Lane — photo43Active

    $3,250,000

    5 bd · — ba · 4,460 sqft

    1200 Indian Neck Lane, Southold, NY

  3. 1140 Park Avenue — photo50Active

    $11,500,000

    5 bd · 5 ba · 5,000 sqft

    1140 Park Avenue, Southold, NY

    Alexis Meadows · Compass Greater NY LLC

  4. 1135 Wildberry Lane — photo43Active

    $2,895,000

    5 bd · 6 ba · 3,240 sqft

    1135 Wildberry Lane, Southold, NY

    Melissa Principi · Douglas Elliman Real Estate

  5. 150 Deer Run — photo45Active

    $3,675,000

    5 bd · 6 ba · 5,285 sqft

    150 Deer Run, Southold, NY

    Jeffrey R. Mead · Corcoran

  6. 605 Cedar Drive — photo33Active

    $2,695,000

    5 bd · 4 ba · 3,500 sqft

    605 Cedar Drive, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  7. 2340 Fairway Drive — photo38Active

    $1,590,000

    5 bd · 4 ba · 3,200 sqft

    2340 Fairway Drive, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  8. 1520 Meday Avenue — photoPrice Reduced32Active

    $795,000

    5 bd · 4 ba · 3,331 sqft

    1520 Meday Avenue, Southold, NY

    Kenneth W. Hacker · All New York Property LLC

  9. 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

  10. 920 Cedar Point Drive E — photoPrice Reduced39Active

    $5,995,000

    5 bd · 5 ba · 3,500 sqft

    920 Cedar Point Drive E, Southold, NY

    William C. McIntosh · Daniel Gale Sothebys Intl Rlty

  11. 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

  12. 26745 Main Road — photo26Active

    $2,300,000

    5 bd · 5 ba · 3,866 sqft

    26745 Main Road, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  13. 2675 Laurel Trail — photoPrice Reduced33Active

    $2,875,000

    5 bd · 6 ba · 5,800 sqft

    2675 Laurel Trail, Southold, NY

    Scott Bortzner CBR · Compass Greater NY LLC

  14. 2200 Laurel Trail — photo3Active

    $2,100,000

    5 bd · 5 ba · 4,000 sqft

    2200 Laurel Trail, Southold, NY

    Dana M. Lindstrand · STOEBE & CO

  15. 3875 Hallock Lane — photoPrice Reduced50Active

    $5,750,000

    5 bd · 8 ba · 8,505 sqft

    3875 Hallock Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  16. 290 Windward Road — photoPrice Reduced31Active

    $2,499,999

    5 bd · 4 ba · 4,200 sqft

    290 Windward Road, Southold, NY

    Maureen J. Orientale CBR · Compass Greater NY LLC

  17. 151 Bay Avenue — photo21Active

    $2,100,000

    5 bd · 5 ba · 3,500 sqft

    151 Bay Avenue, Southold, NY

    Barbara J. Poliwoda · Douglas Elliman Real Estate

  18. 150 N Hillcrest Drive — photo18Active

    $2,900,000

    5 bd · 5 ba · 4,900 sqft

    150 N Hillcrest Drive, Southold, NY

    William J. Walters CBR · Daniel Gale Sothebys Intl Rlty

About 5 Bedroom Homes in Southold, NY

5 Bedroom Homes in Southold, NY: 18 active listings as of October 5, 2026, 02:39 UTC.

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Listing data & MLS disclosures

NY State MLS
The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance 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. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright © 2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
OneKey MLS
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.