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

5 Bedroom Homes in Southold, NY

5 Bedroom Homes in Southold, NY

Show Map
20 Listings
Map

5 Bedroom Homes in Southold, NY

20 Listings

  1. 4595 S Harbor Road — photoNew42

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
Active

$829,000

5 bd · 2 ba · 2,300 sqft

4595 S Harbor Road, Southold, NY

John Z. Savoretti · John Savoretti Realty

  • 440 1st Street — photo19Active

    $1,975,000

    5 bd · 2 ba · 2,659 sqft

    440 1st Street, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  • 2220 Akerly Pond Lane — photoOpen house Sun, Oct 25 · 11:30 AM19Active

    $999,000

    5 bd · 2 ba · 0 sqft

    2220 Akerly Pond Lane, Southold, NY

    Joseph Divello · Century 21 Albertson Realty

  • 270 Pequash Avenue — photo31Active

    $1,800,000

    5 bd · 3 ba · 3,000 sqft

    270 Pequash Avenue, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  • 1000 Sound Drive — photo39Active

    $5,350,000

    5 bd · 5 ba · 3,700 sqft

    1000 Sound Drive, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  • 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

  • 1200 Indian Neck Lane — photoPrice Reduced43Active

    $2,950,000

    5 bd · — ba · 4,460 sqft

    1200 Indian Neck Lane, Southold, NY

  • 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

  • 1135 Wildberry Lane — photoPrice ReducedOpen house Sun, Oct 25 · 12:00 PM45Active

    $2,795,000

    5 bd · 6 ba · 4,750 sqft

    1135 Wildberry Lane, Southold, NY

    Melissa Principi · Douglas Elliman Real Estate

  • 150 Deer Run — photo45Active

    $3,675,000

    5 bd · 6 ba · 5,285 sqft

    150 Deer Run, Southold, NY

    Jeffrey R. Mead · Corcoran

  • 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

  • 2340 Fairway Drive — photoPrice ReducedOpen house Sat, Oct 24 · 12:30 PM29Active

    $1,499,999

    5 bd · 4 ba · 3,200 sqft

    2340 Fairway Drive, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  • 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

  • 920 Cedar Point Drive E — photoPrice Reduced39Active

    $5,395,000

    5 bd · 5 ba · 3,500 sqft

    920 Cedar Point Drive E, Southold, NY

    William C. McIntosh · Daniel Gale Sothebys Intl Rlty

  • 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

  • 2200 Laurel Trail — photo3Active

    $2,100,000

    5 bd · 5 ba · 4,000 sqft

    2200 Laurel Trail, Southold, NY

    Dana M. Lindstrand · STOEBE & CO

  • 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

  • 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

  • 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

  • 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

  • Explore Southold homes

    By price

    • Homes Under $900K
    • Homes Under $1M
    • Homes Under $1.25M
    • Homes Under $1.5M
    • Homes Under $1.75M
    • Homes Under $2M
    • Homes Under $2.25M
    • Homes Under $2.5M
    • Homes Under $2.75M
    • Homes Under $3M
    • Homes Over $3M
    • Luxury Homes

    By bedrooms

    • 3 Bedroom Homes
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    By feature

    • Homes with a Pool
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    • Open Houses
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    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

    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.

    Southold, NY community profile

    Area
    15.2 sq. mi.

    Source: HJN community data