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3 bedsWith a pool
Homes with a Pool in Southold, NY
68 listings

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

  1. 1635 Ships Drive — photo19Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$869,000

3 bd · 2 ba · 1,567 sqft

1635 Ships Drive, Southold, NY

Erin R. Kaelin CBR · Signature Premier Properties

  • 2785 Sigsbee Road — photo23Active

    $1,200,000

    3 bd · 2 ba · 1,200 sqft

    2785 Sigsbee Road, Southold, NY

    Erica S. McKenzie · Andrew Stype Realty Inc

  • 205 Grange Road — photo7Active

    $2,195,000

    4 bd · 4 ba · 3,900 sqft

    205 Grange Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  • 1165 Shipyard Lane — photo39Active

    $1,990,000

    4 bd · 5 ba · 3,050 sqft

    1165 Shipyard Lane, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  • 39595 Main Road — photo16Active

    $1,350,000

    4 bd · 3 ba · 2,400 sqft

    39595 Main Road, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  • 1000 Sound Drive — photo38Active

    $5,350,000

    5 bd · 5 ba · 3,700 sqft

    1000 Sound Drive, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  • 845 Orchard Street — photo23Active

    $1,890,000

    3 bd · 3 ba · 1,690 sqft

    845 Orchard Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  • Main Bayview Main Bayview — photoOpen house Sun, Oct 25 · 1:00 PM49Active

    $999,000

    4 bd · 4 ba · 3,000 sqft

    Main Bayview Main Bayview, Southold, NY

    Jared Eisenberg · Corcoran SRG Residential

  • 1050 Tasker Lane — photoOpen house Sun, Oct 25 · 11:00 AM37Active

    $2,795,000

    7 bd · 7 ba · 4,562 sqft

    1050 Tasker Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  • 1355 Little Peconic Bay Road — photoOpen house Sun, Oct 25 · 1:00 PM32Active

    $3,200,000

    6 bd · 7 ba · 4,760 sqft

    1355 Little Peconic Bay Road, Southold, NY

    Alex Giannikas · Corcoran

  • 3825 Stars Road — photo18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  • 1430 Bay Haven Lane — photoPrice Reduced36Active

    $2,548,000

    4 bd · 4 ba · 3,035 sqft

    1430 Bay Haven Lane, Southold, NY

    Basil Boziotis · Compass Greater NY LLC

  • 860 Hillcrest Drive — photo24Active

    $2,350,000

    3 bd · 4 ba · 2,700 sqft

    860 Hillcrest Drive, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  • 225 Marion Lane — photoPrice ReducedOpen house Sun, Oct 25 · 12:00 PM50Active

    $1,675,000

    3 bd · 4 ba · 3,457 sqft

    225 Marion Lane, Southold, NY

    Laura Wanamaker · Howard Hanna Coach

  • 5750 Aldrich Lane — photoOpen house Sun, Oct 25 · 12:00 PM23Active

    $1,565,000

    4 bd · 3 ba · 2,577 sqft

    5750 Aldrich Lane, Southold, NY

    Bryce Levy CBR · Daniel Gale Sothebys Intl Rlty

  • 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

  • 985 Silver Colt Road — photo31Active

    $950,000

    3 bd · 2 ba · 1,321 sqft

    985 Silver Colt Road, Southold, NY

    Deborah A. Dooley CBR · Signature Premier Properties

  • 3360 Wunneweta Road — photo27Active

    $4,750,000

    6 bd · 9 ba · 8,500 sqft

    3360 Wunneweta Road, Southold, NY

    Marco L. Maida · Compass Greater NY LLC

  • 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

  • 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

  • 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

  • 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

  • 405 Birch Lane — photo27Active

    $1,425,000

    3 bd · 3 ba · 2,679 sqft

    405 Birch Lane, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  • 1200 Indian Neck Lane — photoPrice Reduced43Active

    $2,950,000

    5 bd · 5 ba · 4,460 sqft

    1200 Indian Neck Lane, Southold, NY

    Esteban Gomez · Compass Greater NY LLC

  • 123

    Explore Southold homes

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    • Homes Under $900K
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Listing data & MLS disclosures

    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, 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.