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3 bedsWith a pool
Luxury Homes in Southold, NY
132 listings

Luxury Homes in Southold, NY

Luxury Homes in Southold, NY

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24 of 132 Listings
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Luxury Homes in Southold, NY

24 of 132 Listings

  1. 1050 Tasker Lane — photoNew3

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
Active

$2,795,000

7 bd · 7 ba · 4,562 sqft

1050 Tasker Lane, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

  • 1455 Cedar Point Drive E — photoNew20Active

    $2,150,000

    3 bd · 2 ba · 1,250 sqft

    1455 Cedar Point Drive E, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  • 1045 Fanning Road — photoNew15Active

    $1,250,000

    2 bd · 2 ba · 1,620 sqft

    1045 Fanning Road, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  • 1355 Little Peconic Bay Road — photoNew32Active

    $3,200,000

    6 bd · 7 ba · 7,885 sqft

    1355 Little Peconic Bay Road, Southold, NY

    Alex Giannikas · Corcoran

  • 3825 Stars Road — photoOpen house Sat, Oct 10 · 1:00 PM18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  • 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

  • 1600 Westview Drive — photo27Active

    $1,349,000

    3 bd · 3 ba · 2,925 sqft

    1600 Westview Drive, Southold, NY

    Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

  • 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

  • 13700 Oregon Road — photo35Active

    $1,150,000

    3 bd · 2 ba · 1,204 sqft

    13700 Oregon Road, Southold, NY

    Thomas J. Uhlinger · Douglas Elliman Real Estate

  • 9680 N Bayview Road — photo32Active

    $2,999,000

    4 bd · 6 ba · 7,000 sqft

    9680 N Bayview Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  • 2000 Westphalia Road — photo43Active

    $1,149,999

    3 bd · 2 ba · 1,775 sqft

    2000 Westphalia Road, Southold, NY

    Stephen Zappalla · Keller Williams Realty Elite

  • 225 Marion Lane — photo50Active

    $1,850,000

    3 bd · 4 ba · 3,457 sqft

    225 Marion Lane, Southold, NY

    Laura Wanamaker · Howard Hanna Coach

  • 3645 and 3651 Soundview Avenue — photo49Active

    $6,200,000

    7 bd · 5 ba · 4,628 sqft

    3645 and 3651 Soundview Avenue, Southold, NY

    Nicholas S. Liappas · Compass Greater NY LLC

  • 25105 Main Road N — photoOpen house Sat, Oct 10 · 12:00 PM31Active

    $1,189,000

    4 bd · 4 ba · 3,000 sqft

    25105 Main Road N, Southold, NY

    Suzette Reiss CBR · Douglas Elliman Real Estate

  • 5750 Aldrich Lane — photoOpen house Fri, Oct 9 · 6:00 PM23Active

    $1,565,000

    4 bd · 3 ba · 2,577 sqft

    5750 Aldrich Lane, Southold, NY

    Bryce Levy CBR · Daniel Gale Sothebys Intl Rlty

  • 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

  • 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

  • 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

  • 775 Mulford Court — photo43Active

    $1,750,000

    4 bd · 4 ba · 2,930 sqft

    775 Mulford Court, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  • 1405 Village Lane — photoOpen house Sat, Oct 10 · 11:00 AM23Active

    $1,200,000

    2 bd · 2 ba · 886 sqft

    1405 Village Lane, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  • 750 Reeve Avenue — photoPrice Reduced27Active

    $1,325,000

    3 bd · 3 ba · 3,200 sqft

    750 Reeve Avenue, Southold, NY

    Scott Bortzner CBR · Compass Greater NY LLC

  • 61341 Route 25 — photoOpen house Sat, Oct 10 · 12:00 PM36Active

    $1,100,000

    4 bd · 3 ba · 2,000 sqft

    61341 Route 25, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  • 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

  • 12…6

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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #10311208632

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    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.