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Luxury Homes in Southold, NY
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144 listings
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Luxury Homes in Southold, NY

Luxury Homes in Southold, NY

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24 of 144 Listings
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Luxury Homes in Southold, NY

24 of 144 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 2025 Little Peconic Bay Lane — photo47Active

    $1,695,000

    3 bd · 2 ba · 2,050 sqft

    2025 Little Peconic Bay Lane, Southold, NY

    Thomas J. Uhlinger · Douglas Elliman Real Estate

  2. 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

  3. 1480 Factory Avenue — photo11Active

    $1,200,000

    4 bd · 3 ba · 1,400 sqft

    1480 Factory Avenue, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  4. 650 Grove Drive — photoOpen house Sun, Oct 2528Active

    $1,100,000

    4 bd · 2 ba · 2,000 sqft

    650 Grove Drive, Southold, NY

    Barbara J. Poliwoda · Douglas Elliman Real Estate

  5. 1165 Shipyard Lane — photoOpen house Sat, Oct 24 · 1:00 PM39Active

    $1,990,000

    4 bd · 5 ba · 3,050 sqft

    1165 Shipyard Lane, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  6. 1200 Deep Hole Drive — photoNew45Active

    $2,495,000

    3 bd · 3 ba · 2,791 sqft

    1200 Deep Hole Drive, Southold, NY

    John J. Glennon · Howard Hanna Coach

  7. 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

  8. 216 Monsell Place — photo22Active

    $1,100,000

    3 bd · 2 ba · 1,200 sqft

    216 Monsell Place, Southold, NY

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

  9. 402 5th Street — photo26Active

    $1,300,000

    4 bd · 2 ba · 1,850 sqft

    402 5th Street, Southold, NY

    Jill H. Dunbar · Douglas Elliman Real Estate

  10. 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

  11. 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

  12. 1000 Sound Drive — photo31Active

    $5,350,000

    5 bd · 5 ba · 3,700 sqft

    1000 Sound Drive, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  13. 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

  14. 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

  15. 1050 Tasker Lane — photoOpen house Sun, Oct 25 · 11:00 AM3Active

    $2,795,000

    7 bd · 7 ba · 4,562 sqft

    1050 Tasker Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  16. 1455 Cedar Point Drive E — photo20Active

    $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

  17. 1355 Little Peconic Bay Road — photo32Active

    $3,200,000

    6 bd · 7 ba · 4,760 sqft

    1355 Little Peconic Bay Road, Southold, NY

    Alex Giannikas · Corcoran

  18. 1045 Fanning Road — photo15Active

    $1,250,000

    2 bd · 2 ba · 1,620 sqft

    1045 Fanning Road, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  19. 3825 Stars Road — photo18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  20. 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

  21. 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

  22. 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

  23. 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

  24. 9680 N Bayview Road — photoOpen house Sun, Oct 25 · 1:00 PM39Active

    $2,999,000

    4 bd · 6 ba · 7,000 sqft

    9680 N Bayview Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

12…6

About Luxury Homes in Southold, NY

Luxury Homes in Southold, NY: 144 active listings as of October 19, 2026, 18:42 UTC.

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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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    TO

    Thomas O'Leary

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    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.