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Southold, NY Homes for Sale — Page 3 | Realty.com
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Homes for Sale in Southold, NY

Homes for Sale in Southold, NY

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24 of 175 Listings
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Homes for Sale in Southold, NY

24 of 175 Listings

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Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 790 Vanston Road — photoPrice Reduced44Active

    $1,499,000

    3 bd · 3 ba · 2,370 sqft

    790 Vanston Road, Southold, NY

    Andrea Parks · Douglas Elliman Real Estate

  2. 410 6th Street — photo12Active

    $864,200

    3 bd · 2 ba · 1,500 sqft

    410 6th Street, Southold, NY

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

  3. 1541 Stillwater Avenue — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM50Active

    $1,549,000

    4 bd · 3 ba · 2,500 sqft

    1541 Stillwater Avenue, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  4. 3645 Soundview Avenue — photoOpen house Sat, Oct 10 · 11:30 AM40Active

    $3,300,000

    4 bd · 3 ba · 3,028 sqft

    3645 Soundview Avenue, Southold, NY

    Nicholas S. Liappas · Compass Greater NY LLC

  5. 3651 Soundview Avenue — photoOpen house Sat, Oct 10 · 11:30 AM34Active

    $3,100,000

    3 bd · 2 ba · 1,600 sqft

    3651 Soundview Avenue, Southold, NY

    Nicholas S. Liappas · Compass Greater NY LLC

  6. 390 Wildberry Lane — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM11Active

    $3,095,000

    4 bd · 5 ba · 5,100 sqft

    390 Wildberry Lane, Southold, NY

    Shaun McQuilkin · Migrate Realty LLC

  7. 2600 Boisseau Avenue — photoPrice Reduced37Active

    $549,999

    3 bd · 1 ba · 1,100 sqft

    2600 Boisseau Avenue, Southold, NY

    Zachary Scher CBR · Signature Premier Properties

  8. 1405 Bay Avenue — photo27Active

    $1,200,000

    2 bd · 2 ba · 1,100 sqft

    1405 Bay Avenue, Southold, NY

    Jasmeet Kaur-Soni · Signature Premier Properties

  9. 44 (1180) Sound Road — photo22Active

    $799,000

    2 bd · 1 ba · 1,090 sqft

    44 (1180) Sound Road, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  10. 2625 Great Peconic Bay Boulevard — photoPrice ReducedOpen house Sat, Oct 10 · 1:30 PM44Active

    $774,000

    3 bd · 2 ba · 1,500 sqft

    2625 Great Peconic Bay Boulevard, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  11. 435 Sound Road — photo23Active

    $1,100,000

    3 bd · 2 ba · 1,800 sqft

    435 Sound Road, Southold, NY

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

  12. 515 The Greenway — photo44Active

    $1,250,000

    3 bd · 3 ba · 2,083 sqft

    515 The Greenway, Southold, NY

    Michael Graziose · Redfin Real Estate

  13. 275 Pinewood Road — photoOpen house Sat, Oct 10 · 12:30 PM45Active

    $1,799,000

    6 bd · 4 ba · 2,509 sqft

    275 Pinewood Road, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  14. 40495 Main Road — photo26Active

    $1,699,999

    4 bd · 3 ba · 2,081 sqft

    40495 Main Road, Southold, NY

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

  15. 429 Kaplan Avenue — photoPrice Reduced10Active

    $775,000

    3 bd · 2 ba · 2,200 sqft

    429 Kaplan Avenue, Southold, NY

    Mary E. Terry · MCKENNASHEA LLC

  16. 225 Lakeside Drive S — photoOpen house Sat, Oct 10 · 2:00 PM28Active

    $2,200,000

    3 bd · 3 ba · 2,600 sqft

    225 Lakeside Drive S, Southold, NY

    Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

  17. 380 The Strand — photo37Active

    $3,250,000

    3 bd · 2 ba · 2,254 sqft

    380 The Strand, Southold, NY

    Sheri Winter Parker · Corcoran

  18. 1025 Seawood Drive — photo33Active

    $1,277,000

    4 bd · 4 ba · 3,000 sqft

    1025 Seawood Drive, Southold, NY

    Clorinda F. Tagios · Douglas Elliman Real Estate

  19. 130 Tasker Lane — photo25Active

    $1,175,000

    4 bd · 3 ba · 2,400 sqft

    130 Tasker Lane, Southold, NY

    Kristen E. Rishe CBR · Signature Premier Properties

  20. 2820 Shipyard Lane 1B2 — photoPrice ReducedOpen house Sat, Oct 10 · 1:00 PM35Active

    $779,000

    2 bd · 2 ba · 1,100 sqft

    2820 Shipyard Lane 1B2, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  21. 2850 Main Bayview Road — photo44Active

    $2,695,000

    3 bd · 2 ba · 1,650 sqft

    2850 Main Bayview Road, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  22. 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

  23. listing photo6Active

    $4,500,000

    2 bd · 2 ba · 1,500 sqft

    Address withheld · Southold, NY

    Sheri Winter Parker · Corcoran

  24. 395 Uhl Lane — photo25Active

    $950,000

    2 bd · 2 ba · 1,688 sqft

    395 Uhl Lane, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

1234…8

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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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    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.

    Nearby areas

    ZIP codes

    • 11937 (113)
    • 11968 (110)
    • 11946 (101)
    • 11901 (99)
    • 11978 (61)
    • 11949 (52)
    • 11933 (51)
    • 11963 (51)

    Cities

    • Southampton (476)
    • Riverhead (181)
    • East Hampton (142)
    • Brookhaven (140)
    • Shelter Island (40)
    • Hampton Bays (14)
    • Sag Harbor (14)
    • Water Mill (9)