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Southold, NY Homes for Sale — Page 4 | 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. 2200 Aldrich Lane — photoPrice ReducedOpen house Sat, Oct 10 · 11:00 AM40Active

    $915,000

    4 bd · 2 ba · 2,300 sqft

    2200 Aldrich Lane, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  2. 1135 Wildberry Lane — photo43Active

    $2,895,000

    5 bd · 6 ba · 3,240 sqft

    1135 Wildberry Lane, Southold, NY

    Melissa Principi · Douglas Elliman Real Estate

  3. 365 Rachels Road — photo26Active

    $1,150,000

    4 bd · 4 ba · 2,053 sqft

    365 Rachels Road, Southold, NY

    Jon L. Tomlinson · Daniel Gale Sothebys Intl Rlty

  4. 1600 King Street — photo34Active

    $8,400,000

    6 bd · 7 ba · 5,700 sqft

    1600 King Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  5. 36595 County Rd 48 — photo16Active

    $799,000

    4 bd · 3 ba · 1,800 sqft

    36595 County Rd 48, Southold, NY

    Donna J. Fakiris · Modern Age Realty Group LLC

  6. 270 Opechee Avenue — photoOpen house Sat, Oct 10 · 12:00 PM47Active

    $969,000

    3 bd · 2 ba · 1,600 sqft

    270 Opechee Avenue, Southold, NY

    Patricia Shackel · Douglas Elliman Real Estate

  7. 21515 Soundview Avenue — photoPrice Reduced48Active

    $2,595,000

    3 bd · 2 ba · 1,840 sqft

    21515 Soundview Avenue, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  8. 1850 Highland Road — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM30Active

    $1,375,000

    4 bd · 3 ba · 2,096 sqft

    1850 Highland Road, Southold, NY

    Phyllis L. Caldwell ABR SFR · Daniel Gale Sothebys Intl Rlty

  9. 705 Gus Drive — photo24Active

    $2,249,000

    4 bd · 4 ba · 3,800 sqft

    705 Gus Drive, Southold, NY

    Donna J. Fakiris · Modern Age Realty Group LLC

  10. 150 Deer Run — photoOpen house Sat, Oct 10 · 10:30 AM45Active

    $3,675,000

    5 bd · 6 ba · 5,285 sqft

    150 Deer Run, Southold, NY

    Jeffrey R. Mead · Corcoran

  11. listing photo36Active

    $5,700,000

    4 bd · 3 ba · 3,200 sqft

    Address withheld · Southold, NY

    Sheila M. Izzo CBR · Century 21 Albertson Realty

  12. 1492 Skunk Lane — photo50Active

    $2,499,000

    4 bd · 5 ba · 5,000 sqft

    1492 Skunk Lane, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  13. 605 Cedar Drive — photoPrice ReducedOpen house Sat, Oct 10 · 11:30 AM38Active

    $2,395,000

    5 bd · 4 ba · 3,500 sqft

    605 Cedar Drive, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  14. 80 Rabbit Lane — photo30Active

    $1,499,000

    3 bd · 2 ba · 1,013 sqft

    80 Rabbit Lane, Southold, NY

    Patrick J. Carpenter · Signature Premier Properties

  15. 195 Williamsburg Drive — photo27Active

    $2,650,000

    4 bd · 4 ba · 2,600 sqft

    195 Williamsburg Drive, Southold, NY

    Sheri Winter Parker · Corcoran

  16. 308 Monsell Place — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM39Active

    $749,000

    3 bd · 1 ba · 968 sqft

    308 Monsell Place, Southold, NY

    Isaac D. Israel · Richmond Realty Corp

  17. listing photo33Active

    $1,249,000

    3 bd · 4 ba · 1,700 sqft

    Address withheld · Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  18. 2340 Fairway Drive — photoOpen house Sat, Oct 10 · 11:00 AM42Active

    $1,590,000

    5 bd · 4 ba · 3,200 sqft

    2340 Fairway Drive, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  19. 4725 Orchard Street — photo47Active

    $6,000,000

    3 bd · 3 ba · 2,500 sqft

    4725 Orchard Street, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  20. 26170 County Road 48 — photoPrice Reduced2Active

    $649,000

    4 bd · 1 ba · 1,054 sqft

    26170 County Road 48, Southold, NY

    Patrick Hardy PSA ABR SRES C2EX SF · HomeSmart Premier Living Rlty

  21. 8440 Main Road — photoPrice ReducedOpen house Sat, Oct 10 · 12:00 PM28Active

    $1,199,000

    4 bd · 2 ba · 1,378 sqft

    8440 Main Road, Southold, NY

    Peggy VanGorden CBR SFR · Daniel Gale Sothebys Intl Rlty

  22. 1520 Meday Avenue — photoPrice Reduced32Active

    $795,000

    5 bd · 4 ba · 3,331 sqft

    1520 Meday Avenue, Southold, NY

    Kenneth W. Hacker · All New York Property LLC

  23. 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

  24. 6205 Alvahs Lane — photoPrice Reduced21Active

    $725,000

    3 bd · 2 ba · 1,400 sqft

    6205 Alvahs Lane, Southold, NY

    Andrea Parks · Douglas Elliman Real Estate

1…345…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

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    Thomas O'Leary

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    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)