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Southold, NY Homes for Sale | Realty.com
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Buy

Start here

  • Homes for sale by state
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  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
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  • Get pre-approved

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Homes for Sale in Southold, NY

Homes for Sale in Southold, NY

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24 of 179 Listings
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Homes for Sale in Southold, NY

24 of 179 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 2025 Little Peconic Bay Lane — photo48Active

    $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. 39595 Main Road — photoNew16Active

    $1,350,000

    4 bd · 3 ba · 2,400 sqft

    39595 Main Road, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  3. 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

  4. 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

  5. 430 Grove Road — photoNewOpen house Sat, Oct 17 · 12:00 PM17Active

    $699,000

    3 bd · 1 ba · 0 sqft

    430 Grove Road, Southold, NY

    Karyn Flores GRI SFR · Compass Greater NY LLC

  6. 440 1st Street — photoNew19Active

    $1,975,000

    5 bd · 2 ba · 2,659 sqft

    440 1st Street, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  7. 2220 Akerly Pond Lane — photoNew17Active

    $999,000

    5 bd · 2 ba · 0 sqft

    2220 Akerly Pond Lane, Southold, NY

    Joseph Divello · Century 21 Albertson Realty

  8. 4105 Deep Hole Drive — photoNew43Active

    $879,000

    3 bd · 2 ba · 1,560 sqft

    4105 Deep Hole Drive, Southold, NY

    Thomas J. Uhlinger · Douglas Elliman Real Estate

  9. 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

  10. 52325 County Road 48 41 — photoOpen house Sat, Oct 17 · 10:00 AM16Active

    $240,000

    — bd · — ba · — sqft

    52325 County Road 48 41, Southold, NY

  11. 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

  12. 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

  13. 845 Orchard Street — photoOpen house Sat, Oct 17 · 11:00 AM23Active

    $1,890,000

    3 bd · 3 ba · 1,690 sqft

    845 Orchard Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  14. 2605 Grand Avenue — photo1Active

    $799,999

    4 bd · 3 ba · 2,500 sqft

    2605 Grand Avenue, Southold, NY

    Nancy Davila Campo · Four Seasons Realty Team

  15. 1050 Tasker Lane — photoOpen house Sun, Oct 18 · 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. Main Bayview Main Bayview — photoOpen house Sat, Oct 17 · 11:00 AM49Active

    $999,000

    4 bd · 4 ba · 3,000 sqft

    Main Bayview Main Bayview, Southold, NY

    Jared Eisenberg · Corcoran SRG Residential

  17. 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

  18. 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

  19. 1045 Fanning Road — photoOpen house Sat, Oct 17 · 12:00 PM15Active

    $1,250,000

    2 bd · 2 ba · 1,620 sqft

    1045 Fanning Road, Southold, NY

    Eric P. Elkin · Compass Greater NY LLC

  20. 3825 Stars Road — photo18Active

    $1,200,000

    3 bd · 2 ba · 2,100 sqft

    3825 Stars Road, Southold, NY

    Sheri Winter Parker · Corcoran

  21. 1430 Bay Haven Lane — photoOpen house Sun, Oct 18 · 12:00 PM34Active

    $2,698,000

    4 bd · 4 ba · 3,035 sqft

    1430 Bay Haven Lane, Southold, NY

    Basil Boziotis · Compass Greater NY LLC

  22. 29400 County Road 48 — photo18Active

    $795,000

    3 bd · 2 ba · 2,000 sqft

    29400 County Road 48, Southold, NY

    Sheri Winter Parker · Corcoran

  23. 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

  24. 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

12…8

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Listing data & MLS disclosures

NY State MLS
The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the New York State Alliance 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. Real estate listings held by brokerage firms other than Realty.com, are indicated by detailed information about them such as the name of the listing firms. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither the listing broker(s) nor Realty.com shall be responsible for any typographical errors, misinformation, misprints, and shall be held totally harmless. Copyright © 2026 New York State Alliance and participating MLS's - CNYIS, UNYREIS and WNYREIS. All Rights Reserved.
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
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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 (112)
    • 11968 (112)
    • 11946 (107)
    • 11901 (100)
    • 11978 (62)
    • 11949 (51)
    • 11963 (51)
    • 11933 (50)

    Cities

    • Southampton (482)
    • Riverhead (180)
    • East Hampton (141)
    • Brookhaven (136)
    • Shelter Island (40)
    • Hampton Bays (14)
    • Sag Harbor (14)
    • Water Mill (8)