Realty.com
Buy

Start here

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

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Southold, NY Homes for Sale — Page 6 | Realty.com
Realty.com
Buy

Start here

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

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

176 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
3 bedsWith a pool

Homes for Sale in Southold, NY

Homes for Sale in Southold, NY

Hide Map
24 of 176 Listings
Map

Homes for Sale in Southold, NY

24 of 176 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
  1. 380 Clark Road — photo21Active

    $1,150,000

    2 bd · 1 ba · 1,500 sqft

    380 Clark Road, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  2. 820 Gabriella Court — photoPrice Reduced27Active

    $1,249,000

    3 bd · 2 ba · 1,800 sqft

    820 Gabriella Court, Southold, NY

    Nicholas J. Planamento · William Raveis New York LLC

  3. 2015 Kenneys Road — photoPrice Reduced26Active

    $1,445,000

    4 bd · 3 ba · 2,900 sqft

    2015 Kenneys Road, Southold, NY

    Alexis Meadows · Compass Greater NY LLC

  4. 28 (Aka 710) Sound Road — photoPrice Reduced28Active

    $839,000

    3 bd · 3 ba · 2,200 sqft

    28 (Aka 710) Sound Road, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  5. 1895 Pequash Avenue — photoPrice Reduced29Active

    $2,500,000

    4 bd · 5 ba · 3,400 sqft

    1895 Pequash Avenue, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  6. 920 Cedar Point Drive E — photoPrice Reduced39Active

    $5,995,000

    5 bd · 5 ba · 3,500 sqft

    920 Cedar Point Drive E, Southold, NY

    William C. McIntosh · Daniel Gale Sothebys Intl Rlty

  7. 550 Madison Avenue — photoPrice Reduced21Active

    $1,276,000

    3 bd · 3 ba · 1,500 sqft

    550 Madison Avenue, Southold, NY

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

  8. 540 Franklinville Road — photoPrice Reduced16Active

    $699,000

    3 bd · 2 ba · 2,000 sqft

    540 Franklinville Road, Southold, NY

    Arkadiy Munarov · Classic Realty Partners Inc

  9. 790 N Sea Drive — photo44Active

    $3,450,000

    5 bd · 4 ba · 4,500 sqft

    790 N Sea Drive, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  10. 1025 9th Street — photoPrice Reduced50Active

    $1,849,000

    4 bd · 3 ba · 2,200 sqft

    1025 9th Street, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  11. 440 Cases Lane — photoPrice Reduced31Active

    $1,249,000

    4 bd · 2 ba · 2,200 sqft

    440 Cases Lane, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  12. 295 Willow Terrace Lane — photoPrice Reduced50Active

    $1,230,000

    4 bd · 2 ba · 1,700 sqft

    295 Willow Terrace Lane, Southold, NY

    Krystal Kohles · Century 21 Albertson Realty

  13. 100 Sound Drive — photo17Active

    $2,700,000

    3 bd · 3 ba · 1,652 sqft

    100 Sound Drive, Southold, NY

    Christopher Andron · Andron Realty Group Tulip R E

  14. 26745 Main Road — photo26Active

    $2,300,000

    5 bd · 5 ba · 3,866 sqft

    26745 Main Road, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  15. 435 Old Saddle Lane — photoPrice Reduced18Active

    $1,095,000

    3 bd · 2 ba · 1,500 sqft

    435 Old Saddle Lane, Southold, NY

    Scott Bortzner CBR · Compass Greater NY LLC

  16. 35950 Main Road — photo22Active

    $2,600,000

    3 bd · 2 ba · 1,540 sqft

    35950 Main Road, Southold, NY

    Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

  17. 680 Westview Drive — photo31Active

    $949,000

    3 bd · 2 ba · 1,875 sqft

    680 Westview Drive, Southold, NY

    Scott V. Bennett CBR · Douglas Elliman Real Estate

  18. 2675 Laurel Trail — photoPrice ReducedOpen house Sat, Oct 17 · 10:00 AM33Active

    $2,825,000

    4 bd · 6 ba · 5,800 sqft

    2675 Laurel Trail, Southold, NY

    Scott Bortzner CBR · Compass Greater NY LLC

  19. 3000 Grand Avenue — photo1Active

    $1,899,000

    4 bd · 4 ba · 2,250 sqft

    3000 Grand Avenue, Southold, NY

    John Quinn · John Quinn Inc

  20. 240 Lisa Drive — photoPrice Reduced17Active

    $895,000

    4 bd · 3 ba · 1,862 sqft

    240 Lisa Drive, Southold, NY

    Scott V. Bennett CBR · Douglas Elliman Real Estate

  21. 4760 Blue Horizon Bluffs — photoPrice Reduced19Active

    $2,100,000

    4 bd · 4 ba · 2,900 sqft

    4760 Blue Horizon Bluffs, Southold, NY

    Susan M. Orioli · Engel & Volkers North Fork

  22. 2050 Depot Lane — photoPrice Reduced38Active

    $2,850,000

    4 bd · 5 ba · 3,575 sqft

    2050 Depot Lane, Southold, NY

    Sheri Winter Parker · Corcoran

  23. 10940 Main Road — photo38Active

    $1,300,000

    3 bd · 3 ba · 1,815 sqft

    10940 Main Road, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  24. 2600 Oregon Road — photoPrice Reduced32Active

    $4,100,000

    3 bd · 2 ba · 1,474 sqft

    2600 Oregon Road, Southold, NY

    Sheri Winter Parker · Corcoran

1…5678

Explore Southold homes

By price

  • Homes Under $900K
  • Homes Under $1M
  • Homes Under $1.25M
  • Homes Under $1.5M
  • Homes Under $1.75M
  • Homes Under $2M
  • Homes Under $2.25M
  • Homes Under $2.5M
  • Homes Under $2.75M
  • Homes Under $3M
  • Homes Over $3M
  • Luxury Homes

By bedrooms

  • 3 Bedroom Homes
  • 4 Bedroom Homes

By feature

Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

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
    • Homes with a Pool
    • Waterfront Homes

    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

    Nearby areas

    ZIP codes

    • 11937 (114)
    • 11968 (110)
    • 11946 (103)
    • 11901 (99)
    • 11978 (60)
    • 11963 (51)
    • 11933 (50)
    • 11942 (49)

    Cities

    • Southampton (477)
    • Riverhead (182)
    • Brookhaven (147)
    • East Hampton (141)
    • Shelter Island (40)
    • Hampton Bays (14)
    • Sag Harbor (14)
    • Water Mill (8)

    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.