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Summerland, FL Homes for Sale | Realty.com
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Buy

Start here

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  • The buying timeline

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3 beds
24 listings
Sell

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New construction
With a pool

Homes for Sale in Summerland, FL

Homes for Sale in Summerland, FL

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24 Listings
Map

Homes for Sale in Summerland, FL

24 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 24923 Park Drive — photo22Active

    $950,000

    2 bd · — ba · 902 sqft

    24923 Park Drive, Summerland, FL

    Stacy L Shahan · Island Real Estate Company Florida Keys

  2. 27 N Lake Drive — photo34Active

    $889,900

    3 bd · — ba · 1,638 sqft

    27 N Lake Drive, Summerland, FL

    Colbert A Taylor · Taylor & Assoc. RE, Inc.

  3. 486 S Airport Drive — photo20Active

    $1,300,000

    2 bd · — ba · 1,240 sqft

    486 S Airport Drive, Summerland, FL

    Rose M Dell · Keller Williams Key West Compass Realty

  4. 25361 1st Street — photo82Active

    $3,500,000

    3 bd · — ba · 2,535 sqft

    25361 1st Street, Summerland, FL

    Tommy Mack · Coastal Collection Real Estate Inc.

  5. 23950 Overseas Highway — photoPrice Reduced73Active

    $2,999,000

    5 bd · — ba · 3,886 sqft

    23950 Overseas Highway, Summerland, FL

    Walters Luxury Group Gloria, Rachel and Michaela Walters · Ocean Sotheby's International Realty

  6. 24740 Park Drive — photoPrice Reduced52Active

    $649,000

    2 bd · — ba · 960 sqft

    24740 Park Drive, Summerland, FL

    Diane Corliss · Coldwell Banker Schmitt Real Estate Co

  7. 361 Avenue D — photo63Active

    $3,100,000

    2 bd · — ba · 1,819 sqft

    361 Avenue D, Summerland, FL

    Stacy L Shahan · Island Real Estate Company Florida Keys

  8. 23940 Overseas Highway — photo22Active

    $899,000

    3 bd · — ba · 1,242 sqft

    23940 Overseas Highway, Summerland, FL

    Stacy L Shahan · Island Real Estate Company Florida Keys

  9. 96 John Street — photoPrice Reduced22Active

    $535,000

    3 bd · — ba · 1,120 sqft

    96 John Street, Summerland, FL

    Will Langley · Berkshire Hathaway HomeServices Knight & Gardner Realty

  10. 0 Howell Key — photo146Active

    $16,900,000

    5 bd · — ba · 3,352 sqft

    0 Howell Key, Summerland, FL

    Lisa H Ferringo · Coldwell Banker Schmitt Real Estate Co

  11. 466 W Shore Drive — photoPrice Reduced46Active

    $1,250,000

    2 bd · — ba · 1,364 sqft

    466 W Shore Drive, Summerland, FL

    Donna Pezzi · Keller Williams Key West Compass Realty

  12. 706 E Caribbean Drive — photo39Active

    $1,185,000

    3 bd · — ba · 1,188 sqft

    706 E Caribbean Drive, Summerland, FL

    Donna Pezzi · Keller Williams Key West Compass Realty

  13. 848 E Caribbean Drive — photo44Active

    $2,246,000

    3 bd · — ba · 2,016 sqft

    848 E Caribbean Drive, Summerland, FL

    Jonathan Minerick · Homecoin.com

  14. 414 E Caribbean Drive — photo49Active

    $3,495,000

    4 bd · — ba · 2,766 sqft

    414 E Caribbean Drive, Summerland, FL

    Lisa Swanson · The Agency Florida Keys

  15. 637 E Caribbean Drive — photo47Active

    $1,200,000

    2 bd · — ba · 1,040 sqft

    637 E Caribbean Drive, Summerland, FL

    Donna Pezzi · Keller Williams Key West Compass Realty

  16. 667 E Caribbean Drive — photo54Active

    $1,100,000

    2 bd · — ba · 1,095 sqft

    667 E Caribbean Drive, Summerland, FL

    Donna Pezzi · Keller Williams Key West Compass Realty

  17. 937 Gulf Drive — photoPrice Reduced58Active

    $2,220,000

    3 bd · — ba · 1,900 sqft

    937 Gulf Drive, Summerland, FL

    Sandra Tuttle · Island Welcome Real Estate

  18. 24348 Caribbean Drive — photoPrice Reduced65Active

    $3,295,000

    3 bd · — ba · 2,870 sqft

    24348 Caribbean Drive, Summerland, FL

    Caroline Bauer · Key West Sales, LLC

  19. 24347 W Caribbean Drive — photoPrice Reduced48Active

    $1,199,000

    3 bd · — ba · 1,232 sqft

    24347 W Caribbean Drive, Summerland, FL

    Shirley Carey · Berkshire Hathaway HomeServices Knight & Gardner Realty

  20. 360 W Shore Drive — photoPrice Reduced31Active

    $749,500

    3 bd · — ba · 1,562 sqft

    360 W Shore Drive, Summerland, FL

    Brenda Ann Thomas · Island Welcome Real Estate

  21. 24840 Park Drive — photoPrice Reduced20Active

    $950,000

    3 bd · — ba · 1,565 sqft

    24840 Park Drive, Summerland, FL

    Thomas Murphy · LAER Realty

  22. 860 Lagoon Drive — photo27Active

    $1,950,000

    3 bd · — ba · 1,797 sqft

    860 Lagoon Drive, Summerland, FL

    Cheryl Moses · Action Keys Realty of the Lower FL Keys LLC

  23. 231 E Shore Drive 6 — photo40Active

    $4,400,000

    5 bd · — ba · 3,119 sqft

    231 E Shore Drive 6, Summerland, FL

    Stephanie Marie Muzzillo · Serhant Florida LLC - Delray Beach Office

  24. 0 Melody — photo45Active

    $7,000,000

    3 bd · — ba · 2,851 sqft

    0 Melody, Summerland, FL

    Scott P Forman · Royal Palms Realty (KW)

Explore Summerland homes

By price

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  • 3 beds
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  • 5 beds

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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.

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Listing data & MLS disclosures

Key West Association of REALTORS
The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of The Key West Association of REALTORS®. MLS Real Estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. Information deemed reliable but not guaranteed. Copyright ©2026 The Key West Association of REALTORS®. All Rights Reserved.
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

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