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3 bedsNew constructionWith a pool
Homes with a Pool in Islamorada, FL — Page 3
81 listings

Homes with a Pool in Islamorada, FL

Homes with a Pool in Islamorada, FL

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23 of 81 Listings
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Homes with a Pool in Islamorada, FL

23 of 81 Listings

  1. 88181 Old Highway B3 — photoPrice Reduced56

Your local brokerage

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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Active

$870,000

2 bd · 2 ba · 1,224 sqft

88181 Old Highway B3, Islamorada, FL

Christy Hughes · Coldwell Banker Schmitt Islamorada

  • 81801 Overseas Highway 727 — photo23Active

    $585,000

    1 bd · 1 ba · 358 sqft

    81801 Overseas Highway 727, Islamorada, FL

    Jan Keller · Coldwell Banker Schmitt Islamorada

  • 118 Cortez Drive B2 — photoPrice Reduced14Active

    $649,000

    2 bd · 2 ba · 1,079 sqft

    118 Cortez Drive B2, Islamorada, FL

    Ralph Pena · Pena Realty Inc.

  • 82779 Old Highway 8 — photo82Active

    $4,000,000

    4 bd · 5 ba · 2,574 sqft

    82779 Old Highway 8, Islamorada, FL

    Sabrina Wampler & Sarah Ewald · Ocean Sotheby's International Realty

  • 82779 Old Highway 7 — photo84Active

    $4,000,000

    4 bd · 5 ba · 2,574 sqft

    82779 Old Highway 7, Islamorada, FL

    Sabrina Wampler & Sarah Ewald · Ocean Sotheby's International Realty

  • 82779 Old Highway 15 — photo82Active

    $3,800,000

    4 bd · 5 ba · 2,574 sqft

    82779 Old Highway 15, Islamorada, FL

    Sabrina Wampler & Sarah Ewald · Ocean Sotheby's International Realty

  • 136 San Remo Drive — photoPrice Reduced66Active

    $4,445,000

    8 bd · 4 ba · 4,681 sqft

    136 San Remo Drive, Islamorada, FL

    Shane Murray Wilson · Cypress Realty, Inc.

  • 77340 Overseas Highway — photo26Active

    $3,999,999

    2 bd · 2 ba · 928 sqft

    77340 Overseas Highway, Islamorada, FL

    Elizabeth Jolin · Coldwell Banker Schmitt Real E

  • 88351 Old Hwy — photoPrice Reduced62Active

    $14,990,000

    6 bd · 9 ba · 7,590 sqft

    88351 Old Hwy, Islamorada, FL

    Jason Zarco · BHHS EWM Realty

  • 20 Avacado Street — photo44Active

    $15,950,000

    6 bd · 8 ba · 6,680 sqft

    20 Avacado Street, Islamorada, FL

    Steven Koleno · Beycome of Florida, LLC

  • 88351 Old Highway — photoPrice Reduced65Active

    $14,990,000

    6 bd · 9 ba · 7,590 sqft

    88351 Old Highway, Islamorada, FL

    Jason Zarco · Berkshire Hathaway HomeServices EWM Realty

  • 80450 Overseas Highway Apt 106 — photoPrice Reduced35Active

    $550,000

    2 bd · 3 ba · 1,303 sqft

    80450 Overseas Highway Apt 106, Islamorada, FL

    The Lindback Team · Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • 110 Gulfview Drive — photo39Active

    $3,524,000

    7 bd · 4 ba · 3,524 sqft

    110 Gulfview Drive, Islamorada, FL

    Karen V. Jenkins · EXP Realty, LLC

  • 81486 Overseas Highway — photo26Active

    $22,500,000

    7 bd · 9 ba · 8,878 sqft

    81486 Overseas Highway, Islamorada, FL

    KELLY K SHAW PA · American Caribbean Real Estate, Christie's International Real Estate

  • listing photo38Active

    $22,500,000

    7 bd · 9 ba · — sqft

    Address withheld · Islamorada, FL

    Joy Martin · American Caribbean Real Estate

  • 137 Sapodilla Drive — photoPrice Reduced81Active

    $5,999,999

    5 bd · 6 ba · 5,456 sqft

    137 Sapodilla Drive, Islamorada, FL

    Leslie Leopold · Ocean Sotheby's International Realty

  • 87200 N Overseas Highway N2 — photo73Active

    $630,000

    2 bd · 2 ba · 1,365 sqft

    87200 N Overseas Highway N2, Islamorada, FL

    Barbara Eads · Barbara Eads Realty

  • 81906 Overseas Highway 2 — photo55Active

    $2,495,000

    3 bd · 4 ba · 1,829 sqft

    81906 Overseas Highway 2, Islamorada, FL

    Pierre Marc Bellion · Ocean Sotheby's International Realty

  • 87895 Old Highway — photo92Active

    $24,995,000

    5 bd · 8 ba · 9,011 sqft

    87895 Old Highway, Islamorada, FL

    Samuel Davis Williams · Coldwell Banker Schmitt Real Estate Co.

  • 87465 Old Highway 215 — photoPrice Reduced42Active

    $439,000

    2 bd · 2 ba · 1,100 sqft

    87465 Old Highway 215, Islamorada, FL

    Tony Garcia · The Keyes Company

  • 117 Leoni Drive — photoPrice Reduced109Active

    $4,600,000

    5 bd · 6 ba · 4,100 sqft

    117 Leoni Drive, Islamorada, FL

    Michael Jones · Fairchild Partners, Inc.

  • 88540 Overseas Highway 101 — photoPrice Reduced53Active

    $895,000

    3 bd · 2 ba · 1,262 sqft

    88540 Overseas Highway 101, Islamorada, FL

    Brett Newman · Coldwell Banker Schmitt Islamorada

  • 75280 Overseas Highway — photoPrice Reduced104Active

    $10,750,000

    4 bd · 4 ba · 5,100 sqft

    75280 Overseas Highway, Islamorada, FL

    Sabrina Wampler & Sarah Ewald · Ocean Sotheby's International Realty

  • 1234

    Explore Islamorada homes

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    • With a pool
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    Your local brokerage

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    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    BeachesMLS
    All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. 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.
    Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-25 18:41:03 UTC
    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.
    MIAMI REALTORS MLS
    The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
    The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-09-08 20:39:48 UTC

    Islamorada, FL community profile

    Area
    54.6 sq. mi.

    Source: HJN community data