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3 bedsNew constructionWith a pool
Homes with a Pool in Islamorada, FL — Page 2
81 listings

Homes with a Pool in Islamorada, FL

Homes with a Pool in Islamorada, FL

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

22 of 81 Listings

  1. 19 Avacado Street — photo145

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$13,750,000

5 bd · 7 ba · 5,489 sqft

19 Avacado Street, Islamorada, FL

Lisa Swanson · The Agency Florida Keys

  • 107 Valencia Dr — photo47Active

    $2,795,000

    3 bd · 3 ba · 1,632 sqft

    107 Valencia Dr, Islamorada, FL

    Patty Accorto · Keller Williams Legacy

  • 157 Valencia Drive — photo63Active

    $4,600,000

    5 bd · 6 ba · 4,636 sqft

    157 Valencia Drive, Islamorada, FL

    Claire Johnson · Coastal Realty of the Florida Keys

  • 88540 Overseas Highway Apt 304 — photoPrice Reduced29Active

    $599,995

    2 bd · 2 ba · 853 sqft

    88540 Overseas Highway Apt 304, Islamorada, FL

    Elizabeth Jolin · Coldwell Banker Schmitt Islamorada

  • 109 Giardino Drive — photo48Active

    $3,875,000

    4 bd · 3 ba · 3,088 sqft

    109 Giardino Drive, Islamorada, FL

    Alina Davis · Coldwell Banker Schmitt Islamorada

  • 75090 Overseas Highway — photo86Active

    $29,000,000

    4 bd · 6 ba · 8,194 sqft

    75090 Overseas Highway, Islamorada, FL

    Annie Hagen · Ocean Sothebys Intl Realty

  • 87200 Overseas Highway D3 — photo55Active

    $599,000

    2 bd · 2 ba · 1,352 sqft

    87200 Overseas Highway D3, Islamorada, FL

    Lisa Frins P.A. · Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • 194 Buttonwood Lane — photo82Active

    $6,150,000

    6 bd · 7 ba · 5,100 sqft

    194 Buttonwood Lane, Islamorada, FL

    Michael Jones · Fairchild Partners, Inc.

  • 81801 Overseas Highway Highway 714 — photo13Active

    $710,000

    1 bd · 1 ba · 550 sqft

    81801 Overseas Highway Highway 714, Islamorada, FL

    Joseph R Ziolo · United Realty Group, Inc

  • 88540 Overseas Highway 101 & Boat Slip 22 — photo57Active

    $1,100,000

    3 bd · 2 ba · 1,262 sqft

    88540 Overseas Highway 101 & Boat Slip 22, Islamorada, FL

    Brett Newman · Coldwell Banker Schmitt Islamorada

  • 118 Cortez Dr B — photoPrice Reduced14Active

    $659,000

    2 bd · 2 ba · 1,079 sqft

    118 Cortez Dr B, Islamorada, FL

    Ralph Pena Jr. · Pena Realty, Inc.

  • 40 High Point Rd 402 — photo22Active

    $348,000

    2 bd · 2 ba · 1,156 sqft

    40 High Point Rd 402, Islamorada, FL

    Claire Johnson · Coastal Realty Florida Keys

  • 82768 Overseas Highway — photo125Active

    $25,000,000

    7 bd · 10 ba · 8,288 sqft

    82768 Overseas Highway, Islamorada, FL

    Gonzalo Del Negro · Ocean Sothebys Intl Realty

  • 75071 Overseas Highway — photo41Active

    $3,199,000

    3 bd · 2 ba · 1,260 sqft

    75071 Overseas Highway, Islamorada, FL

    Derek Rodberg · Coastal Realty of the Florida Keys

  • 81801 Overseas Highway 637 — photoPrice Reduced31Active

    $715,000

    1 bd · 1 ba · 550 sqft

    81801 Overseas Highway 637, Islamorada, FL

    Kim Bagnell Thaler · Ocean Sotheby's International Realty

  • 80450 Overseas Highway 204 — photoPrice Reduced38Active

    $550,000

    2 bd · 2 ba · 1,261 sqft

    80450 Overseas Highway 204, Islamorada, FL

    Taylor Globus · Palm House Real Estate

  • 44 W Plaza Del Lago — photo83Active

    $4,750,000

    4 bd · 5 ba · 4,464 sqft

    44 W Plaza Del Lago, Islamorada, FL

    Alexander Pinero · Pine River Realty, LLC

  • 1101 Mastic Street — photoPrice Reduced137Active

    $6,999,000

    8 bd · 6 ba · 3,649 sqft

    1101 Mastic Street, Islamorada, FL

    Tracey E. Petrusha · LoKation Real Estate

  • 81801 Overseas Highway #729 — photo64Active

    $699,000

    1 bd · 1 ba · 550 sqft

    81801 Overseas Highway #729, Islamorada, FL

    Diana Lynn Fiddes · Coldwell Banker Schmitt Key Largo

  • 88747 Old Highway — photo18Active

    $8,000,000

    3 bd · 3 ba · 1,728 sqft

    88747 Old Highway, Islamorada, FL

    Ralph Sam · Real Estate Sales Force, Inc.

  • 137 Sapodilla Dr — photoPrice Reduced65Active

    $5,999,999

    5 bd · 6 ba · 5,456 sqft

    137 Sapodilla Dr, Islamorada, FL

    Annie Hagen · Ocean Sothebys Intl Realty

  • 169 Venetian Way — photoPrice Reduced75Active

    $1,550,000

    5 bd · 3 ba · 2,941 sqft

    169 Venetian Way, Islamorada, FL

    Jane Wasmund · RE/MAX All Keys Real Estate

  • 1234

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    • With a pool
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    Your local brokerage

    TO

    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: 2026-09-23 12:06:37 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: 2026-09-01 15:44:39 UTC

    Islamorada, FL community profile

    Area
    54.6 sq. mi.

    Source: HJN community data