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3 bedsWith a pool
Waterfront Homes in Islamorada, FL — Page 2
118 listings

Waterfront Homes in Islamorada, FL

Waterfront Homes in Islamorada, FL

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16 of 118 Listings
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Waterfront Homes in Islamorada, FL

16 of 118 Listings

  1. 148 Giardino Drive — photoPrice Reduced55

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
Active

$3,599,000

5 bd · 3 ba · 2,328 sqft

148 Giardino Drive, Islamorada, FL

Oscar Valencia · The Valencia Group Corp.

  • 100 Iroquois Drive Unit 5 — photo39Active

    $999,999

    3 bd · 3 ba · 1,710 sqft

    100 Iroquois Drive Unit 5, Islamorada, FL

    Nancy Hershoff · Coldwell Banker Schmitt Islamorada

  • 316 N Dr — photoPrice Reduced45Active

    $2,350,000

    3 bd · 4 ba · — sqft

    316 N Dr, Islamorada, FL

    Anthony Askowitz · RE/MAX Advance Realty II

  • 87200 Overseas Highway J 6 — photo37Active

    $999,000

    3 bd · 2 ba · 1,400 sqft

    87200 Overseas Highway J 6, Islamorada, FL

    Alina Davis · Coldwell Banker Schmitt Islamorada

  • 313 North Drive — photo49Active

    $3,700,000

    3 bd · 3 ba · 1,729 sqft

    313 North Drive, Islamorada, FL

    Sharon Kelly-Brown · Sharon J. Kelly Realty, Inc.

  • 122 Court Contessa — photo80Active

    $2,740,000

    3 bd · 4 ba · 2,374 sqft

    122 Court Contessa, Islamorada, FL

    Lourdes Martin-Rosa · The Keyes Company

  • 144 N Rolling Hill Road — photo69Active

    $6,195,000

    4 bd · 5 ba · 3,284 sqft

    144 N Rolling Hill Road, Islamorada, FL

    Karan Moeller, PA · Ocean Sotheby's International Realty

  • 75751 Overseas Highway — photoPrice Reduced134Active

    $10,000,000

    5 bd · 5 ba · 3,421 sqft

    75751 Overseas Highway, Islamorada, FL

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

  • 155 Plantation Avenue — photo63Active

    $2,000,000

    3 bd · 3 ba · 1,771 sqft

    155 Plantation Avenue, Islamorada, FL

    Seanna Lindback Porter · Sea Haven Realty, Inc.

  • 82779 Old Highway Unit 1 — photo80Active

    $4,750,000

    4 bd · 5 ba · 2,574 sqft

    82779 Old Highway Unit 1, Islamorada, FL

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

  • 74049 Overseas Hwy — photoPrice Reduced72Active

    $3,750,000

    4 bd · 4 ba · 2,596 sqft

    74049 Overseas Hwy, Islamorada, FL

    Kimberly Farias · Luxe Properties

  • 109 Valencia Drive — photo100Active

    $4,650,000

    5 bd · 6 ba · 4,354 sqft

    109 Valencia Drive, Islamorada, FL

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

  • 81250 Overseas Highway 2 — photo34Active

    $2,485,000

    3 bd · 3 ba · 2,072 sqft

    81250 Overseas Highway 2, Islamorada, FL

    Drew Moret · Palm House Real Estate

  • 77350 Overseas Hwy — photoPrice Reduced33Active

    $10,950,000

    6 bd · 8 ba · 6,577 sqft

    77350 Overseas Hwy, Islamorada, FL

    Carolyn Ambler · American Caribbean Real Estate

  • 81801 Old Hwy 754 — photo47Active

    $649,000

    1 bd · 1 ba · 550 sqft

    81801 Old Hwy 754, Islamorada, FL

    Joy Martin · American Caribbean Real Estate

  • 87851 Old Highway Unit P3 — photoPrice Reduced81Active

    $1,895,000

    4 bd · 3 ba · 2,668 sqft

    87851 Old Highway Unit P3, Islamorada, FL

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

  • 123…5

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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.
    MiamiSouthFlorida
    Listing information provided by MiamiSouthFlorida.

    Islamorada, FL community profile

    Area
    54.6 sq. mi.

    Source: HJN community data

    Islamorada housing market

    September 2026 · This period is still settling

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 24, 2026

    Median home size
    3,076 sq. ft.