9,138

Islamorada, FL Homes

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  • /53

    $2,495,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,829 Sq Ft

    81906 Overseas Hwy Unit 2, Islamorada, FL 33036

    Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions.Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront

    Agent Photo

    Pierre-Marc Bellion

    Ocean Sotheby's International Realty

    81906 Overseas Hwy Unit 2, Islamorada, FL 33036
  • /35

    $6,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • House for Rent

    130 Plantation Ave Unit Upper, Tavernier, FL 33070

    Furnished 3 Bed / 2 Bath - All Utilities IncludedBeautifully furnished upper-level unit featuring 3 bedrooms and 2 bathrooms. Rent includes utilities, cable, lawn care, and pool service for a truly hassle-free living experience. Located in a quiet neighborhood close to restaurants, shopping, and top-rated schools.Interested in more space? The entire house (6 Bed / 4 Bath) is also

    Tracey Petrusha Venture Realty Group

    130 Plantation Ave Unit Upper, Tavernier, FL 33070
  • /2

    $2,350,000

    Sold Mar 13, 2026

    101 Villa Bella Dr, Islamorada, FL 33036

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $1,506/SF
    • 71 Days On Market

    Current Estimated Value $2,420,905

    Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada

    101 Villa Bella Dr, Islamorada, FL 33036
    • /25

      Not Listed For Sale

      145 Westminster Dr, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 1,579 Sq Ft
      • Built 1976
      145 Westminster Dr, Tavernier, FL 33070

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Jan Keller Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • /33

    $11,700,000

    New Construction
    • 6 Beds
    • 8 Baths
    • 6,577 Sq Ft

    77350 Overseas Hwy, Islamorada, FL 33036

    Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom

    Agent Photo

    Carolyn Ambler

    American Caribbean Real Estate, Christie's International Real Estate

    77350 Overseas Hwy, Islamorada, FL 33036
  • /15

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 9,878 Sq Ft
    • Apartment for Rent

    Unlisted Address

    Great gateway spot Cabana Studio style in Tavernier with private Hot tub. Apartment comes fully furnished and equipped ready for short term. Unit features small kitchen with cook-top, refrigerator and everything needed to makes your dates enjoyable at the keys. Wifi and parking included. All services included, so only come and make this cozy cabana yours for your Florida keys trip. Unit has a

    Yohan Barreras Soltura Prime House Realty, Inc.

    Unlisted Address
  • /29

    $377,500

    Sold Nov 20, 2025

    119 Cortez Dr Unit 1G, Islamorada, FL 33036

    • 1 Bed
    • 1 Bath
    • 518 Sq Ft
    • Built 1980

    Last Sold Summary

    • 2% Below List Price
    • $729/SF
    • 24 Days On Market

    Last Listing Agent Krissy Carnahan Paradise Florida Keys Real Estate, a Luxury Brand

    119 Cortez Dr Unit 1G, Islamorada, FL 33036
    • /37

      Est $937,509

      Not Listed For Sale

      273 Hibiscus St, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 1,305 Sq Ft
      • Built 1992
      273 Hibiscus St, Tavernier, FL 33070

      Last Sold Summary

      • 140 Days On Market

      Last Listing Agent Karan Moeller Ocean Sotheby's International Realty

  • /49

    $795,000

    $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,152 Sq Ft

    136 Aregood Ln, Islamorada, FL 33036

    Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, peaceful oceanfront community of just 10 townhomes, you'll have a beach, pool and your own slip for boat up to 30'. Spend the day on the water, relax by the pool or head up to the rooftop deck for ocean breezes & a peekaboo water

    Christy Hughes Coldwell Banker Schmitt Islamorada

    136 Aregood Ln, Islamorada, FL 33036
  • /86

    $28,000 Per Month

    • 6 Beds
    • 7 Baths
    • 4,108 Sq Ft
    • House for Rent

    146 Mockingbird Rd, Islamorada, FL 33070

    Spectacular waterfront residence built in 2021 showcasing exceptional craftsmanship and high-quality materials throughout. This three-story coastal retreat offers 6 bedrooms and 6.5 bathrooms and is perfectly positioned facing west, capturing breathtaking sunset Gulf views while offering enhanced privacy with no rear neighbors.The first floor features a private guest suite, living area with

    Nancy Jimenez Douglas Elliman

    146 Mockingbird Rd, Islamorada, FL 33070
  • /44

    $900,000

    Sold May 22, 2026

    109 Costa Bravo Dr, Islamorada, FL 33036

    • 2 Beds
    • 1.5 Baths
    • 1,322 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $681/SF
    • 79 Days On Market

    Last Listing Agent Courtney Conley Serhant Florida LLC - Coconut Grove

    109 Costa Bravo Dr, Islamorada, FL 33036
    • /17

      Est $947,520

      Not Listed For Sale

      33 Flamingo Hammock Rd, Islamorada, FL 33036

      33 Flamingo Hammock Rd, Islamorada, FL 33036

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent Jessica Pinder Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • /33

    $530,000

    • 2 Beds
    • 1 Bath
    • 624 Sq Ft

    107 Tavern Dr, Tavernier, FL 33070

    In the heart of Historic Tavernier, this charming Keys cottage offers the kind of character that's getting harder and harder to find. Set on two lots with peekaboo ocean views, the property combines Old Florida charm, outdoor space, and boating convenience in one inviting package. Inside, the two bedroom, one bath home has a cozy, authentic Keys feel. This compact space is full of personality.

    Karin Moerner Cedergren Coldwell Banker Schmitt Islamorada

    107 Tavern Dr, Tavernier, FL 33070
  • /20

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • Townhouse for Rent

    87200 Overseas Hwy Unit 1, Islamorada, FL 33036

    Prestigious Executive Bay Club corner townhouse in Islamorada. Offering 2BD/2Bth and loft. Spacious, updated & completely furnished. Beach front private community with 24 manned gate entrance, private beach to enjoy beautiful sunsets, pool, tennis courts, club house, first come first serve dock. Next door to Founder's Park offering many activities including the famous Nautical flee market. Assoc

    Isabel Ruiz Coldwell Banker Realty

    87200 Overseas Hwy Unit 1, Islamorada, FL 33036
  • /59

    $2,775,000

    Sold May 22, 2026

    226 S Coconut Palm Blvd, Plantation Key, FL 33070

    • 4 Beds
    • 4 Baths
    • 2,853 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $973/SF
    • 138 Days On Market

    Current Estimated Value $2,795,412

    Last Listing Agent AJ Vetter Palm House Real Estate

    226 S Coconut Palm Blvd, Plantation Key, FL 33070
    • /39

      Est $767,386

      Not Listed For Sale

      168 Ocean Dr, Tavernier, FL 33070

      • 2 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1983
      168 Ocean Dr, Tavernier, FL 33070

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Jennifer Miller LoKation Real Estate - Pompano Beach

  • /56

    $875,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    88181 Old Hwy Unit B3, Islamorada, FL 33036

    Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a

    Christy Hughes Coldwell Banker Schmitt Islamorada

    88181 Old Hwy Unit B3, Islamorada, FL 33036
  • /43

    $8,995 Per Month

    • 5 Beds
    • 4 Baths
    • 2,922 Sq Ft
    • House for Rent

    51 W Plaza Del Lago, Islamorada, FL 33036

    Welcome to PARADISE! FL Vacation Living at Key of Islamorada where luxury meets coastal living! This stunning property offers breathtaking bay views, creating the ultimate Florida Keys retreat. The home features a modern kitchen and updated bedroom flooring, 6-car driveway,blending style and comfort seamlessly. Step outside to your private boat ramp, offering direct access to the bay for endless

    Yure Contreras Brickell Realty Group International

    51 W Plaza Del Lago, Islamorada, FL 33036
  • /23

    $650,000

    Sold Dec 30, 2025

    129 S Rd, Upper Matecumbe Key Islamorada, FL 33036

    • 2 Beds
    • 1 Bath
    • 882 Sq Ft
    • Built 1958

    Last Sold Summary

    • 27% Below List Price
    • $737/SF
    • 118 Days On Market

    Current Estimated Value $672,997

    Last Listing Agent Wiebke Westedt LoKation Real Estate - Pompano Beach

    129 S Rd, Upper Matecumbe Key Islamorada, FL 33036
    • /28

      Est $643,578

      Not Listed For Sale

      88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

      • 2 Beds
      • 2 Baths
      • 1,330 Sq Ft
      • Built 1979
      88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Kathleen Denworth Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • /45

    $2,400,000

    • 3 Beds
    • 4 Baths

    316 North Dr, Islamorada, FL 33036

    Simply the best location, exclusive & extremely private. It's tucked away in the prestigious "Plantation Lake Estates," a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and

    Anthony Askowitz RE/MAX Advance Realty II

    316 North Dr, Islamorada, FL 33036
  • /10

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • House for Rent

    223 El Capitan Dr Unit A, Islamorada, FL 33036

    Florida Keys Living at Its Best!Beautifully furnished downstairs 2-bedroom, 1-bath unit available for rent in Islamorada. This move-in-ready home offers comfortable island living with utilities and dockage included.Enjoy the convenience of a fully furnished rental in one of the most desirable areas of the Florida Keys. Bring your boat, settle in, and start enjoying the Keys

    Lizette Miller Coldwell Banker Schmitt Islamorada

    223 El Capitan Dr Unit A, Islamorada, FL 33036
  • /20

    $4,000

    Sold May 14, 2026

    142 Airstream Ln, Tavernier, FL 33070

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 2022

    Last Sold Summary

    • $4/SF
    • 56 Days On Market

    Current Estimated Value $966,038

    Last Listing Agent Megan Jones Coldwell Banker Schmitt Islamorada

    142 Airstream Ln, Tavernier, FL 33070
    • /26

      Est $334,500

      Not Listed For Sale

      84961 Old Hwy Unit 9, Islamorada, FL 33036

      • 2 Beds
      • 2 Baths
      • 400 Sq Ft
      • Built 2023
      84961 Old Hwy Unit 9, Islamorada, FL 33036

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Claudette Mell Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • /56

    $1,850,000

    $145K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 2,936 Sq Ft

    138 Normandy Dr, Tavernier, FL 33070

    This is what Keys living is all about--waterfront, sunshine, and easy ocean access.Welcome to your slice of paradise in desirable Tavernier! This beautifully constructed 4-bedroom, 3 bath waterfront home, built in 2018 with solid CBS construction, offers the perfect blend of modern comfort and coastal living.Designed with both style and durability in mind, the home features plantation

    Kathe Kaile Still Water Properties

    138 Normandy Dr, Tavernier, FL 33070
  • /23

    $3,995 Per Month

    • 4 Beds
    • 2 Baths
    • Property for Rent

    164 Blue Harbor Dr, Tavernier, FL 33070

    PERFECT VACATION HOME! BRING YOUR BOAT! Available Immediately Beautiful & Spacious 4 Bedrooms & 2 Bathrooms POOL HOME with a wraparound porch & Pool Cabana & outdoor kitchen located in Blue Harbor Private Community Home is located Right across from the Boat Ramp Property offers plenty of space for a Big Family to enjoy endless days of fishing and water activities Space for boat and other water

    Ernie Echauri RE/MAX All Keys Real Estate

    164 Blue Harbor Dr, Tavernier, FL 33070
  • /2

    $1,595,000

    Sold Nov 06, 2025

    162 Azalea St, Tavernier, FL 33070

    • 4 Beds
    • 2 Baths
    • 996 Sq Ft
    • Built 1963

    Last Sold Summary

    • 9% Below List Price
    • $1,601/SF
    • 165 Days On Market

    Current Estimated Value $1,592,332

    Last Listing Agent Tracey Petrusha LoKation

    162 Azalea St, Tavernier, FL 33070
    • /38

      Est $623,313

      Not Listed For Sale

      200 Wrenn St Unit 605, Tavernier, FL 33070

      • 2 Beds
      • 2 Baths
      • 1,179 Sq Ft
      • Built 1975
      200 Wrenn St Unit 605, Tavernier, FL 33070

      Last Sold Summary

      • 156 Days On Market

      Last Listing Agent Lorie LaLonde American Caribbean Real Estate, Christie's International Real Estate

  • /103

    $18,999,000

    New Construction $496K PRICE DROP
    • 6 Beds
    • 8 Baths
    • 6,692 Sq Ft

    87429 Old Hwy, Islamorada, FL 33036

    The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand

    TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

    87429 Old Hwy, Islamorada, FL 33036
  • /21

    $2,200 Per Month

    • 1 Bath
    • 500 Sq Ft
    • House for Rent

    113 Mockingbird Rd Unit 1, Tavernier, FL 33070

    Modern, turnkey studio offering a bright and open layout with assigned Parking and Washer & Dryer. Near Mariners Hospital and local shops and Restaurants, the space features a cozy sleeping area with a nautical flair, plus a versatile living space for lounging or entertaining. Enjoy a fully equipped kitchen with white shaker cabinets, quartz counters, stainless steel appliances, and a stylish

    Jennifer Gomez EXP Realty, LLC

    113 Mockingbird Rd Unit 1, Tavernier, FL 33070
  • /8

    Sold Jun 19, 2026

    40 High Point Rd Unit C105, Tavernier, FL 33070

    • 2 Beds
    • 1.5 Baths

    Last Sold Summary

    • 23 Days On Market

    Current Estimated Value $367,746

    Last Listing Agent Sharon Kelly-Brown Reel Keys Realty

    40 High Point Rd Unit C105, Tavernier, FL 33070
    • /12

      Est $293,251

      Not Listed For Sale

      96 Madeira Rd Unit 26, Islamorada, FL 33036

      • 1 Bed
      • 45 Sq Ft
      • Built 2014
      96 Madeira Rd Unit 26, Islamorada, FL 33036

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  • /89

    $2,195,000

    • 2 Beds
    • 2 Baths
    • 1,066 Sq Ft

    179 Plantation Ave, Tavernier, FL 33070

    A Truly Unique Florida Keys Property — Location, Lifestyle & Luxury!This may be the perfect location and the perfect home for those looking for the ultimate Florida Keys lifestyle. Ideally situated in the Upper Keys, and a few houses away from the bay. The ocean is at a short ten minutes boat ride. This unique property is just over an hour from Miami and offers everything you and your family need

    Ricardo Guerra Realty of Miami Inc

    179 Plantation Ave, Tavernier, FL 33070
  • /2

    $3,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,094 Sq Ft
    • House for Rent

    108 Valjean Ln, Tavernier, FL 33070

    For vacation rental families come and enjoy the Florida Keys. This great 3bdrms 2bths house is fully furnished witha modern bath and kitchen, cable, internet, pots and pans, water and more. Ocean access for boat lovers with adock available. Located within minutes of shops, restaurants, and John Pennekamp Park, it is the ideal location forSalt Life, boating, fishing, and scuba diving.

    108 Valjean Ln, Tavernier, FL 33070
  • /37

    $1,720,000

    Sold Jun 01, 2026

    309 Woods Ave, Tavernier, FL 33070

    • 3 Beds
    • 3 Baths
    • 1,248 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $1,378/SF
    • 2 Days On Market

    Current Estimated Value $1,714,681

    Last Listing Agent Jessica Pinder Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    309 Woods Ave, Tavernier, FL 33070
    • /46

      Est $760,772

      Not Listed For Sale

      163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

      • 6 Beds
      • 4 Baths
      • 2,240 Sq Ft
      • Built 1984
      163 Jo-Jean Way Unit Duplex, Tavernier, FL 33070

      Last Sold Summary

      • 42 Days On Market

      Last Listing Agent Aryl and Pati Robison RE/MAX All Keys Real Estate

  • /24

    $1,549,000

    • 3 Beds
    • 3 Baths
    • 1,704 Sq Ft

    135 Tequesta St, Tavernier, FL 33070

    Waterfront 3/3 Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , Split level living layout which works great as in law quarters ,open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in

    Jonathan Minerick Homecoin.com

    135 Tequesta St, Tavernier, FL 33070
  • /7

    $3,300 Per Month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • House for Rent

    1 Meridian Ave, Key Largo, FL 33037

    2/1 Fully furnished/optional. Private Community Close to restaurants. No pets. Fenced yard with fire pit and jacuzzi.Utilities included.

    Billy Joe DeFuria South Florida Premier Realty Group LLC

    1 Meridian Ave, Key Largo, FL 33037
  • /53

    $2,425,000

    Sold Aug 03, 2026

    Unlisted Address

    • 3 Beds
    • 3.5 Baths
    • 1,768 Sq Ft
    • Built 2020

    Last Sold Summary

    • 8% Below List Price
    • $1,372/SF
    • 185 Days On Market

    Current Estimated Value $2,314,555

    Last Listing Agent Ernesto Portuondo American Caribbean Real Estate

    Unlisted Address
    • /32

      Est $1,831,959

      Not Listed For Sale

      87851 Old Hwy Unit P43, Islamorada, FL 33036

      • 4 Beds
      • 3 Baths
      • 2,668 Sq Ft
      • Built 1989
      87851 Old Hwy Unit P43, Islamorada, FL 33036

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada

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