65,010

Monroe County, FL Homes

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  • /41

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,082 Sq Ft

    22822 Buccaneer Ln, Summerland Key, FL 33042

    LOWEST PRICED STILTED WATERFRONT HOME IN CUDJOE KEY! Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional

    Agent Photo

    Cardenas & Krug Team

    Coastal Collection Real Estate Inc.

    (888) 836-2988

    22822 Buccaneer Ln, Summerland Key, FL 33042
  • /22

    $6,451

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    31 Palm Dr Unit SI FL1-ID1546457P, Key West, FL 33040

    The advertised rate of $6,451/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 9, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    31 Palm Dr Unit SI FL1-ID1546457P, Key West, FL 33040
  • /35

    $295,000

    Sold Jul 02, 2025

    439 83rd Street Ocean, Marathon, FL 33050

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $290/SF
    • 20 Days On Market

    Last Listing Agent Mallory Pinto Keys Ocean Realty Inc.

    439 83rd Street Ocean, Marathon, FL 33050
    • /34

      Est $786,553

      Not Listed For Sale

      88181 Old Hwy Unit 2B Slip 45, Islamorada, FL 33036

      • 2 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1979
      88181 Old Hwy Unit 2B Slip 45, Islamorada, FL 33036

      Last Sold Summary

      • 30 Days On Market

  • /28

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,184 Sq Ft

    290 46th St, Summerland Key, FL 33042

    Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport, and enjoy access to the Blanche Bergin Marina Park, complete with boat ramp and available dockage for a fee. This property is a fixer-upper, located on Summerland Key, at the base of the airport runway. 2/1 on one side, and an additional 12 x32 en suite with a separate entrance on the

    Agent Photo

    Christina Davis

    Coldwell Banker Schmitt RE Co.

    (645) 219-1684

    290 46th St, Summerland Key, FL 33042
  • /27

    $3,700 Per Month

    • 3 Beds
    • 2 Baths
    • 4,033 Sq Ft
    • House for Rent

    24 Bonita Ave, Key Largo, FL 33037

    SEASONAL RENTAL:Located in desirable Bowens Addition to Riviera Village in Key Largo, this 3-bedroom, 2-bath single-family home offers over 4,000 sq ft of living space on a 5,000+ sq ft lot. Built in 1990, the property features a spacious layout with ample room for entertaining or extended living. Community homeowners park includes boat ramp and bayfront beach access.Avaiable now till August 1

    Claire Albertson Luxe Properties

    24 Bonita Ave, Key Largo, FL 33037
  • /44

    $1,125,000

    Sold Jan 16, 2026

    283 Golf Club Dr, Key West, FL 33040

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $703/SF
    • 37 Days On Market

    Current Estimated Value $1,187,781

    Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

    283 Golf Club Dr, Key West, FL 33040
    • /41

      Not Listed For Sale

      1001 Hialeah Ln, Key Largo, FL 33037

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      1001 Hialeah Ln, Key Largo, FL 33037

      Last Sold Summary

      • 63 Days On Market

  • /48

    $1,675,000

    $115K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,034 Sq Ft

    159 Iroquois Dr, Islamorada, FL 33036

    Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full

    Agent Photo

    Pierre Bellion

    Ocean Sotheby's International Realty

    (645) 600-8447

    159 Iroquois Dr, Islamorada, FL 33036
  • /17

    $7,491

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,119 Sq Ft
    • Condo for Rent

    97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037

    The advertised rate of $7,492/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 25, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037
  • /38

    $650,000

    Sold May 19, 2026

    420 17th Court Gulf, Marathon, FL 33050

    • 2 Beds
    • 2 Baths
    • 1,199 Sq Ft
    • Built 1970

    Last Sold Summary

    • 7% Below List Price
    • $542/SF
    • 121 Days On Market

    Current Estimated Value $664,893

    Last Listing Agent Mallory Pinto Keys Ocean Realty Inc.

    420 17th Court Gulf, Marathon, FL 33050
    • /36

      Est $947,526

      Not Listed For Sale

      3666 S Seas St, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,519 Sq Ft
      • Built 1988
      3666 S Seas St, Big Pine Key, FL 33043

      Last Sold Summary

      • 89 Days On Market

  • /38

    $355,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,024 Sq Ft

    300 Ocean Dr Unit 26, Key Largo, FL 33037

    UNIQUE! Completely remodeled with a reworked floorplan to optimize space & functionality, this townhome is the crown jewel of the building! Welcome to Holiday by the Sea #26, a beautifully updated 2-bedroom, 2.5-bath townhome in the heart of Key Largo. Thoughtfully redesigned, this home offers a bright, open layout with modern finishes & efficient use of space throughout. The fully renovated

    Agent Photo

    Lorie Leal

    American Caribbean Real Estate

    (786) 882-2534

    300 Ocean Dr Unit 26, Key Largo, FL 33037
  • /17

    $3,995 Per Month

    • 3 Beds
    • 3 Baths
    • 1,428 Sq Ft
    • House for Rent

    94825 Overseas Hwy Unit 178, Key Largo, FL 33037

    BEAUTIFUL MULTI-Level Home INSIDE AN AMAZING WATERFRONT community with tons of amenities Tennis, Basketball, Pickleball Courts, Pool, Gym & more this home boasts 3 Bedrooms & 3 Bathrooms located close to Marina and with amazing views from Front Balcony SHORT TERM RENTAL as well Very spacious, beautiful kitchen, ample rooms A MUST SEE! Don't miss this opportunity to own in Prestigious Key Largo

    Ernie Echauri RE/MAX All Keys Real Estate

    94825 Overseas Hwy Unit 178, Key Largo, FL 33037
  • /44

    $1,675,000

    Sold Jul 30, 2025

    2605 Gulfview Dr, Key West, FL 33040

    • 3 Beds
    • 3 Baths
    • 1,320 Sq Ft
    • Built 1999

    Last Sold Summary

    • 7% Below List Price
    • $1,269/SF
    • 116 Days On Market

    Current Estimated Value $1,699,474

    Last Listing Agent Paige Bethel Island Home Realty Inc.

    2605 Gulfview Dr, Key West, FL 33040
    • /20

      Est $178,088

      Not Listed For Sale

      100 Avenue I Unit 19, Marathon, FL 33050

      • 1 Bed
      • Built 1987
      100 Avenue I Unit 19, Marathon, FL 33050

      Last Sold Summary

      • 31 Days On Market

  • /65

    $2,175,000

    Open Sat 12PM - 2PM $175K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,150 Sq Ft

    1209 Packer St, Key West, FL 33040

    Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (305) 614-6630

    1209 Packer St, Key West, FL 33040
  • /25

    $5,783

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Condo for Rent

    343 Oleander Dr Unit SI FL1-ID1539598P, Tavernier, FL 33070

    The advertised rate of $5,783/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 8, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    343 Oleander Dr Unit SI FL1-ID1539598P, Tavernier, FL 33070
  • /60

    $930,000

    Sold Jan 23, 2026

    27405 Guadaloupe Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2008

    Last Sold Summary

    • 2% Below List Price
    • $722/SF
    • 51 Days On Market

    Current Estimated Value $938,861

    Last Listing Agent Mark Gable Engel & Volkers Marathon

    27405 Guadaloupe Ln, Summerland Key, FL 33042
    • /15

      Est $305,155

      Not Listed For Sale

      21 Sombrero Blvd Unit 210, Marathon, FL 33050

      • 1 Bed
      • 1 Bath
      • 547 Sq Ft
      • Built 1986
      21 Sombrero Blvd Unit 210, Marathon, FL 33050

      Last Sold Summary

      • 14 Days On Market

  • /39

    $1,079,000

    $96K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,948 Sq Ft

    2926 Flagler Ave, Key West, FL 33040

    Welcome to 2926 Flagler Avenue! This single-family home has four bedrooms and two baths, a swimming pool and is nestled on a 6,360 square foot lot located in a wonderful New Town central location. The spacious interior affords you the opportunity to entertain family, friends, and truly relax in comfort. Having been well maintained throughout the years, this CBS home has a v-crimp metal roof,

    Agent Photo

    Terry Garcia

    Keller Williams Key West Compass Realty

    (786) 882-2409

    2926 Flagler Ave, Key West, FL 33040
  • /17

    $5,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,565 Sq Ft
    • House for Rent

    24840 Park Dr, Summerland Key, FL 33042

    { WOW } Try and find a rental in the Lower Florida Keys! Then, yet again, one with 3 bedrooms, 2 Full baths and spacious Kitchen, Livingroom, Dinning open concept layout. Welcome to living in Summerland Key Cove.Live where others vacation -- in Summerland Key Cove, just 25 miles from Key West. Whether you're a boater, pilot, fisherman, or someone who simply enjoys walking their dog by the water,

    Thomas Murphy LAER Realty

    24840 Park Dr, Summerland Key, FL 33042
  • /18

    $380,000

    Sold Mar 10, 2026

    204 Ocean Blvd, Tavernier, FL 33070

    • Land
    • 12,100 Sq Ft
    • $1,368,000 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 169 Days On Market

    Current Estimated Value $396,157

    Last Listing Agent Katie Raskob Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    204 Ocean Blvd, Tavernier, FL 33070
    • /50

      Est $721,949

      Not Listed For Sale

      88540 Overseas & Boat Slip #3 Hwy Unit 605, Plantation Key, FL 33070

      • 2 Beds
      • 2 Baths
      • 853 Sq Ft
      • Built 1985
      88540 Overseas & Boat Slip #3 Hwy Unit 605, Plantation Key, FL 33070

      Last Sold Summary

      • 29 Days On Market

  • /33

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft

    102 Harry Harris Dr, Tavernier, FL 33070

    Legal Duplex, Two electric meters, Two water meters, with two mailboxes and plenty of parking. Concrete building with metal roof. Both apartments have been nicely updated inside & out. Mini split AC's with tankless water heaters. Each apartment is 748 sq. ft. Downstairs is rented at $2,650.00 Upstairs is rented at $2,700.00 per month. Washer & Dryer in Storage building that both tenants can use.

    Agent Photo

    Tom Rodriguez

    American Caribbean Real Estate, Christie's International Real Estate

    (888) 973-0827

    102 Harry Harris Dr, Tavernier, FL 33070
  • /17

    $4,214

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 775 Sq Ft
    • Condo for Rent

    98381 Windward Ave Unit SI FL1-ID1546252P, Key Largo, FL 33037

    The advertised rate of $4,214/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 16, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    98381 Windward Ave Unit SI FL1-ID1546252P, Key Largo, FL 33037
  • /43

    $600,000

    Sold Feb 06, 2026

    601 W Ocean Dr Unit 407, Key Colony Beach, FL 33051

    • 2 Beds
    • 2.5 Baths
    • 1,475 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $407/SF
    • 78 Days On Market

    Current Estimated Value $603,889

    Last Listing Agent Tracy Chacksfield Berkshire Hathaway HomeServices Keys Real Estate

    601 W Ocean Dr Unit 407, Key Colony Beach, FL 33051
    • /58

      Est $804,072

      Not Listed For Sale

      1133 W Ocean Dr Unit 5, Key Colony Beach, FL 33051

      • 3 Beds
      • 3 Baths
      • 1,929 Sq Ft
      • Built 1982
      1133 W Ocean Dr Unit 5, Key Colony Beach, FL 33051

      Last Sold Summary

      • 42 Days On Market

  • /40

    $699,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,666 Sq Ft

    104 Sirius Ln, Key West, FL 33040

    Deep Water Dockage just 15 minutes from Key West! This rare corner canal-front property in Tamarac Park offers approximately 152' of dockage with 5' control depth and quick ocean access, a true boater's opportunity. Situated on one of the largest lots in the neighborhood (7,017 sq ft), this 3 Bedroom, 2 Bathroom home features 1,666 sq ft including a dramatic 2-story Great Room addition with

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (877) 586-7851

    104 Sirius Ln, Key West, FL 33040
  • /26

    $2,850 Per Month

    • 2 Beds
    • 1.5 Baths
    • 981 Sq Ft
    • Condo for Rent

    87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036

    LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED ON PLANTATION KEY/ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT

    Anthony Garcia The Keyes Company

    87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036
  • /9

    $325,000

    Sold Jun 12, 2025

    35 Sombrero Blvd Unit A3, Marathon, FL 33050

    • Built 2004

    Last Sold Summary

    • 18% Below List Price
    • 278 Days On Market

    Current Estimated Value $336,038

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    35 Sombrero Blvd Unit A3, Marathon, FL 33050
    • /8

      Not Listed For Sale

      30 Avenue F, Key Largo, FL 33037

      • 2 Beds
      • 1.5 Baths
      • 840 Sq Ft
      • Built 1984
      30 Avenue F, Key Largo, FL 33037

      Last Sold Summary

      • 2 Days On Market

  • /36

    $6,290,000

    • 13 Beds
    • 7 Baths
    • 5,022 Sq Ft

    21470 Overseas Hwy, Cudjoe Key, FL 33042

    Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest

    Agent Photo

    Jennifer Weeks

    Select Properties of NWFL

    (833) 404-5450

    21470 Overseas Hwy, Cudjoe Key, FL 33042
  • /29

    $4,320

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,345 Sq Ft
    • Condo for Rent

    87001 Overseas Hwy Unit SI FL2-ID1539601P, Islamorada, FL 33036

    The advertised rate of $4,320/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    87001 Overseas Hwy Unit SI FL2-ID1539601P, Islamorada, FL 33036
  • /41

    $320,000

    Sold Apr 28, 2026

    119 Cortez Dr Unit G11, Islamorada, FL 33036

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

    Last Sold Summary

    • 11% Below List Price
    • $618/SF
    • 34 Days On Market

    Current Estimated Value $342,227

    Last Listing Agent Melissa Nowell Coldwell Banker Schmitt Islamorada

    119 Cortez Dr Unit G11, Islamorada, FL 33036
    • /21

      Est $613,058

      Not Listed For Sale

      2601 S 2601 Roosevelt Blvd Unit 119C, Key West, FL 33040

      • 1 Bed
      • 1 Bath
      • 754 Sq Ft
      • Built 1967
      2601 S 2601 Roosevelt Blvd Unit 119C, Key West, FL 33040

      Last Sold Summary

      • 23 Days On Market

  • /7

    $185,000

    Under Contract
    • Land
    • 5,227 Sq Ft
    • $1,541,667 per Acre

    0 Gumbo Limbo Dr, Key Largo, FL 33037

    Build your dream home on this 50 x 105 vacant lot in the heart of Key Largo on a desirable single-family subdivision. Perfect opportunity to submit your set of plans and apply for a permit. Tier 3, with 30 points, starts high on the ROGO list. Proximity to restaurants, shops, Publix and all that Florida Keys have to offer. Only 1 hour from Miami yet a world of difference. Experience the island

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (855) 340-3362

    0 Gumbo Limbo Dr, Key Largo, FL 33037
  • /30

    $3,800 Per Month

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

    95401 Overseas Hwy, Key Largo, FL 33037

    Available July 15th! Fully furnished and renovated, this tropical Keys retreat offers the perfect blend of fun and functionality. Located at MM 95 Oceanside, right on the Overseas Highway, you'll enjoy front-row access to Key Largo's best restaurants, sandbars, and outdoor activities. The fully fenced property provides privacy and ample space to park your boat, RV, or water toys, with access to a

    Lizzet Torres One Family Realty, LLC

    95401 Overseas Hwy, Key Largo, FL 33037
  • /31

    $390,000

    Sold Jan 21, 2026

    585 116th Street Ocean, Marathon, FL 33050

    • 2 Beds
    • 1.5 Baths
    • 984 Sq Ft
    • Built 1955

    Last Sold Summary

    • 38% Below List Price
    • $396/SF
    • 177 Days On Market

    Current Estimated Value $438,162

    Last Listing Agent Paulette Thompson PA Ocean Sotheby's International

    585 116th Street Ocean, Marathon, FL 33050
    • /21

      Est $550,801

      Not Listed For Sale

      3314 Northside Dr Unit 93, Key West, FL 33040

      • 2 Beds
      • 2 Baths
      • 1,050 Sq Ft
      • Built 1986
      3314 Northside Dr Unit 93, Key West, FL 33040

      Last Sold Summary

      • 98 Days On Market

Showing Results 241 - 280, Page 7 of 18

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