65,633

Monroe County, FL Homes

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  • /70

    $789,000

    $14K PRICE INCREASE Under Contract
    • 2 Beds
    • 2 Baths
    • 853 Sq Ft

    88540 Overseas Hwy Unit 503 + Boat Slip, Tavernier, FL 33070

    Beautifully furnished and updated condo offering stunning water and sunset views, plus a deeded boat slip in one of the best-protected marinas in the Keys. Features include impact windows and triple sliding glass doors that showcase panoramic views from the living room and primary bedroom. The kitchen, bathrooms, flooring, and custom dining nook have all been tastefully renovated. High-end

    Agent Photo

    Karol Marsden

    Freewheeler Realty, Inc.

    88540 Overseas Hwy Unit 503 + Boat Slip, Tavernier, FL 33070
  • /20

    $2,834

    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 $2,834/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 29, 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
  • /37

    $875,000

    Sold Jan 30, 2026

    16 Flamingo Rd, Key Largo, FL 33037

    • 2 Beds
    • 1.5 Baths
    • 672 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $1,302/SF
    • 98 Days On Market

    Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

    16 Flamingo Rd, Key Largo, FL 33037
    • /37

      Est $1,164,201

      Not Listed For Sale

      521 8th St, Key Colony Beach, FL 33051

      • 4 Beds
      • 1,830 Sq Ft
      • Built 1994
      521 8th St, Key Colony Beach, FL 33051

      Last Sold Summary

      • 57 Days On Market

  • /41

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 947 Sq Ft

    104350 Overseas Hwy Unit A204, Key Largo, FL 33037

    Turnkey Florida Keys Condo with Weekly Rentals Allowed - Fully Furnished in Moon BayThis fully furnished 2BR / 1.5BA condo plus den (3rd sleeping area) in Moon Bay offers 947 sq ft of bright, comfortable living space and is ready for immediate enjoyment or rental income.The unit features stainless steel appliances, impact windows and doors, spacious bedrooms, a private balcony, in-unit

    Agent Photo

    Philip Kravitz

    Coldwell Banker Schmitt Key Largo

    104350 Overseas Hwy Unit A204, Key Largo, FL 33037
  • /20

    $5,870

    Total Monthly Price

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

    398 Burton Dr Unit SI ID1545789P, Tavernier, FL 33070

    The advertised rate of $5,871/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 1, 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

    398 Burton Dr Unit SI ID1545789P, Tavernier, FL 33070
  • /10

    $450,000

    Sold Oct 24, 2025

    351 20th St, Marathon, FL 33050

    • Land
    • 10,339 Sq Ft
    • $1,895,745 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 126 Days On Market

    Last Listing Agent Greg Dully RE/MAX All Keys Real Estate

    351 20th St, Marathon, FL 33050
    • /63

      Est $3,276,915

      Not Listed For Sale

      314 E Seaview Dr, Duck Key, FL 33050

      • 4 Beds
      • 3.5 Baths
      • 3,295 Sq Ft
      • Built 2020
      314 E Seaview Dr, Duck Key, FL 33050

      Last Sold Summary

      • 171 Days On Market

  • /68

    $37,500

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    617 Front St Unit B-24 Week 45, Key West, FL 33040

    Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    617 Front St Unit B-24 Week 45, Key West, FL 33040
  • /20

    $7,470

    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 $7,470/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 29, 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
  • /64

    $3,580,000

    Sold Sep 17, 2025

    180 13th St, Key Colony Beach, FL 33051

    • 5 Beds
    • 4.5 Baths
    • 2,741 Sq Ft
    • Built 2022

    Last Sold Summary

    • 7% Below List Price
    • $1,306/SF
    • 276 Days On Market

    Current Estimated Value $3,574,949

    Last Listing Agent Becky Newman Better Homes and Gardens Real Estate Destinations

    180 13th St, Key Colony Beach, FL 33051
    • /58

      Est $1,757,195

      Not Listed For Sale

      107 Point Pleasant Dr, Key Largo, FL 33037

      • 5 Beds
      • 4 Baths
      • 2,957 Sq Ft
      • Built 2022
      107 Point Pleasant Dr, Key Largo, FL 33037

      Last Sold Summary

      • 0 Days On Market

  • /28

    $815,000

    $34K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,471 Sq Ft

    124 Ocean Shores Dr, Key Largo, FL 33037

    Exceptional elevated 3BR/2BA CBS residence with metal roof located in one of Key Largo's most desirable areas. This tastefully updated home offers an airy open-concept design highlighted by a designer kitchen featuring quartz countertops, stainless steel appliances, subway tile backsplash, recessed LED lighting, and seamless entertaining space.The spacious primary suite includes a private

    Agent Photo

    Philip Kravitz

    Coldwell Banker Schmitt Key Largo

    124 Ocean Shores Dr, Key Largo, FL 33037
  • /13

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    D4 10th Ave Unit B unit, Stock Island, FL 33040

    Property Id: 2725559 Location : 4D 10th Ave Stock Island $2200 per month rent, all utilities are included. Require security deposit $1000 and first month rent to move in. Pet friendly. Washer, dryer in the unit. 10 minutes to downtown Key West.

    D4 10th Ave Unit B unit, Stock Island, FL 33040
  • /18

    $170,000

    Sold Aug 25, 2025

    1801 N Roosevelt Blvd, Key West, FL 33040

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 26% Below List Price
    • 105 Days On Market

    Last Listing Agent Randy Moss Coldwell Banker Schmitt RE Co

    1801 N Roosevelt Blvd, Key West, FL 33040
    • /10

      Est $305,252

      Not Listed For Sale

      14 Dolphin Rd, Key West, FL 33040

      • 2 Beds
      • Built 1985
      14 Dolphin Rd, Key West, FL 33040

      Last Sold Summary

      • 8 Days On Market

  • /44

    $65,000

    $4K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

    Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040
  • /20

    $3,451

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,377 Sq Ft
    • Condo for Rent

    210 W 2nd Ct Unit SI FL2-ID1546489P, Key Largo, FL 33037

    The advertised rate of $3,452/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 1, 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

    210 W 2nd Ct Unit SI FL2-ID1546489P, Key Largo, FL 33037
  • /60

    $950,000

    Sold Oct 17, 2025

    76 W Shore Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,028 Sq Ft
    • Built 2001

    Last Sold Summary

    • 13% Below List Price
    • $924/SF
    • 369 Days On Market

    Current Estimated Value $951,227

    Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

    76 W Shore Dr, Summerland Key, FL 33042
    • /46

      Not Listed For Sale

      14 Gayton Place, Key Largo, FL 33037

      • 3 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1971
      14 Gayton Place, Key Largo, FL 33037

      Last Sold Summary

      • 155 Days On Market

  • /29

    $499,000

    $66K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 826 Sq Ft

    500 Burton Dr Unit 1202, Tavernier, FL 33070

    Turnkey 2BD/2BA Ocean Pointe Condo - Fully Furnished, Short-Term Rentals Allowed! Welcome to paradise! This beautiful 2-bedroom, 2-bathroom condo in the sought-after Ocean Pointe community offers the perfect blend of luxury, convenience, and income potential. With 826 sq ft of thoughtfully designed living space, this fully furnished, turnkey unit is ready for immediate occupancy or short-term

    Agent Photo

    Philip Kravitz

    Coldwell Banker Schmitt Key Largo

    500 Burton Dr Unit 1202, Tavernier, FL 33070
  • /18

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • House for Rent

    1635 Pandorea Ln, Big Pine Key, FL 33043

    Welcome to your ideal rental in Big Pine Key, Florida! This charming property offers a perfect environment for those seeking a peaceful lifestyle close to nature and conveniences.Key Property Features include a spacious living area designed for comfort, ensuring you have plenty of room to relax and entertain. Enjoy the benefit of central heating and air conditioning, complemented by

    1635 Pandorea Ln, Big Pine Key, FL 33043
  • /93

    $2,600,000

    Sold May 18, 2026

    114 Royal Ln, Islamorada, FL 33036

    • 4 Beds
    • 5 Baths
    • 3,467 Sq Ft
    • Built 2026

    Last Sold Summary

    • 13% Below List Price
    • $750/SF
    • 73 Days On Market

    Current Estimated Value $2,289,498

    Last Listing Agent Dominic Rivera Pine River Realty, LLC.

    114 Royal Ln, Islamorada, FL 33036
    • /27

      Not Listed For Sale

      115 Long Key Rd, Key Largo, FL 33037

      • 2 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1999
      115 Long Key Rd, Key Largo, FL 33037

      Last Sold Summary

      • 7 Days On Market

  • /8

    $259,000

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft

    60 Ed Swift Rd, Key West, FL 33040

    Prime redevelopment opportunity just minutes from Key West! This 1959 single-wide mobile home sits on a desirable lot and is ready for its next chapter. The property is vacant and offered as-is, with no repairs or improvements to be made by the seller. There are no HOA or association fees, adding flexibility for future use or redevelopment. Due to the age of the structure, this is a cash-only

    Agent Photo

    Terry Garcia

    Keller Williams Key West Compass Realty

    60 Ed Swift Rd, Key West, FL 33040
  • /20

    $21,469

    Total Monthly Price

    • 4 Beds
    • 4 Baths
    • 2,594 Sq Ft
    • Condo for Rent

    811 104th St Unit SI ID1325586P, Marathon, FL 33050

    The advertised rate of $21,469/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 17, 2027.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

    811 104th St Unit SI ID1325586P, Marathon, FL 33050
  • /4

    $2,315,000

    Sold Feb 20, 2026

    1309 Petronia St, Key West, FL 33040

    • 3 Beds
    • 3 Baths
    • 1,675 Sq Ft
    • Built 1938

    Last Sold Summary

    • 2% Below List Price
    • $1,382/SF
    • 30 Days On Market

    Current Estimated Value $2,281,386

    Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

    1309 Petronia St, Key West, FL 33040
    • /57

      Est $5,804,923

      Not Listed For Sale

      124 Sunrise Dr, Marathon, FL 33050

      • 5 Beds
      • 5.5 Baths
      • 5,200 Sq Ft
      • Built 2010
      124 Sunrise Dr, Marathon, FL 33050

      Last Sold Summary

      • 53 Days On Market

  • /56

    $872,500

    $3K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    2600 Overseas Hwy Unit 85, Marathon, FL 33050

    Looking for direct Gulf views, space, resort-style amenities, and strong investment potential? This direct gulf-front 3-bedroom, 2.5-bath townhome at Tranquility Bay Resort checks all the boxes. Set on open gulf waters in the heart of Marathon, it offers unobstructed views and a proven rental history--making it ideal as both a personal getaway and income-producing property. Enjoy sweeping water

    Agent Photo

    Lorie Leal

    American Caribbean Real Estate

    2600 Overseas Hwy Unit 85, Marathon, FL 33050
  • /20

    $5,225

    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 $5,226/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 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

    87001 Overseas Hwy Unit SI FL2-ID1539601P, Islamorada, FL 33036
  • /20

    $1,500,000

    Sold Jul 31, 2025

    9922 Aviation Blvd, Marathon, FL 33050

    • 4 Beds
    • 4 Baths
    • 1,666 Sq Ft
    • Built 1980

    Last Sold Summary

    • 20% Below List Price
    • $900/SF
    • 137 Days On Market

    Current Estimated Value $1,561,677

    Last Listing Agent Stanley Rosen The Keyes Company

    9922 Aviation Blvd, Marathon, FL 33050
    • /42

      Est $1,996,270

      Not Listed For Sale

      106 Tequesta St, Tavernier, FL 33070

      • 4 Beds
      • 4 Baths
      • 2,800 Sq Ft
      • Built 2022
      106 Tequesta St, Tavernier, FL 33070

      Last Sold Summary

      • 281 Days On Market

  • /51

    $2,300,000

    $150K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,086 Sq Ft

    1 Bougainvillea Ave, Key West, FL 33040

    Welcome to luxury waterfront living in sought-after Key Haven. Completely reimagined by Affiliated Builders, this stunning residence offers the perfect blend of sophisticated design, modern functionality, and island lifestyle. This home has been thoughtfully renovated with gorgeous designer finishes and meticulous attention to detail, creating a truly turnkey coastal retreat. The spacious floor

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    1 Bougainvillea Ave, Key West, FL 33040
  • /8

    $6,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • House for Rent

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908 Canal front pool home with a double fenced in lot. Enough room for all your boats and toys. Large saltwater pool perfect for soaking up the sun and enjoying a peaceful afternoon. The split layout provides privacy with your own separate areas to unwind. Bring your 4 legged family members. Bonus room could be the 4th bedroom or office. Large AC storage area or workshop and

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • /2

    $1,030,000

    Sold Nov 19, 2025

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 2010

    Last Sold Summary

    • $596/SF
    • 0 Days On Market

    Current Estimated Value $1,122,179

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042
    • /50

      Est $2,159,494

      Not Listed For Sale

      129 Bimini Dr, Duck Key, FL 33050

      • 4 Beds
      • 3.5 Baths
      • 3,319 Sq Ft
      • Built 2020
      129 Bimini Dr, Duck Key, FL 33050

      Last Sold Summary

      • 305 Days On Market

  • /37

    $725,000

    Open Sun 12PM - 2PM $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft

    29160 Primrose Ln, Big Pine Key, FL 33043

    Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key. Featuring a garage and tons of storage inside and out, fenced yard & room for a pool! Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living. Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    29160 Primrose Ln, Big Pine Key, FL 33043
  • /20

    $7,920

    Total Monthly Price

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

    629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040

    The advertised rate of $7,920/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 31, 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

    629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040
  • /33

    $910,000

    Sold Apr 13, 2026

    151 Cutthroat Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2.5 Baths
    • 1,140 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $798/SF
    • 46 Days On Market

    Current Estimated Value $910,802

    Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

    151 Cutthroat Dr, Summerland Key, FL 33042
    • /68

      Est $3,030,177

      Not Listed For Sale

      127 Marina Ave, Key Largo, FL 33037

      • 4 Beds
      • 3.5 Baths
      • 3,470 Sq Ft
      • Built 2017
      127 Marina Ave, Key Largo, FL 33037

      Last Sold Summary

      • 97 Days On Market

Showing Results 121 - 160, Page 4 of 18

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