65,010

Monroe County, FL Homes

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  • /29

    $514,000

    $51K 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

    (786) 686-3080

    500 Burton Dr Unit 1202, Tavernier, FL 33070
  • /20

    Starting at $3,145 Per Month

    • 1 - 3 Beds

    750 Fort St, Key West, FL 33040

    Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

    Lofts at Bahama Village

    (786) 706-4309

    750 Fort St, Key West, FL 33040
  • /45

    $2,900,000

    Sold Jan 09, 2026

    1224 Florida St, Key West, FL 33040

    • 5 Beds
    • 5.5 Baths
    • 2,760 Sq Ft
    • Built 2006

    Last Sold Summary

    • 9% Below List Price
    • $1,051/SF
    • 56 Days On Market

    Current Estimated Value $2,894,232

    Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

    1224 Florida St, Key West, FL 33040
    • /70

      Est $786,176

      Not Listed For Sale

      22933 Buccaneer Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,088 Sq Ft
      • Built 1995
      22933 Buccaneer Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 74 Days On Market

  • /50

    $2,900,000

    $300K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 2,608 Sq Ft

    16 North Dr, Key Largo, FL 33037

    Bayfront living in the Upper Keys at its finest. Located at 16 North Drive, this modern coastal residence offers 3 bedrooms plus a studio and separate in-law quarters, 5 bathrooms, and approximately 2,608 sq ft of living space, set on a 0.26-acre lot with serene open-bay views and calm waters. Designed for relaxed island living, the home features light-filled interiors, seamless indoor-outdoor

    Agent Photo

    Catherine Pineda

    Coldwell Banker - Pinecrest

    (888) 357-4344

    16 North Dr, Key Largo, FL 33037
  • /20

    Starting at $2,702 Per Month

    • 1 - 2 Beds

    21 1st Ave, Key Largo, FL 33037

    Live in a tropical oasis where summer never ends at Playa Apartments in Key Largo. Surrounded by Old Florida Keys architecture and the ocean breeze, our community offers open-concept one- and two-bedroom homes with modern features and easy access to sun-soaked beaches and world-famous diving. Enjoy white sands at Harry Harris Park, explore John Pennekamp Coral Reef State Park, or dine along the

    Playa Apartments

    (844) 210-8152

    21 1st Ave, Key Largo, FL 33037
  • /40

    $522,500

    Sold Oct 10, 2025

    1115 Sombrero Blvd Unit 101A, Marathon, FL 33050

    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $477/SF
    • 228 Days On Market

    Current Estimated Value $525,134

    Last Listing Agent Ally Kelley Ocean Sotheby's International

    1115 Sombrero Blvd Unit 101A, Marathon, FL 33050
    • /53

      Est $861,734

      Not Listed For Sale

      1500 Ocean Bay Dr Unit S3, Key Largo, FL 33037

      • 3 Beds
      • 3 Baths
      • 925 Sq Ft
      • Built 1983
      1500 Ocean Bay Dr Unit S3, Key Largo, FL 33037

      Last Sold Summary

      • 6 Days On Market

  • /20

    $319,900

    $19K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft

    300 Ocean Dr Unit 22, Key Largo, FL 33037

    Discover Key Largo's Hidden Gem - Holiday By the Sea! This solid concrete fortress, nestled in an X-Flood Zone, has been beautifully upgraded with new electrical, air conditioning/heating, hot water tank, doors, flooring, blinds, and fresh paint. Enjoy harbor views from two of your three private balconies and take advantage of this prime location just steps from Key Largo Harbor Marina. Whether

    Agent Photo

    Philip Kravitz

    Coldwell Banker Schmitt Key Largo

    (786) 833-7005

    300 Ocean Dr Unit 22, Key Largo, FL 33037
  • /20

    $3,064

    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 $3,064/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 7, 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

    (855) 684-8966

    210 W 2nd Ct Unit SI FL2-ID1546489P, Key Largo, FL 33037
  • /50

    $1,632,000

    Sold Apr 30, 2026

    29678 Constitution Ave, Big Pine Key, FL 33043

    • 3 Beds
    • 2.5 Baths
    • 2,172 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Below List Price
    • $751/SF
    • 62 Days On Market

    Current Estimated Value $1,632,142

    Last Listing Agent Callie Harris Brenda Donnelly Real Estate LLC

    29678 Constitution Ave, Big Pine Key, FL 33043
    • /34

      Est $708,261

      Not Listed For Sale

      811 United St Unit 3, Key West, FL 33040

      • 1 Bed
      • 1 Bath
      • 622 Sq Ft
      • Built 1938
      811 United St Unit 3, Key West, FL 33040

      Last Sold Summary

      • 76 Days On Market

  • /66

    $31,000

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

    617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

    Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 233-3593

    617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
  • /20

    $25,018

    Total Monthly Price

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

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

    The advertised rate of $25,018/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 2, 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

    (305) 930-7143

    811 104th St Unit SI ID1325586P, Marathon, FL 33050
  • /7

    $1,056,000

    Sold Jul 21, 2025

    972 Shaw Dr, Key Largo, FL 33037

    • Land
    • 9,937 Sq Ft
    • $4,629,099 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 54 Days On Market

    Current Estimated Value $1,161,130

    Last Listing Agent Betsy Perez LoKation Real Estate - Pompano Beach

    972 Shaw Dr, Key Largo, FL 33037
    • /35

      Est $1,631,559

      Not Listed For Sale

      1075 Duval St Unit 1, Key West, FL 33040

      • 2 Beds
      • 2.5 Baths
      • 1,225 Sq Ft
      • Built 1987
      1075 Duval St Unit 1, Key West, FL 33040

      Last Sold Summary

      • 4 Days On Market

  • /70

    $49,900

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

    617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040

    Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café--everything you need for a

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (855) 450-7168

    617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040
  • /8

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    127 Monroe Dr Unit 1, Tavernier, FL 33070

    Property Id: 1434602Spacious one bedroom one bath full kitchen living room bathroom and washer dryer. Includes all appliances freshly renovated with new cabinets counters floors bathroom vanity sink toilet shower. AC units located in all bedrooms and main living room. Screened patio area overlooking a spacious yard, tiki and Canal cut in beautiful Tavernier.

    (656) 223-6596

    127 Monroe Dr Unit 1, Tavernier, FL 33070
  • /3

    $650,000

    Sold Dec 04, 2025

    806 Pearl St, Key West, FL 33040

    • 4 Beds
    • 3 Baths
    • 1,504 Sq Ft
    • Built 1933

    Last Sold Summary

    • $432/SF
    • 0 Days On Market

    Current Estimated Value $788,388

    Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    806 Pearl St, Key West, FL 33040
    • /41

      Est $894,928

      Not Listed For Sale

      8 Whistling Duck Ln, Key West, FL 33040

      • 3 Beds
      • 2.5 Baths
      • 1,060 Sq Ft
      • Built 1996
      8 Whistling Duck Ln, Key West, FL 33040

      Last Sold Summary

      • 62 Days On Market

  • /33

    $779,000

    $76K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 947 Sq Ft

    104350 Overseas Hwy Unit A-402 & Boat Slip, Key Largo, FL 33037

    Stunning Bayfront Condo in Moon Bay - Fully Furnished with Deeded Boat Slip!Experience the best of waterfront living in this beautifully appointed 2-bedroom, 1.5-bath condo in the sought-after Moon Bay community. This fully furnished unit boasts impact windows and doors, offering breathtaking bay views from the living room, patio, and master bedroom.A boater's dream, the property includes

    Agent Photo

    Philip Kravitz

    Coldwell Banker Schmitt Key Largo

    (888) 807-7481

    104350 Overseas Hwy Unit A-402 & Boat Slip, Key Largo, FL 33037
  • /20

    $4,058

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 2,098 Sq Ft
    • Condo for Rent

    115 Marina Ave Unit SI FL2-ID1546182P, Key Largo, FL 33037

    The advertised rate of $4,058/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 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

    (866) 718-0701

    115 Marina Ave Unit SI FL2-ID1546182P, Key Largo, FL 33037
  • /10

    $560,000

    Sold Dec 26, 2025

    2433 Linda Ave, Key West, FL 33040

    • 3 Beds
    • 2 Baths
    • 2,099 Sq Ft
    • Built 1953

    Last Sold Summary

    • 7% Below List Price
    • $267/SF
    • 96 Days On Market

    Current Estimated Value $613,444

    Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

    2433 Linda Ave, Key West, FL 33040
    • /26

      Est $795,866

      Not Listed For Sale

      1010 Snapper Ln, Key Largo, FL 33037

      • 3 Beds
      • 2 Baths
      • 1,375 Sq Ft
      • Built 1997
      1010 Snapper Ln, Key Largo, FL 33037

      Last Sold Summary

      • 108 Days On Market

  • /59

    $31,000

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

    617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

    Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await you from this desirable PENTHOUSE, top-floor end-unit deeded Timeshare week 37! Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café.Enjoy front-row views as Coast Guard

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 238-9517

    617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
  • /14

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 936 Sq Ft
    • House for Rent

    3693 Landers St, Big Pine Key, FL 33043

    Property Id: 2514237Annual Canal-Front Rental on Big Pine Key! Utilities not included. This charming 2-bedroom, 2-bath home sits on a desirable corner lot with water access, offering a relaxed island lifestyle. Enjoy peaceful views. House is on a corner cana. Nice screened-in back porch with sliding doors to living and dining areas.—perfect for morning coffee or evening unwinding. Open

    (786) 933-7769

    3693 Landers St, Big Pine Key, FL 33043
  • /9

    $240,000

    Sold Jun 13, 2025

    100 Morris Ln F-5, Key Largo, FL 33037

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 5% Above List Price
    • 30 Days On Market

    Last Listing Agent Yvette Doherty Coldwell Banker Schmitt R.E.

    100 Morris Ln F-5, Key Largo, FL 33037
    • /32

      Est $1,021,486

      Not Listed For Sale

      1606 United St, Key West, FL 33040

      • 3 Beds
      • 1.5 Baths
      • 1,216 Sq Ft
      • Built 1958
      1606 United St, Key West, FL 33040

      Last Sold Summary

      • 15 Days On Market

  • /58

    $32,500

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

    617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040

    Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (645) 230-1832

    617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040
  • /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 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

    (786) 998-1981

    629 Elizabeth St Unit SI ID1297833P, Key West, FL 33040
  • /4

    $1,200,000

    Sold Nov 20, 2025

    1108 Whitehead St, Key West, FL 33040

    • Land
    • 3,998 Sq Ft
    • $13,071,268 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Terri Spottswood Truman & Co. (KW)

    1108 Whitehead St, Key West, FL 33040
    • /41

      Est $651,210

      Not Listed For Sale

      11332 3rd Avenue Ocean, Marathon, FL 33050

      • 2 Beds
      • 2 Baths
      • 941 Sq Ft
      • Built 2013
      11332 3rd Avenue Ocean, Marathon, FL 33050

      Last Sold Summary

      • 274 Days On Market

  • /68

    $65,000

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

    617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040

    Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots in the resort, showcasing unobstructed, head-on views of the Gulf of Mexico.The residence features vaulted ceilings, extra windows for enhanced natural light, and multiple balconies designed to

    Agent Photo

    Stephanie Herrmann

    Truman & Co. (KW)

    (645) 231-4457

    617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040
  • /17

    $4,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Townhouse for Rent

    3321 Harriet Ave, Key West, FL 33040

    Property Id: 2589714Available July 1, 2026 | $4,850 per MonthWelcome to 3321 Harriet Avenue! A rare opportunity to lease a private pool home in Key West with no HOA restrictions and all the comforts of island living!This charming 3-bedroom, 2-bath home offers approximately 1,280 square feet of thoughtfully designed living space. The flexible floor plan features one bedroom

    (786) 705-8334

    3321 Harriet Ave, Key West, FL 33040
  • /33

    $250,000

    Sold Nov 18, 2025

    300 Duck Key Dr Unit 3, Marathon, FL 33050

    • 1 Bed
    • 1 Bath
    • 510 Sq Ft
    • Built 1969

    Last Sold Summary

    • 37% Below List Price
    • $490/SF
    • 226 Days On Market

    Current Estimated Value $308,645

    Last Listing Agent Ellen Gvili Ocean Sotheby's International Realty

    300 Duck Key Dr Unit 3, Marathon, FL 33050
    • /69

      Est $2,225,017

      Not Listed For Sale

      70 Bay Dr, Key West, FL 33040

      • 5 Beds
      • 2 Baths
      • 2,450 Sq Ft
      • Built 1993
      70 Bay Dr, Key West, FL 33040

      Last Sold Summary

      • 174 Days On Market

  • /58

    $49,900

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

    617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040

    Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove

    Agent Photo

    Stephanie Herrmann

    Truman & Co. Real Estate

    (833) 427-4068

    617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040
  • /20

    $29,551

    Total Monthly Price

    • 5 Beds
    • 5.5 Baths
    • 2,992 Sq Ft
    • Condo for Rent

    247 Pescayo Ave Unit SI ID1325585P, Marathon, FL 33050

    The advertised rate of $29,552/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 19, 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

    (645) 666-1687

    247 Pescayo Ave Unit SI ID1325585P, Marathon, FL 33050
  • /24

    $525,000

    Sold Aug 15, 2025

    3930 S Roosevelt Blvd Unit S405, Key West, FL 33040

    • 3 Beds
    • 2 Baths
    • 1,069 Sq Ft
    • Built 1991

    Last Sold Summary

    • $491/SF
    • 59 Days On Market

    Current Estimated Value $551,658

    Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

    3930 S Roosevelt Blvd Unit S405, Key West, FL 33040
    • /59

      Est $2,914,991

      Not Listed For Sale

      374 Bahia Ave, Key Largo, FL 33037

      • 4 Beds
      • 3 Baths
      • 3,306 Sq Ft
      • Built 1992
      374 Bahia Ave, Key Largo, FL 33037

      Last Sold Summary

      • 75 Days On Market

Showing Results 41 - 80, Page 2 of 18

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