Monroe County, FL Homes

• 

  

  

  /31

  $789,000

  • 4 Beds
  • 3 Baths
  • 2,074 Sq Ft

  908 66th St, Marathon, FL 33050

  Triplex in the heart of Marathon. Configured as 3/1, 1/1, and studio apartment. Great income property fully occupied. On 10,000 sf lot with large storage in back. Great quiet neighborhood close to the oceanLong term tenants want to stay, 3 electric and 1 water.3/1 $2,400 1/1 $1,500 Studio $1,200

  

  Terry Canto

  American Caribbean Real Estate, Christie's International Real Estate

  (786) 822-6653

  908 66th St, Marathon, FL 33050
• 

  

  

  /10

  $3,750 per month

  • 1 Bed
  • 1 Bath
  • 475 Sq Ft
  • Property for Rent

  621 Whitehead St, Key West, FL 33040

  Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush

  

  Damian Vantriglia

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  (786) 882-1353

  621 Whitehead St, Key West, FL 33040
• 

  

  

  /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

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

  806 Pearl St, Key West, FL 33040
• 

  

  

  /18

  Est $347,828 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 403, Key West, FL 33040

  3312 Northside Dr Unit 403, Key West, FL 33040
• 

  

  

  /17

  $345,000

  • Land
  • 0.04 Acre
  • $8,625,000 per Acre

  94825 Overseas Hwy #70, Key Largo, FL 33037

  Design a custom luxury retreat on Lot 70 in prestigious Key Largo Ocean Resort. This prime cleared lot offers space for a multi-level residence with covered parking, just steps from the oceanfront marina with direct access to the Atlantic with no bridges to ocean. Enjoy resort-style amenities: gated entry, clubhouse, pool, gym, courts, pier and private beach. Ideal for elegant island living or

  

  Delainy Quintero

  One Trust Realty Inc.

  (855) 529-0235

  94825 Overseas Hwy #70, Key Largo, FL 33037
• 

  

  /8

  $2,700 - $3,000 per month

  Coco Palms

  2 Beds

  21585 Overseas Hwy, Cudjoe Key, FL 33042

  Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

  21585 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /6

  $235,000 Sold Feb 05, 2025

  31450 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft
  • Built 1963

  Last Sold Summary

  • $490/SF
  • 19 Days On Market

  Last Listing Agent Kirksten Irick Preferred Properties (KW)

  31450 Avenue C, Big Pine Key, FL 33043
• 

  

  /31

  Est $738,324 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft

  4245 Egret Ln, Summerland Key, FL 33042

  4245 Egret Ln, Summerland Key, FL 33042
• 

  

  /42

  $3,195,000

  • 4 Beds
  • 4 Baths
  • 1,653 Sq Ft

  512 Emma St, Key West, FL 33040

  Welcome to 512 Emma Street, an immaculate 4-bedroom, 4-bathroom home located behind the gates of the prestigious Truman Annex, widely regarded as Key West's premier neighborhood. From this coveted address, you're just steps from beaches, shops, restaurants, the amphitheater, nightlife, and all the charm of Old Town.Inside, the first floor offers bright, open living with luxury finishes

  

  Cardenas & Krug Team

  Ocean Sotheby's International Realty

  (786) 833-7181

  512 Emma St, Key West, FL 33040
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  /9

  $3,800 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  179 Jasmine St, Tavernier, FL 33070

  AVAILABLE FEB 1. Three-bedroom, two-bath upstairs home located in a popular neighborhood. Close to schools, hospital, shopping and great restaurants. Concrete home with large kitchen, granite countertops, all appliances, great counter with seating for dining or entertainment. Also has a separate dining room. There are three nicely sized bedrooms - two have sliding glass doors leading out to a

  Gladys Cornell RE/MAX All Keys Real Estate

  179 Jasmine St, Tavernier, FL 33070
• 

  

  /9

  $240,000 Sold Jun 13, 2025

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

  • Land
  • 0 Acre

  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
• 

  

  /43

  Est $1,127,042 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,161 Sq Ft

  23 Harbor Dr, Key Largo, FL 33037

  23 Harbor Dr, Key Largo, FL 33037
• 

  

  /55

  $5,999,995

  • 4 Beds
  • 4 Baths
  • 3,228 Sq Ft

  75560 Overseas Hwy, Islamorada, FL 33036

  Discover Serenity Cove: Where Privacy Meets the Ease of Keys LivingSerenity Cove is a distinctive waterfront estate that offers an exceptional blend of privacy, space, and comfort along the calm waters of Florida Bay. Set on nearly 1.75 acres stretching from the main highway to the bay, this custom designed property invites you to enjoy the easy, relaxed lifestyle that has made the Florida Keys

  

  Krissy Carnahan

  Realty ONE Group Destination (ISL)

  (786) 933-9406

  75560 Overseas Hwy, Islamorada, FL 33036
• 

  /2

  $2,349 - $2,849 per month

  CoCo Vista

  1 - 3 Beds

  96 Coco Plum Dr, Marathon, FL 33050

  96 Coco Plum Dr, Marathon, FL 33050
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  /4

  $1,200,000 Sold Nov 20, 2025

  1108 Whitehead St, Key West, FL 33040

  • Land

  Last Sold Summary

  • 0 Days On Market

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

  1108 Whitehead St, Key West, FL 33040
• 

  

  /38

  Est $4,805,508 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,281 Sq Ft

  508 Virginia St, Key West, FL 33040

  508 Virginia St, Key West, FL 33040
• 

  

  /73

  $620,000

  • 2 Beds
  • 2 Baths
  • 806 Sq Ft

  138 Golf Club Dr, Key West, FL 33040

  Welcome to 138 GC Dr., located in the highly sought-after Key West Golf Club residential community. Surrounded by acres of open space w/Rees-Jones designed 18-hole Championship Golf Course. INVITING, Ready for Immediate Occupancy, ''Fresh as a Daisy,'' Townhome. Just waiting for you! Beautifully maintained home offers the perfect blend of island living and resort-style amenities. Featuring low

  

  Robin Mitchell

  Keller Williams Key West Compass Realty

  (786) 841-2596

  138 Golf Club Dr, Key West, FL 33040
• 

  

  /23

  $3,750 per month

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

  27 Seaside Ave, Key Largo, FL 33037

  This adorable fully furnished 2 bedroom, 2 bathroom home is situated on an exceptionally large, multi-lot parcel offering space and flexibility rarely found in the Florida Keys.The home features an inviting layout with comfortable furnishings, making it ideal for tenants seeking a turnkey, long-term rental. Elevated construction with CBS exterior and metal roof provides durability and peace of

  Kimberly Hamilton Better Homes and Gardens Real Estate Destinations

  27 Seaside Ave, Key Largo, FL 33037
• 

  

  /55

  $1,375,000 Sold May 30, 2025

  158 Iroquois Dr, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1977

  Last Sold Summary

  • 19% Below List Price
  • $716/SF
  • 210 Days On Market

  Current Estimated Value $1,382,741

  Last Listing Agent Jessica Wolf Luxe Properties, LLC.

  158 Iroquois Dr, Islamorada, FL 33036
• 

  

  /43

  Est $2,273,518 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,935 Sq Ft

  340 S Point Dr, Summerland Key, FL 33042

  340 S Point Dr, Summerland Key, FL 33042
• 

  

  /42

  $749,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 632, Key West, FL 33040

  Experience Ultimate Elegance at Key West's Marriott Beachside Resort. This offering includes two luxurious, fully furnished units--a Signature King Room and a Resort View Suite--each designed to deliver an exceptional blend of comfort and sophistication. Together, they provide flexibility as a full-time residence, vacation retreat, or income-producing rental property with two coveted TRANSIENT

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (786) 422-5828

  3841 N Roosevelt Blvd Unit 632, Key West, FL 33040
• 

  

  /25

  $3,900 - $4,650 per month

  NAS Key West Homes

  3 Beds

  800 Sigsbee Rd, Key West, FL 33040

  NAS Key West Homes is located in Key West, Florida. In addition to the prime location, we offer a variety of floor plans and neighborhoods to fit your needs. Our community is all-inclusive, with baseline utilities, exclusive recreational and fitness amenities, lawn care and an award-winning resident events program included in your monthly rent. Our community professional on-site property name

  800 Sigsbee Rd, 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

  Last Listing Agent Ellen Gvili Ocean Sotheby's International Realty

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

  

  /34

  Est $1,974,631 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft

  1406 Pine St, Key West, FL 33040

  1406 Pine St, Key West, FL 33040
• 

  

  /44

  $1,250,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  283 Golf Club Dr, Key West, FL 33040

  Nestled along the lush 16th fairway of the Key West Golf Club, this beautifully upgraded 3-bedroom, 2.5-bath residence offers the perfect blend of privacy, style, and island charm. A rare find, the home also includes a versatile office space that can easily serve as a fourth bedroom , ideal for guests or a growing family.Step inside the 1600 sqft area to discover a bright, open floor plan with an

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 746-8259

  283 Golf Club Dr, Key West, FL 33040
• 

  

  /31

  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Property for Rent

  117 W Sandy Cir, Big Pine Key, FL 33043

  Great 4/2 in Big Pine Key, perfect for a family or roommate situation. Pets allowed!!!Walk right into your living room that over looks the heart of the home, your kitchen. Great for entertaining for family and friends coming over. Split floor plan with three bedrooms on one side and one on the other. Step outside to a great yard, big enough for all your toys and just down the highway is a boat

  Bobby Coe RE/MAX Keys Connection (KW)

  117 W Sandy Cir, Big Pine Key, FL 33043
• 

  

  /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 $556,918

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

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

  

  /47

  Est $1,197,672 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  3827 Dyer Rd, Big Pine Key, FL 33043

  3827 Dyer Rd, Big Pine Key, FL 33043
• 

  

  /49

  $1,998,000

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 788-8217

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /35

  $2,650 - $3,967 per month

  The Quarry

  1 - 3 Beds

  10 Betty Rose Dr, Key West, FL 33040

  Welcome to The Quarry, a residential community in Key West, FL featuring one, two, and three bedroom apartments. Spacious layouts welcome you home, along with exceptional service and an ideal location close to shopping, dining and entertainment.

  10 Betty Rose Dr, Key West, FL 33040
• 

  

  /37

  $1,000,000 Sold Nov 26, 2025

  301 Woods Ave, Tavernier, FL 33070

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft
  • Built 1968

  Last Sold Summary

  • 23% Below List Price
  • $727/SF
  • 155 Days On Market

  Last Listing Agent AJ Vetter Palm House Real Estate

  301 Woods Ave, Tavernier, FL 33070
• 

  

  /3

  Est $1,251,395 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  908 Windsor Ln, Key West, FL 33040

  908 Windsor Ln, Key West, FL 33040
• 

  

  /6

  $499,000

  • Land

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

  7049 sf Oceanfront Lot with beautiful views of Cudjoe Bay ! Build your dream home in Cudjoe Key ! Don't miss out on this great opportunity to build and live in one of the most desirable neighborhoods in the Keys !

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 659-1030

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /36

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Townhouse for Rent

  4903 49th St, Marathon, FL 33050

  Enjoy classic Florida Keys living in this waterfront 2-bedroom, 1-bath home located at 4903 49th Street in Marathon. Situated directly on the water, this is an ideal long-term rental for those looking to enjoy the Keys lifestyle year-round. The home features a functional and comfortable layout with two well-sized bedrooms, a full bathroom, and an open living area filled with natural light. Step

  Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

  4903 49th St, Marathon, FL 33050
• 

  

  /66

  $3,400,000 Sold Feb 04, 2025

  28 Aster Terrace, Key West, FL 33040

  • 4 Beds
  • 4 Baths
  • 2,057 Sq Ft
  • Built 1968

  Last Sold Summary

  • 13% Below List Price
  • $1,653/SF
  • 57 Days On Market

  Current Estimated Value $3,110,219

  Last Listing Agent Suzanne Moore Suzanne Moore Real Estate

  28 Aster Terrace, Key West, FL 33040
• 

  

  /7

  Est $681,012 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 810 Sq Ft

  148 Golf Club Dr, Key West, FL 33040

  148 Golf Club Dr, Key West, FL 33040
• 

  

  /13

  $250,000

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  1801 N Roosevelt Blvd Unit M28, Key West, FL 33040

  LIVEABOARD Houseboat & Slip (Package) at Garrison Bight Marina (Houseboat Row). It's a Leasehold to the City of Key West and with the Transfer of Title to your name. NO RENTALS, VRBO/AIRBNB! This community is Historic. It's a TRUE KEY WEST LIFESTYLE... CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one. Absolutely adorable. This community

  

  Annie Rivera

  Berkshire Hathaway Florida Realty

  (786) 565-6353

  1801 N Roosevelt Blvd Unit M28, Key West, FL 33040
• 

  

  /35

  $2,009 - $3,096 per month

  Playa Apartments

  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

  21 1st Ave, Key Largo, FL 33037
• 

  

  /40

  $975,000 Sold Jul 03, 2025

  13 Garden Cove Dr, Key Largo, FL 33037

  • 5 Beds
  • 3 Baths
  • Built 2024

  Last Sold Summary

  • 18% Below List Price
  • 240 Days On Market

  Current Estimated Value $984,862

  Last Listing Agent Merlin Perez Golden International Realty Corp

  13 Garden Cove Dr, Key Largo, FL 33037
• 

  

  /48

  Est $4,243,022 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,983 Sq Ft

  108 Sunset Dr, Marathon, FL 33050

  108 Sunset Dr, Marathon, FL 33050

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