Cudjoe Key, FL Homes

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  $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
• Explore Cudjoe Key

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  /70

  $12,500 per month

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft
  • Property for Rent

  21640 Overseas Hwy, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 442-3255

  21640 Overseas Hwy, Summerland Key, FL 33042
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  /35

  $217,000 Sold Jan 31, 2025

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 22 Days On Market

  Current Estimated Value $219,771

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
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  /21

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
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  /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
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  /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
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  /2

  $1,030,000 Sold Nov 19, 2025

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • $596/SF
  • 0 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042
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  /8

  Est $242,544 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042
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  /49

  $1,140,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

  Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 891-5684

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
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  /45

  $630,000 Sold Dec 08, 2025

  22970 Sharp Ln, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $1,094/SF
  • 4 Days On Market

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  22970 Sharp Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
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  /39

  $495,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 551-4336

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
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  /15

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Circle Cir, Verifying, FL 33042

  • Land

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  8 Calico Jack Circle Cir, Verifying, FL 33042
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  /2

  Est $268,122 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
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  /20

  $224,500

  • Land

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 418-4615

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
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  /59

  $860,300 Sold May 02, 2025

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Below List Price
  • $996/SF
  • 76 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
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  /44

  $1,150,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
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  /2

  $55,000 Sold Oct 22, 2025

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042
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  /2

  Est $311,309 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
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  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 Sawyer Dr, Summerland Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
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  $1,100,000 Sold Jun 27, 2025

  21014 7th Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $808/SF
  • 102 Days On Market

  Current Estimated Value $1,093,941

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  21014 7th Ave, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
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  /48

  $319,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

  Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

  

  Ian Calderwood

  Bluescape Real Estate

  (305) 570-4554

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
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  /45

  $1,700,000 Sold Feb 13, 2025

  20942 6th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Below List Price
  • $613/SF
  • 42 Days On Market

  Current Estimated Value $1,771,629

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20942 6th Ave W, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042
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  /42

  $1,895,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  20771 2nd Ave W, Summerland Key, FL 33042

  Incredible Florida Keys living! High quality concrete construction, impact windows and doors and custom metal roof- this home is ABOVE FLOOD and has no stairs! Enjoy the ease of one level living, with the storm safety of being above flood. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool and tiki! Exceptional boating- the 100' concrete dock

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-5792

  20771 2nd Ave W, Summerland Key, FL 33042
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  /42

  $1,900,000 Sold Jun 29, 2025

  20867 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $1,116/SF
  • 17 Days On Market

  Current Estimated Value $1,886,599

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20867 5th Ave W, Cudjoe Key, FL 33042
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  /2

  Est $1,399,548 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  22863 Bluegill Ln, Cudjoe Key, FL 33042
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  /6

  $400,000 Open Sun 9AM - 1PM

  • Land

  21865 Spain Blvd, Summerland Key, FL 33042

  Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (305) 614-8634

  21865 Spain Blvd, Summerland Key, FL 33042
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  /71

  $3,150,000 Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $633/SF
  • 118 Days On Market

  Current Estimated Value $3,187,918

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  225 Colson Dr, Summerland Key, FL 33042
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  /3

  Est $604,000 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
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  /17

  $999,000

  • Land

  21082 6th Ave, Summerland Key, FL 33042

  An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
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  /32

  $450,000 Sold Mar 19, 2025

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 256 Days On Market

  Current Estimated Value $442,277

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /39

  $912,250 Sold Apr 03, 2025

  22879 Blackbeard Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $679/SF
  • 43 Days On Market

  Current Estimated Value $909,369

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22879 Blackbeard Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $966/SF
  • 14 Days On Market

  Last Listing Agent Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

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