Cudjoe Key, FL Homes

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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
• 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
• 

  

  /2

  $55,000 Sold Oct 22, 2025

  • Land

  • 2 Days On Market

  Lot 2 Rainbow Beach, Big Torch Key, FL 33042

  This is a 2 point lot to be used toward a building permit in Monroe County. Add to your current ROGO application or use it when submitting a new ROGO application to Monroe County. Contact Monroe County Planning Department for specific details on how and when these points can be used. Seller has several lots worth 1 and 2 points for sale if you are looking for additional points.

  Pamela Stangler Expert Realty LLC

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

  

  

  /58

  Est $1,654,788 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft

  1106 Thatch Ln, Summerland Key, FL 33042

  1106 Thatch Ln, Summerland Key, FL 33042
• 

  

  

  /33

  $329,000

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

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

  Cozy 1-Bedroom 1-bathroom Mobile Home with Enchanting Florida RoomLocated inside the very desirable Venture Out Gated Community.This charming and very well kept mobile home offers a comfortable and affordable living space. Key Features:* Fully tiled.* Comfortable Bedroom: With plenty of large windows. * Fully equipped kitchen with table, chairs and a built in desk.* Full Bathroom: Includes

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 550-7131

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /36

  $685,000 Sold Oct 15, 2025

  • 864 Sq Ft
  • $793/SF
  • 164 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2010

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

  GREAT PRICE for this canal-front, slice of paradise! As a successful, active vacation rental where nightly rentals are allowed, this is an excellent income-generating opportunity in the gated community of Venture Out. It's tastefully furnished and ready for you or your guests to enjoy. With all the amenities this 69-acre gated community offers, you might just decide to make it your primary home

  Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
• 

  

  /8

  Est $382,839 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042
• 

  

  /77

  $12,999,999

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /14

  $6,300 per month

  • 7 Beds
  • 6 Baths
  • 3,249 Sq Ft
  • House for Rent

  21660 Overseas Hwy, Summerland Key, FL 33042

  Private Oceanfront Beach House - Annual Rental Available.Your private slice of the Florida Keys, just 20 minutes from Key West. This direct oceanfront home offers sweeping Atlantic views and the ultimate coastal escape.Inside, you'll find an airy layout with plenty of natural light, stainless steel appliances, French doors, impact-rated sliders, doors, and windows, plus updated AC units for

  Kelly Gardner Bluescape Real Estate

  21660 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /43

  $870,000 Sold Oct 10, 2025

  • 1,452 Sq Ft
  • $599/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  22818 Privateer Dr, Summerland Key, FL 33042

  Waterfront Living Awaits!This spacious 3-bedroom, 2-bath canal front home offers the perfect blend of comfort and Florida lifestyle. Inside, large kitchen with generous counter seating, dining room, & living room designed for gatherings. Step outside to the screened porch and enjoy relaxing breezes year-round.Downstairs features an enclosure for extra space & storage, while outdoors you'll love

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  /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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  /46

  $2,999,999

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  653 Sawyer Dr, Summerland Key, FL 33042

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 238-6782

  653 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /3

  $75,000 Sold Oct 10, 2025

  • Land
  • 1.01 Acres
  • $74,124 per Acre

  • 41 Days On Market

  0 Asturias Rd, Cudjoe Key, FL 33042

  Lush, Tropical, acreage on Cudjoe Key. and Near the Water. Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering privacy and tranquility. Located close to a public boat ramp, you'll have easy access to world-class fishing, boating, and watersports. And with Key West

  Maryann Warren Coldwell Banker - Ft. Lauderdale

  0 Asturias Rd, Cudjoe Key, FL 33042
• 

  /2

  Est $249,892 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
• 

  

  /51

  $1,079,000 Pending

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

  22841 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-8373

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /62

  $1,185,000 Sold Oct 06, 2025

  • 1,344 Sq Ft
  • $882/SF
  • 37 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  22915 Bluegill Ln, Summerland Key, FL 33042

  Discover this beautifully remodeled waterfront residence that blends modern luxury with coastal living. Located on a wide canal perfect for larger boats, this home offers exceptional dockage and direct water access to Kemp Channel. Situated on a larger 10,200 sqft lot, step inside to an open-concept floor plan featuring a fully remodeled interior with luxury fixtures and finishes throughout. The

  Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
• 

  /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
• 

  

  /12

  $299,000 Under Contract

  • Land

  20822 1st Ave, Cudjoe Key, FL 33042

  Located in the prestigious waterfront community of Cudjoe Gardens, this cleared and buildable 10,000 sq. ft. canal front lot offers an exceptional opportunity to create your dream home in the Lower Keys. With deep water, quick ocean access and no bridges, this property is perfect for boating enthusiasts and water lovers alike.Situated on a wide, clean canal just moments from the open ocean, the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 713-1031

  20822 1st Ave, Cudjoe Key, FL 33042
• 

  

  /42

  $775,000 Sold Oct 01, 2025

  • 1,122 Sq Ft
  • $691/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  22988 Port Royal Ln, Summerland Key, FL 33042

  With unbeatable access to oceanside fishing, diving, and lobstering, this canal front home delivers the kind of location boaters rarely find. The west-facing canal sets the stage for vivid sunset views, while the spacious lot offers room for extra parking, trailered boats, or an RV. Inside, the home features three bedrooms, two bathrooms, granite countertops, stainless steel appliances, and

  Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  22988 Port Royal Ln, Summerland Key, FL 33042
• 

  /2

  Est $280,976 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
• 

  

  /57

  $2,999,000 Under Contract

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft

  22967 Redfish Ln, Cudjoe Key, FL 33042

  Custom Luxury Meets Waterfront Living on Cudjoe Key. Welcome to 22967 Redfish Lane -- a one-of-a-kind luxury home crafted by one of the Keys' most respected builders as his personal residence. This 3,747 sq ft coastal estate offers 3 bedrooms, 3.5 baths, and high-end custom finishes throughout.Step inside to find black walnut hardwood flooring, soaring tongue-and-groove ceilings, and a true

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 900-8075

  22967 Redfish Ln, Cudjoe Key, FL 33042
• 

  

  /15

  $250,000 Sold Sep 30, 2025

  • Land

  • 60 Days On Market

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042

  Spacious RV lot with nightly rentals allowed. 35' x 69' RV lot offers ample space for your outdoor living. Venture Out is a 24hr manned gated community with amentities including - Boat Ramp and fueling station, Marina store. Tennis, Pickleball, Bocce, Basketball courts and a playground for the little ones. This golf cart friendly and beautifully maintained property is the perfect balance of

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042
• 

  /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
• 

  

  /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
• 

  

  /41

  $1,105,000 Sold Sep 26, 2025

  • 1,200 Sq Ft
  • $921/SF
  • 255 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  22946 Bluegill Ln, Summerland Key, FL 33042

  If you are looking for the ''Island Life'' with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both

  Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  /2

  $49,000 Sold Sep 22, 2025

  • Land

  • 21 Days On Market

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042

  This is a 2 point lot to be used toward a building permit in Monroe County. Add to your current ROGO application or use it when submitting a new ROGO application to Monroe County. Contact Monroe County Planning Department for specific details on how and when these points can be used. ROGO letter in hand. Seller has several lots worth 1 and 2 points for sale if you are looking for additional

  Pamela Stangler Expert Realty LLC

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042
• 

  /2

  Est $1,339,184 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
• 

  

  /48

  $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
• 

  

  /75

  $830,000 Sold Sep 15, 2025

  • 1,200 Sq Ft
  • $692/SF
  • 84 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  22738 Blackbeard Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Cudjoe Key, this thoughtfully designed waterfront residence offers the ideal blend of comfort, durability, and island style. A large paver driveway leads to a spacious under-home parking area with room for two vehicles, while a concrete drive wraps around to a second covered patio--offering ample space for guests, toys, or trailers.Composite decking leads to a

  Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /3

  Est $318,000 Not Listed For Sale

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

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

  

  /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
• 

  

  /52

  $2,300,000 Sold Sep 12, 2025

  • 2,586 Sq Ft
  • $889/SF
  • 147 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  23086 Snapper Ln, Summerland Key, FL 33042

  Oceanfront CBS Fortress with Breathtaking Atlantic Ocean Views and Deep Draft Protected Dockage. Experience unparalleled coastal living with stunning, unobstructed views of the Atlantic Ocean and Kemp Channel from this oversized 12,000 sq. ft. corner lot. This one-of-a-kind CBS home is built for strength and style, offering the ultimate in durability and design. Featuring 4 bedrooms, 3 baths, and

  Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /6

  $550,000

  • 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
• 

  

  /38

  $775,000 Sold Sep 11, 2025

  • 1,008 Sq Ft
  • $769/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  22957 Drake Ln, Cudjoe Key, FL 33042

  Excellent boating and pretty open water views down the canal at this gorgeous Cudjoe Key retreat! Enjoy quick no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large center island

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /44

  $1,250,000

  • 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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