Cudjoe Key, FL Homes

• 

  

  

  /36

  $820,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

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

  This canal-front, slice of paradise is an excellent income-generating opportunity in the gated community of Venture Out. As a successful, active vacation rental where nightly rentals are allowed, it's tastefully furnished, turnkey 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 in the Lower

  Patti Nickless Coldwell Banker Schmitt RE Co. Lower Keys Office

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

  

  

  /30

  $740,000 Sold Jan 21, 2025

  • 1,064 Sq Ft
  • $695/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  124 Yardarm Rd, Cudjoe Key, FL 33042

  Welcome to this brand-new 3BD/2BA stilted modular home on the Gulfside of Cudjoe Key, just 20 minutes from Key West! Situated on a spacious 6,000 sq. ft. lot, this never-lived-in gem offers an inviting 1,064 sq. ft. open-concept design with soaring ceilings and sunlit interiors from large windows that bring the Florida sunshine indoors.**Enjoy the sleek tile flooring, a modern kitchen with

  Team Spottswood/Vazquez Truman & Co. (KW)

  124 Yardarm Rd, Cudjoe Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
• 

  

  

  /37

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft

  22957 Port Royal Ln, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe Key - A Boater's Dream!Welcome to your own piece of paradise on the highly sought-after island of Cudjoe Key! Just 22 miles from the vibrant energy of Key West, this stunning waterfront home offers the perfect blend of tropical tranquility and modern convenience.Boasting an impressive 120 feet of waterfront, this property provides exceptional boating opportunities

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  22957 Port Royal Ln, Summerland Key, FL 33042
• 

  

  

  /48

  $975,000 Sold Jan 21, 2025

  • 1,465 Sq Ft
  • $666/SF
  • 50 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  22940 Gasparilla Ln, Summerland Key, FL 33042

  Stunning 2-Bedroom, 2-Bath Waterfront Home with Ocean Access! Discover your dream home in the heart of the Florida Keys! This beautifully renovated 2-bedroom, 2-bathroom waterfront home offers everything you need for a perfect island lifestyle. Enjoy direct boating access to the Atlantic Ocean from your private 60' dock and take in the spectacular ocean views from your spacious open floor

  Bobby Krug Ocean Sotheby's International Realty

  22940 Gasparilla Ln, Summerland Key, FL 33042
• 

  

  /47

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  701 Spanish Main Dr Unit 469, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 469, Cudjoe Key, FL 33042
• 

  

  /9

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /27

  $225,000 Sold Jan 13, 2025

  • Land

  • 161 Days On Market

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  Oversized RV Lot for big RVs or Build your home here in the private, gated community of Venture Out on Cudjoe Key. Cleared and paved lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
• 

  

  /64

  Est $392,942 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 340, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 340, Cudjoe Key, FL 33042
• 

  

  /20

  $229,999

  • 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

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

  

  /30

  $649,000 Sold Jan 08, 2025

  • 864 Sq Ft
  • $751/SF
  • 176 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  Welcome to your slice of paradise located in the gated Venture Out community! This stunning 2 bedroom, 2 bathroom home offers unparalleled views of the open water from the living room, kitchen, and outdoor entertaining areas. Step inside to discover a beautifully appointed interior that exudes both comfort and style. The spacious living room is the perfect spot to relax and unwind, while the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
• 

  

  /24

  Est $1,571,884 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,588 Sq Ft

  21011 1st Ave, Cudjoe Key, FL 33042

  21011 1st Ave, Cudjoe Key, FL 33042
• 

  

  /61

  $637,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom home, built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
• 

  

  /51

  $777,000 Sold Dec 23, 2024

  • 864 Sq Ft
  • $899/SF
  • 27 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

  Island Oasis Awaits! Welcome to your dream retreat in the heart of paradise! This turn-key 2 bedroom, 2 bath canal front home offers an idyllic escape with stunning open water views. Picture yourself waking up to the gentle sounds of the waves and enjoying your morning coffee while soaking in the tropical sunshine. Nestled within the secure, gated community of Venture Out on Cudjoe Key, this

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
• 

  

  /17

  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
• 

  

  /42

  $1,175,000

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with your very own

  Terry Garcia Keller Williams Key West Compass Realty

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /35

  $1,025,000 Sold Dec 16, 2024

  • 1,313 Sq Ft
  • $781/SF
  • 196 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2005

  21024 2nd Ave, Summerland Key, FL 33042

  Presenting a stunning waterfront residence in the prestigious Cudjoe Gardens of Cudjoe Key, Florida. This exquisitely designed 2-bedroom, 2-bath home offers an abundance of natural light through its expansive windows and seamless indoor-outdoor flow via sliding glass doors, ideal for hosting and entertaining. The property features modern, upgraded appliances and is offered fully furnished with

  Britannie Wesley Bascom Grooms Real Estate (KW)

  21024 2nd Ave, Summerland Key, FL 33042
• 

  /2

  Est $433,408 Not Listed For Sale

  • Studio
  • 1 Bath

  701 Spanish Main Dr Unit 452, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 452, Cudjoe Key, FL 33042
• 

  

  /31

  $369,000

  • Land

  701 Spanish Main Dr Unit 355, Cudjoe Key, FL 33042

  Oversized RV lot with nice open water views down the 60' wide canal with enjoyable tropical breezes. A 17' stepdown concrete seawall with cleats is perfect for your boating needs. Easy access to both the gulf and ocean. Impeccable lot with concrete pad, tropical landscaping, picnic table & electric hookup with 30 & 50 amp. Venture Out has extensive amenities including 80' heated pool, spa, tennis

  Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

  701 Spanish Main Dr Unit 355, Cudjoe Key, FL 33042
• 

  

  /14

  $385,000 Sold Dec 11, 2024

  • Land

  • 183 Days On Market

  0 La Fitte Dr, Cudjoe Key, FL 33042

  2 Tier III Highly visible Commercial Lots on US 1. These lots are located between Cudjoe Sales and The Square Grouper for maximum exposure. Access from LaFitte Dr and US 1 make it super accessible. Zoned SC

  Greg MacLaren Internet Realty of the Florida Keys

  0 La Fitte Dr, Cudjoe Key, FL 33042
• 

  

  /41

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042
• 

  

  /70

  $824,000

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  22933 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to your dream waterfront property! Nestled in tranquil and desirable Cudjoe Key, this exquisite canal-front residence offers an unparalleled fusion of luxury, convenience, and tranquility. Whether you seek a permanent residence, a vacation retreat, or an investment property, this home offers a waterfront paradise for any lifestyle. This meticulously crafted two-bedroom, two-bathroom,

  Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /44

  $685,000 Sold Nov 27, 2024

  • 1,152 Sq Ft
  • $595/SF
  • 108 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  Assumable VA mortgage at 2.2% Waterfront home with quick and easy access to open water and 135 feet of concrete seawall. Home is solid CBS construction with three bedrooms and one and a half bathrooms. Home has many updates, including new impact windows, fresh paint, light fixtures and roof coating. Large attached screeded in patio and laundry room are an extra bonus spaces. There is an

  Monique Thiel Sunshine State Realty Services

  22903 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  701 Spanish Main Dr Unit 649, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 649, Cudjoe Key, FL 33042
• 

  

  /36

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  165 Colson Dr, Cudjoe Key, FL 33042

  Welcome Home! As you step inside of this Brand New contemporary coastal designed Florida Keys home, you will discover what you have been looking for in today's market. This property was built to last by using the finest available materials and sits on over a half-acre of land. The main great room features 15 ft. vaulted ceilings, an open concept living area with a combined high-end kitchen with a

  Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042
• 

  

  /34

  $910,000 Sold Nov 26, 2024

  • 1,056 Sq Ft
  • $862/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  320 Spanish Main Dr, Summerland Key, FL 33042

  Beautifully remodeled open floor plan 2 bed, 2 bath waterfront oasis offering stunning canal and sunset views, a large screened porch, and a 10,000 lb. boat lift. Inside, enjoy a modern kitchen with granite countertops, updated bathrooms, and wood-look tile flooring. The den off the living room is perfect for a home office or potential small 3rd bedroom.. The lower level (permitted 634 sqft)

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  320 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /95

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft

  701 Spanish Main Dr Unit 531, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 531, Cudjoe Key, FL 33042
• 

  

  /29

  $504,000

  • Land

  701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042

  BUILDABLE Waterfront RV Lot with Transient 1 day Rental Opportunity!! This RV site is perfect for your needs. Can accommodate a large RV, easy when parking and has room for storage shed and the rights to build a home in the future. The lot it is located in a private street, providing privacy and enjoyment. 24 hour Gated Security entry. Located near Key West (19 Miles) this property is perfect

  Howard & Lily Leitner Robert Slack LLC

  701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042
• 

  /2

  $60,000 Sold Nov 19, 2024

  • Land

  • 255 Days On Market

  22861 John Silver Ln, Cudjoe Key, FL 33042

  Tier III canal front lot in Cudjoe Key!

  Tommy Mack Coastal Collection Real Estate Inc.

  22861 John Silver Ln, Cudjoe Key, FL 33042
• 

  

  /97

  Est $2,312,741 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,693 Sq Ft

  1124 Labat Ln, Cudjoe Key, FL 33042

  1124 Labat Ln, Cudjoe Key, FL 33042
• 

  

  /5

  $299,000

  • Land

  21731 Asturias Rd, Summerland Key, FL 33042

  Private Acre on Cudjoe Key - Lush, Tropical, and Near the WaterEscape 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 unmatched privacy and tranquility.Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and watersports.

  Coby Taylor Expert Realty LLC (HQ)

  21731 Asturias Rd, Summerland Key, FL 33042
• 

  

  /21

  $435,000 Sold Nov 18, 2024

  • 770 Sq Ft
  • $565/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1978

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

  This is your chance to own an income property or full-time retreat in the Florida Keys! Cuddie cottage is currently the most competitively priced ocean front single family unit in Venture Out on Cudjoe Key.Make this 2-bedroom, 1-bath island home yours. World class boating and fishing from your own concrete dock equipped with filet table and ladder for quick salt water dips. Following is a

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

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

  

  /65

  Est $286,060 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042
• 

  

  /13

  $525,000

  • Land

  1147 Basque Ln, Cudjoe Key, FL 33042

  PERMIT IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water Views all with a

  Brad Baker RE/MAX Keys To The Key

  1147 Basque Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $250,000 Sold Nov 15, 2024

  • 316 Sq Ft
  • $791/SF
  • 193 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1980

  701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042

  Possible Seller Financing, Motivated seller! Income producing property! Welcome to your tropical paradise retreat on Cudjoe Key! This charming mobile home, nestled within the Venture Out community, offers the perfect balance of comfort, convenience, and island living. As you step inside, you'll be greeted by a cozy yet efficiently designed living space, complete with dining area, living room,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
• 

  

  /55

  Est $1,254,297 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  266 Colson Dr, Summerland Key, FL 33042

  266 Colson Dr, Summerland Key, FL 33042
• 

  

  /51

  $459,000

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  Charming Opportunity in Venture Out on Cudjoe Key! Welcome to your next project in the sought-after gated community of Venture Out! This one-bedroom, one-bath mobile home is brimming with potential, offering a unique chance for investors or DIY enthusiasts looking to create their dream getaway. As you step inside, you'll find a cozy layout that provides a blank canvas for your creative vision.

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
• 

  

  /47

  $1,120,000 Sold Nov 14, 2024

  • 1,780 Sq Ft
  • $629/SF
  • 128 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  133 Galleon Ln, Summerland Key, FL 33042

  CANAL-FRONT POOL HOME IN CUDJOE KEY - step inside and you'll be impressed by the soaring, tongue and groove ceilings and exposed cedar beams throughout this custom-built design. Just shy of 1800 sq. ft., the living area is light and airy, a brand-new kitchen offers abundant white cabinets and quartz counters; all floors are tile. Pocket sliders open onto porches on both levels allowing the

  Patti Nickless Coldwell Banker Schmitt Real E

  133 Galleon Ln, Summerland Key, FL 33042
• 

  

  /35

  Est $1,245,431 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,735 Sq Ft

  22977 Port Royal Ln, Cudjoe Key, FL 33042

  22977 Port Royal Ln, Cudjoe Key, FL 33042
• 

  

  /19

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  Team Spottswood/Vazquez Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

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