Cudjoe Key, FL Homes

• 

  

  

  /47

  Est $2,243,697 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  22684 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  

  /61

  $595,000

  • 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
• 

  

  

  /45

  $1,700,000 Sold Feb 13, 2025

  • 2,772 Sq Ft
  • $613/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Stunning canal front home in desirable Cudjoe Gardens, with Southern Exposure, massive 15,600 Sq. Ft. double lot, and deep-water access to Open Ocean and backcountry! Expertly outfitted with 125' of concrete seawall with running water, fillet station, swim ladders, 15K boat lift, davits, and turning basin! Situated on a clean flow-through canal, excellent for swimming and capable of accommodating

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20942 6th Ave W, Summerland Key, FL 33042
• 

  

  

  /60

  Est $911,028 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  52 Cutthroat Dr, Summerland Key, FL 33042

  52 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  

  /30

  $470,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
• 

  

  /41

  $2,075,000 Sold Feb 03, 2025

  • 3,056 Sq Ft
  • $679/SF
  • 19 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2004

  20864 4th Ave W, Summerland Key, FL 33042

  This elegantly designed custom built ground level home was created by local architect Glenn Gray. Boasting a spacious open floor plan @ 3,056 sq ft. Two master bedrooms with ensuite baths, third bedroom, full bath and a half, and office all on first floor. Up the flight of stairs leads to a huge open loft space for a fourth bedroom/bunk room, theater room, art room or whatever your needs.

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  20864 4th Ave W, Summerland Key, FL 33042
• 

  /2

  Est $725,065 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  53 Treasure Chest Dr, Summerland Key, FL 33042

  53 Treasure Chest Dr, Summerland Key, FL 33042
• 

  

  /39

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  21073 7th Ave, Summerland Key, FL 33042

  Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  21073 7th Ave, Summerland Key, FL 33042
• 

  

  /35

  $217,000 Sold Jan 31, 2025

  • Land

  • 22 Days On Market

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

  TRANSIENT RENTALS ALLOWED!!Live the Island Life in Your Own Slice of Paradise! Ahoy, fellow adventurers! Set your sails for this dreamy RV lot nestled in the vibrant Venture Out Community, just a breezy 19 miles from the heart of Key West. This spacious 35' x 69' lot is ready to welcome even the biggest rigs, so bring your home on wheels and let the good times roll! With lush landscaping already

  Kelly Gardner Bluescape Real Estate

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

  

  /77

  Est $5,919,099 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,514 Sq Ft

  200 Erie Dr, Summerland Key, FL 33042

  200 Erie Dr, Summerland Key, FL 33042
• 

  

  /43

  $559,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Welcome to your tropical retreat! This 2-bed, 1.5-bath canal-front mobile home in Cudjoe Key offers open ocean access and the perfect blend of comfort and affordability. Located in the desirable Venture Out community, this property is also a proven income-producing vacation rental, making it a fantastic investment opportunity.Venture Out is a residential condominium community with 24-hour gated

  Justyn Ewald Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
• 

  

  /31

  $800,000 Sold Jan 31, 2025

  • 1,008 Sq Ft
  • $794/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  Idyllic Canal-Front Cudjoe Key retreat on a generous fenced-in lot in a prime location! This bright and spacious Cutthroat Harbor Estates home boasts an open concept main living space and three generous bedrooms! Coming soon, the seller is replacing the existing roof with a new metal roof. Upon entry, this turnkey home is tailor-made for entertaining. The living room flows seamlessly with a

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /43

  Est $1,270,826 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft

  408 Sawyer Dr, Summerland Key, FL 33042

  408 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /24

  $475,000

  • Land

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  Welcome to your own slice of paradise at Venture Out, a premier gated community in the heart of the Florida Keys, located at Mile Marker 23 on Cudjoe Key. This exceptional RV lot, measuring 35' x 69', offers the perfect blend of comfort and functionality for the ultimate outdoor lifestyle. Features of this lot include a sturdy concrete seawall equipped with a convenient fish cleaning table and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
• 

  

  /43

  $2,520,000 Sold Jan 31, 2025

  • 2,156 Sq Ft
  • $1,169/SF
  • 165 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Indulge in the epitome of Keys living with this delightful turnkey 3-bedroom, 3 1/2 bathroom stilt home on 1 1/2 lots. Embracing the coastal allure, this residence features serene blue to aqua tones indoors, complemented by elegant white plantation shutters that evoke a sense of timeless charm. Step onto the expansive covered patio, where panoramic views of the pool and a long canal stretch

  Laura Derrickson Keller Williams Coastal Partners

  622 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $2,239,391 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,561 Sq Ft

  683 Sawyer Dr, Summerland Key, FL 33042

  683 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /26

  $268,000

  • 2 Beds
  • 1 Bath
  • 664 Sq Ft

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

  2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

  Deirdre Praught Florida Keys Realty, Inc.

  701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
• 

  

  /34

  $775,000 Sold Jan 30, 2025

  • 1,340 Sq Ft
  • $578/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Located on a spacious corner lot of a quarter acre in the heart of Cudjoe Key, this home offers both peace and potential. The large, fenced-in yard provides endless opportunities for outdoor activities, with plenty of space for water toys, gardening, or just relaxing in a private, open space. The 25K boat lift makes it an ideal spot for those who love life on the water, while the expansive lot

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  191 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /32

  Est $1,796,223 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,966 Sq Ft

  21018 4th Ave, Summerland Key, FL 33042

  21018 4th Ave, Summerland Key, FL 33042
• 

  

  /19

  $329,000

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042

  NIGHTLY RENTALS ALLOWED! Welcome to this immaculate 2-bedroom, 1-bathroom vacation retreat nestled at the picturesque southern tip of Venture Out, where the land gracefully meets the sea. The attention to detail is evident with luxurious travertine flooring added to this home. Don't let the square footage fool you. This home offers an open floor plan with an open kitchen over looking the family

  Susan Halligan Live Local Realty of the Florida Keys

  701 Spanish Main Dr Unit 62, 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

  The Spottswood Team Truman & Co. (KW)

  124 Yardarm Rd, Cudjoe Key, FL 33042
• 

  

  /28

  Est $770,726 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  21702 Asturias Rd, Summerland Key, FL 33042

  21702 Asturias Rd, Summerland Key, FL 33042
• 

  

  /30

  $790,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

  Dream Island Living Awaits!Discover this move-in ready, fully furnished 2 bed/2bath canal front home in the secure gated community of Venture Out in CUDJOE KEY. This beautifully appointed property features a 35 ft concrete seawall, perfect for boaters and water enthusiasts, offering stunning open water views that create a serene backdrop for your island lifestyle. Enjoy ample downstairs space,

  Katrina Vanek Bluescape Real Estate

  701 Spanish Main Dr Unit 468, Cudjoe 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
• 

  /2

  Est $1,009,886 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,744 Sq Ft

  21790 Spain Blvd, Summerland Key, FL 33042

  21790 Spain Blvd, Summerland Key, FL 33042
• 

  

  /46

  $497,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe 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
• 

  

  /29

  Est $1,060,752 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  23034 Wahoo Ln, Summerland Key, FL 33042

  23034 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /19

  $319,000

  • Land

  701 Spanish Main Dr Unit 236, Cudjoe Key, FL 33042

  Lush landscape on this corner lot adds to the privacy you will get her at Lot 236 in the gated community of Venture Out on Cudjoe Key. Located on a beautiful boating canal, this lot has a 13.25' concrete seawall. The lot has a separate seating area nestled under the shade of the palm trees.Looking to build in the future? This lot is ROGO exempt. Build your high rise home and capture the open

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 236, 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
• 

  

  /39

  Est $1,339,963 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft

  21076 3rd Ave, Summerland Key, FL 33042

  21076 3rd Ave, Summerland Key, FL 33042
• 

  

  /55

  $899,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2018, 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 serene retreat at the end of the

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 97, 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
• 

  /2

  Est $832,377 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22968 Drake Ln, Summerland Key, FL 33042

  22968 Drake Ln, Summerland Key, FL 33042
• 

  

  /31

  $645,000

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  701 Spanish Main Dr Unit 324, Cudjoe Key, FL 33042

  Step into a dreamy haven: this 2-bedroom, 1-bathroom mobile oasis perfectly situated in the Keys. Compact yet bursting with charm, this home offers direct Marina access, complete with a boat ramp, inviting you to embrace the serene waterside life. Thanks to the unparalleled weather of the Keys, the property's rear beckons you for perfect tanning sessions under the clear blue skies. For those with

  Monika Turek Karem Kramer Realty (KW)

  701 Spanish Main Dr Unit 324, 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
• 

  

  /28

  Est $932,544 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  340 Spanish Main Dr, Summerland Key, FL 33042

  340 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /12

  $550,000

  • Land

  701 Spanish Main Dr Unit 323, Cudjoe Key, FL 33042

  Waterfront Wonder in Venture Out Resort. Nestled in the heart of the coveted Venture Out Resort, this waterfront property promises unparalleled location and countless amenities. Situated on a prestigious street, you are moments away from the resort's best offerings. Be swept away by breathtaking ocean views that showcase landmarks like Pelican Pt & Summerland Key. A spacious 40' concrete dock

  Monika Turek Karem Kramer Realty (KW)

  701 Spanish Main Dr Unit 323, Cudjoe Key, FL 33042
• 

  

  /14

  $385,000 Sold Dec 11, 2024

  • Land
  • 0.57 Acre
  • $670,824 per Acre

  • 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
• 

  

  /36

  Est $1,457,830 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  20878 5th Ave W, Summerland Key, FL 33042

  20878 5th Ave W, Summerland Key, FL 33042

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