Cudjoe Key, FL Homes

• 

  

  

  /47

  $925,000

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft

  22880 Blackbeard Ln, Summerland Key, FL 33042

  This gorgeous and unique waterfront 2 bedroom, 1.5 bathroom home with a 3rd guest room/office that has panoramic views of Cudjoe Key and Cudjoe Bay offers everything you need to start enjoying the Florida Keys Lifestyle. Pride of ownership with every detail for comfortable and convenient waterfront living and it comes turn-key! Fully furnished inside and out, all indoor/outdoor furniture,

  Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  

  /68

  $2,600,000 Sold May 30, 2025

  • 2,604 Sq Ft
  • $998/SF
  • 57 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1985

  531 Seminole Dr, Summerland Key, FL 33042

  Welcome to this stunning CBS (Concrete Block Stucco) Home located in the desirable Cudjoe Gardens neighborhood on Cudjoe Key. This charming 4-bedroom, 3-bathroom residence offers 255 feet of seawall, perfect for boating enthusiasts with ample dock space and 2 boat lifts.As you approach this meticulously landscaped property, on a lot & half, you'll be greeted by the serene ambiance of the tropical

  Karen Haack Coldwell Banker Schmitt RE Co.

  531 Seminole Dr, Summerland Key, FL 33042
• 

  

  

  /81

  Est $1,464,792 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland Key, FL 33042
• 

  

  

  /17

  $265,000

  • Land

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

  Spacious RV lot measuring approximately 35 x 69 in the highly desirable Venture Out Resort on Cudjoe Key. This ROGO exempt lot is ready for your RV with both 30- and 50-amp service, water, and sewer hookups, plus the flexibility to build in the future. The community offers resort-style amenities including a heated pool, hot tub, private marina with boat ramp, fuel dock and community store,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
• 

  

  

  /38

  $900,000 Sold May 30, 2025

  • 1,142 Sq Ft
  • $788/SF
  • 46 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  22971 Hawkins Ln, Summerland Key, FL 33042

  Don't miss this immaculate home at 22971 Hawkins Ln Cudjoe Key. This completely furnished 3 bedroom 3 bath home is in impeccable condition with recent upgrades to include all new kitchen and appliances, new baths, impact windows, AC, metal roof and paint. The third bedroom could be utilized as an office, gym, yoga or media room. The home also has a walk around deck with a covered screened porch.

  Greg MacLaren Internet Realty of the Florida Keys

  22971 Hawkins Ln, Summerland Key, FL 33042
• 

  

  /19

  Est $803,996 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /14

  $265,000

  • Land

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
• 

  

  /46

  $550,000 Sold May 28, 2025

  • 754 Sq Ft
  • $729/SF
  • 72 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

  This super cute, meticulous maintained property is all you need to start living and enjoying paradise in the Florida Keys. It comes completely furnished with coastal charm and includes 2 bedrooms and 2 baths, a stunning kitchen and dining room and views out to the patio overlooking the canal. The patio is perfect for those beautiful evenings outside for entertaining, grilling, or sipping adult

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
• 

  

  /41

  Est $394,837 Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
• 

  

  /43

  $1,165,000

  • 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 298 sq. ft. of

  Terry Garcia Keller Williams Key West Compass Realty

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $970,000 Sold May 27, 2025

  • 1,390 Sq Ft
  • $698/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  366 Sawyer Dr, Summerland Key, FL 33042

  Welcome to your own tropical paradise! This stunning oceanside retreat offers everything you need for the ultimate waterfront lifestyle. With an 80-ft concrete dock, you'll have plenty of space for your boat, making it easy to set off on incredible fishing adventures--just minutes to the open ocean via direct canal or the serene backcountry waters.This inviting 3-bedroom, 2-bathroom home is

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  366 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /37

  Est $873,552 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  139 Le Grand Ln, Summerland Key, FL 33042

  139 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /29

  $395,000 Sold May 19, 2025

  • Land

  • 78 Days On Market

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a 35' concrete seawall, dock posts, swim ladder, full hookups including water, sewer, and 30, 50 and 110 amp electric service. Enjoy the convenience of a

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,675,084 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
• 

  /2

  $57,000

  • Land

  Lot 17 Treasure Chest Dr, Cudjoe 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.

  Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /58

  $2,025,000 Sold May 13, 2025

  • 1,292 Sq Ft
  • $1,567/SF
  • 85 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1988

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated

  Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /40

  Est $983,584 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  22983 Anne Bonny Ln, Summerland Key, FL 33042
• 

  /2

  $57,000

  • Land

  Lot 16 Treasure Chest Dr, Cudjoe 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.

  Pamela Stangler Expert Realty LLC

  Lot 16 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /115

  $12,250,000 Sold May 07, 2025

  • 4,888 Sq Ft
  • $2,506/SF
  • 44 Days On Market

  • 7 Beds
  • 6 Baths
  • Built 2019

  785 Sawyer Dr, Cudjoe Key, FL 33042

  Welcome to Cypress Point, an exceptional and highly private, 7-Bed, 6-Bath, 4,888 Sq Ft oceanfront estate spanning almost a full acre on Cudjoe Key, where luxury and coastal beauty uniquely blend. This custom D'Asign Source built home is privately nestled behind an electric gate and boasts the finest finishes and amenities which include an oceanfront pool, outdoor theater, 6-hole golf green,

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $2,266,458 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  20820 7th Ave W, Summerland Key, FL 33042

  20820 7th Ave W, Summerland Key, FL 33042
• 

  

  /39

  $650,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

  Randal Longo Keys Realty Redefined LLC

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
• 

  

  /59

  $860,300 Sold May 02, 2025

  • 864 Sq Ft
  • $996/SF
  • 76 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

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

  This home is BIG BOAT friendly and ready for you to move in. Turn key, fully furnished home located in the gated community of Venture Out on Cudjoe Key at Mile Marker 23. 2 Bedrooms and 2 Baths mid-rise sits on open water with an oversized massive 60' of concrete seawall. When you walk inside, you will feel like you are floating on the ocean with the large windows and picturesque ocean views. The

  Kelly Gardner Bluescape Real Estate

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

  

  /17

  Est $1,033,273 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,334 Sq Ft

  248 Spanish Main Dr, Summerland Key, FL 33042

  248 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /65

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
• 

  

  /36

  $330,000 Sold Apr 17, 2025

  • 728 Sq Ft
  • $453/SF
  • 63 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1983

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  Welcome to your slice of paradise! This beautifully updated home is on the quiet, serene southwest side of the highly sought-after Venture Out Resort. With no neighbors behind you, you can enjoy added privacy and tranquility. The home is conveniently located next to the bathhouse for added convenience. Featuring two bedrooms and one bathroom, there is plenty of space to spread out and relax. The

  Frank Griffiths Lokation Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
• 

  

  /50

  Est $1,682,856 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft

  21025 Hamilton Ave, Summerland Key, FL 33042

  21025 Hamilton Ave, Summerland Key, FL 33042
• 

  

  /15

  $999,965

  • Land

  701 Spanish Main Dr Unit 369, 370, Cudjoe Key, FL 33042

  Boater's Paradise with Expansive Waterfront Views! Rare opportunity to own one of only three double lots in Venture Out on Cudjoe Key with unbeatable waterfront views and a newer 70-ft concrete seawall equipped with davits, bumpers, swim ladder, fish cleaning station, and upgraded dock posts and cleats--perfect for accommodating your large boats. Take advantage of the double buildable lot

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  701 Spanish Main Dr Unit 369, 370, Cudjoe Key, FL 33042
• 

  

  /44

  $650,000 Sold Apr 17, 2025

  • 1,056 Sq Ft
  • $616/SF
  • 86 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  268 Spanish Main Dr, Summerland Key, FL 33042

  Charming fishing bungalow located on oceanside Cudjoe Key just waiting to be yours. This waterfront haven features two bedrooms, two bathrooms and just under 1,100 square feet inside plus a permitted downstairs enclosure with plumbing and electric. Enjoy room for all to entertain in the open concept living area that seamlessly leads into the kitchen and dining. Waterside screened porch allows for

  Ally Kelley Ocean Sotheby's International

  268 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /9

  Est $728,832 Not Listed For Sale

  • 2 Beds

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042
• 

  

  /53

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  /57

  $1,375,000 Sold Apr 17, 2025

  • 1,797 Sq Ft
  • $765/SF
  • 215 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1972

  468 Sawyer Dr, Summerland Key, FL 33042

  Discover a Rare Gem in Cudjoe Gardens: Double Waterfront Lot with Private Boat BasinNestled in the Cudjoe Gardens costal community, this unique canal-front home boasts 4 bedrooms and 4 bathrooms, with an expansive upper deck offering stunning waterway views and breathtaking sunsets. The main house is ground level CBS construction and features terrazzo flooring throughout, capturing the true

  Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /56

  Est $1,731,195 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft

  20966 8th Ave W, Summerland Key, FL 33042

  20966 8th Ave W, Summerland Key, FL 33042
• 

  

  /23

  $3,750,000

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

  22815 Port Royal Ln, Summerland Key, FL 33042

  DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

  Rhonda Gailey Gailey Enterprises Real Estate

  22815 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /39

  $912,250 Sold Apr 03, 2025

  • 1,344 Sq Ft
  • $679/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  22879 Blackbeard Ln, Summerland Key, FL 33042

  Beautiful 3 bedroom 2 bathroom elevated island retreat on Cudjoe Key. This property features a private dock so you can keep your boat on site and enjoy immediate access to world class fishing and diving the stunning waters of the Florida Keys. Located just 25 minutes to Key West and 3 hours from Miami with grocery store, restaurants and bars close by. The exterior features hard plank siding and

  Sandra Tuttle Island Welcome Real Estate

  22879 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /36

  Est $896,907 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft

  21066 3rd Ave, Summerland Key, FL 33042

  21066 3rd Ave, Summerland Key, FL 33042
• 

  

  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
• 

  

  /40

  $850,000 Sold Mar 31, 2025

  • 1,312 Sq Ft
  • $648/SF
  • 59 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  20914 7th Ave W, Summerland Key, FL 33042

  Welcome to your perfect coastal retreat! This inviting 2-bedroom, 2-bath home plus office offers the ideal blend of comfort and convenience for boating enthusiasts. Nestled on the Oceanside with no bridges to navigate, it boasts a private 15,000 lb boatlift on 80 ft concrete dock a generous 4-ft draft making it a dream for those who love the water. Relax and unwind in the screened patio, perfect

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  20914 7th Ave W, Summerland Key, FL 33042
• 

  /2

  Est $1,282,486 Not Listed For Sale

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

  23047 Bluegill Ln, Summerland Key, FL 33042

  23047 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

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