Cudjoe Key, FL Homes

• 

  

  

  /66

  Not Listed For Sale

  • 2 Beds

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  

  /28

  $896,000

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  This 3-bedroom, 2-bathroom stilted home offers 1,200 sq ft of thoughtfully designed space on a spacious canal-front lot.Enjoy the convenience of a 40 ft seawall, 10,000 lb boat lift, outdoor shower, and an enclosed garage with plenty of room for vehicles, boats, and water toys.Inside, the open-concept kitchen, living, and dining areas are equipped with brand-new appliances, ample cabinet space,

  Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  

  /50

  $550,000 Sold Jul 14, 2025

  • 864 Sq Ft
  • $637/SF
  • 245 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  MOTIVATED SELLER. BRING THE OFFERS! BEST VALUE IN VENTURE OUT! HUGE PRICE DROP! NEGOTIABLE.! 2-YEAR HOME WARRANTY. TOTAL ELEGANCE! Experience the pinnacle of stilt-home living in this stunning residence at Venture Out, built just 3.5 years ago and meticulously designed with premium upgrades throughout. This 2-bedroom, 2-bathroom manufactured gem is move-in ready and fully furnished, offering a

  Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042
• 

  

  

  /43

  $1,799,999

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

  Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /54

  $615,000 Sold Jul 11, 2025

  • 864 Sq Ft
  • $712/SF
  • 194 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

  Are you dreaming of owning a piece of paradise in the Fabulous Florida Keys? Look no further than this gorgeous 2 bedroom, 2 bath waterfront home in the highly desired Venture Out Park in Cudjoe Key. This clean and updated home features a 35' concrete dock with whips, heavy duty aluminum posts, and easy access to enjoy both the gulf and ocean for world-class fishing and diving adventures. Inside,

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 131, 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
• 

  

  /29

  $1,549,000

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  20841 8th Ave W, Cudjoe Key, FL 33042

  Meticulously maintained and located in the desirable boating community of Cudjoe Gardens, this nearly 1,900 sq ft home includes 90 feet of dockage, a 10,000 lb boat lift, hurricane impact windows, doors, and garage door, as well as a gorgeous pool creating your own private oasis. A boater's paradise with easy access to both ocean side and gulf side! The inside boasts 3 spacious bedrooms and an

  Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

  20841 8th Ave W, Cudjoe Key, FL 33042
• 

  

  /45

  $2,090,000 Sold Jul 07, 2025

  • 1,938 Sq Ft
  • $1,078/SF
  • 65 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  23066 Tarpon Ln, Summerland Key, FL 33042

  ''BRAND NEW' CBS Construction ready for occupancy!!! Amazing New Oceanside Home with 4 Bedrooms, 3.5 Baths, in Beautiful Cudjoe Ocean Shores, (Custom Built by Dream Builders of the Florida Keys). This home offers Open Water Views, Instant Deep Draft Boating for Big Boat Action, Protected Concrete step-down Dock, Open Floor plan, Dining Area, two Master Suites, High Ceilings, Chefs Kitchen with

  Greg MacLaren Internet Realty of the Florida Keys

  23066 Tarpon Ln, Summerland Key, FL 33042
• 

  

  /35

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 849 Sq Ft

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

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042
• 

  

  /70

  $1,899,000

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  20889 7th Ave W, Summerland Key, FL 33042

  Luxury Waterfront Living in Prestigious Cudjoe Gardens, ROOM FOR A POOL! Discover refined island living in the heart of one of the Florida Keys' most exclusive waterfront communities renowned for its deepwater access, upscale ambiance, and close proximity to Key West.This elegantly designed residence is positioned on an 8,000sf lot, offering exceptional canal frontage on a 50ft wide canal only 6

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20889 7th Ave W, Summerland Key, FL 33042
• 

  

  /41

  $650,000 Sold Jul 01, 2025

  • 1,120 Sq Ft
  • $580/SF
  • 81 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  22882 Buccaneer Ln, Summerland Key, FL 33042

  Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22882 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /58

  Est $1,646,392 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
• 

  

  /42

  $2,300,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, Cudjoe Key, FL 33042
• 

  

  /44

  $650,000 Sold Jun 30, 2025

  • 828 Sq Ft
  • $785/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

  Turnkey Waterfront Vacation Rental with Ocean Views in Venture Out.Welcome to your Florida Keys escape--a fully furnished, income-producing 2-bedroom, 2-bath home ideally positioned on a wide canal with stunning ocean views and 35 feet of concrete seawall dockage. Located in the vibrant, gated community of Venture Out on Cudjoe Key, this well-maintained property is not just a serene coastal

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, 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
• 

  

  /45

  $1,950,000

  • 2 Beds
  • 2 Baths
  • 1,281 Sq Ft

  489 Sawyer Dr, Summerland Key, FL 33042

  OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  489 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /26

  $239,000 Sold Jun 30, 2025

  • Land

  • 74 Days On Market

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

  Embrace the island lifestyle with this prime RV lot in Venture Out, a premier gated community on Cudjoe Key! Nestled in a quiet section of the park, this lot offers peak-a-boo ocean views and stunning sunsets from the rear of the property, making it the perfect tropical retreat. Whether you're looking for a personal getaway or a smart investment, this lot is a rare find--Venture Out is one of the

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  701 Spanish Main Dr Unit 6, 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
• 

  

  /41

  $2,500,000

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft

  1176 Thatch Ln, Summerland Key, FL 33042

  Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

  Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /42

  $1,900,000 Sold Jun 29, 2025

  • 1,702 Sq Ft
  • $1,116/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2011

  20867 5th Ave W, Cudjoe Key, FL 33042

  Enjoy deep draft dockage, 2 Boat Lifts, Garage and Pool plus no steps to climb at this 3 Bedroom 2 Bath home located in Cudjoe Gardens, an upscale waterfront community of CBS constructed Above Flood ground level homes offering a neighborhood full service marina and waterfront restaurant and bar. Enter into the open Great Room where a wall of impact glass doors overlooks the pool and water. The

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20867 5th Ave W, Cudjoe Key, FL 33042
• 

  

  /65

  Est $255,571 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
• 

  

  /59

  $1,599,999 New Construction

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /47

  $1,100,000 Sold Jun 27, 2025

  • 1,361 Sq Ft
  • $808/SF
  • 102 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  21014 7th Ave, Summerland Key, FL 33042

  Nestled in one of the Lower Keys' most coveted boating communities, this meticulously renovated 3 bedroom 2 bathroom coastal retreat is more than just a home...it's a gateway to endless aquatic adventures. Situated on a deep-draft, flow-through canal with direct access to both the Atlantic and Gulf, this property is a dream for fishing, diving, and island-hopping enthusiasts. The brand-new

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  21014 7th Ave, Summerland Key, FL 33042
• 

  

  /55

  Est $1,226,595 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
• 

  

  /4

  $85,000

  • Land

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

  Tier I property, County letter in the documents tab. Buildable, but also worth 1 point if you are looking for lots for land dedication purposes. No surveys have been done. It is the responsibilty of the buyer to verify the provided information

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
• 

  

  /36

  $1,225,000 Sold Jun 13, 2025

  • 1,696 Sq Ft
  • $722/SF
  • 104 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2023

  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
• 

  /2

  Est $900,271 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft

  22842 Buccaneer Ln, Summerland Key, FL 33042

  22842 Buccaneer Ln, Summerland Key, FL 33042
• 

  /2

  $210,000

  • Land

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

  Excellent value for ROGO allocation points.Includes three Tier-1 dedication lots totaling 8 points with letter in hand. Approximately three acres of conservation land offered solely for ROGO point purposes--not buildable. Sale subject to court approval.

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /107

  $5,300,000 Sold Jun 13, 2025

  • 4,981 Sq Ft
  • $1,064/SF
  • 165 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  Experience unparalleled luxury in this 2025 Custom Built Smart Home. Concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an infinity-edge pool and

  Stacy Shahan Island Real Estate Company Florida Keys

  220 E Caribbean Dr, Summerland Key, FL 33042
• 

  

  /40

  Est $2,081,758 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, Summerland Key, FL 33042
• 

  

  /55

  $1,199,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  164 Tortuga Ln, Summerland Key, FL 33042

  Experience the best of island living at this beautifully updated Cudjoe Key retreat with quick ocean access. Built in 1990 and extensively renovated in 2020 this stilted coastal home blends modern comfort with timeless Keys style.The 1,400 sq ft interior features a bright open layout, custom kitchen, and spa-inspired bathrooms.Outside enjoy a resort-style saltwater pool with both heater and

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  164 Tortuga Ln, Summerland Key, FL 33042
• 

  /2

  $49,000 Sold Jun 06, 2025

  • Land
  • 0.19 Acre
  • $257,895 per Acre

  • 168 Days On Market

  7 Lot, Lower Keys, FL 33042

  2 Point Lot with point letter in hand. Can purchase with MLS# A 11685133, which is another 2 point lot with letter in hand for 110,00 for both (total of 4 points). For lot dedication and points used to build on another dedicated lot in Monroe County. Call the Monroe County Planning Department for more details.

  Pamela Stangler MMLS Assoc.-Inactive Member

  7 Lot, Lower Keys, FL 33042
• 

  /2

  Est $913,294 Not Listed For Sale

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

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042
• 

  

  /30

  $485,000

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
• 

  /2

  $49,000 Sold Jun 06, 2025

  • Land

  • 163 Days On Market

  Lot 7 Block 14, Cudjoe Key, FL 33042

  2 Point Lot with point letter in hand. Can purchase with MLS# 612010, which is another 2 point lot with letter in hand for 135,00 for both (total of 4 points).

  Pamela Stangler Expert Realty LLC

  Lot 7 Block 14, Cudjoe Key, FL 33042
• 

  

  /19

  Est $870,874 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /51

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft

  20844 4th Ave W, Summerland Key, FL 33042

  Welcome to 20844 4th Ave W, a remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping and tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence blends timeless elegance with coastal

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
• 

  

  /70

  $721,000 Sold Jun 03, 2025

  • 1,088 Sq Ft
  • $663/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1995

  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
• 

  /2

  Est $1,355,984 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,274 Sq Ft

  21082 6th Ave, Summerland Key, FL 33042

  21082 6th Ave, Summerland Key, FL 33042

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