Cudjoe Key, FL Homes

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  /115

  $13,500,000 Pending

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft

  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)

  (855) 571-2719

  785 Sawyer Dr, Cudjoe Key, FL 33042
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• 

  

  

  /24

  $4,900 per month

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft
  • House for Rent

  1060 Coxon Ln, Cudjoe Key, FL 33042

  A waterfront two bedroom, two bath home, with huge walk in closet. Home is fully furnished, but we are also willing to rent unfurnished or partially furnished to suit your needs. Located seconds from open water, this home boasts all of the outdoor space you need, including a 60 ft seawall and parking for your vehicles and boat trailers. A fish cleaning station, grill, bait freezer, and outdoor

  1060 Coxon Ln, Cudjoe Key, FL 33042
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  /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 Ocean Sotheby's International Realty

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /2

  Est $263,335 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
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  /58

  $2,195,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft

  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

  (866) 646-5291

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /7

  $750 per month

  • 1 Bath
  • Property for Rent

  22966 Overseas Hwy Unit 3, Cudjoe Key, FL 33042

  Commercial office space, highway frontage, casual commercial rental, half bath, small coffee bar area. Laminate flooring, central air, ceiling fans, approx 400 sqft. Plus electric, water included. This is not a livable space, it's office space only.Owner is licensed Realtor

  Susan Rich Select Properties of NWFL

  22966 Overseas Hwy Unit 3, 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 Realty

  268 Spanish Main Dr, Summerland Key, FL 33042
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  /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
• 

  

  /71

  $3,499,000

  • 6 Beds
  • 7 Baths
  • 4,976 Sq Ft

  225 Colson Dr, Summerland Key, FL 33042

  Experience the epitome of island luxury in this custom built 5,000 sq. ft. CBS estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated coastal living. Step into the light-filled, open-concept Great

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 563-4761

  225 Colson Dr, Summerland 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
• 

  /2

  Est $1,359,609 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
• 

  

  /26

  $245,000

  • Land

  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)

  (786) 847-7836

  701 Spanish Main Dr Unit 6, Cudjoe 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
• 

  

  /3

  Est $411,000 Not Listed For Sale

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

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

  

  /42

  $885,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  22739 Buccaneer Ln, Summerland Key, FL 33042

  If you're looking for the ultimate ''Island Life'' this charming canal-front home in sought-after Cutthroat Harbor Estates is exactly what you need. This 2 Bedroom 2 Bath home is located on the ocean side with excellent boating access to the Atlantic & Gulf. This home includes a #10,000 pound boat lift, full concrete seawall, large storage area below, and a fully fenced yard, making it a

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 560-1602

  22739 Buccaneer Ln, Summerland 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
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /46

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  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)

  (888) 611-7990

  21014 7th Ave, Summerland Key, FL 33042
• 

  

  /46

  $1,900,000 Sold Mar 27, 2025

  • 2,358 Sq Ft
  • $806/SF
  • 342 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2023

  271 W Indies Dr, Ramrod Key, FL 33042

  Brand new construction in Breezeswept Beach Estates! This modern 2,358 sq. ft. pool home offers unbeatable Open Water Views and high-end finishes. The open-concept layout features a Chef's Kitchen with premium stainless steel appliances, quartz countertops, ample storage, and a large island. A separate bar with a wine cooler adds convenience. Impact sliding glass doors lead to a covered veranda

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  271 W Indies Dr, Ramrod Key, FL 33042
• 

  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /41

  $1,196,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  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)

  (305) 787-3949

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /32

  $450,000 Sold Mar 19, 2025

  • Land

  • 256 Days On Market

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  A Fisherman's Paradise for the Big Boaters! This 40' seawall RV site located in the coveted Venture Out community is the perfect vacation and or income producing property for nightly/weekly rentals. The 60' wide canal is one of the best in the park providing deep draft clear water with ample maneuverability for the big boats. The canal provides a straight shot out to Kemp Channel and the open

  Paul Rogers Coldwell Banker Schmitt RE Co. Lower Keys Office

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
• 

  /2

  Est $524,031 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  /33

  $1,599,000

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft

  20883 4th Ave, Cudjoe Key, FL 33042

  Tucked away in the boating community of Cudjoe Gardens, this spacious 3 Bedroom plus Loft canal front home boasts over 2,500 sq. ft. with soaring ceilings and a 2-car garage. Thoughtfully designed for both relaxation and functionality, the space is filled with natural light which flows seamlessly from room to room. The massive Kitchen is highly functional featuring lots of granite counter space

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 971-2593

  20883 4th Ave, Cudjoe Key, FL 33042
• 

  

  /47

  $312,500 Sold Mar 17, 2025

  • 520 Sq Ft
  • $601/SF
  • 194 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2000

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

  OPEN WATER VIEWS with TRANSIENT RENTAL. This home is well cared for with newer construction (2000) offers a inviting opportunity to soak up Florida Keys sunshine with amenities readily available. Turnkey features allow you to move right in or get immediately into the rental market. Upgraded vinyl plank flooring, newly added stackable washer and dryer, all new drywall, accordion hurricane

  Anne Press Lokation Real Estate

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

  /2

  Est $1,131,847 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  21034 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /42

  $2,300,000

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  20771 2nd Ave W, Summerland Key, FL 33042

  Wonderful Cudjoe Gardens property! High quality concrete construction and custom metal roof. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool, tiki and firepit. Exceptional boating- the 100' concrete dock is set up for 2 boats- with a 20,000 lb lift and davits rated to 10,000 lbs. Enjoy easy boating access to world class fishing and diving

  

  Sandra Tuttle

  Island Welcome Real Estate

  (833) 402-1042

  20771 2nd Ave W, Summerland Key, FL 33042
• 

  

  /41

  $1,375,000 Sold Mar 13, 2025

  • 1,499 Sq Ft
  • $917/SF
  • 77 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Welcome to your waterfront paradise in Cudjoe Gardens! This exceptional 2-bedroom, 2-bathroom home boasts a stunning outdoor oasis and stylish interior, perfect for relaxation and entertaining. Step outside to a beautiful paver pool deck surrounding a sparkling pool, ideal for sunbathing and gatherings. Enjoy the convenience of a fillet station for your catch of the day, and take advantage of the

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20785 5th Ave W, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  1138 Basque Ln, Summerland Key, FL 33042
• 

  

  /53

  $2,499,000

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft

  23086 Snapper Ln, Summerland Key, FL 33042

  Luxury Waterfront Fortress with Breathtaking Atlantic Ocean Views. 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 a spacious two-car garage,

  Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
• 

  

  /40

  $837,000 Sold Mar 12, 2025

  • 1,184 Sq Ft
  • $707/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  22994 Anne Bonny Ln, Summerland Key, FL 33042

  Canal home on a corner lot offers amazing water views and boating access to the Atlantic and Gulf. This Cudjoe Key home is just 21 miles from Key West. Elevated home on a cul-de-sac boasting tropical landscape and stunning views. This well-maintained home has been owner occupied and features three bedrooms, two baths including an updated en suite primary bathroom, spacious kitchen with gorgeous

  Bascom Grooms Bascom Grooms Real Estate (KW)

  22994 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /39

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
• 

  

  /39

  $1,375,000

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

  164 Tortuga Ln, Summerland Key, FL 33042

  PRICE DROP - EASY TO SEE- MUST SEE - WATERFRONT HOME IN CUDJOE KEY! THIS Renovated 3-bedroom, 2-bath waterfront home located on a quiet canal with quick and easy access to the ocean. The open kitchen features a large island, new cabinetry, and high-end appliances, ideal for entertaining. The primary bedroom includes a walk-in closet and a private bathroom with a frameless glass shower and updated

  Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

  164 Tortuga Ln, Summerland Key, FL 33042
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  /14

  $225,000 Sold Mar 07, 2025

  • Land

  • 246 Days On Market

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Transient RV/Buildable lot in the much sought after Venture Out at Cudjoe Key. This is your chance to own a piece of paradise at an affordable price! The Venture Out Community is located only 19 miles from Key West, but with all of the amenities here you may never want to leave! There is a heated pool, hot tub, fuel docks, boat ramps, fish cleaning stations, bocce ball and tennis courts, pickle

  Mary Conklin Action Keys Realty FL Keys Inc

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
• 

  

  /43

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft

  701 Spanish Main Dr Unit 256, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 256, Cudjoe Key, FL 33042
• 

  

  /29

  $1,749,000

  • 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
• 

  

  /48

  $940,000 Sold Feb 28, 2025

  • 2,320 Sq Ft
  • $405/SF
  • 184 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1963

  184 Cutthroat Dr, Summerland Key, FL 33042

  Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home is being sold fully furnished and with kayaks! Has a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
• 

  /2

  Est $411,000 Not Listed For Sale

  • Studio

  0 Disturbed Pine Rd Unit 602265, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit 602265, Cudjoe Key, FL 33042
• 

  

  /55

  $2,199,000

  • 4 Beds
  • 4 Baths
  • 2,638 Sq Ft

  22925 John Avery Ln, Summerland Key, FL 33042

  Guaranteed to impress! You will not find another one like this solid, custom-built, fully furnished, waterfront island home located on crystal-clear waters filled with tropical fish. Room for pool and seller offering POOL CREDIT! From the moment you enter this large, luxury, British West Indies Island inspired home thru the custom 8ft solid mahogany arched double doors into a stunning foyer, you

  Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  • 828 Sq Ft
  • $966/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Beautiful open water home with direct ocean access. Completely furnished, ready to rent, future bookings in place. 52 foot concrete seawall with dock posts. Downstairs locked storage for all your fishing gear and what not, open deck for sunning, covered area for grilling and entertaining, fishing off the seawall. Gorgeous sunrise and sunsets. Community offers full service marina, convenience

  Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

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