Cudjoe Key, FL Homes for Sale

• 

  

  

  /77

  $13,995,000

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
• 

  Explore Cudjoe Key

• 

  

  

  /39

  $699,000

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft

  181 Doubloon Ln, Summerland Key, FL 33042

  This super cute 2 Bedroom 2 Bath home in Cutthroat Harbor Estates on Cudjoe Key offers easy ocean access with no bridges from the 60' long concrete dock. The open concept floorpan features a remodeled kitchen with center island, new cabinetry, stainless appliances and granite countertops. The enclosed Florida Room and adjacent outdoor Porch both overlook the water and are the perfect places to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 882-0498

  181 Doubloon Ln, Summerland Key, FL 33042
• 

  

  

  /38

  $810,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  22957 Drake Ln, Cudjoe Key, FL 33042

  Excellent boating and pretty open water views down the canal at this gorgeous Cudjoe Key retreat! Enjoy quick no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large center island

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 964-3201

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  

  

  /42

  $1,999,000

  • 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

  (786) 952-5792

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

  

  

  /49

  $1,749,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 900-5290

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /51

  $1,099,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  22841 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-8373

  22841 Buccaneer Ln, Summerland 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. ICF (super energy efficient insulated concrete forms) constructed 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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 563-4761

  225 Colson Dr, Summerland Key, FL 33042
• 

  

  /36

  $755,000

  • 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 Lower Keys (KW)

  (645) 205-1034

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

  

  /5

  $285,000

  • 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)

  (786) 398-5093

  21731 Asturias Rd, Summerland Key, FL 33042
• 

  

  /41

  $1,172,000 Open Fri 3PM - 5PM

  • 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
• 

  

  /45

  $1,950,000 Open Fri 12PM - 2PM

  • 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
• 

  

  /39

  $1,199,000

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

  164 Tortuga Ln, Summerland Key, FL 33042

  JUST REDUCED $206,000Now Offered at $1,119,000 Welcome to 164 Tortuga Lane, a solid concrete stilted home perfectly positioned on a wide canal with quick access to open water. Recently repriced over $200,000 below original list, this is one of the best values in the Lower Keys waterfront market.This move-in-ready property features 3 bedrooms, 2 bathrooms, 1,400 sq ft of living space, and a 6,000

  Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

  164 Tortuga Ln, Summerland 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
• 

  

  /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
• 

  

  /35

  $1,380,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  22822 John Silver Ln, Summerland Key, FL 33042

  Submit all offers to listing agent

  Halley Haack Coldwell Banker Schmitt Real E

  22822 John Silver Ln, Summerland Key, FL 33042
• 

  

  /43

  $1,135,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers ! Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland 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
• 

  

  /40

  $998,000

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  22846 Port Royal Ln, Cudjoe Key, FL 33042

  Stunning open-water views, unforgettable sunsets over the bay, and direct ocean access from this beautifully updated 2BD/2BA Cudjoe Key retreat! Enjoy panoramic bay views, a highly sought-after private boat launch (no longer permitted to be built), and canal with quick access to the Atlantic and Back Country. Upgrades include hurricane-rated impact windows and sliders, a new hurricane-proof

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22846 Port Royal Ln, Cudjoe 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
• 

  

  /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
• 

  

  /9

  $199,500

  • Land

  Vacant Picard Ln, Cudjoe Key, FL 33042

  Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desireable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity to build your dream home,complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open water. It's off the beaten

  lee Sanders KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  

  /29

  $239,000

  • Land

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

  RV Lot 621 - Priced to Sell!! Calling investors, locals and snowbirds - This is an active vacation rental, it also has rights to build a home, or just enjoy this for yourself year round or as a second homebase. Lushly Landscaped 35' x 69' Lot with Ocean Views & Full Hookups. This beautifully landscaped RV lot offers amazing privacy and is located in the gated, community of Venture out on Cudjoe

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
• 

  

  /52

  $439,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

  Transient Rental License! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen, featuring a full line of new

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 635, Cudjoe 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
• 

  

  /15

  $285,000

  • Land

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042

  Spacious RV lot with nightly rentals allowed. 35' x 69' RV lot offers ample space for your outdoor living. Venture Out is a 24hr manned gated community with amentities including - Boat Ramp and fueling station, Marina store. Tennis, Pickleball, Bocce, Basketball courts and a playground for the little ones. This golf cart friendly and beautifully maintained property is the perfect balance of

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042
• 

  

  /35

  $875,000 Open Fri 2PM - 4PM

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft

  22878 Privateer Dr, Summerland Key, FL 33042

  Adorable 2 bed, 2 bath home with many new improvements! New impact windows and doors, new hardie-board siding installed on exterior of house, newer 60 foot concrete dock with cut-ins for a boat lift, roof replaced in October 2017 and newer hot water heater. All the heavy lifting has been done on this house located in sought after Cudjoe Key. Quick boating access to the Gulf and Atlantic,

  Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  

  /40

  $344,999

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

  Step in to your new tropical paradise! This cozy 2 bedroom, 1 bathroom mobile home in Cudjoe Key offers affordable keys living. Enjoy all of the amenities that come with being located in the well known Venture Out community. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
• 

  

  /44

  $997,000

  • 2 Beds
  • 2 Baths
  • 779 Sq Ft

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

  Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
• 

  

  /56

  $295,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

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

  Welcome to this well-maintained home located in the desirable all-age community of Venture Out on Cudjoe Key. This home offers more than meets the eye, featuring a spacious addition that includes a carpeted living area and a versatile flex room currently used as an extra sleeping space--ideal for guests or a home office.While the exterior is modest, the inside offers a comfortable, well-kept

  Kimberly Didrichsons Bluescape Real Estate

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

  

  /60

  $539,000

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
• 

  

  /42

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft

  22988 Port Royal Ln, Summerland Key, FL 33042

  With unbeatable access to oceanside fishing, diving, and lobstering, this canal front home delivers the kind of location boaters rarely find. The west-facing canal sets the stage for vivid sunset views, while the spacious lot offers room for extra parking, trailered boats, or an RV. Inside, the home features three bedrooms, two bathrooms, granite countertops, stainless steel appliances, and

  Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  22988 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /44

  $549,900

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Transient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroom, 2 bathroom home in Cudjoe Key offers the perfect blend of comfort and island living. Enjoy the open-concept living and dining area, perfect for entertaining guests and take in all of the sunrise and sunset views from your porch! Take advantage of all the amenities that come with being located in the well

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
• 

  

  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rent license. The floor plan makes the open water views as its main focus. Cook the catch of the day over looking the waters that you just caught that prized fish in. Sit back and watch

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
• 

  

  /49

  $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
• 

  

  /75

  $889,000

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

  22738 Blackbeard Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Cudjoe Key, this thoughtfully designed waterfront residence offers the ideal blend of comfort, durability, and island style. A large paver driveway leads to a spacious under-home parking area with room for two vehicles, while a concrete drive wraps around to a second covered patio--offering ample space for guests, toys, or trailers.Composite decking leads to a

  Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /40

  $300,000

  • Land

  701 Spanish Main Dr Unit 403, 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 private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042
• 

  

  /19

  $250,000

  • Land

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
• 

  

  /49

  $1,140,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

  Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property 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

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
• 

  

  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

  Rayden Vega CASA MIAMI REAL ESTATE

  22961 John Avery Ln, Summerland Key, FL 33042
• 

  

  /26

  $999,965

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main 369 370 Dr Unit 369, 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! This 2-bedroom, 2-bath home offers unbeatable waterfront living with 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. Enjoy sweeping

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

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

Showing Results 1 - 40, Page 1 of 2

Why Live in Cudjoe Key

Cudjoe Key, FL, is a small community known for its waterfront properties and unique attractions. The island, which began as a U.S. Air Force base in the late 1950s, features a mix of single-family homes and resort rentals, with much of the land remaining undeveloped. The National Key Deer Refuge, a 9,000-acre preserve, protects the endangered Key deer on the island. A notable feature is the aerostat site at the northern tip, where a large white blimp, nicknamed “Fat Albert,” hovers. Residential areas like Cutthroat Harbor Estates and Cudjoe Gardens offer stilt homes and canal-front properties, with prices ranging from $600,000 to over $3 million. The island lacks traditional parks, but residents enjoy water activities such as deep-sea diving, boating, and fishing. Bahia Honda State Park, located 15 miles away, provides additional outdoor recreation with its beach, hiking trails, and snorkeling sites. Dining options include Broil, a gourmet steakhouse, and The Bent Prop, known for its happy hour specials. For groceries, Murray’s Market is 2 miles away on Summerland Key, and a Winn-Dixie is 9 miles away on Big Pine Key. Students attend highly rated schools like Key West High School and Big Pine Academy. The Overseas Highway connects Cudjoe Key to Key West, 20 miles south, and Marathon, 30 miles north. Residents face high home and flood insurance premiums due to the island's susceptibility to hurricanes.

Learn more about living in Cudjoe Key

Frequently Asked Questions

What is the average home price in Cudjoe Key, FL?

Homes for sale in Cudjoe Key, FL have an average home price of $1,307,395.

Are home prices dropping in Cudjoe Key?

Yes, home prices in Cudjoe Key are down 25% in the last 12 months.

How many homes have sold over the last 12 months in Cudjoe Key, FL?

34 homes have sold in Cudjoe Key, FL over the last 12 months.

What are the most popular zip codes in Cudjoe Key, FL?

The most popular zip codes in Cudjoe Key, FL include 33042, 33040 and 33043.

How much do you need to make to afford a house in Cudjoe Key?

The median home price in Cudjoe Key is $1,249,000. If you put a 20% down payment of $249,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $6,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $277K a year to afford the median home price in Cudjoe Key.

How are the schools in Cudjoe Key, FL?

Cudjoe Key, FL has highly rated public and private schools. Some of the best schools in Cudjoe Key based on Niche Grades are Sugarloaf School and Key West High School. Browse all the schools in Cudjoe Key, FL to learn more.

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 145 days on the market compared to the national average of 70 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $1,350,000, down 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,350,000

Median Single Family Sale Price

$1,175,000

Average Price Per Sq Ft

$931

Number of Homes for Sale

4

Last 12 months Home Sales

34

Months of Supply

1.40

Median List Price

$1,249,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

-19%