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Cudjoe Key, FL Homes for Sale with AC

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  • /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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (833) 402-1042

    20771 2nd Ave W, Summerland Key, FL 33042
  • /44

    $2,990,000

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

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, you will love this Private Oasis! Enjoy the Cudjoe Key lifestyle in this fabulous 2 bedroom, 2 bath home. Built in 1984 with a well-planned 1577 sqft floorplan, perfectly situated on a corner, oceanfront 24,829 sqft lot. This beautiful home will sell fast!! Granite kitchen countertops, brand new stainless steel appliances, new AC, new tankless water heater, impact doors

    Jonathan Minerick Homecoin.com

    1176 Thatch 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
  • /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
  • /71

    $3,400,000

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

    1083 Labat Ln, Cudjoe Key, FL 33042

    Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact-resistant doors and windows, concrete dock, and poolside cabana featuring a bar, sink, and ice machine, ensures a luxurious haven. Lush landscaping, meticulously maintained on a weekly basis, adds to

    Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /36

    $2,400,000 New Construction

    • 4 Beds
    • 4 Baths
    • 1,938 Sq Ft

    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
  • /27

    $1,290,000

    • 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
  • /12

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key - Priced to Sell!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 level offers a private in-law suite

    Rayden Vega CASA MIAMI REAL ESTATE

    22961 John Avery Ln, Summerland Key, FL 33042
  • /55

    $407,000

    • 2 Beds
    • 2 Baths
    • 748 Sq Ft

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

    Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • /36

    $795,000

    • 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 RE Co. Lower Keys Office

    701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
  • /37

    $1,250,000

    • 3 Beds
    • 2 Baths
    • 1,482 Sq Ft

    22957 Port Royal Ln, Summerland Key, FL 33042

    Waterfront Paradise in Cudjoe Key - A Boater's Dream!Welcome to your own piece of paradise on the highly sought-after island of Cudjoe Key! Just 22 miles from the vibrant energy of Key West, this stunning waterfront home offers the perfect blend of tropical tranquility and modern convenience.Boasting an impressive 120 feet of waterfront, this property provides exceptional boating opportunities

    Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    22957 Port Royal Ln, Summerland Key, FL 33042
  • /61

    $637,000

    • 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
  • /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
  • /39

    $495,000

    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /33

    $345,000

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    Cozy 1-Bedroom 1-bathroom Mobile Home with Enchanting Florida RoomLocated inside the very desirable Venture Out Gated Community.This charming and very well kept mobile home offers a comfortable and affordable living space. Key Features:* Fully tiled.* Comfortable Bedroom: With plenty of large windows. * Fully equipped kitchen with table, chairs and a built in desk.* Full Bathroom: Includes

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
  • /34

    $1,495,000

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

    22822 John Silver Ln, Summerland Key, FL 33042

    Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

    Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

    22822 John Silver Ln, Summerland Key, FL 33042
  • /30

    $849,900

    • 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
  • /46

    $549,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

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

    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 open-concept layout,

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
  • /54

    $699,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    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. Lower Keys Office

    701 Spanish Main Dr Unit 131, Cudjoe 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
  • /50

    $635,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

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

    MOTIVATED SELLER. BRING THE OFFERS! BEST VALUE IN VENTURE OUT! HUGE PRICE DROP! NEGOTIABLE.! 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 seamless blend of

    Joe Sappington Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
  • /48

    $915,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

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

    Panoramic Ocean Views! Transient Rental License! This 2 bedroom, 1 bathroom home has panoramic ocean views, southern exposure, direct oceanfront access with a 45-foot concrete seawall to dock your boat with swim ladder and fish-cleaning station. Views of the ocean abound in your large, bright living room, well equipped kitchen, large bathroom, washer and dryer, a covered porch overlooking the

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
  • /52

    $699,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

    Introducing an incredible investment opportunity in the heart of the Florida Keys! This stunning waterfront property on Cudjoe Key is not only zoned for minimum one-day vacation rentals but also located in the highly desirable gated community of Venture Out, making it a perfect choice for investors and buyers alike. As you enter this completely remodeled residence, you'll be greeted by a sense of

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
  • /32

    $477,000

    • 2 Beds
    • 2 Baths
    • 814 Sq Ft

    701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

    Charming Florida Keys Retreat at Venture Out on Cudjoe Key: Your Slice of Paradise Awaits! Welcome to your dream getaway nestled in the vibrant Venture Out community! This beautifully designed 2 BR, 2 BA home, built in 2016, is perfect for those seeking a blend of relaxation and adventure. Fully furnished and ready for you to move in or rent out nightly, this property is a true gem in the heart

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
  • /44

    $1,135,000

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

    22837 Calico Jack Cir, Summerland Key, FL 33042

    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 too. Quick commute to Key

    Beata Sharpe Coldwell Banker Vanguard Realty

    22837 Calico Jack Cir, Summerland Key, FL 33042
  • /71

    $565,000

    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

    JUST REDUCED! Motivated Seller! BRING YOUR OFFER! Turn-key, updated 2/2 with 35' of private dockage is ready to generate a lucrative income with nightly rentals allowed. The furniture is included and so is the golf cart! BRAND NEW PAVER PATIO! This amenity-rich, gated community is perfect for investors or seasonal/full-time residents! DON'T MISS YOUR OPPORTUNITY IN THIS HIGHLY SOUGHT-AFTER PIECE

    Laurie Keiling Engel & Volkers Marathon

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • /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

    21470 Overseas Hwy, Cudjoe Key, FL 33042
  • /44

    $1,025,000

    • 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
  • /24

    $550,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 343, Cudjoe Key, FL 33042

    Motivated seller! Income producing property, located on Cudjoe Key, just 20 miles from Key West. Located in Venture Out community, with many amenities, olympic size pool, heated pool, hot tub, baby pool, tennis courts, bocce ball, full service marina, convenience store and 24 hour security, just to name a few. 2 bedroom, 2 bath, open living and kitchen, screened porch overlooking canal with a 35

    Susan Rich Select Properties of NWFL

    701 Spanish Main Dr Unit 343, Cudjoe Key, FL 33042
  • /66

    $998,000

    • 3 Beds
    • 2 Baths
    • 1,541 Sq Ft

    246 Colson Dr, Summerland Key, FL 33042

    SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet

    Tracey Petrusha Venture Realty Group

    246 Colson Dr, Summerland Key, FL 33042
  • /107

    $5,992,000 New Construction

    • 5 Beds
    • 7 Baths
    • 4,981 Sq Ft

    220 E Caribbean Dr, Summerland Key, FL 33042

    Experience unparalleled luxury in this Brand New 2025 Custom Built Smart Home. 6,128 SQ FT 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

    Stacy Shahan Island Real Estate Company Florida Keys

    220 E Caribbean Dr, Summerland Key, FL 33042
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