Waterfront Homes for Sale in Cudjoe Key, FL

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  $535,000

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  /50

  $289,000

  • 1 Bed
  • 1 Bath
  • 340 Sq Ft

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042

  Welcome to Coconut Cottage #653, a charming island retreat located in the gated waterfront community of Venture Out on Cudjoe Key. This cozy 1BD/1BA home is the perfect Florida Keys getaway, ideal as a vacation rental investment, seasonal escape, or personal retreat. Turn-key and ready to enjoy or rent immediately, this property offers excellent income potential with nightly rentals allowed in

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 653, Cudjoe Key, FL 33042
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  /45

  $1,150,000

  $100K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  20868 5th Ave W, Summerland Key, FL 33042

  Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

  Karen Haack Coldwell Banker Schmitt RE Co.

  20868 5th Ave W, Summerland Key, FL 33042
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  $1,299,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  21025 3rd Ave, Summerland Key, FL 33042

  Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21025 3rd Ave, Summerland Key, FL 33042
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  /16

  $895,900

  $94K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million!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

  Rayden Vega Casa Miami Real Estate

  22961 John Avery Ln, Summerland Key, FL 33042
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  $449,999

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

  Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key.NIGHTLY RENTALS ALLOWEDEnjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home,

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
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  $275,000

  • Land
  • 6,969 Sq Ft
  • $1,718,750 per Acre

  1155 Thatch Ln, Cudjoe Key, FL 33042

  Build your Florida Keys dream in Cudjoe Key just 3 lots from open water. Dock has already been approved and house plans are ready to submit to the county to begin the ROGO process.

  Tommy Mack Coastal Collection Real Estate Inc.

  1155 Thatch Ln, Cudjoe Key, FL 33042
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  $5,995,000

  $295K PRICE DROP

  • 13 Beds
  • 7 Baths
  • 5,022 Sq Ft

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest

  Jennifer Weeks Select Properties of NWFL

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  $487,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

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

  Seller is Motivated!Coastal Charm Meets Modern ComfortWelcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key.Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
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  /6

  $225,000

  $25K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  124 Cutthroat Dr, Cudjoe Key, FL 33042

  Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

  Jimmy Lane Island Life Realty Experts

  124 Cutthroat Dr, Cudjoe Key, FL 33042
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  $365,000

  • Land
  • 2,178 Sq Ft
  • $7,300,000 per Acre

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
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  $460,000

  $20K PRICE DROP

  • Land
  • 1,742 Sq Ft
  • $11,500,000 per Acre

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
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  $12,999,999

  $1M PRICE DROP

  • 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
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  $499,000

  • Land
  • 6,969 Sq Ft
  • $3,118,750 per Acre

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042

  Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22552 Jolly Roger Dr, Cudjoe Key, FL 33042
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  /4

  $985,000

  • Land
  • 6,098 Sq Ft
  • $7,035,714 per Acre

  Unlisted Address

  ROGO EXEMPT CANALFRONT WITH GREAT SUNSETS AND OPEN WATER VIEWS READY FOR YOU TO BRING YOUR BOAT WITH STEP DOWN DOCK. DOCK NEEDS SOME TLC. ACTIVE WATER METER ON SITE, SEWER STUBBED IN AND READY FOR CONNECTION AS A PRIOR HOME WAS DEMOLISHED. BUYER TO VERIFY ALL INFORMATION. POWER IN FRONT. SURVEY AVIALABLE. TWO STORY HOME WOULD PROVIDE SPECTACULAR VIEWS AND A TREMENDOUS OPPORTUNITY FOR YOUR VISION,

  Unlisted Address

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