Cudjoe Key, FL Homes

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  /34

  $1,300,000 Sold Aug 18, 2025

  22822 John Silver Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2002

  Last Sold Summary

  • 19% Below List Price
  • $619/SF
  • 214 Days On Market

  Current Estimated Value $1,318,755

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
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  /2

  Est $2,415,418 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  20820 7th Ave W, Summerland Key, FL 33042

  20820 7th Ave W, Summerland Key, FL 33042
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  /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
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  /2

  $55,000 Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
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  /50

  Est $1,910,301 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft

  21025 Hamilton Ave, Summerland Key, FL 33042

  21025 Hamilton Ave, Summerland Key, FL 33042
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  /65

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
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  /29

  $235,000 Sold Oct 31, 2025

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

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 76 Days On Market

  Current Estimated Value $245,569

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
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  /9

  Est $680,226 Not Listed For Sale

  • 2 Beds

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042
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  /2

  $324,999

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement. The value of this property is in the ROGO EXEMPT status. All the utilities are there and I can give you clear title for this property upon closing.Adjacent to this property is lots #35 & 36. They are also available making a total parcel of 18,000 square feet.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
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  /2

  $495,000 Sold Feb 25, 2025

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 773 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Below List Price
  • $640/SF
  • 78 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042
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  /56

  Est $1,784,236 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft

  20966 8th Ave W, Summerland Key, FL 33042

  20966 8th Ave W, Summerland Key, FL 33042
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  /34

  $980,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  131 Doubloon Ln, Summerland Key, FL 33042

  3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

  Jenifer Hirsch Bluescape Real Estate

  131 Doubloon Ln, Summerland Key, FL 33042
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  /36

  $685,000 Sold Oct 15, 2025

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

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $793/SF
  • 164 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
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  /36

  Est $974,538 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft

  21066 3rd Ave, Summerland Key, FL 33042

  21066 3rd Ave, Summerland Key, FL 33042
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  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
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  /12

  $269,000 Sold Sep 29, 2025

  20822 1st Ave, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 10% Below List Price
  • 18 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20822 1st Ave, Cudjoe Key, FL 33042
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  /2

  Est $1,352,511 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  23047 Bluegill Ln, Summerland Key, FL 33042

  23047 Bluegill Ln, Summerland Key, FL 33042
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  /27

  $350,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
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  /20

  $250,000 Sold Feb 21, 2025

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 6% Below List Price
  • 167 Days On Market

  Current Estimated Value $260,534

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
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  /49

  Est $1,803,224 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  22766 Jolly Roger Dr, Summerland Key, FL 33042
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  /47

  $455,000

  • Land

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
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  /51

  $990,000 Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,045,727

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22841 Buccaneer Ln, Summerland Key, FL 33042
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  /2

  Est $872,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  154 Cutthroat Dr, Summerland Key, FL 33042

  154 Cutthroat Dr, Summerland Key, FL 33042
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  /49

  $329,000

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
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  /46

  $550,000 Sold May 28, 2025

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 754 Sq Ft
  • Built 1989

  Last Sold Summary

  • 12% Below List Price
  • $729/SF
  • 72 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
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  /39

  Est $957,305 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  22716 Privateer Dr, Summerland Key, FL 33042

  22716 Privateer Dr, Summerland Key, FL 33042
• 

  

  /18

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
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  /36

  $1,225,000 Sold Jun 13, 2025

  165 Colson Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 2023

  Last Sold Summary

  • 5% Below List Price
  • $722/SF
  • 104 Days On Market

  Current Estimated Value $1,251,341

  Last Listing Agent Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042
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  /29

  Est $855,634 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

  22774 Cudjoe Dr, Summerland Key, FL 33042

  22774 Cudjoe Dr, Summerland Key, FL 33042
• 

  

  /19

  $465,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
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  /7

  $1,600,000 Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
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  /45

  Est $1,177,627 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,280 Sq Ft

  23058 Sailfish Ln, Summerland Key, FL 33042

  23058 Sailfish Ln, Summerland Key, FL 33042
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  /21

  $475,000

  • 1 Bed
  • 1 Bath
  • 668 Sq Ft

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

  Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
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  /47

  $895,000 Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
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  /16

  Est $1,781,186 Not Listed For Sale

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

  23076 Tarpon Ln, Summerland Key, FL 33042

  23076 Tarpon Ln, Summerland Key, FL 33042
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  /9

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /38

  $775,000 Sold Sep 11, 2025

  22957 Drake Ln, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $769/SF
  • 7 Days On Market

  Current Estimated Value $797,296

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22957 Drake Ln, Cudjoe Key, FL 33042
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  /27

  Est $1,611,514 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,645 Sq Ft

  23092 Snapper Ln, Summerland Key, FL 33042

  23092 Snapper 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
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  /24

  $430,000 Sold Nov 25, 2025

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 13% Below List Price
  • 287 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

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