Cudjoe Key, FL Homes

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  /49

  Est $351,493 Not Listed For Sale

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

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

  

  

  /77

  $12,999,999

  • 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
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  /51

  $420,000 Sold Nov 21, 2025

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 185 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
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  /8

  Est $469,191 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042
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  /49

  $1,145,000

  • 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 298 sq. ft. of

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 321-8407

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
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  /4

  $50,000 Sold Dec 19, 2025

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 41% Below List Price
  • 25 Days On Market

  Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /52

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  21250 Conch Dr, Summerland Key, FL 33042

  Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 614-3802

  21250 Conch Dr, Summerland Key, FL 33042
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  /39

  $705,000 Sold Sep 08, 2025

  181 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $647/SF
  • 7 Days On Market

  Current Estimated Value $710,204

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

  181 Doubloon Ln, Summerland Key, FL 33042
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  /14

  Est $478,047 Not Listed For Sale

  • 1 Bed

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

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

  

  /29

  $1,325,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  22974 Anne Bonny Ln, Summerland Key, FL 33042

  Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago, allowing a new owner to

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 869-3656

  22974 Anne Bonny Ln, Summerland Key, FL 33042
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  /16

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 8% Below List Price
  • 212 Days On Market

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
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  /2

  Est $883,002 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
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  /39

  $485,000

  • 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

  (786) 551-4336

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
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  /58

  $2,025,000 Sold May 13, 2025

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $1,567/SF
  • 85 Days On Market

  Current Estimated Value $2,021,525

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
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  /69

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042
• 

  

  /20

  $214,500

  • Land

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 418-4615

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
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  /48

  $940,000 Sold Feb 28, 2025

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 1963

  Last Sold Summary

  • 22% Below List Price
  • $405/SF
  • 184 Days On Market

  Current Estimated Value $1,009,244

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
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  /66

  Not Listed For Sale

  • 2 Beds

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

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

  

  /44

  $1,150,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
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  /46

  $998,000 Sold Sep 09, 2025

  1117 Basque Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft
  • Built 2013

  Last Sold Summary

  • $757/SF
  • 16 Days On Market

  Current Estimated Value $1,000,542

  Last Listing Agent Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

  1117 Basque Ln, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042
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  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 Sawyer Dr, Summerland Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
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  /2

  $73,000 Sold Feb 21, 2025

  00 Valencia Rd, Cudjoe Key, FL 33042

  • Land
  • 1.01 Acres
  • $72,277 per Acre

  Last Sold Summary

  • 64% Below List Price
  • 36 Days On Market

  Last Listing Agent Jennifer Withers EXP REALTY LLC

  00 Valencia Rd, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

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

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

  

  /47

  $629,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, 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 2024, 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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
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  /33

  $1,350,000 Sold Jul 24, 2025

  20883 4th Ave, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2011

  Last Sold Summary

  • 21% Below List Price
  • $535/SF
  • 215 Days On Market

  Current Estimated Value $1,619,297

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

  20883 4th Ave, Cudjoe Key, FL 33042
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  /35

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 849 Sq Ft

  701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

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

  

  /31

  $430,000

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  Acre of Privacy, your Keys cottage/bungalow in the woods. Artist retreat, man cave or maybe just because you love privacy and want an escape. Horse stables nearby and you can ride horses in this area. Connected to the house by sidewalk and decking is a Screen porch 13 X 18 plus a storge room 9 X 12. Additionally, there are 2 carports, 3 sheds. Space in yard to park your cars, boats, RV. Property

  Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
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  /44

  $650,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $785/SF
  • 8 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042
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  /58

  Est $1,726,076 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft

  1106 Thatch Ln, Summerland Key, FL 33042

  1106 Thatch Ln, Summerland Key, FL 33042
• 

  

  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 618 Sq Ft

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

  Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

  Suzanne Moore Suzanne Moore Real Estate

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042
• 

  

  /41

  $1,350,000 Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,356,755

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

  20735 5th Ave W, Summerland Key, FL 33042
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  /30

  Est $738,861 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  124 Yardarm Rd, Cudjoe Key, FL 33042

  124 Yardarm Rd, Cudjoe Key, FL 33042
• 

  

  /59

  $1,569,999 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
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  /32

  $450,000 Sold Aug 20, 2025

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

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

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

  

  /17

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
• 

  

  /41

  $2,395,000 Pending

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

  1176 Thatch Ln, Summerland Key, FL 33042

  Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

  Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /36

  $330,000 Sold Apr 17, 2025

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

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $453/SF
  • 63 Days On Market

  Last Listing Agent Frank Griffiths Lokation Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /41

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

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