Cudjoe Key, FL Homes

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  /42

  $2,200,000

  • 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
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  /47

  $1,075,000 Sold Jul 30, 2025

  128 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1999

  Last Sold Summary

  • 16% Below List Price
  • $960/SF
  • 189 Days On Market

  Current Estimated Value $1,075,962

  Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

  128 Le Grand Ln, Summerland Key, FL 33042
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  /65

  Est $259,975 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042
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  /69

  $2,249,000 Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 230K-300K for 2026!! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room!

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland Key, FL 33042
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  /42

  $775,000 Sold Oct 01, 2025

  22988 Port Royal Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $691/SF
  • 68 Days On Market

  Current Estimated Value $783,998

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

  22988 Port Royal Ln, Summerland Key, FL 33042
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  /55

  Est $1,350,771 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  266 Colson Dr, Summerland Key, FL 33042

  266 Colson Dr, Summerland Key, FL 33042
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  /29

  $1,549,000 Under Contract

  • 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
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  /41

  $970,000 Sold May 27, 2025

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $698/SF
  • 4 Days On Market

  Current Estimated Value $1,004,635

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  366 Sawyer Dr, Summerland Key, FL 33042
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  /2

  Est $913,994 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft

  22842 Buccaneer Ln, Summerland Key, FL 33042

  22842 Buccaneer Ln, Summerland Key, FL 33042
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  /45

  $1,399,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  1185 Hakluyt Ln, Summerland Key, FL 33042

  Location, location, location!Situated on the desirable southern tip of Cudjoe Key, this exceptional oceanside property offers everything you could dream of in a true Florida Keys retreat. Enjoy breathtaking open-water views from every room and an inviting open floor plan featuring a newer kitchen, updated appliances, modern bathrooms, refreshed flooring, and upgraded impact windows and

  Greg MacLaren Internet Realty of the Florida Keys

  1185 Hakluyt Ln, Summerland Key, FL 33042
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  /41

  $650,000 Sold Jul 01, 2025

  22882 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $580/SF
  • 81 Days On Market

  Current Estimated Value $689,014

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  22882 Buccaneer Ln, Summerland Key, FL 33042
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  /40

  Est $2,216,185 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, Summerland Key, FL 33042
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  /61

  $1,749,900 Open Sun 11AM - 1PM

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

  1163 de Lussan Ln, Summerland Key, FL 33042

  Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

  Jan Fritz Coldwell Banker Schmitt RE Co.

  1163 de Lussan Ln, Summerland Key, FL 33042
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  /52

  $2,300,000 Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,373,365

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
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  /2

  Est $927,454 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  22974 John Avery Ln, Summerland Key, FL 33042

  22974 John Avery Ln, Summerland Key, FL 33042
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  /38

  $1,599,000

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  1113 de Lussan Ln, Summerland Key, FL 33042

  Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED!Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle.Main Living Area:Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the surrounding water

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1113 de Lussan Ln, Summerland Key, FL 33042
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  /17

  $16,000 Sold Oct 28, 2025

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 23% Below List Price
  • 12 Days On Market

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042
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  /19

  Est $909,148 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  221 Cutthroat Dr, Summerland Key, FL 33042

  221 Cutthroat Dr, Summerland Key, FL 33042
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  /68

  $879,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

  This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
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  /54

  $615,000 Sold Jul 11, 2025

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $712/SF
  • 194 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042
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  /81

  Est $1,526,474 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  23041 Snapper Ln, Summerland Key, FL 33042

  23041 Snapper Ln, Summerland Key, FL 33042
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  /33

  $949,000 Pending

  • 2 Beds
  • 3 Baths
  • 1,140 Sq Ft

  151 Cutthroat Dr, Summerland Key, FL 33042

  Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

  Heather Bennett Keller Williams Key West Compass Realty

  151 Cutthroat Dr, Summerland Key, FL 33042
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  /58

  $1,164,000 Sold Dec 12, 2025

  164 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $831/SF
  • 27 Days On Market

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  164 Tortuga Ln, Summerland Key, FL 33042
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  /19

  Est $830,494 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22910 Privateer Dr, Summerland Key, FL 33042

  22910 Privateer Dr, Summerland Key, FL 33042
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  /37

  $275,000

  • Land

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

  Buildable RV Lot. Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Located in a serene, well-maintained gated community at Mile Marker 23. This RV/Buildable lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with landscaping, pea rock, storage box and concrete parking pad. Lot is equipped with full hookups

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
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  /41

  $1,375,000 Sold Mar 13, 2025

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $917/SF
  • 77 Days On Market

  Current Estimated Value $1,395,438

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

  20785 5th Ave W, Summerland Key, FL 33042
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  /34

  Est $927,088 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  320 Spanish Main Dr, Summerland Key, FL 33042

  320 Spanish Main Dr, Summerland Key, FL 33042
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  /17

  $265,000

  • Land

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
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  /107

  $5,300,000 Sold Jun 13, 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 7 Baths
  • 4,981 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $1,064/SF
  • 165 Days On Market

  Current Estimated Value $5,015,474

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  220 E Caribbean Dr, Summerland Key, FL 33042
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  /41

  Est $441,828 Not Listed For Sale

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
• 

  

  /49

  $280,000

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

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

  Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
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  /2

  $49,000 Sold Jun 06, 2025

  7 Lot, Lower Keys, FL 33042

  • Land
  • 0.19 Acre
  • $257,895 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 168 Days On Market

  Last Listing Agent Pamela Stangler MMLS Assoc.-Inactive Member

  7 Lot, Lower Keys, FL 33042
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  /37

  Est $899,714 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  139 Le Grand Ln, Summerland Key, FL 33042

  139 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /43

  $1,125,000

  • 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
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  /28

  $853,000 Sold Jan 09, 2026

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • Built 2012

  Last Sold Summary

  • 14% Below List Price
  • $714/SF
  • 105 Days On Market

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,853,054 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
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  /24

  $265,000

  • Land

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
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  /62

  $1,185,000 Sold Oct 06, 2025

  22915 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $882/SF
  • 37 Days On Market

  Current Estimated Value $1,181,064

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
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  /40

  Est $1,049,862 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  22983 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /24

  $375,000

  • Land

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

  The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeyEscape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig and start relaxing

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

Showing Results 121 - 160, Page 4 of 18