Cudjoe Key, FL Homes

• 

  

  /2

  Est $855,000 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
• 

  

  

  /39

  $995,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

  Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 221, 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
• 

  

  /2

  Est $766,978 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22775 Privateer Dr, Summerland Key, FL 33042

  22775 Privateer Dr, Summerland Key, FL 33042
• 

  

  

  /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 ALLOWED! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! 5 bedrooms and 3 baths in this charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views, balconies from almost every room! Original hardwood floor, tons of character and warmth in this lovely home! Large

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland 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

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /39

  Est $957,759 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
• 

  

  /33

  $278,500

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

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

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

  Jenifer Hirsch Bluescape Real Estate

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

  

  /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 $1,318,826

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $792,210 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
• 

  

  /17

  $265,000

  • Land

  701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

  Spacious RV lot measuring approximately 35 x 69 in the highly desirable Venture Out Resort on Cudjoe Key. This ROGO exempt lot is ready for your RV with both 30- and 50-amp service, water, and sewer hookups, plus the flexibility to build in the future. The community offers resort-style amenities including a heated pool, hot tub, private marina with boat ramp, fuel dock and community store,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 642, 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
• 

  /2

  Est $1,040,660 Not Listed For Sale

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

  22974 Anne Bonny Ln, Summerland Key, FL 33042

  22974 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /29

  $1,549,000

  • 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
• 

  

  /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

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
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  /45

  Est $1,235,859 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
• 

  

  /61

  $595,000

  • 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
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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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  /16

  Est $1,762,440 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
• 

  

  /59

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,951 Sq Ft

  20844 4th Ave W, Summerland Key, FL 33042

  SOLD TURNKEY! PRICE INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! A remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, 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
• 

  

  /27

  Est $1,565,206 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
• 

  

  /37

  $979,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  PROTECTED DOCKAGE! LOOK AT THIS VIEW! You have open water views from this impeccably maintained, fully stilted 2BR/2 BATH unit! A 43' SEAWALL with heavy duty dock posts, cleats, fish cleaning table and swim ladder add to the allure of this home perfect for the avid boater! North winds are NO PROBLEM with this protected dockage! The oversized patio off the main living area upstairs is the perfect

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe 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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  /42

  Est $1,350,389 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  1172 Coates Ln, Summerland Key, FL 33042

  1172 Coates Ln, Summerland Key, FL 33042
• 

  

  /43

  $559,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

  Welcome to your tropical retreat! This 2-bed, 1.5-bath canal-front mobile home in Cudjoe Key offers open ocean access and the perfect blend of comfort and affordability. Located in the desirable Venture Out community, this property is also a proven income-producing vacation rental, making it a fantastic investment opportunity.Venture Out is a residential condominium community with 24-hour gated

  Justyn Ewald Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
• 

  

  /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 $259,144

  Last Listing Agent Kelly Gardner Bluescape Real Estate

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

  /2

  Est $1,196,646 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  22943 Dirk Ln, Summerland Key, FL 33042

  22943 Dirk Ln, Summerland Key, FL 33042
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  /7

  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, Cudjoe Key, FL 33042
• 

  

  /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

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

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  /2

  Est $801,471 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  22973 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

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

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
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  /30

  $649,000 Sold Jan 08, 2025

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 13% Below List Price
  • $751/SF
  • 176 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
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  /44

  Est $705,903 Not Listed For Sale

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

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  22903 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /59

  $549,000

  • 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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  /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
• 

  /2

  Est $785,174 Not Listed For Sale

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

  201 Cutthroat Dr, Summerland Key, FL 33042

  201 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /18

  $470,000

  • Land

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, 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 $1,234,469

  Last Listing Agent Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042
• 

  

  /45

  Est $1,233,124 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  22820 Blackbeard Ln, Summerland Key, FL 33042

  22820 Blackbeard Ln, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18