Cudjoe Key, FL Homes

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  /32

  Est $454,519 Not Listed For Sale

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1988

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $1,103/SF
  • 256 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
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  /58

  $3,750,000

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

  755 & 744 Sawyer Dr, Cudjoe 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

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
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  /75

  $830,000 Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $848,119

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
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  /30

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • $751/SF
  • 176 Days On Market

  Last Sold Price $649,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
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  /34

  $1,575,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /41

  $1,105,000 Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,091,395

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
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  /14

  Est $238,014 Not Listed For Sale

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 2000

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $402/SF
  • 246 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Mary Conklin Action Keys Realty of the Lower FL Keys LLC
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  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
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  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,387,846

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  Last Sold Summary

  • $551/SF

  Last Sold Price $450,000
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  /72

  $2,995,000

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  

  Miriam Novotny

  Compass Florida, LLC

  (786) 667-5744

  20920 5th Ave W, Summerland Key, FL 33042
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  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $6,513,006

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  785 Sawyer Dr, Cudjoe Key, FL 33042
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  /2

  Est $251,086 Not Listed For Sale

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  • Studio
  • Built 1981

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  Last Sold Summary

  • 5% Below List Price

  Last Sold Price $265,000
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  /73

  $3,500,000

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

  Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 841-9203

  1083 Labat Ln, Cudjoe Key, FL 33042
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  /43

  $1,700,000 Sold Jan 30, 2026

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $820/SF
  • 140 Days On Market

  Current Estimated Value $1,690,104

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  Last Sold Summary

  • $736/SF

  Last Sold Price $660,000

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
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  /51

  $1,999,999 Under Contract

  • 3 Beds
  • 4 Baths
  • 2,100 Sq Ft

  23087 Sailfish Ln, Summerland Key, FL 33042

  Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 807-9315

  23087 Sailfish Ln, Summerland Key, FL 33042
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  /26

  $239,000 Sold Jun 30, 2025

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

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 74 Days On Market

  Current Estimated Value $244,972

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
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  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • $828/SF
  • 66 Days On Market

  Last Sold Price $715,000
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  /91

  $1,200,000 Under Contract

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

  21855 Spain Blvd, Summerland Key, FL 33042

  Imagine owning a pool home and 3.3 private acres in the Florida Keys - this rare opportunity is in Cudjoe Acres, an equestrian area just 20 miles from Key West, with two equestrian facilities just around the corner. The home sits on one secluded acre surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 225-2307

  21855 Spain Blvd, Summerland Key, FL 33042
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  /57

  $2,800,000 Sold Oct 30, 2025

  22967 Redfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $747/SF
  • 37 Days On Market

  Current Estimated Value $2,800,667

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22967 Redfish Ln, Cudjoe Key, FL 33042
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  /2

  Est $1,467,072 Not Listed For Sale

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft
  • Built 2019

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 13% Below List Price
  • $655/SF

  Last Sold Price $1,300,000

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

  

  /19

  $215,000

  • Land

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 761-5180

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
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  /44

  $700,000 Sold Jan 09, 2026

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $810/SF
  • 23 Days On Market

  Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
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  /3

  Est $571,000 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  Last Sold Summary

  • 128% Above List Price
  • 4 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Carmen David Xcellence Realty
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  /39

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  20838 5th Ave W, Summerland Key, FL 33042

  Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 952-7261

  20838 5th Ave W, Summerland Key, FL 33042
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  /48

  $291,000 Sold Mar 03, 2026

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $404/SF
  • 133 Days On Market

  Last Listing Agent Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  Last Sold Price $50,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
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  /60

  $487,500

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 981-9841

  701 Spanish Main Dr Unit 602, 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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  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  Last Sold Price $50,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
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  /66

  $799,000

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

  Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 841-6970

  701 Spanish Main Dr Unit 172, 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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  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 543 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.
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  /47

  $559,000 Open Fri 10:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

  701 Spanish Main Dr Unit 510, Cudjoe 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 $709,229

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  181 Doubloon Ln, Summerland Key, FL 33042
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  /2

  Est $426,128 Not Listed For Sale

  20874 4th Ave, Cudjoe Key, FL 33042

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  Last Sold Summary

  • 5% Below List Price

  Last Sold Price $450,000

  Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)
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  /74

  $799,000 Pending

  • 2 Beds
  • 2 Baths
  • 766 Sq Ft

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042

  Canal Front Oasis with Resort Amenities!Nightly Rentals Allowed!Income Producing Gem!RARE-DOUBLE LOT!! Allows 2 cars with 2 separate driveways. Massive 69' Seawall!RARE-DAVITS for your boat!! Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom mid-rise home offers the ultimate Florida Keys

  

  Ian Calderwood

  Bluescape Real Estate

  (844) 482-8589

  701 Spanish Main Dr Unit 333,334, 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 $2,062,598

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,158,249 Not Listed For Sale

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft
  • Built 2022

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  Last Sold Summary

  • 5% Below List Price
  • $808/SF

  Last Sold Price $1,100,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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