Cudjoe Key, FL Homes

• 

  

  

  /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
• 

  

  

  /19

  $225,000

  • 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
• 

  

  

  /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
• 

  

  

  /8

  Est $469,191 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042
• 

  

  

  /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 Lower Keys (KW)

  (786) 952-7261

  20838 5th Ave W, Summerland Key, FL 33042
• 

  

  /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
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /60

  $490,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /55

  $1,500,000 Under Contract

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

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042

  Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (866) 528-5667

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  

  /61

  $2,150,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  743 Pattison Dr, Summerland Key, FL 33042

  Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 756-9163

  743 Pattison Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  

  /50

  $1,599,000 Under Contract

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

  56 Colson Dr, Summerland Key, FL 33042

  Exceptional waterfront living awaits at 56 Colson Drive in Cudjoe Gardens on Cudjoe Key--a fully renovated 3 Bedroom 2 Bathroom home offering 1,645 sq. ft. of thoughtfully planned interior space on a sprawling 11,900 sq. ft. lot. Built with CBS construction and impact doors and windows, this property combines durability with modern coastal appeal and is designed to take full advantage of the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 841-7430

  56 Colson Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  /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
• 

  

  /38

  $1,200,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  218 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 218 Spanish Main Dr., a turnkey, recently renovated Florida Keys waterfront home offering the perfect blend of coastal charm and modern comfort. This 2-story, 3 bed, 3 bath fully fenced retreat boasts 2,016 sq ft of thoughtfully designed space with water views from nearly every room. Enjoy porches on both levels, ideal for morning coffee or sunset cocktails. The main level features an

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 876-6037

  218 Spanish Main Dr, Summerland Key, FL 33042
• 

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 18