Cudjoe Key, FL Homes

• 

  

  

  /55

  $374,000

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
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  /40

  $550,000 Sold Feb 19, 2025

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1996

  Last Sold Summary

  • 15% Below List Price
  • $674/SF
  • 22 Days On Market

  Last Listing Agent Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
• 

  

  

  /49

  Est $1,370,738 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,790 Sq Ft

  21790 Spain Blvd, Summerland Key, FL 33042

  21790 Spain Blvd, Summerland Key, FL 33042
• 

  

  

  /54

  $839,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
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  /114

  $1,477,000 Sold Sep 02, 2025

  153 Galleon Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $947/SF
  • 49 Days On Market

  Current Estimated Value $1,454,813

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,095,553 Not Listed For Sale

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

  23034 Wahoo Ln, Summerland Key, FL 33042

  23034 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /18

  $265,000

  • Land

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

  Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

  Jenifer Hirsch Bluescape Real Estate

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

  

  /19

  $505,000 Sold Jul 30, 2025

  134 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 11% Below List Price
  • $478/SF
  • 4 Days On Market

  Current Estimated Value $538,152

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

  134 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /39

  Est $1,407,942 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft

  21076 3rd Ave, Summerland Key, FL 33042

  21076 3rd Ave, Summerland Key, FL 33042
• 

  

  /53

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  /47

  $312,500 Sold Mar 17, 2025

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

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • Built 2000

  Last Sold Summary

  • 22% Below List Price
  • $601/SF
  • 194 Days On Market

  Last Listing Agent Anne Press Lokation Real Estate

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

  /2

  Est $824,480 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22968 Drake Ln, Summerland Key, FL 33042

  22968 Drake Ln, Summerland Key, FL 33042
• 

  

  /75

  $939,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

  This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
• 

  /2

  $175,000 Sold Dec 10, 2025

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 17% Below List Price
  • 23 Days On Market

  Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /28

  Est $965,549 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  340 Spanish Main Dr, Summerland Key, FL 33042

  340 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /42

  $650,000

  • Land

  22948 Drake Ln, Summerland Key, FL 33042

  Canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water: Views and more views. 70-foot concrete seawall with boat slip/basin and 10,000 pound boat lift make this the perfect location for boater/angler's new home. Previous house removed and lot is ready for your new vision. Electric was in place, buyer to verify FKAA

  Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland Key, FL 33042
• 

  

  /45

  $2,090,000 Sold Jul 07, 2025

  23066 Tarpon Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3.5 Baths
  • 1,938 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Below List Price
  • $1,078/SF
  • 65 Days On Market

  Current Estimated Value $2,104,333

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23066 Tarpon Ln, Summerland Key, FL 33042
• 

  

  /36

  Est $1,528,669 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  20878 5th Ave W, Summerland Key, FL 33042

  20878 5th Ave W, Summerland Key, FL 33042
• 

  

  /46

  $419,000

  • 1 Bed
  • 1 Bath
  • 833 Sq Ft

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

  This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
• 

  

  /27

  $905,000 Sold Dec 11, 2025

  22852 John Silver Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $559/SF
  • 75 Days On Market

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  22852 John Silver Ln, Summerland Key, FL 33042
• 

  

  /53

  Est $939,954 Not Listed For Sale

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

  22977 Long Ben Ln, Summerland Key, FL 33042

  22977 Long Ben Ln, Summerland Key, FL 33042
• 

  

  /56

  $579,900

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

  Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
• 

  

  /46

  $1,900,000 Sold Mar 27, 2025

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  Last Sold Summary

  • 36% Below List Price
  • $806/SF
  • 342 Days On Market

  Current Estimated Value $1,914,073

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

  271 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /23

  Est $1,269,364 Not Listed For Sale

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

  21044 7th Ave, Summerland Key, FL 33042

  21044 7th Ave, Summerland Key, FL 33042
• 

  

  /39

  $625,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

  Randal Longo Keys Realty Redefined LLC

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
• 

  /2

  $49,000 Sold Sep 22, 2025

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /62

  Est $1,688,233 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  1008 Calico Jack Cir, Summerland Key, FL 33042

  1008 Calico Jack Cir, Summerland Key, FL 33042
• 

  

  /30

  $460,000

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
• 

  

  /74

  $3,300,000 Sold Feb 18, 2025

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  Last Sold Summary

  • 27% Below List Price
  • $1,023/SF
  • 313 Days On Market

  Current Estimated Value $3,225,004

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  22572 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /35

  Est $1,067,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,313 Sq Ft

  21024 2nd Ave, Summerland Key, FL 33042

  21024 2nd Ave, Summerland Key, FL 33042
• 

  

  /25

  $569,700

  • 2 Beds
  • 1 Bath
  • 718 Sq Ft

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

  Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
• 

  

  /44

  $650,000 Sold Apr 17, 2025

  268 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $616/SF
  • 86 Days On Market

  Current Estimated Value $670,224

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  268 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /31

  Est $489,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22953 John Silver Ln, Summerland Key, FL 33042

  22953 John Silver Ln, Summerland Key, FL 33042
• 

  

  /46

  $487,000 Open Mon 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

  Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
• 

  

  /33

  $725,000 Sold Feb 21, 2025

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $507/SF
  • 175 Days On Market

  Current Estimated Value $772,347

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22918 Cudjoe Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $869,792 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft

  22812 Buccaneer Ln, Summerland Key, FL 33042

  22812 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /45

  $879,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 950 Sq Ft

  23012 Snapper Ln, Summerland Key, FL 33042

  Welcome to 23012 Snapper Lane in Beautiful Cudjoe Key, FL.This Three (3) bedroom and Two (2) bathroom elevated, waterfront on a corner lot is the one you have been looking for, with a great price too!This home is built to last and has been meticulously cared for. Come bring your boat and sit back and enjoy your favorite beverage on this oversized backyard. Tons of storage for all your toys, and

  Bobby Coe RE/MAX Keys Connection (KW)

  23012 Snapper Ln, Summerland Key, FL 33042
• 

  

  /38

  $900,000 Sold May 30, 2025

  22971 Hawkins Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,142 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $788/SF
  • 46 Days On Market

  Current Estimated Value $918,402

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  22971 Hawkins Ln, Summerland Key, FL 33042
• 

  

  /47

  Est $1,182,640 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,780 Sq Ft

  133 Galleon Ln, Summerland Key, FL 33042

  133 Galleon Ln, Summerland Key, FL 33042
• 

  

  /29

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  463 Lesrohde Dr, Ramrod Key, FL 33042

  Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

  Sarah Dolson Keller Williams Key West Compass Realty

  463 Lesrohde Dr, Ramrod Key, FL 33042

Showing Results 241 - 280, Page 7 of 18