Homes in ZIP Code 33042

• 

  

  /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 $1,235,523 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft

  19563 Canal Dr, Summerland Key, FL 33042

  19563 Canal Dr, 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
• 

  

  /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
• 

  

  /3

  $300,000

  • Land

  0 Candice Ave, Little Torch Key, FL 33042

  Rare opportunity to acquire a 6-parcel assemblage totaling approx. 13.67 acres on Little Torch Key. Includes five 6,000 sq. ft. Mates Beach lots on Candice Avenue (two Tier 3 Infill) and a 12.97+/- acre tract with 2.61 acres upland and 10.36 acres environmentally sensitive land. Perfect for agricultural or beekeeping use, conservation project, or long-term investment. Located in a desirable Lower

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  0 Candice Ave, Little Torch Key, FL 33042
• 

  /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
• 

  /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
• 

  

  /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
• 

  

  /29

  $390,000 Sold May 28, 2025

  28131 Helen Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $456/SF
  • 91 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  28131 Helen Ave, Little Torch 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
• 

  

  /94

  $3,875,000

  • 4 Beds
  • 4 Baths
  • 2,766 Sq Ft

  414 Caribbean Dr E, Summerland Key, FL 33042

  Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft.

  Lisa Swanson The Agency Florida Keys

  414 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /42

  $1,000,000 Sold Jun 20, 2025

  27330 Barbados Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1991

  Last Sold Summary

  • 16% Below List Price
  • $567/SF
  • 79 Days On Market

  Current Estimated Value $1,005,937

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
• 

  

  /29

  Est $906,204 Not Listed For Sale

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

  27359 Jamaica Ln, Summerland Key, FL 33042

  27359 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /47

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
• 

  

  /48

  $360,000 Sold Jan 10, 2025

  19461 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,136 Sq Ft
  • Built 1963

  Last Sold Summary

  • 40% Below List Price
  • $317/SF
  • 84 Days On Market

  Current Estimated Value $516,713

  Last Listing Agent Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  19461 Canal Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,031,115 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  479 Blackbeard Rd, Summerland Key, FL 33042

  479 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /59

  $2,950,000 Open Sun 1PM - 3PM

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /25

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **Motivated Sellers, all reasonable offers considered**This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor seating

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /23

  Est $769,585 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  283 Pirates Rd, Summerland Key, FL 33042

  283 Pirates Rd, 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
• 

  

  /12

  $300,000 Sold Jan 27, 2025

  27007 Angelfish Rd, Summerland Key, FL 33042

  • 1,201 Sq Ft
  • Built 1967

  Last Sold Summary

  • 50% Below List Price
  • $250/SF
  • 281 Days On Market

  Current Estimated Value $517,271

  Last Listing Agent Sabrina Liguori Key West Vacation Properties & Realty, LLC (KW)

  27007 Angelfish Rd, Summerland Key, FL 33042
• 

  

  /33

  Est $1,072,046 Not Listed For Sale

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

  131 W Indies Dr, Summerland Key, FL 33042

  131 W Indies Dr, Summerland Key, FL 33042
• 

  

  /47

  $370,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  27945 Tarpon Terrace, Little Torch Key, FL 33042

  Lots of new upgrades : Remodeled* New 40 gallon Hot Water Heater, several new mini splits, New Tiled floors throughout, New kitchen, New bathroom , new cabinet in the Laundry room area lots of new shelving added throughout, New electric box on the exterior, most of the appliances kitchen and laundry are newly added upgrades completely newly painted interior. Lots of money put into this remodeled

  Anne Press Lokation Real Estate

  27945 Tarpon Terrace, Little Torch 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 $690,479 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  19720 Date Palm Dr, Summerland Key, FL 33042

  19720 Date Palm Dr, 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
• 

  

  /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
• 

  

  /4

  Est $833,682 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,108 Sq Ft

  27456 Martinique Ln, Summerland Key, FL 33042

  27456 Martinique Ln, Summerland Key, FL 33042
• 

  

  /13

  $395,000

  • Land

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key while the building permit is in-process for a 4 bedroom / 2 bath stilted single family residence (home is additional). The plans shown are for a 1920 sq ft' / 2 story Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment,

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /45

  Est $1,801,467 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft

  19527 Indian Mound Dr, Summerland Key, FL 33042

  19527 Indian Mound Dr, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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 $1,123,786 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft

  1981 Sugarloaf Blvd, Summerland Key, FL 33042

  1981 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /116

  $19,750,000

  • 6 Beds
  • 7 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson The Agency Florida Keys

  15760 Old State Road 4a, Summerland Key, FL 33042
• 

  

  /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

Showing Results 441 - 480, Page 12 of 18