Cudjoe Key, FL Homes

• 

  

  

  /31

  $750,000

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft

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

  Calling All Boating Enthusiasts! Experience the ultimate in waterfront living with this stunning 2-bedroom, 1.5 -bathroom house nestled on a spacious double lot, this gem boasts a 70-foot concrete seawall with davits -- perfect for your big boat! Plus, enjoy the convenience of two-car parking right at your doorstep. Step onto the large covered porch and soak in the breathtaking water views that

  Monika Turek Karem Kramer Realty (KW)

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

  

  

  /44

  $685,000 Sold Nov 27, 2024

  • 1,152 Sq Ft
  • $595/SF
  • 108 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  Assumable VA mortgage at 2.2% Waterfront home with quick and easy access to open water and 135 feet of concrete seawall. Home is solid CBS construction with three bedrooms and one and a half bathrooms. Home has many updates, including new impact windows, fresh paint, light fixtures and roof coating. Large attached screeded in patio and laundry room are an extra bonus spaces. There is an

  Monique Thiel Sunshine State Realty Services

  22903 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  

  /53

  Est $849,727 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
• 

  

  

  /20

  $470,000

  • Land

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

  New Listing! This 35' x 69' canal front lot has ocean views and excellent boating. Bring your RV and live simply by the sea in the private, gated community of Venture Out on Cudjoe Key. Are you looking to build without having to go through the ROGO process? Look no further! This Lot provides you the Right to Build your future home.This Lot has a concrete parking pad and lush tropical landscaping

  Kelly Gardner Bluescape Real Estate

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

  

  

  /34

  $910,000 Sold Nov 26, 2024

  • 1,056 Sq Ft
  • $862/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  320 Spanish Main Dr, Summerland Key, FL 33042

  Beautifully remodeled open floor plan 2 bed, 2 bath waterfront oasis offering stunning canal and sunset views, a large screened porch, and a 10,000 lb. boat lift. Inside, enjoy a modern kitchen with granite countertops, updated bathrooms, and wood-look tile flooring. The den off the living room is perfect for a home office or potential small 3rd bedroom.. The lower level (permitted 634 sqft)

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  320 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /23

  Est $1,207,616 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
• 

  

  /33

  $625,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

  Affordable piece of paradise! Move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and dehumidify! Plus, a 5 stage reverse osmosis water

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
• 

  /2

  $60,000 Sold Nov 19, 2024

  • Land

  • 255 Days On Market

  22861 John Silver Ln, Cudjoe Key, FL 33042

  Tier III canal front lot in Cudjoe Key!

  Tommy Mack Coastal Collection Real Estate Inc.

  22861 John Silver Ln, Cudjoe Key, FL 33042
• 

  

  /62

  Est $1,656,168 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
• 

  

  /24

  $265,000

  • Land

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
• 

  

  /21

  $435,000 Sold Nov 18, 2024

  • 770 Sq Ft
  • $565/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1978

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  This is your chance to own an income property or full-time retreat in the Florida Keys! Cuddie cottage is currently the most competitively priced ocean front single family unit in Venture Out on Cudjoe Key.Make this 2-bedroom, 1-bath island home yours. World class boating and fishing from your own concrete dock equipped with filet table and ladder for quick salt water dips. Following is a

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
• 

  

  /31

  Est $522,000 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
• 

  

  /43

  $1,135,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers ! Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, FL 33042
• 

  

  /41

  $250,000 Sold Nov 15, 2024

  • 316 Sq Ft
  • $791/SF
  • 193 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1980

  701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042

  Possible Seller Financing, Motivated seller! Income producing property! Welcome to your tropical paradise retreat on Cudjoe Key! This charming mobile home, nestled within the Venture Out community, offers the perfect balance of comfort, convenience, and island living. As you step inside, you'll be greeted by a cozy yet efficiently designed living space, complete with dining area, living room,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 423, Cudjoe Key, FL 33042
• 

  /2

  Est $885,530 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
• 

  

  /32

  $1,399,000 New Construction

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

  22872 Buccaneer Ln, Cudjoe Key, FL 33042

  Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  22872 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  

  /47

  $1,120,000 Sold Nov 14, 2024

  • 1,780 Sq Ft
  • $629/SF
  • 128 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  133 Galleon Ln, Summerland Key, FL 33042

  CANAL-FRONT POOL HOME IN CUDJOE KEY - step inside and you'll be impressed by the soaring, tongue and groove ceilings and exposed cedar beams throughout this custom-built design. Just shy of 1800 sq. ft., the living area is light and airy, a brand-new kitchen offers abundant white cabinets and quartz counters; all floors are tile. Pocket sliders open onto porches on both levels allowing the

  Patti Nickless Coldwell Banker Schmitt Real E

  133 Galleon Ln, Summerland Key, FL 33042
• 

  

  /31

  Est $921,919 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft

  23038 Sailfish Ln, Summerland Key, FL 33042

  23038 Sailfish Ln, Summerland Key, FL 33042
• 

  

  /38

  $779,000 Pending

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  22464 La Fitte Dr, Summerland Key, FL 33042

  Cudjoe Key Canal Front Living -- Newly renovated home with covered carport, custom master bath, real wood slim shaker cabinets, quartz countertops, and new appliances and A/C. Features impact doors/sliders, new floors, and fresh P-rock landscaping. Two open porches overlook a 60' canal for relaxing or entertaining. Permitted storage below is ideal for gear or tools. Yard is a blank slate--build

  Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  

  /49

  $1,800,000 Sold Nov 14, 2024

  • 1,884 Sq Ft
  • $955/SF
  • 80 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  COASTAL BEAUTY and MODERN COMFORT in the Fabulous Florida Keys. This fully remodeled Atlantic Oceanfront residence offers a seamless fusion of modern comforts and the natural beauty that surrounds it. A spacious front yard, professionally landscaped with native flora, welcomes you to the property. Each of the three oversized bedrooms accommodate king size beds and walk-in or double door

  Donna Pezzi Keller Williams Key West Compass Realty

  22766 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /42

  Est $1,157,463 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft

  23028 Sailfish Ln, Summerland Key, FL 33042

  23028 Sailfish Ln, Summerland Key, FL 33042
• 

  

  /66

  $3,599,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,817 Sq Ft

  20816 4th Ave W, Cudjoe Key, FL 33042

  LUXURY COLLECTION WATERFRONT ESTATE in the prestigious Cudjoe Gardens. A STUNNING TURNKEY PARADISE, SOLD AS IS WITH HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, & SERENA AND LILY. ALSO 2 HOBIE CATS. This Custom Built Home with a total of 5,373sf under roof is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20816 4th Ave W, Cudjoe Key, FL 33042
• 

  

  /34

  $1,600,000 Sold Nov 14, 2024

  • 1,288 Sq Ft
  • $1,242/SF
  • 157 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  22532 Jolly Roger Dr, Cudjoe Key, FL 33042

  Welcome 22532 Jolly Roger Dr. This impressive open water 3/2 home was built in 2020. The home is finished with all impact rated doors and windows, plank tile flooring, stone countertops, metal roof, Hardie board siding, waterfront balcony and a spacious and inviting open floor plan. The lower level area is finished with street facing garage doors for privacy and security, seamlessly pavered

  Lynn Lucas Berkshire Hathaway HomeServices Keys Real Estate

  22532 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /23

  Est $763,355 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  300 Spanish Main Dr, Summerland Key, FL 33042

  300 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /6

  $200,000 Under Contract

  • Land

  124 Cutthroat Dr, Cudjoe Key, FL 33042

  Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

  Jimmy Lane Island Life Realty Experts

  124 Cutthroat Dr, Cudjoe Key, FL 33042
• 

  /2

  $42,500 Sold Oct 31, 2024

  • Land

  • 94 Days On Market

  Lot 7 Blk 14, Cudjoe Key, FL 33042

  ROGO Lot for dedication purposes. Buyer to confirm points & process with Monroe County Dept. of Planning.

  Paul Rogers Coldwell Banker Schmitt RE Co.

  Lot 7 Blk 14, Cudjoe Key, FL 33042
• 

  /2

  Est $1,594,506 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  1124 de Lussan Ln, Summerland Key, FL 33042

  1124 de Lussan Ln, Summerland Key, FL 33042
• 

  

  /17

  $20,900 Under Contract

  • Land

  0 Budd Key Alley Unit 616603, Cudjoe Key, FL 33042

  Come get your getaway piece of peace in The Florida Keys. Budd Key is an unbelievable but unbuildable island off of the grind and looking for the right buyer. This property cannot be built on or used for any camping. Please confirm with county for all uses.

  Bobby Coe RE/MAX Keys Connection (KW)

  0 Budd Key Alley Unit 616603, Cudjoe Key, FL 33042
• 

  /2

  $49,000 Sold Oct 03, 2025

  • Land

  • 50 Days On Market

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  This is a 2 point lot to be used toward a building permit in Monroe County. Add to your current ROGO application or use it when submitting a new ROGO application to Monroe County. Contact Monroe County Planning Department for specific details on how and when these points can be used. Seller has several lots worth 1 and 2 points for sale if you are looking for additional points. Possible

  Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
• 

  /2

  Est $881,412 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,022 Sq Ft

  1060 Coxon Ln, Summerland Key, FL 33042

  1060 Coxon Ln, Summerland Key, FL 33042
• 

  

  /9

  $199,500 Under Contract

  • Land

  Vacant Picard Ln, Cudjoe Key, FL 33042

  Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desireable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity to build your dream home,complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open water. It's off the beaten

  Sunnie San Lorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  /2

  $600,000 Sold Jul 14, 2025

  • 816 Sq Ft
  • $735/SF
  • 56 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1993

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

  Beautiful Transient Rental Home in Gated Florida Keys Community with Boat Dock and Davits! Welcome to your dream home in the Florida Keys! This updated 2-bedroom, 2-bath home offers an open-concept living area with a fully stocked kitchen, living room, guest bedroom & bathroom and the primary bedroom offers an en suite bathroom all beautifully furnished. The kitchen comes equipped with a full

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
• 

  

  /40

  Est $981,042 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  22939 Gasparilla Ln, Summerland Key, FL 33042

  22939 Gasparilla Ln, Summerland Key, FL 33042
• 

  

  /29

  $239,000 Under Contract

  • Land

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

  RV Lot 621 - Priced to Sell!! Calling investors, locals and snowbirds - This is an active vacation rental, it also has rights to build a home, or just enjoy this for yourself year round or as a second homebase. Lushly Landscaped 35' x 69' Lot with Ocean Views & Full Hookups. This beautifully landscaped RV lot offers amazing privacy and is located in the gated, community of Venture out on Cudjoe

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
• 

  /2

  $495,000 Sold Feb 25, 2025

  • 773 Sq Ft
  • $640/SF
  • 78 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042

  Welcome to coastal living in the Florida Keys! This fully furnished two-bed, two-bath home located within the highly desirable Venture Out Community offers a spacious and well equipped eat-in kitchen with a full line of appliances to cook your catch and entertain friends. Located on a 35-foot seawall, this is a boaters paradise just waiting for you to hit the crystal clear waters of the Florida

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042
• 

  

  /15

  Est $3,253,492 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,578 Sq Ft

  783 Pattison Dr, Summerland Key, FL 33042

  783 Pattison Dr, Summerland Key, FL 33042
• 

  

  /51

  $420,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  Charming Opportunity in Venture Out on Cudjoe Key! Welcome to your next project in the sought-after gated community of Venture Out! This one-bedroom, one-bath mobile home is brimming with potential, offering a unique chance for investors or DIY enthusiasts looking to create their dream getaway. As you step inside, you'll find a cozy layout that provides a blank canvas for your creative vision.

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
• 

  /2

  $73,000 Sold Feb 21, 2025

  • Land
  • 1.01 Acres
  • $72,147 per Acre

  • 30 Days On Market

  0 Valencia Rd, Cudjoe Key, FL 33042

  1.01 ACRE LOT in Beautiful Cudjoe Key. First time available since 1972. Never been built on. Tier 1 Lot. Buyer must do their own due diligence with Monroe County. No building rights!

  Lauren Elliott EXP Realty, LLC

  0 Valencia Rd, Cudjoe Key, FL 33042
• 

  /2

  Est $1,120,698 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,726 Sq Ft

  21056 3rd Ave, Summerland Key, FL 33042

  21056 3rd Ave, Summerland Key, FL 33042
• 

  

  /7

  $1,900,000 Under Contract

  • Land
  • 1.37 Acres
  • $1,382,880 per Acre

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  Prime Location! Rare waterfront commercial lots with high visibility off US1. Truly a sight to be seen with over an acre of property and 500ft of canal frontage! This could be the perfect spot to build your dream business and become a staple in the Key's community. The lots are cleared and fully fenced. Centrally located in the Lower Keys, only 22 miles from Key West and 29 miles to Marathon.

  Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042

Showing Results 241 - 280, Page 7 of 18