Cudjoe Key, FL Homes

• 

  

  /2

  Est $270,000 Not Listed For Sale

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  27328 St Vincent Ln, Ramrod Key, FL 33042
• 

  

  

  /34

  $1,495,000

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

  22822 John Silver Ln, Summerland Key, FL 33042

  Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

  Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

  22822 John Silver Ln, Summerland Key, FL 33042
• 

  

  

  /15

  $165,000 Sold Feb 24, 2025

  • Land

  • 18 Days On Market

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

  Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  8 Calico Jack Circle Cir, Verifying, FL 33042
• 

  

  

  /49

  Est $346,223 Not Listed For Sale

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
• 

  

  

  /42

  $2,300,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, Cudjoe Key, FL 33042
• 

  

  /16

  $165,000 Sold Feb 24, 2025

  • Land

  • 212 Days On Market

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  Great Cudjoe Key Location with good boating access and sunset skies views down the canal. This lot can be purchased with house next door 22837 Calico Jack Circle. Picture a pool, tiki hut, family fun with beautiful Florida Keys waters... See lot survey in documents tab. Property outline in pictures is approximate. There is a possibility of change to AE zone. Reach out for further information.

  Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  /8

  Est $582,098 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042
• 

  

  /84

  $2,100,000

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

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  Welcome to paradise at 22562 Jolly Roger Dr in beautiful Cudjoe Key! This custom built, 4-bedroom, 2-bath home features open water views, a designer kitchen with high-end finishes and Viking appliances. In addition, on the first floor there are two guest bedrooms, an office and bathroom. The second floor is where you will find the third bedroom as well the primary bedroom complete with private

  LoRetta Godwin eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /33

  $725,000 Sold Feb 21, 2025

  • 1,431 Sq Ft
  • $507/SF
  • 175 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2016

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  This beautifully maintained 3 bedroom, 2 bathroom home built in 2016 sits on a 7,500 square foot lot in highly sought after Cudjoe Key. Large open floorplan with dedicated dining area, well-appointed kitchen with granite countertops, stainless steel appliances and large center island offering plenty of space for family and friends to gather. Great insurance rates with metal roof, impact

  Pamela Stangler Expert Realty LLC

  22918 Cudjoe Dr, Cudjoe Key, FL 33042
• 

  

  /33

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 396 Sq Ft

  701 Spanish Main Dr Unit 329, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 329, Cudjoe Key, FL 33042
• 

  

  /38

  $1,599,000

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  1113 de Lussan Ln, Summerland Key, FL 33042

  Breathtaking Open Water Home in Cudjoe Key thats comes FULLY FURNISHED. Welcome to paradise! This stunning 2-bedroom, 2-bath home offers magnificent open water views and the ultimate Florida Keys lifestyle.Main Floor: Spanning 784 sq. ft., the first floor features an open-concept kitchen, living room, and dining area, all bathed in natural light. A full bath completes this level, providing

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  1113 de Lussan Ln, Summerland Key, FL 33042
• 

  

  /20

  $250,000 Sold Feb 21, 2025

  • Land

  • 167 Days On Market

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  NIGHTLY RENTALS ALLOWED! Or build your Florida Keys dream home.Come on down to the ultimate RV paradise at this picture perfect lot in Venture Out! 35' x 69' of pure potential for your dream RV setup! Feel the good vibes as you park your rig and let the adventures begin! Dive into the laid-back lifestyle of Venture Out and make memories that will last a lifetime! Build your home here in the

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /32

  $1,399,000 New Construction

  • 3 Beds
  • 2 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
• 

  

  /40

  $550,000 Sold Feb 19, 2025

  • 816 Sq Ft
  • $674/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

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

  Waterfront Paradise Awaits!This charming two-bedroom, two-bath mobile home offers a truly unique waterfront living experience. Enjoy breathtaking views and direct access to the sparkling waters of Cudjoe Key.Key Features:* Prime Waterfront Location: Situated directly on the water with a 35-foot concrete seawall, providing deep water access for boating enthusiasts.* Large windows for amazing views

  Ian Calderwood Bluescape Real Estate

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

  

  /3

  Est $413,000 Not Listed For Sale

  00 Red Legs Ln, Cudjoe Key, FL 33042

  00 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /48

  $850,000

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

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

  Beautiful canal front home with open water views from your spacious open-air porch. Located in a gated community with TRANSIENT RENTALS and tons of amenities. 35' custom-tiled concrete seawall and covered carport w/storage room. Beautiful kitchen with double oven, stainless appliances, Corian countertops and lots of cabinets for all your storage needs. Open floor plan w/dedicated dining area,

  Kim Babenzien Expert Realty LLC (HQ)

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

  

  /74

  $3,300,000 Sold Feb 18, 2025

  • 3,225 Sq Ft
  • $1023/SF
  • 313 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1963

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  A luxury waterfront estate with panoramic ocean views, this walled and gated masterpiece surrounded by gorgeous landscaping provides utmost privacy and the perfect Keys lifestyle and comes completely furnished. The unique 6-bedroom, 4-bathroom layout offers ample space for family and guests with breathtaking ocean vistas from almost every room. A secluded backyard oasis features a private beach,

  Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

  22572 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $442,955 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
• 

  

  /55

  $427,000

  • 2 Beds
  • 2 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
• 

  

  /45

  $1,700,000 Sold Feb 13, 2025

  • 2,772 Sq Ft
  • $613/SF
  • 42 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Stunning canal front home in desirable Cudjoe Gardens, with Southern Exposure, massive 15,600 Sq. Ft. double lot, and deep-water access to Open Ocean and backcountry! Expertly outfitted with 125' of concrete seawall with running water, fillet station, swim ladders, 15K boat lift, davits, and turning basin! Situated on a clean flow-through canal, excellent for swimming and capable of accommodating

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20942 6th Ave W, 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
• 

  

  /42

  $685,999

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to a stunning brand-new construction in the sought-after Venture Out community on Cudjoe Key. This turnkey investment property is designed for comfort and style offering high-quality upgrades and modern features. Built on 9-foot concrete columns with hardy board siding, metal roof and concrete stairs/decking, all meeting 2023 installation standards. Features open concept floor plan with

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
• 

  

  /41

  $2,075,000 Sold Feb 03, 2025

  • 3,056 Sq Ft
  • $679/SF
  • 19 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2004

  20864 4th Ave W, Summerland Key, FL 33042

  This elegantly designed custom built ground level home was created by local architect Glenn Gray. Boasting a spacious open floor plan @ 3,056 sq ft. Two master bedrooms with ensuite baths, third bedroom, full bath and a half, and office all on first floor. Up the flight of stairs leads to a huge open loft space for a fourth bedroom/bunk room, theater room, art room or whatever your needs.

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  20864 4th Ave W, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042

  BK 3 Lot 4 Antigua Ln, Ramrod Key, FL 33042
• 

  

  /53

  $685,999

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

  Welcome to a stunning brand-new construction in the sought-after Venture Out community on Cudjoe Key. This turnkey investment property is designed for comfort and style offering high-quality upgrades and modern features. Built on 9-foot concrete columns with hardy board siding, metal roof and concrete stairs/decking, all meeting 2023 installation standards. Features open concept floor plan with

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
• 

  

  /35

  $217,000 Sold Jan 31, 2025

  • Land

  • 22 Days On Market

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

  TRANSIENT RENTALS ALLOWED!!Live the Island Life in Your Own Slice of Paradise! Ahoy, fellow adventurers! Set your sails for this dreamy RV lot nestled in the vibrant Venture Out Community, just a breezy 19 miles from the heart of Key West. This spacious 35' x 69' lot is ready to welcome even the biggest rigs, so bring your home on wheels and let the good times roll! With lush landscaping already

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
• 

  

  /45

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 574 Sq Ft

  701 Spanish Main Dr Unit 394, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 394, Cudjoe Key, FL 33042
• 

  

  /42

  $425,000

  • 2 Beds
  • 2 Baths
  • 556 Sq Ft

  701 Spanish Main Dr Unit 145, Cudjoe Key, FL 33042

  Welcome to the epitome of comfort and convenience in this fully furnished two-bedroom, one and a half bath home located within the highly desirable Venture Out Community. Step into the quaint and well-equipped kitchen, featuring a full line of appliances, laminate countertops, and natural light throughout. Beyond your private backyard you'll find a haven of amenities and recreational

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 145, Cudjoe Key, FL 33042
• 

  

  /31

  $800,000 Sold Jan 31, 2025

  • 1,008 Sq Ft
  • $794/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  Idyllic Canal-Front Cudjoe Key retreat on a generous fenced-in lot in a prime location! This bright and spacious Cutthroat Harbor Estates home boasts an open concept main living space and three generous bedrooms! Coming soon, the seller is replacing the existing roof with a new metal roof. Upon entry, this turnkey home is tailor-made for entertaining. The living room flows seamlessly with a

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /19

  Est $429,111 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 570, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 570, Cudjoe Key, FL 33042
• 

  

  /44

  $2,990,000

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft

  1176 Thatch Ln, Summerland Key, FL 33042

  Unobstructed Ocean views, you will love this Private Oasis! Enjoy the Cudjoe Key lifestyle in this fabulous 2 bedroom, 2 bath home. Built in 1984 with a well-planned 1577 sqft floorplan, perfectly situated on a corner, oceanfront 24,829 sqft lot. This beautiful home will sell fast!! Granite kitchen countertops, brand new stainless steel appliances, new AC, new tankless water heater, impact doors

  Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /43

  $2,520,000 Sold Jan 31, 2025

  • 2,156 Sq Ft
  • $1169/SF
  • 165 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1986

  622 Sawyer Dr, Summerland Key, FL 33042

  Indulge in the epitome of Keys living with this delightful turnkey 3-bedroom, 3 1/2 bathroom stilt home on 1 1/2 lots. Embracing the coastal allure, this residence features serene blue to aqua tones indoors, complemented by elegant white plantation shutters that evoke a sense of timeless charm. Step onto the expansive covered patio, where panoramic views of the pool and a long canal stretch

  Laura Derrickson Keller Williams Coastal Partners

  622 Sawyer 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
• 

  

  /46

  $599,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

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

  Beautifully renovated 2 bedroom, 2 bathroom canal front home in a gated community with TRANSIENT RENTALS PERMITTED! Well appointed eat-in kitchen and open concept living with family room that opens onto your spacious outdoor porch overlooking the clear boating canal. 35-foot concrete seawall with quick boating access to the Gulf of Mexico and Atlantic Ocean. Home comes fully furnished and has

  Kim Babenzien Expert Realty LLC (HQ)

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

  

  /34

  $775,000 Sold Jan 30, 2025

  • 1,340 Sq Ft
  • $578/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  191 Doubloon Ln, Summerland Key, FL 33042

  Located on a spacious corner lot of a quarter acre in the heart of Cudjoe Key, this home offers both peace and potential. The large, fenced-in yard provides endless opportunities for outdoor activities, with plenty of space for water toys, gardening, or just relaxing in a private, open space. The 25K boat lift makes it an ideal spot for those who love life on the water, while the expansive lot

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  191 Doubloon Ln, Summerland 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
• 

  

  /52

  $699,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  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
• 

  

  /27

  $240,000 Sold Jan 28, 2025

  • Land

  • 210 Days On Market

  701 Spanish Main Dr Unit 403, Cudjoe Key, FL 33042

  Escape to your own piece of paradise in the Venture Out community, where the amenities are as plentiful as the margaritas at a Jimmy Buffett tribute. Picture yourself lounging by the heated pool overlooking the sparkling ocean. Serve up some friendly competition on the tennis courts or Pickleball courts, or head over to the marina to gas up for a day out on your boat. This is not just a property

  Katrina Vanek Bluescape Real Estate

  701 Spanish Main Dr Unit 403, 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

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