Cudjoe Key, FL Homes

• 

  

  

  /46

  $1,900,000 Sold Mar 27, 2025

  • 2,358 Sq Ft
  • $806/SF
  • 342 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2023

  271 W Indies Dr, Ramrod Key, FL 33042

  Brand new construction in Breezeswept Beach Estates! This modern 2,358 sq. ft. pool home offers unbeatable Open Water Views and high-end finishes. The open-concept layout features a Chef's Kitchen with premium stainless steel appliances, quartz countertops, ample storage, and a large island. A separate bar with a wine cooler adds convenience. Impact sliding glass doors lead to a covered veranda

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  271 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /2

  Est $884,000 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
• 

  

  

  /52

  $425,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

  Transient Rental License! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen, featuring a full line of new

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
• 

  

  

  /32

  $450,000 Sold Mar 19, 2025

  • Land

  • 256 Days On Market

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  A Fisherman's Paradise for the Big Boaters! This 40' seawall RV site located in the coveted Venture Out community is the perfect vacation and or income producing property for nightly/weekly rentals. The 60' wide canal is one of the best in the park providing deep draft clear water with ample maneuverability for the big boats. The canal provides a straight shot out to Kemp Channel and the open

  Paul Rogers Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
• 

  

  /2

  Est $735,087 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
• 

  

  /35

  $875,000

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft

  22878 Privateer Dr, Summerland Key, FL 33042

  Adorable 2 bed, 2 bath home with many new improvements! New impact windows and doors, new hardie-board siding installed on exterior of house, newer 60 foot concrete dock with cut-ins for a boat lift, roof replaced in October 2017 and newer hot water heater. All the heavy lifting has been done on this house located in sought after Cudjoe Key. Quick boating access to the Gulf and Atlantic,

  Pamela Stangler Expert Realty LLC

  22878 Privateer Dr, Summerland Key, FL 33042
• 

  

  /47

  $312,500 Sold Mar 17, 2025

  • 520 Sq Ft
  • $601/SF
  • 194 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2000

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

  OPEN WATER VIEWS with TRANSIENT RENTAL. This home is well cared for with newer construction (2000) offers a inviting opportunity to soak up Florida Keys sunshine with amenities readily available. Turnkey features allow you to move right in or get immediately into the rental market. Upgraded vinyl plank flooring, newly added stackable washer and dryer, all new drywall, accordion hurricane

  Anne Press Lokation Real Estate

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

  

  /39

  Est $959,888 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
• 

  

  /44

  $949,000

  • 2 Beds
  • 2 Baths
  • 779 Sq Ft

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

  Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
• 

  

  /41

  $1,375,000 Sold Mar 13, 2025

  • 1,499 Sq Ft
  • $917/SF
  • 77 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  20785 5th Ave W, Summerland Key, FL 33042

  Welcome to your waterfront paradise in Cudjoe Gardens! This exceptional 2-bedroom, 2-bathroom home boasts a stunning outdoor oasis and stylish interior, perfect for relaxation and entertaining. Step outside to a beautiful paver pool deck surrounding a sparkling pool, ideal for sunbathing and gatherings. Enjoy the convenience of a fillet station for your catch of the day, and take advantage of the

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20785 5th Ave W, Summerland Key, FL 33042
• 

  

  /29

  Est $922,665 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
• 

  

  /56

  $279,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to this well-maintained home located in the desirable all-age community of Venture Out on Cudjoe Key. This home offers more than meets the eye, featuring a spacious addition that includes a carpeted living area and a versatile flex room currently used as an extra sleeping space--ideal for guests or a home office.While the exterior is modest, the inside offers a comfortable, well-kept

  Kimberly Didrichsons Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  /40

  $837,000 Sold Mar 12, 2025

  • 1,184 Sq Ft
  • $707/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  22994 Anne Bonny Ln, Summerland Key, FL 33042

  Canal home on a corner lot offers amazing water views and boating access to the Atlantic and Gulf. This Cudjoe Key home is just 21 miles from Key West. Elevated home on a cul-de-sac boasting tropical landscape and stunning views. This well-maintained home has been owner occupied and features three bedrooms, two baths including an updated en suite primary bathroom, spacious kitchen with gorgeous

  Bascom Grooms Bascom Grooms Real Estate (KW)

  22994 Anne Bonny Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,027,313 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  22974 Anne Bonny Ln, Summerland Key, FL 33042

  22974 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rent license. The floor plan makes the open water views as its main focus. Cook the catch of the day over looking the waters that you just caught that prized fish in. Sit back and watch

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
• 

  

  /14

  $225,000 Sold Mar 07, 2025

  • Land

  • 246 Days On Market

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Transient RV/Buildable lot in the much sought after Venture Out at Cudjoe Key. This is your chance to own a piece of paradise at an affordable price! The Venture Out Community is located only 19 miles from Key West, but with all of the amenities here you may never want to leave! There is a heated pool, hot tub, fuel docks, boat ramps, fish cleaning stations, bocce ball and tennis courts, pickle

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
• 

  

  /45

  Est $1,107,265 Not Listed For Sale

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

  23058 Sailfish Ln, Summerland Key, FL 33042

  23058 Sailfish Ln, Summerland Key, FL 33042
• 

  

  /40

  $300,000

  • Land

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

  Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Buildable RV Lot. Nestled in a serene, well-maintained community, this RV lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with new landscaping, pea rock and concrete parking pad and is equipped with full hookups including water, sewer, and 30, and 50 amp electric

  Kim Babenzien Expert Realty LLC (HQ)

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

  

  /48

  $940,000 Sold Feb 28, 2025

  • 2,320 Sq Ft
  • $405/SF
  • 184 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1963

  184 Cutthroat Dr, Summerland Key, FL 33042

  Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home is being sold fully furnished and with kayaks! Has a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /16

  Est $1,652,448 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  23076 Tarpon Ln, Summerland Key, FL 33042

  23076 Tarpon Ln, Summerland Key, FL 33042
• 

  

  /16

  $989,999

  • 3 Beds
  • 3 Baths
  • 960 Sq Ft

  22961 John Avery Ln, Summerland Key, FL 33042

  Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

  Rayden Vega CASA MIAMI REAL ESTATE

  22961 John Avery Ln, Summerland Key, FL 33042
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  • 828 Sq Ft
  • $966/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Beautiful open water home with direct ocean access. Completely furnished, ready to rent, future bookings in place. 52 foot concrete seawall with dock posts. Downstairs locked storage for all your fishing gear and what not, open deck for sunning, covered area for grilling and entertaining, fishing off the seawall. Gorgeous sunrise and sunsets. Community offers full service marina, convenience

  Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
• 

  

  /27

  Est $1,540,460 Not Listed For Sale

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

  23092 Snapper Ln, Summerland Key, FL 33042

  23092 Snapper Ln, Summerland Key, FL 33042
• 

  

  /46

  $999,965

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main 369 370 Dr Unit 369, Cudjoe Key, FL 33042

  Boater's Paradise with Expansive Waterfront Views!Rare opportunity to own one of only three double lots in Venture Out on Cudjoe Key! This 2-bedroom, 2-bath home offers unbeatable waterfront living with a newer 70-ft concrete seawall equipped with davits, bumpers, swim ladder, fish cleaning station, and upgraded dock posts and cleats--perfect for accommodating your large boats. Enjoy sweeping

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  701 Spanish Main 369 370 Dr Unit 369, Cudjoe 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
• 

  

  /42

  Est $1,301,761 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  1172 Coates Ln, Summerland Key, FL 33042

  1172 Coates Ln, Summerland 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
• 

  

  /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
• 

  /2

  Est $1,152,121 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  22943 Dirk Ln, Summerland Key, FL 33042

  22943 Dirk Ln, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /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
• 

  /2

  Est $804,152 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  22973 Anne Bonny Ln, Summerland Key, FL 33042
• 

  /2

  $350,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe 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

  Est $775,057 Not Listed For Sale

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

  201 Cutthroat Dr, Summerland Key, FL 33042

  201 Cutthroat Dr, Summerland Key, FL 33042
• 

  /2

  $80,000

  • Land

  248 Yardarm Rd, Cudjoe Key, FL 33042

  This is a listing for two transferable lots. lots # 35 & 36 each lot is 6000 sq. ft.

  Joseph Ordini Keller Williams Key West Compass Realty

  248 Yardarm Rd, 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
• 

  

  /45

  Est $1,206,490 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  22820 Blackbeard Ln, Summerland Key, FL 33042

  22820 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /9

  $849,000

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

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /74

  $3,300,000 Sold Feb 18, 2025

  • 3,225 Sq Ft
  • $1,023/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.

  22572 Jolly Roger Dr, Summerland Key, FL 33042

Showing Results 161 - 200, Page 5 of 18