Cudjoe Key, FL Homes

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  /49

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 900-5290

  22865 Redfish Ln, Summerland Key, FL 33042
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  Explore Cudjoe Key

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  /114

  $1,477,000 Sold Sep 02, 2025

  • 1,560 Sq Ft
  • $947/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2018

  153 Galleon Ln, Summerland Key, FL 33042

  Welcome home to this beautifully maintained waterfront retreat in the heart of the Florida Keys! Located on the highly sought-after Cudjoe Key, this spacious & elegant home blends casual island living with refined comfort, all custom-designed & cared for with exceptional pride & attention to detail.From the moment you arrive, you'll notice the peaceful, private setting of this stunning tropical

  Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
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  /2

  Est $226,971 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
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  /51

  $1,079,000

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  22841 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to ''Cayo Casa Cudjoe,'' a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this angler's paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-8373

  22841 Buccaneer Ln, Summerland Key, FL 33042
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  /71

  $3,150,000 Sold Aug 28, 2025

  • 4,976 Sq Ft
  • $633/SF
  • 118 Days On Market

  • 6 Beds
  • 7 Baths
  • Built 2010

  225 Colson Dr, Summerland Key, FL 33042

  Experience the epitome of island luxury in this custom built 5,000 sq. ft. ICF (super energy efficient insulated concrete forms) constructed estate, where masterful design, refined finishes, and breathtaking ocean views come together in perfect harmony. Situated on over an acre of prime oceanfront land, this gated and walled compound offers the ultimate in privacy, serenity, and sophisticated

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  225 Colson Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
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  /36

  $699,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

  GREAT PRICE for this canal-front, slice of paradise! As a successful, active vacation rental where nightly rentals are allowed, this is an excellent income-generating opportunity in the gated community of Venture Out. It's tastefully furnished, turnkey and ready for you or your guests to enjoy. With all the amenities this 69-acre gated community offers, you might just decide to make it your

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 205-1034

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
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  /32

  $450,000 Sold Aug 20, 2025

  • 814 Sq Ft
  • $553/SF
  • 283 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  Charming Florida Keys Retreat at Venture Out on Cudjoe Key: Your Slice of Paradise Awaits! Welcome to your dream getaway nestled in the vibrant Venture Out community! This beautifully designed 2 BR, 2 BA home, built in 2016, is perfect for those seeking a blend of relaxation and adventure. Fully furnished and ready for you to move in or rent out nightly, this property is a true gem in the heart

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
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  /2

  Est $295,661 Not Listed For Sale

  • Studio

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

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
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  /77

  $13,995,000

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  /41

  $1,350,000 Sold Aug 18, 2025

  • 1,582 Sq Ft
  • $853/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  20735 5th Ave W, Summerland Key, FL 33042

  This beautifully renovated 3 Bedroom 2 Bathroom home is located in Cudjoe Gardens, a premiere boating community offering wide crystal clear deep draft canals, quick ocean access, neighborhood restaurant and a full service marina with fuel, bait, ice, refreshments and boat ramp. As you enter into this lovely and impeccably kept home a bright and sunny Great Room greets you highlighted with a

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20735 5th Ave W, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042
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  /46

  $2,999,999

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  653 Sawyer Dr, Summerland Key, FL 33042

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 238-6782

  653 Sawyer Dr, Summerland Key, FL 33042
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  /34

  $1,300,000 Sold Aug 18, 2025

  • 2,100 Sq Ft
  • $619/SF
  • 214 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  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.

  22822 John Silver Ln, Summerland Key, FL 33042
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  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042
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  /39

  $699,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft

  181 Doubloon Ln, Summerland Key, FL 33042

  This super cute 2 Bedroom 2 Bath home in Cutthroat Harbor Estates on Cudjoe Key offers easy ocean access with no bridges from the 60' long concrete dock. The open concept floorpan features a remodeled kitchen with center island, new cabinetry, stainless appliances and granite countertops. The enclosed Florida Room and adjacent outdoor Porch both overlook the water and are the perfect places to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 882-0498

  181 Doubloon Ln, Summerland Key, FL 33042
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  /33

  $665,000 Sold Aug 14, 2025

  • 855 Sq Ft
  • $778/SF
  • 74 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  21161 Old State Road 4a, Summerland Key, FL 33042

  Island life awaits! Beautiful, elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Fenced yard with ample parking. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise

  Bascom Grooms Bascom Grooms Real Estate (KW)

  21161 Old State Road 4a, Summerland Key, FL 33042
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  /2

  Est $1,319,148 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  22863 Bluegill Ln, Cudjoe Key, FL 33042
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  /38

  $810,000 Under Contract

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

  22957 Drake Ln, Cudjoe Key, FL 33042

  Excellent boating and pretty open water views down the canal at this gorgeous Cudjoe Key retreat! Enjoy quick no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large center island

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 964-3201

  22957 Drake Ln, Cudjoe Key, FL 33042
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  /47

  $350,000 Sold Aug 14, 2025

  • 675 Sq Ft
  • $519/SF
  • 228 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1984

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

  Currently the LOWEST priced waterfront property in Venture Out! Seller says bring an offer! Welcome to a slice of paradise tucked away in the gated community of Venture Out on Cudjoe Key, where your dream of coastal living becomes a reality. This charming 2-bedroom, 1.5-bathroom home invites you to embrace the tropical lifestyle, offering the perfect blend of comfort and tranquility. The interior

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
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  /3

  Est $308,333 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
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  /41

  $1,172,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  22946 Bluegill Ln, Summerland Key, FL 33042

  If you are looking for the ''Island Life'' with the best boating access in the Keys, this is the property for you. This beautifully updated tropical Keys home on a lushly landscaped spacious 10,200 square foot lot, is located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable for its premier boating access to world class fishing and diving in both

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 787-3949

  22946 Bluegill Ln, Summerland Key, FL 33042
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  /19

  $505,000 Sold Jul 30, 2025

  • 1,056 Sq Ft
  • $478/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  134 Tortuga Ln, Summerland Key, FL 33042

  Waterfront Fixer-Upper with Endless Potential on Cudjoe Key in the Magical Lower Keys!Embrace the opportunity to transform this waterfront gem into your Florida Keys dream retreat! Nestled in the desirable community behind the famous Square Grouper Restaurant this property offers direct boating access to the Atlantic Ocean--no bridges, no hassle, just open water in mere minutes.Situated on a

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  134 Tortuga Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
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  /4

  $285,000

  • Land

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
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  /47

  $1,075,000 Sold Jul 30, 2025

  • 1,120 Sq Ft
  • $960/SF
  • 189 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  128 Le Grand Ln, Summerland Key, FL 33042

  Welcome to your stunning 3-bedroom, 2-bathroom oasis, nestled at the end of a peaceful cul-de-sac on a double canal. Surrounded by lush fruit trees, this home offers the perfect blend of tranquility and luxury. Step inside to find a spacious open floor plan that creates a bright and airy atmosphere, ideal for entertaining. The chef-friendly kitchen is equipped with modern appliances, making it a

  Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

  128 Le Grand Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
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  /36

  $999,000

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

  22954 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1509

  22954 Buccaneer Ln, Summerland Key, FL 33042
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  /33

  $1,350,000 Sold Jul 24, 2025

  • 2,524 Sq Ft
  • $535/SF
  • 215 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2011

  20883 4th Ave, Cudjoe Key, FL 33042

  Tucked away in the boating community of Cudjoe Gardens, this spacious 3 Bedroom plus Loft canal front home boasts over 2,500 sq. ft. with soaring ceilings and a 2-car garage. Thoughtfully designed for both relaxation and functionality, the space is filled with natural light which flows seamlessly from room to room. The massive Kitchen is highly functional featuring lots of granite counter space

  Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20883 4th Ave, Cudjoe Key, FL 33042
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  /2

  Est $431,370 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  /57

  $2,999,000

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft

  22967 Redfish Ln, Cudjoe Key, FL 33042

  Custom Luxury Meets Waterfront Living on Cudjoe Key. Welcome to 22967 Redfish Lane -- a one-of-a-kind luxury home crafted by one of the Keys' most respected builders as his personal residence. This 3,747 sq ft coastal estate offers 3 bedrooms, 3.5 baths, and high-end custom finishes throughout.Step inside to find black walnut hardwood flooring, soaring tongue-and-groove ceilings, and a true

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 900-8075

  22967 Redfish Ln, Cudjoe Key, FL 33042
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  /66

  $910,000 Sold Jul 23, 2025

  • 1,541 Sq Ft
  • $591/SF
  • 427 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  246 Colson Dr, Summerland Key, FL 33042

  SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet

  Tracey Petrusha Venture Realty Group

  246 Colson Dr, Summerland Key, FL 33042
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  /2

  Est $1,120,871 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  21034 Overseas Hwy, Cudjoe Key, FL 33042
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  /42

  $1,999,000

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  20771 2nd Ave W, Summerland Key, FL 33042

  Wonderful Cudjoe Gardens property! High quality concrete construction and custom metal roof. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool, tiki and firepit. Exceptional boating- the 100' concrete dock is set up for 2 boats- with a 20,000 lb lift and davits rated to 10,000 lbs. Enjoy easy boating access to world class fishing and diving

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-5792

  20771 2nd Ave W, Summerland Key, FL 33042
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  /55

  $1,800,000 Sold Jul 18, 2025

  • 2,638 Sq Ft
  • $682/SF
  • 164 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1993

  22925 John Avery Ln, Summerland Key, FL 33042

  Welcome to your forever island home! Fully furnished and turnkey! One of a kind, solid, custom-built (no modular here) coastal home with magnificent sunset, ocean and bay views from your wrap around porches and balconies. Located on crystal-clear waters filled with tropical fish, a boat ramp for beach launching kayaks or small boats and 60ft of waterfront with dock that can accommodate a 36ft

  Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  1138 Basque Ln, Summerland Key, FL 33042
• 

  

  /48

  $3,499,000

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  653 Sawyer Dr, Summerland Key, FL 33042

  Spectacular Oceanfront Retreat with canal front dockage! Experience the ultimate in Keys living at this beautifully renovated 3 bedroom, 2 bath oceanfront oasis with an additional canal-front lot featuring boat dockage just across the street. This smart, solar-powered home with 6 Tesla Powerwalls, 2 EV chargers, plus an annual check for excess energy production offers eco-conscious luxury with

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 400-8268

  653 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /50

  $550,000 Sold Jul 14, 2025

  • 864 Sq Ft
  • $637/SF
  • 245 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2021

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  MOTIVATED SELLER. BRING THE OFFERS! BEST VALUE IN VENTURE OUT! HUGE PRICE DROP! NEGOTIABLE.! 2-YEAR HOME WARRANTY. TOTAL ELEGANCE! Experience the pinnacle of stilt-home living in this stunning residence at Venture Out, built just 3.5 years ago and meticulously designed with premium upgrades throughout. This 2-bedroom, 2-bathroom manufactured gem is move-in ready and fully furnished, offering a

  Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
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  /61

  Est $2,660,078 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft

  20886 4th Ave W, Summerland Key, FL 33042

  20886 4th Ave W, Summerland Key, FL 33042
• 

  

  /28

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  This 3-bedroom, 2-bathroom stilted home offers 1,200 sq ft of thoughtfully designed space on a spacious canal-front lot.Enjoy the convenience of a 40 ft seawall, 10,000 lb boat lift, outdoor shower, and an enclosed garage with plenty of room for vehicles, boats, and water toys.Inside, the open-concept kitchen, living, and dining areas are equipped with brand-new appliances, ample cabinet space,

  Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

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