2,462

Cudjoe Key, FL Homes

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  • /35

    $817,500 Sold Dec 01, 2025

    22878 Privateer Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1989

    Last Sold Summary

    • 7% Below List Price
    • $862/SF
    • 133 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, Summerland Key, FL 33042
    • /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
  • /58

    $3,750,000

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    755 Sawyer Dr, Summerland Key, FL 33042

    In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

    Agent Photo

    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 204-2360

    755 Sawyer Dr, Summerland Key, FL 33042
  • /3

    $75,000 Sold Oct 10, 2025

    0 Asturias Rd, Cudjoe Key, FL 33042

    • Land
    • 1.01 Acres
    • $74,124 per Acre

    Last Sold Summary

    • 62% Below List Price
    • 41 Days On Market

    Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

    0 Asturias Rd, Cudjoe Key, FL 33042
    • /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
  • /48

    $299,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

    Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (305) 570-4554

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
  • /2

    $600,000 Sold Jul 14, 2025

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

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft
    • Built 1993

    Last Sold Summary

    • 14% Below List Price
    • $735/SF
    • 56 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
    • /2

      Est $1,434,557 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
  • /71

    $525,000

    • 2 Beds
    • 1.5 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall.* Community

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 977-2397

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • /2

    $49,000 Sold Oct 03, 2025

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042

    • Land

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042
    • /3

      Est $498,667 Not Listed For Sale

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

      0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
  • /42

    $1,845,000 Under Contract

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

    20771 2nd Ave W, Summerland Key, FL 33042

    ACTIVELY SHOWING FOR OFFERS!!! Call to see! Incredible Florida Keys living! High quality concrete construction, impact windows and doors and custom metal roof- this home is ABOVE FLOOD and has no stairs! Enjoy the ease of one level living, with the storm safety of being above flood. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool and tiki!

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (786) 952-5792

    20771 2nd Ave W, Summerland Key, FL 33042
  • /3

    $420,000 Sold Jun 27, 2025

    701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 488 Sq Ft
    • Built 1999

    Last Sold Summary

    • 13% Below List Price
    • $861/SF
    • 0 Days On Market

    Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
    • /2

      Not Listed For Sale

      13 Red Legs Ln, Cudjoe Key, FL 33042

      13 Red Legs Ln, Cudjoe Key, FL 33042
  • /49

    $2,299,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    Welcome to coastal living in one of the most desirable neighborhoods in Cudjoe Key. This beautifully renovated 4-bedroom, 3-bath oceanfront residence sits proudly on a rare double lot, offering unmatched space, privacy, and breathtaking open-water views. Step inside to discover a bright, airy living space with stylish coastal finishes, vaulted ceilings, and walls of windows that frame the

    Agent Photo

    Emily Lombard

    Ocean Sotheby's International Realty

    (786) 952-5159

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /75

    $830,000 Sold Sep 15, 2025

    22738 Blackbeard Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1989

    Last Sold Summary

    • 17% Below List Price
    • $692/SF
    • 84 Days On Market

    Current Estimated Value $841,761

    Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

    22738 Blackbeard Ln, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      12 Red Legs Ln, Cudjoe Key, FL 33042

      12 Red Legs Ln, Cudjoe Key, FL 33042
  • /6

    $400,000

    • Land

    21865 Spain Blvd, Summerland Key, FL 33042

    Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    (305) 614-8634

    21865 Spain Blvd, Summerland Key, FL 33042
  • /41

    $1,105,000 Sold Sep 26, 2025

    22946 Bluegill Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1975

    Last Sold Summary

    • 14% Below List Price
    • $921/SF
    • 255 Days On Market

    Current Estimated Value $1,096,128

    Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

    22946 Bluegill Ln, Summerland Key, FL 33042
    • /9

      Not Listed For Sale

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      22819 Blackbeard Ln, Cudjoe Key, FL 33042
  • /16

    $999,000

    • Land

    21082 6th Ave, Summerland Key, FL 33042

    An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 300-6302

    21082 6th Ave, Summerland Key, FL 33042
  • /57

    $1,375,000 Sold Apr 17, 2025

    468 Sawyer Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 1,797 Sq Ft
    • Built 1972

    Last Sold Summary

    • 19% Below List Price
    • $765/SF
    • 215 Days On Market

    Current Estimated Value $1,372,540

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    468 Sawyer Dr, Summerland Key, FL 33042
    • /2

      Est $544,100 Not Listed For Sale

      • Studio

      20874 4th Ave, Cudjoe Key, FL 33042

      20874 4th Ave, Cudjoe Key, FL 33042
  • /66

    $539,000

    • 2 Beds
    • 2 Baths
    • 836 Sq Ft

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

    Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 882-1915

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • /115

    $12,250,000 Sold May 07, 2025

    785 Sawyer Dr, Cudjoe Key, FL 33042

    • 7 Beds
    • 6 Baths
    • 4,888 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $2,506/SF
    • 44 Days On Market

    Current Estimated Value $4,507,572

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    785 Sawyer Dr, Cudjoe Key, FL 33042
    • /2

      Est $1,161,430 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
  • /58

    $3,750,000

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

    In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

    Agent Photo

    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 465-7217

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
  • /43

    $1,700,000 Sold Jan 30, 2026

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $820/SF
    • 140 Days On Market

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, 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
  • /34

    $1,595,000

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

    22865 Redfish Ln, Summerland Key, FL 33042

    The Best Boating Access in the Lower Keys, hands down!!! 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

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 241-6029

    22865 Redfish Ln, Summerland Key, FL 33042
  • /26

    $239,000 Sold Jun 30, 2025

    701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 2% Below List Price
    • 74 Days On Market

    Current Estimated Value $245,086

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
    • /61

      Est $2,762,544 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
  • /41

    $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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 230-1509

    22954 Buccaneer Ln, Summerland Key, FL 33042
  • /57

    $2,800,000 Sold Oct 30, 2025

    22967 Redfish Ln, Cudjoe Key, FL 33042

    • 3 Beds
    • 4 Baths
    • 3,747 Sq Ft
    • Built 2019

    Last Sold Summary

    • 7% Below List Price
    • $747/SF
    • 37 Days On Market

    Current Estimated Value $2,811,102

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

    22967 Redfish Ln, Cudjoe Key, FL 33042
    • /39

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft

      701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042
  • /38

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,203 Sq Ft

    153 Peg Leg Ln, Summerland Key, FL 33042

    Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (833) 853-7147

    153 Peg Leg Ln, Summerland Key, FL 33042
  • /44

    $700,000 Sold Jan 09, 2026

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 2000

    Last Sold Summary

    • 10% Below List Price
    • $810/SF
    • 23 Days On Market

    Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
    • /2

      Est $330,333 Not Listed For Sale

      • Studio

      27328 St Vincent Ln, Ramrod Key, FL 33042

      27328 St Vincent Ln, Ramrod Key, FL 33042
  • /48

    $1,999,999

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

    23087 Sailfish Ln, Summerland Key, FL 33042

    Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 807-9315

    23087 Sailfish Ln, Summerland Key, FL 33042
  • /29

    $395,000 Sold May 19, 2025

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 5% Below List Price
    • 78 Days On Market

    Current Estimated Value $392,764

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

Showing Results 41 - 80, Page 2 of 18

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