2,330

Cudjoe Key, FL Homes

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  • /38

    $1,399,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Summerland Key, FL 33042

    Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    51 Drost 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 Prudential Keyswide Properties

    0 Asturias Rd, Cudjoe Key, FL 33042
    • /2

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1987
      701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  • /43

    $1,799,000

    • 3 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    51 Sawyer Dr, Cudjoe Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

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

    $49,000

    Sold Oct 03, 2025

    Lot 24 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,499 Sq Ft
    • $388,080 per Acre

    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
    • /2

      Est $255,518

      Not Listed For Sale

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

      • Studio
      • Built 1981
      701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  • /5

    $285,000

    • Land
    • 1.01 Acres
    • $282,178 per Acre

    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

    Agent Photo

    Coby Taylor

    Expert Realty LLC (HQ)

    Unlisted Address
  • /61

    $2,675,000

    Sold Jun 01, 2026

    20844 4th Ave W, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft
    • Built 1997

    Last Sold Summary

    • 4% Below List Price
    • $906/SF
    • 10 Days On Market

    Current Estimated Value $2,666,734

    Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

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

      • 2 Beds
      • 1 Bath
      • 897 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • /49

    $1,399,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21250 Conch Dr, Cudjoe Key, FL 33042

    Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21250 Conch Dr, Cudjoe 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 $864,164

    Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

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

      Est $779,974

      Not Listed For Sale

      53 Treasure Chest Dr, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1991
      53 Treasure Chest Dr, Cudjoe Key, FL 33042

  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 5 Unit 619550, Cudjoe 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 $1,125,577

    Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt RE Co.

    22946 Bluegill Ln, Summerland Key, FL 33042
    • /34

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1998
      701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

      Last Sold Summary

      • 66 Days On Market

  • /2

    $30,000

    $20K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $187,500 per Acre

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

    Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
  • /47

    $1,075,000

    Sold May 13, 2026

    110 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Built 1968

    Last Sold Summary

    • 7% Below List Price
    • $853/SF
    • 9 Days On Market

    Current Estimated Value $1,060,317

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    110 Doubloon Ln, Summerland Key, FL 33042
    • /9

      Not Listed For Sale

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      22819 Blackbeard Ln, Cudjoe Key, FL 33042

      Last Sold Summary

      • 543 Days On Market

      Last Listing Agent Amy Prumo Coldwell Banker Schmitt Real Estate Co.

  • /49

    $849,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    22832 John Silver Ln, Summerland Key, FL 33042

    CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES.Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle.New Upgrades Include -Fully remodeled

    Agent Photo

    Mike Kane

    Internet Realty of the Florida Keys

    22832 John Silver Ln, Summerland Key, FL 33042
  • 22963 Anne Bonny Ln, Summerland Key, FL 33042

    $560,000

    Sold Jun 18, 2026

    22963 Anne Bonny Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 834 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $671/SF
    • 43 Days On Market

    Current Estimated Value $580,735

    Last Listing Agent Judith Exposito Luxe Properties

    22963 Anne Bonny Ln, Summerland Key, FL 33042
    • /2

      Est $466,078

      Not Listed For Sale

      20874 4th Ave, Cudjoe Key, FL 33042

      • Studio
      20874 4th Ave, Cudjoe Key, FL 33042

  • /39

    $485,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home withFlorida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.*

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /34

    $840,207

    Sold Jul 03, 2026

    131 Doubloon Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $577/SF
    • 61 Days On Market

    Current Estimated Value $972,572

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    131 Doubloon Ln, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      1138 Basque Ln, Summerland Key, FL 33042

      • 7,000 Sq Ft
      1138 Basque Ln, Summerland Key, FL 33042

  • /19

    $199,000

    $16K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $3,980,000 per Acre

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

    Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • /14

    $205,000

    Sold May 20, 2026

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,125,000 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 56 Days On Market

    Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
    • /61

      Est $2,845,053

      Not Listed For Sale

      20886 4th Ave W, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 3,042 Sq Ft
      • Built 2008
      20886 4th Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  • /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 homenestled 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 453, 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

    Current Estimated Value $1,683,143

    Last Listing Agent Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
    • /107

      Est $5,194,037

      Not Listed For Sale

      220 E Caribbean Dr, Summerland Key, FL 33042

      • 5 Beds
      • 7 Baths
      • 4,981 Sq Ft
      • Built 2025
      220 E Caribbean Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 165 Days On Market

      Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  • /66

    $525,000

    $14K PRICE DROP
    • 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 deck—an ideal spot for your morning coffee or evening

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • /156

    $1,400,000

    Sold Jul 23, 2026

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft
    • Built 2024

    Last Sold Summary

    • 12% Below List Price
    • $655/SF
    • 324 Days On Market

    Current Estimated Value $1,509,137

    Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER

    142 Peg Leg Ln, Cudjoe Key, FL 33042
    • /2

      Est $223,400

      Not Listed For Sale

      27328 St Vincent Ln, Ramrod Key, FL 33042

      • Studio
      27328 St Vincent Ln, Ramrod Key, FL 33042

  • /59

    $649,000

    New Construction $5K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

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

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • /57

    $2,800,000

    Sold Oct 30, 2025

    22967 Redfish Ln, Cudjoe Key, FL 33042

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

    Last Sold Summary

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

    Current Estimated Value $2,872,240

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22967 Redfish Ln, Cudjoe Key, FL 33042
    • /2

      Est $841,518

      Not Listed For Sale

      22727 Jolly Roger Dr, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 2001
      22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  • /47

    $649,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

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

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 30, Cudjoe 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

      Not Listed For Sale

      23008 Overseas Hwy, Cudjoe Key, FL 33042

      23008 Overseas Hwy, Cudjoe Key, FL 33042

  • /68

    $879,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

    This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

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