2,329

Cudjoe Key, FL Homes

Section Image Section Image
  • 21023 2nd Ave, Summerland Key, FL 33042
    21023 2nd Ave, Summerland Key, FL 33042
    21023 2nd Ave, Summerland Key, FL 33042
    /65

    $2,499,000

    • 4 Beds
    • 2 Baths
    • 2,739 Sq Ft

    21023 2nd Ave, Summerland Key, FL 33042

    Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21023 2nd Ave, Summerland Key, FL 33042
  • 22777 Jolly Roger Dr, Summerland Key, FL 33042
    22777 Jolly Roger Dr, Summerland Key, FL 33042
    22777 Jolly Roger Dr, Summerland Key, FL 33042
    /8

    $5,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • House for Rent

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Property Id: 1197908 Canal front pool home with a double fenced in lot. Enough room for all your boats and toys. Large saltwater pool perfect for soaking up the sun and enjoying a peaceful afternoon. The split layout provides privacy with your own separate areas to unwind. Bring your 4 legged family members. Bonus room could be the 4th bedroom or office. Large AC storage area or workshop and

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • 22410 Jolly Roger Dr, Summerland Key, FL 33042
    22410 Jolly Roger Dr, Summerland Key, FL 33042
    22410 Jolly Roger Dr, Summerland Key, FL 33042
    /62

    $1,500,000

    Sold Aug 10, 2026

    22410 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,587 Sq Ft
    • Built 1982

    Last Sold Summary

    • $945/SF
    • 10 Days On Market

    Current Estimated Value $1,674,544

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22410 Jolly Roger Dr, Summerland Key, FL 33042
    • 701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
      /3

      Not Listed For Sale

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

      • 1 Bed
      • 1 Bath
      • 488 Sq Ft
      • Built 1999
      701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  • 1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    /69

    $3,300,000

    $200K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    1083 Labat Ln, Cudjoe Key, FL 33042
  • 22860 Blackbeard Ln, Cudjoe Key, FL 33042
    22860 Blackbeard Ln, Cudjoe Key, FL 33042
    22860 Blackbeard Ln, Cudjoe Key, FL 33042
    /17

    $4,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • House for Rent

    22860 Blackbeard Ln, Cudjoe Key, FL 33042

    Enjoy the Florida Keys lifestyle in this beautifully upgraded 3-bedroom, 2-bathroom canal front home, now available for long-term rental in the highly desirable community of Cudjoe Key. Situated on a quiet dead-end street, this home offers privacy and minimal traffic, making it an ideal retreat.Boaters will appreciate the 10,000-pound boat lift, commercial ice maker downstairs, and quick,

    Maria Sanchez LoKation Real Estate

    22860 Blackbeard Ln, Cudjoe Key, FL 33042
  • 22521 Jolly Roger Dr, Cudjoe Key, FL 33042
    22521 Jolly Roger Dr, Cudjoe Key, FL 33042
    /2

    $1,030,000

    Sold Nov 19, 2025

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042

    • 4 Beds
    • 2.5 Baths
    • 1,728 Sq Ft
    • Built 2010

    Last Sold Summary

    • $596/SF
    • 0 Days On Market

    Current Estimated Value $1,100,994

    Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

    22521 Jolly Roger Dr, Cudjoe Key, FL 33042
    • 23066 Tarpon Ln, Summerland Key, FL 33042
      23066 Tarpon Ln, Summerland Key, FL 33042
      23066 Tarpon Ln, Summerland Key, FL 33042
      /45

      Est $1,788,950

      Not Listed For Sale

      23066 Tarpon Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 1,938 Sq Ft
      • Built 2025
      23066 Tarpon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • 21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland Key, FL 33042
    21012 6th Ave, Summerland Key, FL 33042
    /61

    $1,399,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,372 Sq Ft

    21012 6th Ave, Summerland Key, FL 33042

    Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21012 6th Ave, Summerland Key, FL 33042
  • 21074 Hamilton Ave, Cudjoe Key, FL 33042
    21074 Hamilton Ave, Cudjoe Key, FL 33042
    21074 Hamilton Ave, Cudjoe Key, FL 33042
    /12

    $3,700 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    21074 Hamilton Ave, Cudjoe Key, FL 33042

    Enjoy the Florida Keys lifestyle in this spacious 3 bedroom, 2 bath waterfront duplex located in the desirable Cudjoe Gardens community. Step outside and enjoy dock space with direct boating access, making it easy to spend your days on the water. The property is conveniently located just seconds from the local marina.Please note that this is a duplex, so there are some shared

    Halley Haack Coldwell Banker Schmitt RE Co.

    21074 Hamilton Ave, Cudjoe Key, FL 33042
  • 151 Cutthroat Dr, Summerland Key, FL 33042
    151 Cutthroat Dr, Summerland Key, FL 33042
    151 Cutthroat Dr, Summerland Key, FL 33042
    /33

    $910,000

    Sold Apr 13, 2026

    151 Cutthroat Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2.5 Baths
    • 1,140 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $798/SF
    • 46 Days On Market

    Current Estimated Value $920,617

    Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

    151 Cutthroat Dr, Summerland Key, FL 33042
    • 701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
      /26

      Est $253,545

      Not Listed For Sale

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

      • Built 1978
      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • 22832 John Silver Ln, Summerland Key, FL 33042
    22832 John Silver Ln, Summerland Key, FL 33042
    22832 John Silver Ln, Summerland Key, FL 33042
    /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
  • 142 Sawyer Dr, Summerland Key, FL 33042
    142 Sawyer Dr, Summerland Key, FL 33042
    142 Sawyer Dr, Summerland Key, FL 33042
    /19

    $11,600 Per Month

    • 5 Beds
    • 3 Baths
    • 2,528 Sq Ft
    • House for Rent

    142 Sawyer Dr, Summerland Key, FL 33042

    Welcome to Paradise!Enjoy this beautiful 5-bedroom, 3-bathroom waterfront rental featuring 120 feet of private dockage--perfect for boating enthusiasts and families alike. Shore power would be an additional charge.This fully furnished home is move-in ready and offers everything you need for a comfortable and relaxing stay. Whether you're planning a vacation getaway or an extended

    Tracey Petrusha Venture Realty Group

    142 Sawyer Dr, Summerland Key, FL 33042
  • 22970 Sharp Ln, Summerland Key, FL 33042
    22970 Sharp Ln, Summerland Key, FL 33042
    22970 Sharp Ln, Summerland Key, FL 33042
    /45

    $630,000

    Sold Dec 08, 2025

    22970 Sharp Ln, Summerland Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $1,094/SF
    • 4 Days On Market

    Current Estimated Value $656,089

    Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

    22970 Sharp Ln, Summerland Key, FL 33042
    • 8 Calico Jack Circle Cir, Verifying, FL 33042
      8 Calico Jack Circle Cir, Verifying, FL 33042
      8 Calico Jack Circle Cir, Verifying, FL 33042
      /15

      Not Listed For Sale

      8 Calico Jack Circle Cir, Verifying, FL 33042

      8 Calico Jack Circle Cir, Verifying, FL 33042

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

  • 701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, 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
  • 701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    /37

    $268,000

    Sold Apr 27, 2026

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $5,360,000 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 52 Days On Market

    Current Estimated Value $269,729

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
    • 701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
      /40

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 816 Sq Ft
      • Built 1996
      701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  • 701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 610, Cudjoe 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
  • Lot 2 Rainbow Beach, Big Torch Key, FL 33042
    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
    /2

    $55,000

    Sold Oct 22, 2025

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042

    • Land
    • 5,000 Sq Ft
    • $479,160 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 2 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 2 Rainbow Beach, Big Torch Key, FL 33042
    • 701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
      /50

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2021
      701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

      Last Sold Summary

      • 245 Days On Market

      Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

  • 701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, 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 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
  • 701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    /49

    $280,000

    Sold Jun 03, 2026

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft
    • Built 1976

    Last Sold Summary

    • $406/SF
    • 98 Days On Market

    Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    • 701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
      /32

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 814 Sq Ft
      • Built 2016
      701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

      Last Sold Summary

      • 283 Days On Market

      Last Listing Agent Kelly Gardner Bluescape Real Estate

  • 701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    /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
  • 22939 Privateer Dr, Summerland Key, FL 33042
    22939 Privateer Dr, Summerland Key, FL 33042
    22939 Privateer Dr, Summerland Key, FL 33042
    /41

    $775,000

    Sold May 01, 2026

    22939 Privateer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1988

    Last Sold Summary

    • $602/SF
    • 3 Days On Market

    Current Estimated Value $774,846

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
    • 1135 Hakluyt Ln, Cudjoe Key, FL 33042
      1135 Hakluyt Ln, Cudjoe Key, FL 33042
      1135 Hakluyt Ln, Cudjoe Key, FL 33042
      /8

      Est $233,432

      Not Listed For Sale

      1135 Hakluyt Ln, Cudjoe Key, FL 33042

      1135 Hakluyt Ln, Cudjoe Key, FL 33042

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall

  • 22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    /34

    $1,575,000

    $20K PRICE DROP
    • 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 RE Co.

    22865 Redfish Ln, Summerland Key, FL 33042
  • 270 E Caribbean Dr, Summerland Key, FL 33042
    270 E Caribbean Dr, Summerland Key, FL 33042
    270 E Caribbean Dr, Summerland Key, FL 33042
    /67

    $3,150,000

    Sold Jun 09, 2026

    270 E Caribbean Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,326/SF
    • 22 Days On Market

    Current Estimated Value $3,070,667

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
    • 701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
      /27

      Est $248,869

      Not Listed For Sale

      701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

      • 1 Bed
      • Built 1974
      701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

      Last Sold Summary

      • 161 Days On Market

      Last Listing Agent Kelly Gardner Bluescape Real Estate

  • 23057 Bluegill Ln, Summerland Key, FL 33042
    23057 Bluegill Ln, Summerland Key, FL 33042
    23057 Bluegill Ln, Summerland Key, FL 33042
    /38

    $1,349,000

    • 3 Beds
    • 2 Baths
    • 1,270 Sq Ft

    23057 Bluegill Ln, Summerland Key, FL 33042

    Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt RE Co.

    23057 Bluegill Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    /20

    $207,000

    Sold Apr 09, 2026

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

    • Land
    • 1,742 Sq Ft
    • $5,175,000 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 375 Days On Market

    Current Estimated Value $208,609

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
    • 8 Calico Jack Cir, Cudjoe Key, FL 33042
      8 Calico Jack Cir, Cudjoe Key, FL 33042
      8 Calico Jack Cir, Cudjoe Key, FL 33042
      /16

      Not Listed For Sale

      8 Calico Jack Cir, Cudjoe Key, FL 33042

      8 Calico Jack Cir, Cudjoe Key, FL 33042

      Last Sold Summary

      • 212 Days On Market

      Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  • 20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    /71

    $2,795,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest.Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    20920 5th Ave W, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    /24

    $310,000

    Sold Apr 16, 2026

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    • Land
    • 2,178 Sq Ft
    • $6,200,000 per Acre

    Last Sold Summary

    • 19% Below List Price
    • 118 Days On Market

    Current Estimated Value $318,560

    Last Listing Agent Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    • 7 Calico Jack Cir, Cudjoe Key, FL 33042
      7 Calico Jack Cir, Cudjoe Key, FL 33042
      /2

      Not Listed For Sale

      7 Calico Jack Cir, Cudjoe Key, FL 33042

      7 Calico Jack Cir, Cudjoe Key, FL 33042

  • 21640 Overseas Hwy, Summerland Key, FL 33042
    21640 Overseas Hwy, Summerland Key, FL 33042
    21640 Overseas Hwy, Summerland Key, FL 33042
    /70

    $2,800,000

    Pending
    • 4 Beds
    • 3 Baths
    • 3,286 Sq Ft

    21640 Overseas Hwy, Summerland Key, FL 33042

    SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    21640 Overseas Hwy, Summerland Key, FL 33042
  • 22878 Privateer Dr, Summerland Key, FL 33042
    22878 Privateer Dr, Summerland Key, FL 33042
    22878 Privateer Dr, Summerland Key, FL 33042
    /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

    Current Estimated Value $818,350

    Last Listing Agent Pamela Stangler Expert Realty LLC

    22878 Privateer Dr, Summerland Key, FL 33042
    • 701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
      701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042
      /14

      Est $230,434

      Not Listed For Sale

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

      • 2 Beds
      • Built 2000
      701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

      Last Sold Summary

      • 246 Days On Market

      Last Listing Agent Mary Conklin Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

Showing Results 1 - 40, Page 1 of 18

Florida Monroe County

Real Estate & Homes

Home Prices in Cudjoe Key, FL

The median home sale price in Cudjoe Key, FL is $1,014,000, down 17% year-over-year. Homes in Cudjoe Key sell in 134 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$1,014,000
Median Single Family Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$730,000
Average Price Per Sq Ft
$826
Number of Homes for Sale
12
Last 12 months Home Sales
20
Months of Supply
7.20
Median List Price
$1,494,500
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-17%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group