2,458

Cudjoe Key, FL Homes

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  • /32

    $450,000 Sold Aug 20, 2025

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

    • 2 Beds
    • 2 Baths
    • 814 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $553/SF
    • 283 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
    • /19

      Est $806,158 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft

      22910 Privateer Dr, Summerland Key, FL 33042

      22910 Privateer Dr, Summerland Key, FL 33042
  • /44

    $725,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

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

    Priced to sell....Enjoy sweeping ocean views from this desirable 2-bed/2-bath residence, featuring a 35' dock on a pristine 60' wide canal, an exceptional setting for avid boaters with immediate access to both the Atlantic Ocean and the Gulf of Mexico. This charming home offers a wonderful canvas for personalized upgrades or serves perfectly as a serene vacation retreat. Additional highlights

    Holly Burger RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
  • /27

    $225,000 Sold Jan 13, 2025

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

    • Land

    Last Sold Summary

    • 13% Below List Price
    • 161 Days On Market

    Current Estimated Value $230,278

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
    • /34

      Est $884,523 Not Listed For Sale

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

      320 Spanish Main Dr, Summerland Key, FL 33042

      320 Spanish Main Dr, Summerland Key, FL 33042
  • /4

    $85,000 Pending

    • Land

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

    Tier I property, County letter in the documents tab. Buildable, but also worth 1 point if you are looking for lots for land dedication purposes. No surveys have been done. It is the responsibilty of the buyer to verify the provided information

    Sabre Mendoza Coldwell Banker Schmitt RE Co.

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
  • /36

    $330,000 Sold Apr 17, 2025

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft
    • Built 1983

    Last Sold Summary

    • 8% Below List Price
    • $453/SF
    • 63 Days On Market

    Last Listing Agent Frank Griffiths Lokation Real Estate

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    • /41

      Est $422,468 Not Listed For Sale

      701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 416, Cudjoe Key, FL 33042
  • /49

    $329,000 Open House 1/03

    • 2 Beds
    • 1 Bath
    • 738 Sq Ft

    701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

    BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
  • /47

    $1,075,000 Sold Jul 30, 2025

    128 Le Grand Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1999

    Last Sold Summary

    • 16% Below List Price
    • $960/SF
    • 189 Days On Market

    Current Estimated Value $1,077,753

    Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

    128 Le Grand Ln, Summerland Key, FL 33042
    • /37

      Est $901,243 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,300 Sq Ft

      139 Le Grand Ln, Summerland Key, FL 33042

      139 Le Grand Ln, Summerland Key, FL 33042
  • /18

    $600,000

    • Land

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

    Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
  • /42

    $775,000 Sold Oct 01, 2025

    22988 Port Royal Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $691/SF
    • 68 Days On Market

    Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    22988 Port Royal Ln, Summerland Key, FL 33042
    • /27

      Est $1,806,287 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,406 Sq Ft

      22836 Port Royal Ln, Summerland Key, FL 33042

      22836 Port Royal Ln, Summerland Key, FL 33042
  • /19

    $475,000

    • Land

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

    Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • /41

    $970,000 Sold May 27, 2025

    366 Sawyer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • Built 1988

    Last Sold Summary

    • 19% Below List Price
    • $698/SF
    • 4 Days On Market

    Current Estimated Value $1,003,167

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    366 Sawyer Dr, Summerland Key, FL 33042
    • /40

      Est $994,120 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,320 Sq Ft

      22983 Anne Bonny Ln, Summerland Key, FL 33042

      22983 Anne Bonny 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
  • /2

    $305,000 Sold Jan 29, 2025

    701 Spanish Main Dr Unit 502, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 4% Below List Price
    • 0 Days On Market

    Current Estimated Value $304,016

    Last Listing Agent Susan Halligan Live Local Realty of the Florida Keys

    701 Spanish Main Dr Unit 502, Cudjoe Key, FL 33042
    • /2

      Est $2,288,471 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,000 Sq Ft

      20820 7th Ave W, Summerland Key, FL 33042

      20820 7th Ave W, Summerland Key, FL 33042
  • /19

    $329,000

    • 2 Beds
    • 1 Bath
    • 756 Sq Ft

    701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042

    NIGHTLY RENTALS ALLOWED! Welcome to this immaculate 2-bedroom, 1-bathroom vacation retreat nestled at the picturesque southern tip of Venture Out, where the land gracefully meets the sea. The attention to detail is evident with luxurious travertine flooring added to this home. Don't let the square footage fool you. This home offers an open floor plan with an open kitchen over looking the family

    Susan Halligan Live Local Realty of the Florida Keys

    701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042
  • /41

    $650,000 Sold Jul 01, 2025

    22882 Buccaneer Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1984

    Last Sold Summary

    • 19% Below List Price
    • $580/SF
    • 81 Days On Market

    Current Estimated Value $685,138

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    22882 Buccaneer Ln, Summerland Key, FL 33042
    • /50

      Est $1,868,690 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 4,060 Sq Ft

      21025 Hamilton Ave, Summerland Key, FL 33042

      21025 Hamilton Ave, Summerland Key, FL 33042
  • /30

    $485,000

    • 2 Beds
    • 1.5 Baths
    • 604 Sq Ft

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

    Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
  • /52

    $2,300,000 Sold Sep 12, 2025

    23086 Snapper Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3 Baths
    • 2,586 Sq Ft
    • Built 1985

    Last Sold Summary

    • 8% Below List Price
    • $889/SF
    • 147 Days On Market

    Current Estimated Value $2,262,159

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    23086 Snapper Ln, Summerland Key, FL 33042
    • /9

      Est $639,046 Not Listed For Sale

      • 2 Beds

      701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

      701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042
  • /9

    $199,500

    • Land

    Vacant Picard Ln, Cudjoe Key, FL 33042

    Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

    Sunnie San Lorenzo KeyIsle Realty

    Vacant Picard Ln, Cudjoe Key, FL 33042
  • /17

    $16,000 Sold Oct 28, 2025

    0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 23% Below List Price
    • 12 Days On Market

    Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

    0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042
    • /56

      Est $1,770,790 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,166 Sq Ft

      20966 8th Ave W, Summerland Key, FL 33042

      20966 8th Ave W, Summerland Key, FL 33042
  • /39

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    21073 7th Ave, Summerland Key, FL 33042

    Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    21073 7th Ave, Summerland Key, FL 33042
  • /54

    $615,000 Sold Jul 11, 2025

    701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft
    • Built 1999

    Last Sold Summary

    • 14% Below List Price
    • $712/SF
    • 194 Days On Market

    Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042
    • /36

      Est $960,357 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,245 Sq Ft

      21066 3rd Ave, Summerland Key, FL 33042

      21066 3rd Ave, Summerland Key, FL 33042
  • /41

    $2,450,000

    • 2 Beds
    • 2 Baths
    • 1,577 Sq Ft

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

    Jonathan Minerick Homecoin.com

    1176 Thatch Ln, Summerland Key, FL 33042
  • /58

    $1,164,000 Sold Dec 12, 2025

    164 Tortuga Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $831/SF
    • 27 Days On Market

    Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

    164 Tortuga Ln, Summerland Key, FL 33042
    • /2

      Est $1,322,427 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,440 Sq Ft

      23047 Bluegill Ln, Summerland Key, FL 33042

      23047 Bluegill Ln, Summerland Key, FL 33042
  • /42

    $2,200,000

    • 5 Beds
    • 3 Baths
    • 1,978 Sq Ft

    94 Sacarma Dr, Cudjoe Key, FL 33042

    Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

    Michelle Blades Realty Executives Florida Keys Old Town

    94 Sacarma Dr, Cudjoe Key, FL 33042
  • /41

    $1,375,000 Sold Mar 13, 2025

    20785 5th Ave W, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,499 Sq Ft
    • Built 1990

    Last Sold Summary

    • 8% Below List Price
    • $917/SF
    • 77 Days On Market

    Current Estimated Value $1,358,706

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

    20785 5th Ave W, Summerland Key, FL 33042
    • /49

      Est $1,788,782 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,884 Sq Ft

      22766 Jolly Roger Dr, Summerland Key, FL 33042

      22766 Jolly Roger Dr, Summerland Key, FL 33042
  • /39

    $995,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

    Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
  • /107

    $5,300,000 Sold Jun 13, 2025

    220 E Caribbean Dr, Summerland Key, FL 33042

    • 5 Beds
    • 7 Baths
    • 4,981 Sq Ft
    • Built 2025

    Last Sold Summary

    • 18% Below List Price
    • $1,064/SF
    • 165 Days On Market

    Current Estimated Value $5,003,432

    Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

    220 E Caribbean Dr, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18

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