2,330

Cudjoe Key, FL Homes

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  • /48

    $291,000

    Sold Mar 03, 2026

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

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1985

    Last Sold Summary

    • 9% Below List Price
    • $404/SF
    • 133 Days On Market

    Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

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

      Est $843,058

      Not Listed For Sale

      53 Gold Boullion Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2016
      53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • /17

    $255,000

    $10K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /51

    $420,000

    Sold Nov 21, 2025

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft
    • Built 1979

    Last Sold Summary

    • 8% Below List Price
    • $515/SF
    • 185 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
    • /69

      Not Listed For Sale

      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 420 Sq Ft
      • Built 1988
      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      Last Sold Summary

      • 461 Days On Market

      Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.

  • /58

    $267,000

    $28K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /4

    $50,000

    Sold Dec 19, 2025

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

    • Land
    • 7,450 Sq Ft
    • $292,349 per Acre

    Last Sold Summary

    • 41% Below List Price
    • 25 Days On Market

    Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

    0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
    • /47

      Not Listed For Sale

      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 520 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      Last Sold Summary

      • 194 Days On Market

      Last Listing Agent Anne Press Lokation Real Estate

  • /2

    $235,000

    $20K PRICE DROP
    • Land
    • 7.09 Acres
    • $33,145 per Acre

    Lot 7 Parcel 10, Cudjoe Key, FL 33042

    This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

    Pamela Stangler Expert Realty LLC

    Lot 7 Parcel 10, Cudjoe Key, FL 33042
  • /39

    $705,000

    Sold Sep 08, 2025

    181 Doubloon Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,090 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Above List Price
    • $647/SF
    • 7 Days On Market

    Current Estimated Value $749,570

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    181 Doubloon Ln, Summerland Key, FL 33042
    • /46

      Est $1,896,703

      Not Listed For Sale

      271 W Indies Dr, Ramrod Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 2,358 Sq Ft
      • Built 2023
      271 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 342 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /24

    $259,000

    $6K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,180,000 per Acre

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /49

    $278,000

    Sold Apr 30, 2026

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

    • 2 Beds
    • 1 Bath
    • 738 Sq Ft
    • Built 1986

    Last Sold Summary

    • 16% Below List Price
    • $377/SF
    • 149 Days On Market

    Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
    • /35

      Not Listed For Sale

      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 849 Sq Ft
      • Built 1992
      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      Last Sold Summary

      • 191 Days On Market

  • /51

    $425,000

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

    Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

    Justyn Ewald Expert Realty LLC

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
  • /2

    $185,000

    Sold Mar 20, 2026

    1223 Rogers Ln, Cudjoe Key, FL 33042

    • Land
    • 6,969 Sq Ft
    • $1,156,250 per Acre

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $185,105

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    1223 Rogers Ln, Cudjoe Key, FL 33042
    • /58

      Est $1,817,028

      Not Listed For Sale

      1106 Thatch Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2016
      1106 Thatch Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real E

  • /60

    $2,699,999

    • 4 Beds
    • 2.5 Baths
    • 2,452 Sq Ft

    20833 4th Ave W, Cudjoe Key, FL 33042

    Welcome to one of Cudjoe Gardens' most desirable waterfront addressesBuilt in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and

    Diane Corliss Coldwell Banker Schmitt RE Co.

    20833 4th Ave W, Cudjoe Key, FL 33042
  • /18

    $480,000

    Sold Apr 01, 2026

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

    • Land
    • 2,307 Sq Ft
    • $9,059,272 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 126 Days On Market

    Current Estimated Value $480,696

    Last Listing Agent The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
    • /30

      Est $823,470

      Not Listed For Sale

      124 Yardarm Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,064 Sq Ft
      • Built 2023
      124 Yardarm Rd, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent The Spottswood Team Truman & Co. (KW)

  • /42

    $1,449,000

    New Construction Under Contract
    • 3 Beds
    • 3 Baths
    • 1,500 Sq Ft

    22872 Buccaneer Ln, Cudjoe Key, FL 33042

    *SWIMMING POOL BEING BUILT NOW! Construction process underway. *Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own.

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    22872 Buccaneer Ln, Cudjoe Key, FL 33042
  • /36

    $1,100,000

    Sold Jun 12, 2026

    22874 Bluegill Ln, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,518 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Below List Price
    • $725/SF
    • 7 Days On Market

    Current Estimated Value $1,121,314

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    22874 Bluegill Ln, Summerland Key, FL 33042
    • /21

      Not Listed For Sale

      701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft
      • Built 1978
      701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  • /52

    $1,725,000

    $174K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /46

    $998,000

    Sold Sep 09, 2025

    1117 Basque Ln, Cudjoe Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,318 Sq Ft
    • Built 2013

    Last Sold Summary

    • $757/SF
    • 16 Days On Market

    Current Estimated Value $1,034,068

    Last Listing Agent Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

    1117 Basque Ln, Cudjoe Key, FL 33042
    • /31

      Est $843,482

      Not Listed For Sale

      22918 Cudjoe Dr, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,431 Sq Ft
      • Built 2016
      22918 Cudjoe Dr, Cudjoe Key, FL 33042

      Last Sold Summary

      • 174 Days On Market

      Last Listing Agent ANTHONY GUADALUPE Non Member Listing Office

  • /27

    $320,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

    Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
  • /42

    $1,750,000

    Sold Feb 26, 2026

    20771 2nd Ave W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,047 Sq Ft
    • Built 2010

    Last Sold Summary

    • 17% Below List Price
    • $855/SF
    • 161 Days On Market

    Current Estimated Value $1,771,553

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    20771 2nd Ave W, Summerland Key, FL 33042
    • /33

      Est $644,424

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 855 Sq Ft
      • Built 1975
      21161 Old State Road 4a, Summerland Key, FL 33042

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

  • /47

    $445,000

    $10K PRICE DROP
    • Land
    • 2,078 Sq Ft
    • $9,328,296 per Acre

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

    ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
  • /16

    $925,000

    Sold Jun 24, 2026

    21082 6th Ave, Cudjoe Key, FL 33042

    • Land
    • 16,552 Sq Ft
    • $2,434,211 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 135 Days On Market

    Current Estimated Value $1,014,864

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    21082 6th Ave, Cudjoe Key, FL 33042
    • /38

      Est $937,968

      Not Listed For Sale

      22971 Hawkins Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,142 Sq Ft
      • Built 1987
      22971 Hawkins Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • /19

    $425,000

    $50K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $8,500,000 per Acre

    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

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • /30

    $440,000

    Sold Apr 30, 2026

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

    • 2 Beds
    • 1.5 Baths
    • 604 Sq Ft
    • Built 1976

    Last Sold Summary

    • 9% Below List Price
    • $728/SF
    • 170 Days On Market

    Last Listing Agent Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    • /55

      Est $1,424,874

      Not Listed For Sale

      266 Colson Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,943 Sq Ft
      • Built 1975
      266 Colson Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /13

    $450,000

    $92K PRICE DROP
    • Land
    • 6,969 Sq Ft
    • $2,812,500 per Acre

    1147 Basque Ln, Cudjoe Key, FL 33042

    BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

    Brad Baker Key to the Keys Real Estate, Inc

    1147 Basque Ln, Cudjoe Key, FL 33042
  • /9

    $175,000

    Sold Apr 06, 2026

    Vacant Picard Ln, Cudjoe Key, FL 33042

    • Land
    • 6,000 Sq Ft
    • $1,270,500 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 219 Days On Market

    Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

    Vacant Picard Ln, Cudjoe Key, FL 33042
    • /2

      Est $913,429

      Not Listed For Sale

      22842 Buccaneer Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,326 Sq Ft
      • Built 1998
      22842 Buccaneer Ln, Summerland Key, FL 33042

  • /4

    $350,000

    • Land
    • 8,276 Sq Ft
    • $1,842,105 per Acre

    22776 Overseas, Cudjoe Key, FL 33042

    Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial

    Rose Dell Keller Williams Key West Compass Realty

    22776 Overseas, Cudjoe Key, FL 33042
  • /46

    $860,000

    Sold Aug 11, 2026

    288 Spanish Main Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft
    • Built 1984

    Last Sold Summary

    • 18% Below List Price
    • $752/SF
    • 108 Days On Market

    Current Estimated Value $926,039

    Last Listing Agent Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042

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