2,463

Cudjoe Key, FL Homes

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  • /19

    $430,000

    • 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

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • /47

    $350,000 Sold Aug 14, 2025

    701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 675 Sq Ft
    • Built 1984

    Last Sold Summary

    • 22% Below List Price
    • $519/SF
    • 228 Days On Market

    Last Listing Agent Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
    • /39

      Est $961,391 Not Listed For Sale

      22716 Privateer Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft
      • Built 2007
      22716 Privateer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 3% Above List Price
      • $830/SF
      • 9 Days On Market

      Last Sold Price $989,000

      Last Listing Agent Kelly Gardner Bluescape Real Estate

  • /13

    $475,000

    • Land

    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 RE/MAX Keys To The Key

    1147 Basque Ln, Cudjoe Key, FL 33042
  • /44

    $870,000 Sold Feb 05, 2026

    701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 779 Sq Ft
    • Built 2005

    Last Sold Summary

    • 13% Below List Price
    • $1,117/SF
    • 224 Days On Market

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
    • /29

      Est $823,984 Not Listed For Sale

      22774 Cudjoe Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 1987
      22774 Cudjoe Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $617/SF
      • 44 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  • /21

    $459,000

    • 1 Bed
    • 1 Bath
    • 668 Sq Ft

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

    Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
  • /38

    $785,000 Sold Nov 04, 2025

    22464 La Fitte Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 860 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $913/SF
    • 41 Days On Market

    Current Estimated Value $773,228

    Last Listing Agent Steven Koleno Beycome of Florida, LLC

    22464 La Fitte Dr, Summerland Key, FL 33042
    • /64

      Est $1,121,819 Not Listed For Sale

      184 Cutthroat Dr, Summerland Key, FL 33042

      • 4 Beds
      • 2 Baths
      • 2,320 Sq Ft
      • Built 1963
      184 Cutthroat Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 19% Above List Price
      • $405/SF
      • 151 Days On Market

      Last Sold Price $940,000

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

  • /30

    $449,700 Under Contract

    • 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 the gated community of Venture Out on Cudjoe Key--offering move-in-ready comfort and an easy Florida Keys lifestyle. Bright and inviting, the home features a flexible layout with a sliding pocket door that creates a private guest space with its own half bath--ideal for visitors.The main bedroom is furnished with a queen bed, while the

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
  • /2

    $49,000 Sold Jun 06, 2025

    Lot 7 Block 14, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 29% Below List Price
    • 163 Days On Market

    Last Listing Agent Pamela Stangler Expert Realty LLC

    Lot 7 Block 14, Cudjoe Key, FL 33042
    • /45

      Est $1,115,203 Not Listed For Sale

      23058 Sailfish Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,280 Sq Ft
      • Built 1980
      23058 Sailfish Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $918/SF
      • 145 Days On Market

      Last Sold Price $1,175,000

      Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  • /9

    $185,000 Pending

    • 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
  • /2

    $1,650,000 Sold Oct 30, 2025

    22864 Bluegill Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2002

    Last Sold Summary

    • $992/SF
    • 0 Days On Market

    Current Estimated Value $1,605,848

    Last Listing Agent Melissa Graham Bluescape Real Estate

    22864 Bluegill Ln, Summerland Key, FL 33042
    • /16

      Est $1,880,803 Not Listed For Sale

      23076 Tarpon Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,122 Sq Ft
      • Built 1975
      23076 Tarpon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $1,872/SF
      • 82 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  • /38

    $1,049,000

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

    288 Spanish Main Dr, Summerland Key, FL 33042

    Beautifully renovated canalfront home on Cudjoe Key offering the perfect blend of modern upgrades and classic Florida Keys charm. This 3-bedroom, 2-bath stilted home has been completely updated for serene, worry-free living.Inside, you'll find a beautiful kitchen with stainless steel appliances and quartz countertops, along with a comfortable living area. Step outside to enjoy spacious covered

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042
  • /66

    $3,275,000 Sold Oct 28, 2025

    20816 4th Ave W, Cudjoe Key, FL 33042

    • 5 Beds
    • 4 Baths
    • 3,817 Sq Ft
    • Built 2021

    Last Sold Summary

    • 32% Below List Price
    • $858/SF
    • 206 Days On Market

    Current Estimated Value $3,233,047

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

    20816 4th Ave W, Cudjoe Key, FL 33042
    • /27

      Est $1,586,581 Not Listed For Sale

      23092 Snapper Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,645 Sq Ft
      • Built 1985
      23092 Snapper Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $957/SF
      • 7 Days On Market

      Last Sold Price $1,575,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /41

    $2,395,000 Pending

    • 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
  • /29

    $1,300,000 Sold Jan 09, 2026

    141 Arica Ln, Cudjoe Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • Built 2010

    Last Sold Summary

    • 6% Below List Price
    • $777/SF
    • 19 Days On Market

    Current Estimated Value $1,308,726

    Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

    141 Arica Ln, Cudjoe Key, FL 33042
    • /42

      Est $1,269,952 Not Listed For Sale

      1172 Coates Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 1,794 Sq Ft
      • Built 2002
      1172 Coates Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $747/SF
      • 138 Days On Market

      Last Sold Price $1,340,000

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

  • /72

    $595,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

    Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
  • /114

    $1,477,000 Sold Sep 02, 2025

    153 Galleon Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Below List Price
    • $947/SF
    • 49 Days On Market

    Current Estimated Value $1,452,952

    Last Listing Agent Lindsay Ryan EXP Realty LLC

    153 Galleon Ln, Summerland Key, FL 33042
    • /2

      Est $1,198,774 Not Listed For Sale

      22943 Dirk Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,598 Sq Ft
      • Built 1998
      22943 Dirk Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Below List Price
      • $798/SF

      Last Sold Price $1,275,000

      Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  • /39

    $899,000

    • 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
  • /19

    $505,000 Sold Jul 30, 2025

    134 Tortuga Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1988

    Last Sold Summary

    • 11% Below List Price
    • $478/SF
    • 4 Days On Market

    Current Estimated Value $633,359

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

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

      Est $1,019,359 Not Listed For Sale

      22973 Anne Bonny Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 992 Sq Ft
      • Built 1988
      22973 Anne Bonny Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 36% Below List Price
      • $756/SF

      Last Sold Price $750,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /41

    $790,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    22920 Privateer Dr, Summerland Key, FL 33042

    Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • /2

    $175,000 Sold Dec 10, 2025

    ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 17% Below List Price
    • 23 Days On Market

    Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

    ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
    • /44

      Est $741,535 Not Listed For Sale

      22903 Jolly Roger Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1972
      22903 Jolly Roger Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 8% Above List Price
      • $595/SF
      • 108 Days On Market

      Last Sold Price $685,000

      Last Listing Agent Monique Thiel Sunshine State Realty Services

  • /33

    $255,000

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

    Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • /45

    $2,090,000 Sold Jul 07, 2025

    23066 Tarpon Ln, Summerland Key, FL 33042

    • 4 Beds
    • 3.5 Baths
    • 1,938 Sq Ft
    • Built 2025

    Last Sold Summary

    • 13% Below List Price
    • $1,078/SF
    • 65 Days On Market

    Current Estimated Value $1,959,009

    Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

    23066 Tarpon Ln, Summerland Key, FL 33042
    • /2

      Est $792,620 Not Listed For Sale

      201 Cutthroat Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1983
      201 Cutthroat Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Below List Price
      • $724/SF

      Last Sold Price $765,000

      Last Listing Agent Mark Peterson

  • /45

    $519,000

    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

    MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • /5

    $840,000 Sold Mar 03, 2026

    23012 Snapper Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 950 Sq Ft
    • Built 2004

    Last Sold Summary

    • 7% Below List Price
    • $884/SF
    • 113 Days On Market

    Current Estimated Value $888,030

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

    23012 Snapper Ln, Summerland Key, FL 33042
    • /45

      Est $1,215,642 Not Listed For Sale

      22820 Blackbeard Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,420 Sq Ft
      • Built 1989
      22820 Blackbeard Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $863/SF
      • 3 Days On Market

      Last Sold Price $1,225,000

      Last Listing Agent Jamie Caudill Lokation Real Estate

  • /12

    $495,000

    • Land

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

    Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

    Anay Ramos Miami New Realty

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
  • /27

    $905,000 Sold Dec 11, 2025

    22852 John Silver Ln, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $559/SF
    • 75 Days On Market

    Current Estimated Value $907,294

    Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

    22852 John Silver Ln, Summerland Key, FL 33042
    • /47

      Est $2,259,209 Not Listed For Sale

      22684 Jolly Roger Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,819 Sq Ft
      • Built 1977
      22684 Jolly Roger Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 8% Below List Price
      • $1,347/SF
      • 17 Days On Market

      Last Sold Price $2,450,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /4

    $750,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    53 Treasure Chest Dr, Summerland Key, FL 33042

    53 Treasure Chest Drive in Cudjoe Key is more than a home--it's your chance to own a piece of paradise. From the moment you arrive, you'll feel the laid-back island vibe paired with the comfort and security today's buyers demand, including impact windows and doors for year-round peace of mind.Bright, airy, and designed for easy living, this property invites you to slow down, entertain more, and

    Mary Bryant Keller Williams Key West Compass Realty

    53 Treasure Chest Dr, Summerland Key, FL 33042

Showing Results 201 - 240, Page 6 of 18

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