Cudjoe Key, FL Homes

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  /34

  Est $879,566 Not Listed For Sale

  320 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  320 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $862/SF
  • 18 Days On Market

  Last Sold Price $910,000

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  

  /34

  $469,000

  • 1 Bed
  • 1.5 Baths
  • 735 Sq Ft

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

  Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home offers

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
• 

  

  

  /36

  $1,225,000 Sold Jun 13, 2025

  165 Colson Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 2023

  Last Sold Summary

  • 5% Below List Price
  • $722/SF
  • 104 Days On Market

  Current Estimated Value $1,268,907

  Last Listing Agent Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042
• 

  

  

  /41

  Est $391,406 Not Listed For Sale

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

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

  Last Sold Summary

  • 4% Below List Price
  • 95 Days On Market

  Last Sold Price $408,000

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.
• 

  

  

  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
• 

  

  /7

  $1,600,000 Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Current Estimated Value $465,000

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /37

  Est $885,501 Not Listed For Sale

  139 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1994

  139 Le Grand Ln, Summerland Key, FL 33042

  Last Sold Summary

  • $684/SF
  • 48 Days On Market

  Last Sold Price $889,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
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  /61

  $2,795,000

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

  20844 4th Ave W, Summerland Key, FL 33042

  FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

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

  

  /47

  $895,000 Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Current Estimated Value $889,231

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /27

  Est $1,664,887 Not Listed For Sale

  22836 Port Royal Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 1987

  22836 Port Royal Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 17% Above List Price
  • $1,422/SF
  • 6 Days On Market

  Last Sold Price $2,000,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  /34

  $980,000 Under Contract

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

  131 Doubloon Ln, Summerland Key, FL 33042

  3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024).The downstairs area includes two large storage rooms, one of which features a fully functioning

  Bea Evelyn Citron Compass Florida, LLC

  131 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /38

  $775,000 Sold Sep 11, 2025

  22957 Drake Ln, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $769/SF
  • 7 Days On Market

  Current Estimated Value $788,607

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  

  /45

  Est $1,975,971 Not Listed For Sale

  20942 6th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 16% Above List Price
  • $613/SF
  • 42 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /24

  $430,000 Sold Nov 25, 2025

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 13% Below List Price
  • 287 Days On Market

  Current Estimated Value $421,591

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
• 

  

  /74

  Est $3,253,962 Not Listed For Sale

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $1,023/SF
  • 313 Days On Market

  Last Sold Price $3,300,000

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.
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  /49

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

  Kim Babenzien Expert Realty LLC (HQ)

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

  

  /61

  $2,000,000 Sold Mar 18, 2026

  743 Pattison Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1997

  Last Sold Summary

  • 11% Below List Price
  • $1,195/SF
  • 135 Days On Market

  Current Estimated Value $2,118,685

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  743 Pattison Dr, Summerland Key, FL 33042
• 

  

  /40

  Est $1,038,344 Not Listed For Sale

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1986

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $814/SF
  • 109 Days On Market

  Last Sold Price $1,075,000

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

  

  /14

  $258,000

  • Land

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

  Venture Out RV Lot - Prime Location Near the StoreOpportunity to own a spacious RV lot in the highly desirable Venture Out community in Cudjoe Key. This pie-shaped lot measures approximately 65' x 67' x 63', offering generous space for your RV, outdoor living area, and parking.Conveniently located just a short distance from the community store and amenities, this lot provides easy access to

  Lisa Carter Florida Keys Realty, Inc.

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

  

  /50

  $1,550,000 Sold Feb 23, 2026

  56 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Below List Price
  • $942/SF
  • 12 Days On Market

  Current Estimated Value $1,555,236

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  56 Colson Dr, Summerland Key, FL 33042
• 

  /2

  Est $2,524,383 Not Listed For Sale

  20820 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1972

  20820 7th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 11% Below List Price
  • $1,425/SF

  Last Sold Price $2,850,000

  Last Listing Agent Steven Koleno Beycome of Florida, LLC
• 

  

  /27

  $350,000

  • 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

  Bea Evelyn Citron Compass Florida, LLC

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

  

  /55

  $1,800,000 Sold Jul 18, 2025

  22925 John Avery Ln, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,638 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $682/SF
  • 164 Days On Market

  Current Estimated Value $1,775,129

  Last Listing Agent Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  

  /50

  Est $1,822,427 Not Listed For Sale

  21025 Hamilton Ave, Summerland Key, FL 33042

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft
  • Built 1983

  21025 Hamilton Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 35% Above List Price
  • $333/SF
  • 47 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Mike Kane Internet Realty of the Florida Keys
• 

  

  /47

  $445,000

  • Land

  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
• 

  

  /50

  $550,000 Sold Jul 14, 2025

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

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2021

  Last Sold Summary

  • 18% Below List Price
  • $637/SF
  • 245 Days On Market

  Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

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

  

  /9

  Est $631,762 Not Listed For Sale

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

  • 2 Beds
  • Built 1991

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

  Last Sold Summary

  • 8% Above List Price
  • $851/SF
  • 200 Days On Market

  Last Sold Price $685,000

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
• 

  

  /49

  $329,000

  • 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
• 

  

  /43

  $870,000 Sold Oct 10, 2025

  22818 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1997

  Last Sold Summary

  • $599/SF
  • 1 Day On Market

  Current Estimated Value $863,179

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

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  

  /56

  Est $1,768,603 Not Listed For Sale

  20966 8th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft
  • Built 1982

  20966 8th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $831/SF
  • 31 Days On Market

  Last Sold Price $1,799,000

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

  

  /18

  $499,000 Under Contract

  • 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
• 

  

  /30

  $710,000 Sold Dec 01, 2025

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2002

  Last Sold Summary

  • 25% Below List Price
  • $822/SF
  • 328 Days On Market

  Last Listing Agent Katrina Vanek Bluescape Real Estate

  701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
• 

  

  /36

  Est $964,915 Not Listed For Sale

  21066 3rd Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft
  • Built 1974

  21066 3rd Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Above List Price
  • $715/SF
  • 326 Days On Market

  Last Sold Price $890,000

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.
• 

  /2

  $175,000

  • Land
  • 0.16 Acre
  • $1,093,750 per Acre

  0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key's desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys'. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys

  Jaysen Larrieux LoKation

  0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042
• 

  

  /38

  $1,170,000 Sold Mar 02, 2026

  218 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Below List Price
  • $580/SF
  • 11 Days On Market

  Current Estimated Value $1,184,579

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  218 Spanish Main Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,308,681 Not Listed For Sale

  23047 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1991

  23047 Bluegill Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $920/SF

  Last Sold Price $1,325,500

  Last Listing Agent Daniel Cloud Water Vista Realty, Inc.
• 

  

  /36

  $1,175,000

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

  22874 Bluegill Ln, Summerland Key, FL 33042

  Prestigious ''Cudjoe Ocean Shores'' home with quick, deep boating access to both the Atlantic and the Gulf. 85 feet of concrete dock with heavy duty davits and a large step-down water entrance for your backyard swimming and boating pleasure. This immaculate 3 bedroom, 3 bath home comes with a 10,200 Square Foot Lot, New Kitchen with Stainless Appliances, New Full Bath, Impact Windows and Doors,

  Greg MacLaren Internet Realty of the Florida Keys

  22874 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /70

  $721,000 Sold Jun 03, 2025

  22933 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1995

  Last Sold Summary

  • 18% Below List Price
  • $663/SF
  • 74 Days On Market

  Current Estimated Value $766,007

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /49

  Est $1,756,910 Not Listed For Sale

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft
  • Built 1989

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $955/SF
  • 80 Days On Market

  Last Sold Price $1,800,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

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