Cudjoe Key, FL Homes

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  /42

  Est $1,399,354 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,794 Sq Ft

  1172 Coates Ln, Summerland Key, FL 33042

  1172 Coates Ln, Summerland Key, FL 33042
• 

  

  

  /9

  $185,000 Under Contract

  • 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
• 

  

  

  /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 $1,751,695

  Last Listing Agent Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  

  /2

  Est $1,230,624 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft

  22943 Dirk Ln, Summerland Key, FL 33042

  22943 Dirk Ln, Summerland Key, FL 33042
• 

  

  

  /39

  $1,050,000

  • 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
• 

  

  /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
• 

  /2

  Est $868,494 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  22973 Anne Bonny Ln, Summerland Key, FL 33042

  22973 Anne Bonny Ln, 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
• 

  

  /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 $867,593

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

  22818 Privateer Dr, Summerland Key, FL 33042
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  /44

  Est $739,908 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  22903 Jolly Roger Dr, Summerland Key, FL 33042

  22903 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /45

  $2,995,000 Open House 2/22

  • 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

  Miriam Novotny Compass Florida, LLC

  20920 5th Ave W, Summerland 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
• 

  

  /45

  Est $1,215,239 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  22820 Blackbeard Ln, Summerland Key, FL 33042

  22820 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /33

  $268,500

  • 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

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
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  /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 $750,641

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /47

  Est $2,338,073 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,819 Sq Ft

  22684 Jolly Roger Dr, Summerland Key, FL 33042

  22684 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /61

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

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

  Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom 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 cozy and

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
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  /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
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  /60

  Est $915,123 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  52 Cutthroat Dr, Summerland Key, FL 33042

  52 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /67

  $2,875,000

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

  20844 4th Ave W, Summerland Key, FL 33042

  SOLD TURNKEY! INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! DEEP WATER! A remarkable waterfront estate 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

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  20844 4th Ave W, Summerland Key, FL 33042
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  /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
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  /2

  Est $827,814 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  53 Treasure Chest Dr, Summerland Key, FL 33042

  53 Treasure Chest Dr, Summerland Key, FL 33042
• 

  

  /37

  $879,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  NEW YEAR, NEW PRICE on this heavily rented PROTECTED DOCKAGE property! LOOK AT THIS VIEW! You have open water views from this impeccably maintained, fully stilted 2BR/2 BATH unit! A 43' SEAWALL with heavy duty dock posts, cleats, fish cleaning table and swim ladder add to the allure of this home perfect for the avid boater! North winds are NO PROBLEM with this protected dockage! The oversized

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  /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 $780,217

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  

  /77

  Est $5,843,929 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,514 Sq Ft

  200 Erie Dr, Summerland Key, FL 33042

  200 Erie Dr, Summerland Key, FL 33042
• 

  

  /7

  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, 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. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, 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 $2,013,748 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,156 Sq Ft

  622 Sawyer Dr, Summerland Key, FL 33042

  622 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /55

  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit

  Bobby Coe RE/MAX Keys Connection (KW)

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

  

  /40

  $837,000 Sold Mar 12, 2025

  22994 Anne Bonny Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $707/SF
  • 62 Days On Market

  Current Estimated Value $848,101

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

  22994 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $1,366,785 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft

  408 Sawyer Dr, Summerland Key, FL 33042

  408 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /59

  $549,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, 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 $1,634,799

  Last Listing Agent Melissa Graham Bluescape Real Estate

  22864 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /14

  Est $2,573,473 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,561 Sq Ft

  683 Sawyer Dr, Summerland Key, FL 33042

  683 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /18

  $470,000

  • Land

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
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  /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 $3,311,133

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

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

  

  /32

  Est $1,935,629 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,966 Sq Ft

  21018 4th Ave, Summerland Key, FL 33042

  21018 4th Ave, Summerland Key, FL 33042
• 

  /2

  $65,000

  • Land

  248 Yardarm Rd, Cudjoe Key, FL 33042

  This is a listing for two transferable lots. lots # 35 & 36 each lot is 6000 sq. ft.

  Joseph Ordini Keller Williams Key West Compass Realty

  248 Yardarm Rd, Cudjoe 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

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  141 Arica Ln, Cudjoe Key, FL 33042
• 

  

  /28

  Est $825,065 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  21702 Asturias Rd, Summerland Key, FL 33042

  21702 Asturias Rd, Summerland Key, FL 33042

Showing Results 201 - 240, Page 6 of 18