Homes in ZIP Code 33042

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  /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
• 

  

  

  /29

  $390,000 Sold May 28, 2025

  28131 Helen Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $456/SF
  • 91 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  28131 Helen Ave, Little Torch Key, FL 33042
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  /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.
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  /100

  $8,995,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
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  /45

  $1,300,000 Sold Mar 03, 2026

  1185 Hakluyt Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1989

  Last Sold Summary

  • 7% Below List Price
  • $1,128/SF
  • 10 Days On Market

  Current Estimated Value $1,283,605

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  1185 Hakluyt Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $916,863 Not Listed For Sale

  447 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1991

  447 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $925/SF
  • 51 Days On Market

  Last Sold Price $910,000

  Last Listing Agent Jennifer Newman Truman & Co. (KW)
• 

  /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
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  /61

  $3,900,000 Sold Feb 27, 2026

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,986/SF
  • 25 Days On Market

  Current Estimated Value $2,370,275

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  16200 Old State Rd Unit 4A, Sugarloaf 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.
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  /36

  $1,175,000 Under Contract

  • 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
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  /42

  $1,000,000 Sold Jun 20, 2025

  27330 Barbados Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1991

  Last Sold Summary

  • 16% Below List Price
  • $567/SF
  • 79 Days On Market

  Current Estimated Value $1,028,334

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
• 

  

  /20

  Est $795,492 Not Listed For Sale

  27370 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1992

  27370 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $667/SF
  • 118 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
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  /56

  $3,025,000

  • 3 Beds
  • 3 Baths
  • 2,288 Sq Ft

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042

  A rare double-parcel waterfront opportunity in Lower Sugarloaf Key - offering a newly constructed home plus an adjacent buildable lot, creating the ultimate private boating compound.The newly built 3BD/2.5BA residence with an office/den & laundry/utility room spans 2,288sf on a 16,445sf lot and is thoughtfully designed with an open-concept layout, abundant natural light, and sweeping water views

  The Spottswood Team Truman & Co. (KW)

  17210 Angelfish Ln Unit + 17220, Summerland Key, FL 33042
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  /36

  $685,000 Sold Oct 15, 2025

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $793/SF
  • 164 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
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  /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
• 

  

  /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
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  /12

  $269,000 Sold Sep 29, 2025

  20822 1st Ave, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 10% Below List Price
  • 18 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20822 1st Ave, Cudjoe Key, FL 33042
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  /29

  Est $1,689,405 Not Listed For Sale

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 1963

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Below List Price
  • $957/SF
  • 275 Days On Market

  Last Sold Price $1,800,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /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
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  /51

  $990,000 Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,041,499

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,306,826 Not Listed For Sale

  19563 Canal Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 1990

  19563 Canal Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Below List Price
  • $580/SF

  Last Sold Price $1,225,000

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)
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  /7

  $500,000

  • Land

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Build your dream home in prestigious Sugarloaf Shores, an upscale coastal waterfront community just 20 minutes from the magic of Key West. This oversized 16,361 SqFt canal-front lot offers approximately 80 feet of waterfront frontage with excellent boating access to both the Atlantic Ocean and Florida Bay.The property includes permits for dock installation, clearing, and grading, with ROGO

  Anay Ramos Miami New Realty

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /46

  $550,000 Sold May 28, 2025

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 754 Sq Ft
  • Built 1989

  Last Sold Summary

  • 12% Below List Price
  • $729/SF
  • 72 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
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  /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
• 

  

  /24

  $399,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  27735 Sea Whip St, Summerland Key, FL 33042

  Amazing opportunity to own a canal-front 2-bedroom, 2-bath home in Coral Shores Estates. Tucked away in a quiet subdivision, this waterfront property is conveniently located just minutes from a public boat ramp, restaurants, and shopping. Whether you are looking for a full-time residence, vacation getaway, or investment opportunity, this home offers an affordable way to enjoy the true island

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  27735 Sea Whip St, Summerland 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
• 

  

  /29

  Est $882,744 Not Listed For Sale

  27359 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  27359 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $851/SF
  • 33 Days On Market

  Last Sold Price $899,000

  Last Listing Agent Fred Mullins Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  /57

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 1,964 Sq Ft

  27385 Saint Lucie Ln, Summerland Key, FL 33042

  Tropical Keys Oasis -- Waterfront Luxury LivingCome experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most

  Amedeo Belmonte William Raveis Florida LLC

  27385 Saint Lucie Ln, Summerland Key, FL 33042
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  /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
• 

  

  /31

  Est $744,139 Not Listed For Sale

  4245 Egret Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2002

  4245 Egret Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Above List Price
  • $672/SF
  • 34 Days On Market

  Last Sold Price $715,000

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
• 

  

  /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
• 

  

  /29

  $1,245,000 Sold Jul 28, 2025

  17081 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $807/SF
  • 199 Days On Market

  Current Estimated Value $1,287,625

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  17081 Starfish Ln W, Summerland 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)
• 

  

  /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
• 

  

  /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
• 

  

  /23

  Est $699,083 Not Listed For Sale

  283 Pirates Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1964

  283 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Below List Price
  • $977/SF
  • 148 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
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  /3

  $179,000 Pending

  • Land
  • 0.11 Acre
  • $1,627,273 per Acre

  Lot 32 Caloosa St, Sugarloaf, FL 33042

  Lot with ROGO letter for 5 points. Not ROGO exempt, use points towards building on another lot or contact the Monroe County Planning Department for information about building on this lot or how to use these points. Tier 3 AE11. Contact Monroe County to verify all information. ROGO letter available upon request.

  Pamela Stangler MMLS Assoc.-Inactive Member

  Lot 32 Caloosa St, Sugarloaf, FL 33042
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  /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
• 

  

  /33

  Est $1,070,906 Not Listed For Sale

  131 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1996

  131 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Above List Price
  • $732/SF
  • 250 Days On Market

  Last Sold Price $1,025,000

  Last Listing Agent Team Connect Coastal Collection Real Estate Inc.
• 

  

  /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

Showing Results 441 - 480, Page 12 of 18