Homes in ZIP Code 33042

• 

  

  

  /54

  $899,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 97, 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

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

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  

  /2

  Est $801,471 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
• 

  

  

  /4

  $31,000

  • Land
  • 0.14 Acre
  • $227,941 per Acre

  0 Adams Rd, Sugarloaf, FL 33042

  No RV's, no camping, no clearing, and most likely unbuildable. No utilities to property. Not surveyed. ROGO LETTER IN HAND FOR 1 ROGO POINT. This lot is for dedication to receive 1 Rogo Point, Buyer Verify with County. Being sold as-is. Include extra time in offers to verify marketable title and conduct due diligence. Owner/Agent.

  Carmen David Xcellence Realty

  0 Adams Rd, Sugarloaf, FL 33042
• 

  

  

  /56

  $2,599,000 Sold Jun 18, 2025

  28595 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 1975

  Last Sold Summary

  • $2,254/SF
  • 11 Days On Market

  Current Estimated Value $2,561,019

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  28595 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /44

  Est $705,903 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
• 

  

  /117

  $11,000,000

  • 6 Beds
  • 8 Baths
  • 4,894 Sq Ft

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

  Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress-- built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on

  Lisa Swanson The Agency Florida Keys

  1041 Buttonwood Dr E, Sugarloaf 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
• 

  /2

  Est $785,174 Not Listed For Sale

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

  201 Cutthroat Dr, Summerland Key, FL 33042

  201 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /53

  $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
• 

  

  /34

  $735,000 Sold May 16, 2025

  27373 Anguila Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,077 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $682/SF
  • 117 Days On Market

  Current Estimated Value $756,897

  Last Listing Agent Tracy Shields KeyIsle Realty

  27373 Anguila Ln, Summerland Key, FL 33042
• 

  

  /45

  Est $1,233,124 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
• 

  

  /15

  $399,000

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  27977 Coral Shores Rd, Little Torch Key, FL 33042

  This 2 bedroom 1 bath with a screened in covered porch mobile home on just over 4100 sqft waterfront lot with great boating access.

  Dasha Ray Conch Realty LLC (KW)

  27977 Coral Shores Rd, Little Torch Key, FL 33042
• 

  

  /92

  $1,050,000 Sold May 14, 2025

  27436 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2020

  Last Sold Summary

  • 19% Below List Price
  • $852/SF
  • 129 Days On Market

  Current Estimated Value $1,032,399

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  27436 Tobago Ln, Summerland Key, FL 33042
• 

  

  /47

  Est $2,326,423 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

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  27332 St Martin Ln, Ramrod Key, FL 33042

  Welcome to Breezeswept Beach Estates-- In the heart of the Florida Keys! Here, boating, diving, and fishing are a way of life. This waterfront concrete block (CBS) 3-bed, 2-bath home sits on a deep, ocean-side canal just minutes to open water; Looe Key's clear blue reef is about a 15-minute boat ride away, and Key West is roughly 30 minutes by car. Thoughtfully updated for low-maintenance Keys

  Mark Gable Engel & Volkers Marathon

  27332 St Martin Ln, Ramrod 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 $746,156

  Last Listing Agent Bobby Baker Brightwild Real Estate

  22933 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /60

  Est $885,208 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
• 

  

  /17

  $998,000

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  17171 Seagrape Ln, Summerland Key, FL 33042

  RARE OPPORTUNITY HERE! This home is perfect for a DIY or Builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large lot on 70' wide flow through canal. Bay views.

  Marie Howe Century 21 Circle - Key West

  17171 Seagrape Ln, Summerland Key, FL 33042
• 

  

  /40

  $785,000 Sold Mar 12, 2025

  17236 Keystone Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1974

  Last Sold Summary

  • 21% Below List Price
  • $680/SF
  • 184 Days On Market

  Current Estimated Value $844,688

  Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty

  17236 Keystone Rd, Summerland Key, FL 33042
• 

  /2

  Est $786,512 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
• 

  

  /42

  $650,000

  • Land

  22948 Drake Ln, Summerland Key, FL 33042

  Canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water: Views and more views. 70-foot concrete seawall with boat slip/basin and 10,000 pound boat lift make this the perfect location for boater/angler's new home. Previous house removed and lot is ready for your new vision. Electric was in place, buyer to verify FKAA

  Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland 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
• 

  

  /77

  Est $5,864,670 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
• 

  

  /68

  $1,900,000

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  27385 Saint Lucie Ln, Summerland Key, FL 33042

  Tropical Keys Oasis -- Waterfront Luxury Living -- Come 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

  Amedeo Belmonte William Raveis Real Estate

  27385 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /37

  $765,000 Sold Jul 28, 2025

  27255 Mariposa Rd, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2019

  Last Sold Summary

  • 8% Below List Price
  • $531/SF
  • 113 Days On Market

  Current Estimated Value $802,057

  Last Listing Agent Melissa Graham Bluescape Real Estate

  27255 Mariposa Rd, Ramrod Key, FL 33042
• 

  

  /43

  Est $1,316,370 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
• 

  

  /7

  $4,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 2, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 2, Summerland 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

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  22464 La Fitte Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $2,422,657 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
• 

  

  /50

  $1,675,000

  • 3 Beds
  • 2 Baths
  • 1,995 Sq Ft

  643 Indies Rd, Summerland Key, FL 33042

  Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for

  Greg MacLaren Internet Realty of the Florida Keys

  643 Indies Rd, Summerland 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
• 

  

  /32

  Est $1,901,405 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
• 

  

  /44

  $949,000

  • 2 Beds
  • 2 Baths
  • 779 Sq Ft

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

  Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 214, 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 $842,058

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

  22994 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /8

  Est $694,847 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  19514 Canal Dr, Summerland Key, FL 33042

  19514 Canal Dr, Summerland Key, FL 33042
• 

  

  /15

  $290,000

  • Land

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

  Discover an exceptional canal-front lot that boasts direct bridge-free boating access, making it a fisherman's paradise and an ideal spot for your dream home. Nestled conveniently close to US 1 between Key West and Marathon, this location offers easy access to an array of restaurants, shopping, and mini golf--everything you need for the perfect Keys lifestyle. This Tier III lot is currently in

  Scott Brisson KeyIsle Realty

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /43

  $910,000 Sold Mar 04, 2025

  447 Pirates Rd, Summerland Key, FL 33042

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

  Last Sold Summary

  • 7% Below List Price
  • $925/SF
  • 51 Days On Market

  Current Estimated Value $917,933

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

  447 Pirates Rd, Summerland Key, FL 33042
• 

  

  /26

  Est $523,228 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  19910 Flamingo Rd, Summerland Key, FL 33042

  19910 Flamingo Rd, Summerland Key, FL 33042
• 

  

  /17

  $751,900

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  56 W Shore Dr, Summerland Key, FL 33042

  Rare waterfront opportunity in Summerland Key Cove! This 3-bedroom, 2-bath home offers 1,380 sq ft of living area on an oversized 7,000+ sq ft lot with direct access to world-class boating and fishing. Located on a deep, wide ocean-side canal, the property provides a quick ride out to open water -- perfect for enjoying the Lower Keys lifestyle.Summerland Key Cove is a highly desirable,

  Veronica Crego-Flores

  56 W Shore Dr, Summerland Key, FL 33042

Showing Results 521 - 560, Page 14 of 18