Homes in ZIP Code 33042

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  /58

  $3,335,000

  Sold Jun 13, 2025

  23971 Henry St, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $1,131/SF
  • 37 Days On Market

  Current Estimated Value $3,197,257

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  23971 Henry St, Summerland Key, FL 33042
• 

  

  

  /33

  Est $871,791

  Not Listed For Sale

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 175 Days On Market
• 

  

  

  /49

  $275,000

  $5K PRICE DROP Under Contract

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

  Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
• 

  

  

  /24

  $360,000

  Sold Apr 27, 2026

  27735 Sea Whip St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Built 1978

  Last Sold Summary

  • 16% Below List Price
  • $349/SF
  • 12 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  27735 Sea Whip St, Summerland Key, FL 33042
• 

  

  /2

  Est $827,386

  Not Listed For Sale

  677 Heck Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 875 Sq Ft
  • Built 1977

  677 Heck Ave, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /24

  $259,000

  $6K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,180,000 per Acre

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
• 

  

  /33

  $1,350,000

  Sold Jul 24, 2025

  20883 4th Ave, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2011

  Last Sold Summary

  • 21% Below List Price
  • $535/SF
  • 215 Days On Market

  Current Estimated Value $1,621,342

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20883 4th Ave, Cudjoe Key, FL 33042
• 

  

  /19

  Est $1,016,009

  Not Listed For Sale

  825 Pirates Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,920 Sq Ft
  • Built 1982

  825 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 32 Days On Market
• 

  /2

  $275,000

  • Land
  • 0 Sq Ft

  0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

  Seller Financing available.Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

  Pamela Stangler Expert Realty LLC

  0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
• 

  

  /96

  $1,575,000

  Sold Mar 23, 2026

  17176 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $669/SF
  • 63 Days On Market

  Current Estimated Value $1,716,087

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
• 

  /2

  Est $902,625

  Not Listed For Sale

  337 46th St, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1958

  337 46th St, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /33

  $469,000

  • 1 Bed
  • 2 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

  Jenifer Hirsch Bluescape Real Estate

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

  

  /44

  $650,000

  Sold Jun 30, 2025

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 4% Below List Price
  • $785/SF
  • 8 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042
• 

  

  /35

  Est $934,555

  Not Listed For Sale

  346 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 1996

  346 Blackbeard Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 62 Days On Market
• 

  

  /32

  $1,125,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  27821 Leeward South Rd, Little Torch Key, FL 33042

  ***OPEN HOUSE*** Sunday May 17th from 11am-1pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan

  Kate Zhang Kylin Realty LLC

  27821 Leeward South Rd, Little Torch Key, FL 33042
• 

  

  /30

  $440,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 604 Sq Ft
  • Built 1976

  Last Sold Summary

  • 9% Below List Price
  • $728/SF
  • 170 Days On Market

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

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

  

  /3

  Est $1,141,387

  Not Listed For Sale

  Unlisted Address

  • 5 Beds
  • 4 Baths
  • 1,702 Sq Ft
  • Built 1967

  Unlisted Address

  Last Sold Summary

  • 1 Day On Market
• 

  

  /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
• 

  /2

  $1,400,000

  Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,398,606

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /55

  Est $1,444,417

  Not Listed For Sale

  266 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 1975

  266 Colson Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market
• 

  

  /10

  $335,000

  • Land
  • 6,000 Sq Ft
  • $2,432,100 per Acre

  0 Indies Rd, Ramrod Key, FL 33042

  Waterfront vacant lot located on Ramrod Key in an established canal community on the oceanside of the Lower Keys. This property offers boating access to the Atlantic with connectivity to Florida Bay. No building permit is currently in place; buyers may pursue development through ROGO or obtain a separate building right. Conveniently situated between Marathon and Key West, offering easy access to

  Bea Evelyn Citron Compass Florida, LLC

  0 Indies Rd, Ramrod Key, FL 33042
• 

  

  /9

  $175,000

  Sold Apr 06, 2026

  Vacant Picard Ln, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $1,270,500 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 219 Days On Market

  Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  

  /37

  Est $1,838,393

  Not Listed For Sale

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 2008

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 42 Days On Market
• 

  

  /51

  $425,000

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

  701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

  Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

  Justyn Ewald Expert Realty LLC

  701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
• 

  

  /30

  $430,000

  Sold May 11, 2026

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft
  • Built 1975

  Last Sold Summary

  • $1,036/SF
  • 94 Days On Market

  Current Estimated Value $454,210

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  

  /46

  Est $3,082,659

  Not Listed For Sale

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft
  • Built 1967

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  Last Sold Summary

  • 78 Days On Market
• 

  

  /12

  $599,000

  • Land
  • 11,950 Sq Ft
  • $2,183,468 per Acre

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042

  **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

  Daiane Sardinas Carvalho Centennial Realty Group, LLC

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042
• 

  

  /23

  $710,000

  Sold Aug 20, 2025

  19603 Seminole St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $747,060

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
• 

  

  /46

  Est $1,342,141

  Not Listed For Sale

  137 Caribbean Dr E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  137 Caribbean Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /42

  $1,095,000

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  27345 Barbuda Ln, Summerland Key, FL 33042

  Looking for brand-new waterfront construction with excellent boating access to both the Atlantic and Gulf? This custom home, completed in fall 2025 on the southern end of Ramrod Key, puts you exactly where you want to be; close to deep, open water and far enough from US-1 to enjoy true peace and quiet. Built with hurricane impact-rated construction for added peace of mind, the home offers 3

  Madeleine Lowe Expert Realty LLC (HQ)

  27345 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /73

  $809,300

  Sold Aug 18, 2025

  547 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1991

  Last Sold Summary

  • $736/SF
  • 39 Days On Market

  Current Estimated Value $838,342

  Last Listing Agent Litney Ellis Dalton Wade Inc

  547 Heck Ave, Little Torch Key, FL 33042
• 

  /2

  Est $1,738,423

  Not Listed For Sale

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2005

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  Last Sold Summary
• 

  

  /42

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  750 W Indies Dr, Summerland Key, FL 33042

  This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen! The exterior of the property has several updates, including

  Mary Conklin Action Keys Realty of the Lower FL Keys LLC

  750 W Indies Dr, Summerland Key, FL 33042
• 

  

  /41

  $2,280,000

  Sold Apr 02, 2026

  1176 Thatch Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1984

  Last Sold Summary

  • 24% Below List Price
  • $1,446/SF
  • 359 Days On Market

  Current Estimated Value $2,497,954

  Last Listing Agent Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  /2

  Est $958,012

  Not Listed For Sale

  22842 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft
  • Built 1998

  22842 Buccaneer Ln, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /61

  $2,795,000

  Under Contract

  • 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
• 

  

  /41

  $1,350,000

  Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,363,708

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
• 

  

  /24

  Est $1,037,219

  Not Listed For Sale

  19453 Seminole St, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft
  • Built 1986

  19453 Seminole St, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 2 Days On Market
• 

  

  /40

  $894,000

  Open Fri 10AM - 12:30PM $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large

  Diane Corliss Coldwell Banker Schmitt RE Co.

  28571 Buccaneer Rd, Summerland Key, FL 33042
• 

  

  /37

  $725,000

  Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $732,212

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042

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