Homes in ZIP Code 33042

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  /55

  $5,003,500 Sold Jan 05, 2026

  1151 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $1,266/SF
  • 47 Days On Market

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  1151 Ocean Dr, Summerland Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042
• 

  

  

  /16

  $999,000

  • Land

  21082 6th Ave, Summerland Key, FL 33042

  An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
• 

  

  

  /45

  $1,700,000 Sold Feb 13, 2025

  20942 6th Ave W, Summerland Key, FL 33042

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

  Last Sold Summary

  • 6% Below List Price
  • $613/SF
  • 42 Days On Market

  Current Estimated Value $1,821,365

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20942 6th Ave W, Summerland Key, FL 33042
• 

  

  

  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042
• 

  

  /68

  $2,985,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 686-4688

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /34

  $600,000 Sold Sep 22, 2025

  19557 Mayan St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $607/SF
  • 186 Days On Market

  Current Estimated Value $606,004

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042
• 

  

  /33

  Est $872,275 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  28120 County Rd, Little Torch Key, FL 33042

  28120 County Rd, Little Torch Key, FL 33042
• 

  

  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /64

  $815,422 Sold Nov 06, 2025

  554 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Below List Price
  • $580/SF
  • 34 Days On Market

  Current Estimated Value $847,656

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,086,543 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  17277 Dolphin St E, Summerland Key, FL 33042

  17277 Dolphin St E, Summerland Key, FL 33042
• 

  

  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  /42

  $1,900,000 Sold Jun 29, 2025

  20867 5th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 2011

  Last Sold Summary

  • 5% Below List Price
  • $1,116/SF
  • 17 Days On Market

  Current Estimated Value $1,897,096

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  20867 5th Ave W, Cudjoe Key, FL 33042
• 

  /2

  Est $1,161,785 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  421 W Indies, Ramrod Key, FL 33042

  421 W Indies, Ramrod Key, FL 33042
• 

  

  /30

  $800,000

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft

  630 Barry Ave, Summerland Key, FL 33042

  Set on a rare 0.68-acre property spanning four lots, this private canal-front home offers exceptional space, water access, and tranquility. With 204.5 feet of canal frontage, a 40-foot wood dock, and less than a 5-minute boat ride to Pine Channel, this location is ideal for boating enthusiasts. The 3-bedroom, 2-bath residence features a roof-covered deck perfect for entertaining friends and

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 822-8419

  630 Barry Ave, Summerland Key, FL 33042
• 

  

  /75

  $950,000 Sold Apr 30, 2025

  529 W Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1991

  Last Sold Summary

  • 21% Below List Price
  • $990/SF
  • 75 Days On Market

  Current Estimated Value $1,061,034

  Last Listing Agent Everett Smith Ocean Sotheby's International Realty

  529 W Shore Dr, Summerland Key, FL 33042
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  /2

  Est $2,151,514 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,096 Sq Ft

  17015 Wahoo Ln W, Summerland Key, FL 33042

  17015 Wahoo Ln W, Summerland Key, FL 33042
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  /34

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27940 Lobster Tail Trail, Summerland Key, FL 33042

  Discover one of the best waterfront buying opportunities in the Lower Keys! This spacious and well-maintained 3-bedroom, 2-bath manufactured home offers incredible value and lifestyle at just $650,000. Inside, you'll find an open floor plan with updated laminate floors, a bright kitchen, and a large primary suite featuring a big bedroom and a relaxing bath with a soaking tub.Outdoors, enjoy 46

  

  Sandra Tuttle

  Island Welcome Real Estate

  (645) 218-8749

  27940 Lobster Tail Trail, Summerland Key, FL 33042
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  /71

  $3,150,000 Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $633/SF
  • 118 Days On Market

  Current Estimated Value $3,193,088

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  225 Colson Dr, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 273, Cudjoe Key, FL 33042
• 

  

  /34

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland Key, FL 33042
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  /32

  $450,000 Sold Mar 19, 2025

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 256 Days On Market

  Current Estimated Value $443,650

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042
• 

  

  /5

  Est $1,368,015 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,881 Sq Ft

  354 Airport Dr S, Summerland Key, FL 33042

  354 Airport Dr S, Summerland Key, FL 33042
• 

  

  /40

  $1,300,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft

  537 Heck Ave, Summerland Key, FL 33042

  Welcome to island living at its finest. This stunning 3-bedroom, 2-bath canal-front home is packed with every bell and whistle you could want in a Florida Keys retreat. Designed for both comfort and entertaining, the property features a private pool, tiki hut, 3 screened in porches boat lift with direct canal access and close to open water with no bridges. Perfect for days on the water and

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (786) 410-6602

  537 Heck Ave, Summerland Key, FL 33042
• 

  

  /32

  $1,830,000 Sold Apr 02, 2025

  17023 Allamanda Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $1,658/SF
  • 77 Days On Market

  Current Estimated Value $1,787,980

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17023 Allamanda Dr W, Summerland Key, FL 33042
• 

  

  /11

  Not Listed For Sale

  0 4th St Unit A&B 608914, Summerland Key, FL 33042

  0 4th St Unit A&B 608914, Summerland Key, FL 33042
• 

  

  /41

  $999,000

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

  22954 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1509

  22954 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /43

  $1,150,000 Sold Sep 22, 2025

  1032 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1990

  Last Sold Summary

  • 18% Below List Price
  • $833/SF
  • 175 Days On Market

  Current Estimated Value $1,142,264

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
• 

  /2

  Est $306,879 Not Listed For Sale

  • Studio

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 40, Cudjoe Key, FL 33042
• 

  

  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
• 

  

  /37

  $705,000 Sold Aug 21, 2025

  27312 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $614/SF
  • 127 Days On Market

  Current Estimated Value $734,941

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  27312 Anguila Ln, Summerland Key, FL 33042
• 

  /2

  Est $570,623 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  27188 Dolphin Rd, Ramrod Key, FL 33042

  27188 Dolphin Rd, Ramrod Key, FL 33042
• 

  

  /43

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Summerland Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 666-1028

  420 W Indies Dr, Summerland Key, FL 33042
• 

  

  /39

  $912,250 Sold Apr 03, 2025

  22879 Blackbeard Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $679/SF
  • 43 Days On Market

  Current Estimated Value $935,603

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22879 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /3

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  27732 Astrangia Ave, Little Torch Key, FL 33042

  27732 Astrangia Ave, Little Torch Key, FL 33042
• 

  

  /45

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  195 W Shore Dr, Summerland Key, FL 33042

  Welcome to a truly unique aviation property in the heart of Summerland Key! Located at the end of the exclusive Summerland Key airstrip on a 12,425 sq. ft. double lot, this concrete block home offers the ultimate blend of sky, sea, and space. Featuring a 37' x 27' airplane hangar, 2-car garage, and expansive driveway, this 3-bedroom, 2-bathroom plus bonus/4th Bedroom residence is tailor-made for

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-8438

  195 W Shore Dr, Summerland Key, FL 33042
• 

  

  /31

  $725,000 Sold Jan 05, 2026

  27235 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $532/SF
  • 127 Days On Market

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft

  27772 Astrangia Ave, Summerland Key, FL 33042

  27772 Astrangia Ave, Summerland Key, FL 33042
• 

  

  /12

  $789,900

  • Land

  0 Dominica Ln Unit 615842, Ramrod Key, FL 33042

  Gorgeous Open Ocean location totaling 4 lots, boasting over a quarter acre of land with sheltered canal and private beach; an incredible investment opportunity! Build your dream home in paradise with a transferable building right, which are readily available on the market and provide an easy path to development. This unique opportunity is in the ideal location, on one of the last remaining Open

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 744-6884

  0 Dominica Ln Unit 615842, Ramrod Key, FL 33042
• 

  

  /29

  $800,000 Sold Feb 27, 2025

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $966/SF
  • 14 Days On Market

  Last Listing Agent Susan Rich Select Properties of NWFL

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

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