Homes in ZIP Code 33042

• 

  

  /2

  $49,000 Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /2

  Est $468,984 Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $500,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty
• 

  

  

  /88

  $745,000 Under Contract

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

  40 Munson Ave, Summerland Key, FL 33042

  Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

  

  Lindsay Ryan

  EXP Realty LLC

  (786) 952-6862

  40 Munson Ave, Summerland Key, FL 33042
• 

  

  

  /3

  $420,000 Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  Last Sold Summary

  • $736/SF

  Last Sold Price $660,000

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
• 

  

  /29

  $1,325,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  22974 Anne Bonny Ln, Summerland Key, FL 33042

  Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. Perfect 1031 opportunity! This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago,

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 869-3656

  22974 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /75

  $830,000 Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $848,119

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /2

  Est $183,993 Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 7% Below List Price

  Last Sold Price $172,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
• 

  

  /41

  $775,000

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

  22939 Privateer Dr, Summerland Key, FL 33042

  Welcome to your private slice of paradise in desirable Cudjoe Key. this charming well maintained 3-bedroom, 2-bath home sits on an oversized double lot, offering space, privacy, and endless Keys lifestyle potential.With 1,144 square feet of living space, the home is thoughtfully laid out and surrounded by lush tropical surroundings. The property backs up to a private wooded area, creating a

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (833) 381-1226

  22939 Privateer Dr, Summerland Key, FL 33042
• 

  

  /50

  $1,900,000 Sold Mar 27, 2026

  711 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 62 Days On Market

  Current Estimated Value $2,060,214

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
• 

  /2

  Est $3,059,776 Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $850/SF

  Last Sold Price $3,000,000

  Last Listing Agent Lee Sanders KeyIsle Realty
• 

  

  /39

  $485,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 551-4336

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
• 

  

  /41

  $1,105,000 Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Current Estimated Value $1,091,395

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

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • $828/SF
  • 66 Days On Market

  Last Sold Price $715,000
• 

  

  /20

  $214,500 Pending

  • Land

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

  RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 418-4615

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
• 

  

  /61

  $1,750,000 Sold Mar 09, 2026

  876 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $1,493/SF
  • 122 Days On Market

  Current Estimated Value $1,614,886

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,024,636 Not Listed For Sale

  18954 Acosta Trail, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2013

  18954 Acosta Trail, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $991/SF

  Last Sold Price $999,000

  Last Listing Agent Lisa Swanson The Agency Florida Keys
• 

  

  /71

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  16941 Driftwood Ln, Summerland Key, FL 33042

  There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (855) 606-6133

  16941 Driftwood Ln, Summerland Key, FL 33042
• 

  

  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,387,846

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
• 

  /2

  Est $456,014 Not Listed For Sale

  520 Blackbeard Rd, Little Torch Key, FL 33042

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $485,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
• 

  

  /49

  $945,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  683 Blackbeard Rd, Summerland Key, FL 33042

  Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 982-0551

  683 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $6,513,006

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Last Sold Summary

  Last Sold Price $30,000

  Last Listing Agent Allan Leder Preferred Properties (KW)
• 

  

  /71

  $1,349,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  403 Indies Rd, Ramrod Key, FL 33042

  Private Ramrod Key Sanctuary with Sunset Views & Exceptional Boating Access.A rare find, spanning over a 15,000 sq ft, fully fenced lot, offering remarkable privacy, natural beauty, and spectacular sunrise and sunset views. The main home features expansive impact glass door systems in the front and rear, filling the living space with natural light and framing canal views, distant views of the

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-7871

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /26

  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 686 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
• 

  

  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  Last Sold Summary

  • 198 Days On Market

  Last Sold Price $242,000

  Last Listing Agent Carmen David Xcellence Realty
• 

  

  /49

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  110 Doubloon Ln, Summerland Key, FL 33042

  Welcome to island life--this charming 2-bedroom, 2-bath waterfront cottage captures everything we love about the Florida Keys. Tucked on a desirable corner lot with canals on two sides, the property offers exceptional privacy, sea breezes, and inviting views from multiple vantage points. Inside, the home is bright, fresh, and thoughtfully updated, featuring a crisp white kitchen with quartz

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 957-4255

  110 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /33

  $799,000 Sold Apr 28, 2025

  24833 Park Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $685/SF
  • 115 Days On Market

  Current Estimated Value $773,012

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  24833 Park Dr, Summerland Key, FL 33042
• 

  /2

  Est $897,445 Not Listed For Sale

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2022

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 4% Below List Price
  • $756/SF

  Last Sold Price $865,000

  Last Listing Agent Mark Gable Engel & Volkers Marathon
• 

  

  /92

  $3,799,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  493 Coral Ave, Summerland Key, FL 33042

  There are homes in the Florida Keys... and then there are legacy properties. Conceived and built by internationally recognized Keys architect Glenn Gray as his personal residence, 493 Coral Avenue is a rare architectural offering positioned on a premier point lot with open Gulf frontage and protected canal dockage. With water on two sides and panoramic sunrise-to-sunset views, the setting is

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 300-3164

  493 Coral Ave, Summerland Key, FL 33042
• 

  

  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
• 

  /2

  Est $2,208,823 Not Listed For Sale

  305 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft
  • Built 1986

  305 S Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Below List Price
  • $975/SF

  Last Sold Price $2,300,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /48

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  823 Indies Rd, Ramrod Key, FL 33042

  Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (305) 614-6847

  823 Indies Rd, Ramrod Key, FL 33042
• 

  

  /21

  $380,000 Sold Jun 24, 2025

  27848 Lobster Tail Trail, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft
  • Built 1971

  Last Sold Summary

  • 24% Below List Price
  • $688/SF
  • 248 Days On Market

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  27848 Lobster Tail Trail, Little Torch Key, FL 33042
• 

  /2

  Est $1,467,072 Not Listed For Sale

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft
  • Built 2019

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 13% Below List Price
  • $655/SF

  Last Sold Price $1,300,000

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

  

  /62

  $5,200,000

  • 4 Beds
  • 4 Baths
  • 2,660 Sq Ft

  17013 Coral Dr, Summerland Key, FL 33042

  Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 882-3659

  17013 Coral Dr, Summerland Key, FL 33042
• 

  

  /21

  $775,000 Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $848,279

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
• 

  

  /3

  Est $571,000 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  Last Sold Summary

  • 128% Above List Price
  • 4 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Carmen David Xcellence Realty
• 

  

  /58

  $3,750,000

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

  755 Sawyer Dr, Summerland 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 for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /58

  $760,000 Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $759,784

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042

Showing Results 121 - 160, Page 4 of 18