Homes in ZIP Code 33042

• 

  

  

  /41

  $835,000

  Sold May 29, 2026

  154 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $870/SF
  • 50 Days On Market

  Current Estimated Value $872,000

  Last Listing Agent Pamela Stangler Expert Realty LLC

  154 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  

  /31

  Est $1,383,499

  Not Listed For Sale

  949 Bay Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 1980

  949 Bay Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 50 Days On Market
• 

  

  

  /60

  $175,000

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
• 

  

  

  /52

  $1,006,000

  Sold Mar 19, 2026

  27360 Barbados Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Below List Price
  • $967/SF
  • 21 Days On Market

  Current Estimated Value $993,530

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27360 Barbados Ln, Summerland Key, FL 33042
• 

  

  /2

  Est $1,520,178

  Not Listed For Sale

  28537 John Silver Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,552 Sq Ft
  • Built 1985

  28537 John Silver Rd, Summerland Key, FL 33042
• 

  

  /29

  $3,000

  • 2 Beds
  • 1.5 Baths
  • 700 Sq Ft

  1656 Pine Channel Dr, Little Torch Key, FL 33042

  Well-maintained 2 bedroom, 1.5 bathroom house located on a boating canal. Spacious kitchen with stainless steel appliances and dining area, plus a separate living room for relaxing. Off main area there is screened back porch overlooking the water. Approximately 45 ft of concrete dockage with a 5,000 lb boat lift and fish cleaning station. Deep-water canal with easy Gulf and Atlantic access. Boat

  Deni Heintzelman KeyIsle Realty

  1656 Pine Channel Dr, Little Torch Key, FL 33042
• 

  

  /39

  $1,100,000

  Sold Apr 27, 2026

  857 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1987

  Last Sold Summary

  • 15% Below List Price
  • $914/SF
  • 112 Days On Market

  Current Estimated Value $1,136,892

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  857 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /45

  Est $2,137,142

  Not Listed For Sale

  1126 Lagoon Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1996

  1126 Lagoon Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 101 Days On Market
• 

  

  /6

  $225,000

  $25K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,607,143 per Acre

  124 Cutthroat Dr, Cudjoe Key, FL 33042

  Canal front lot in beautiful Cutthroat Harbor Estates. Excellent opportunity to be on the water in a great location. Property currently has concrete columns and slab in place. Possible short sale.

  Jimmy Lane Island Life Realty Experts

  124 Cutthroat Dr, Cudjoe Key, FL 33042
• 

  /2

  $175,000

  Sold Dec 10, 2025

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.78 Acres
  • $98,361 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 23 Days On Market

  Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  ROGO LOTS Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /41

  Est $725,066

  Not Listed For Sale

  22882 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  22882 Buccaneer Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 81 Days On Market
• 

  

  /22

  $839,000

  New Construction

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

  27215 Mariposa Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION! This charming 1,500 sqft home is a true retreat, perfectly positioned in the Lower Keys, just a moments walk from the popular Looe Key Tiki Bar and Boondocks restaurants. Tucked away in a quiet, low-traffic neighborhood, this property offers the ideal combination of peace and convenience, allowing you to embrace the relaxed Keys lifestyle. Inside, you'll find: A spacious, open

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27215 Mariposa Rd, Summerland Key, FL 33042
• 

  /2

  $2,030,000

  Sold Nov 17, 2025

  27450 W Indies Dr, Summerland Key, FL 33042

  • 2 Beds
  • 4 Baths
  • 1,968 Sq Ft
  • Built 1984

  Last Sold Summary

  • 22% Below List Price
  • $1,032/SF
  • 273 Days On Market

  Current Estimated Value $2,089,953

  Last Listing Agent Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  27450 W Indies Dr, Summerland Key, FL 33042
• 

  

  /80

  Est $3,988,525

  Not Listed For Sale

  24826 Calle Real, Summerland Key, FL 33042

  • 5 Beds
  • 4.5 Baths
  • 4,068 Sq Ft
  • Built 1960

  24826 Calle Real, Summerland Key, FL 33042

  Last Sold Summary

  • 41 Days On Market
• 

  

  /8

  $365,000

  • Land
  • 2,178 Sq Ft
  • $7,300,000 per Acre

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  Discover your own piece of paradise in Venture Out! This beautifully maintained waterfront lot offers 17 feet of seawall and a private tropical setting enhanced by mature landscaping and thoughtful care. Whether you're looking for the perfect RV getaway, seasonal retreat, or future homesite, this property provides the ideal blend of privacy, beauty, and waterfront living.Located within the

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
• 

  

  /30

  $400,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft
  • Built 1987

  Last Sold Summary

  • 20% Below List Price
  • $535/SF
  • 481 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
• 

  /2

  Est $1,993,478

  Not Listed For Sale

  494 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1989

  494 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /51

  $890,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH,Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys

  Guadalupe Perez Douglas Elliman

  813 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /60

  $938,000

  Sold Dec 11, 2025

  460 Barry Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1985

  Last Sold Summary

  • 22% Below List Price
  • $651/SF
  • 196 Days On Market

  Current Estimated Value $982,571

  Last Listing Agent Noel Betancourt Tropic Shores Realty

  460 Barry Ave, Summerland Key, FL 33042
• 

  

  /7

  Est $302,314

  Not Listed For Sale

  25074 45th St, Summerland Key, FL 33042

  • 3 Beds
  • Built 1982

  25074 45th St, Summerland Key, FL 33042

  Last Sold Summary

  • 130 Days On Market

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