Homes in ZIP Code 33042

• 

  

  

  /61

  $1,875,000

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

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
• 

  

  

  /39

  $1,725,000 Sold Apr 25, 2025

  474 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1973

  Last Sold Summary

  • 21% Below List Price
  • $1,037/SF
  • 127 Days On Market

  Current Estimated Value $1,684,471

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

  474 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  

  /37

  Est $1,714,767 Not Listed For Sale

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

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  1008 Buttonwood Dr E, Summerland Key, FL 33042
• 

  

  

  /39

  $969,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  437 Pirates Rd, Little Torch Key, FL 33042

  Now offered in the sought after Jolly Roger Estates, this beautifully maintained one owner, free-flowing canal front home is just 10 years old and move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence features three bedrooms and two bathrooms with refined details such as crown molding, tray ceilings, tile showers, and an open-concept living area. A new metal roof was

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
• 

  

  

  /46

  $1,750,000 Sold Feb 13, 2025

  17194 Kingfish Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,073 Sq Ft
  • Built 2011

  Last Sold Summary

  • 17% Below List Price
  • $844/SF
  • 150 Days On Market

  Current Estimated Value $1,721,190

  Last Listing Agent Samantha Barrabeitg Taylor & Assoc. RE, Inc.

  17194 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /46

  Est $2,774,656 Not Listed For Sale

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

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  661 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /73

  $1,050,000 Sold Jan 03, 2025

  103 Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1989

  Last Sold Summary

  • 12% Below List Price
  • $931/SF
  • 24 Days On Market

  Current Estimated Value $1,046,630

  Last Listing Agent Stephany Duvall Engel & Volkers Marathon

  103 Shore Dr, Summerland Key, FL 33042
• 

  

  /46

  Est $1,281,511 Not Listed For Sale

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

  137 Caribbean Dr E, Summerland Key, FL 33042

  137 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 6 Date Palm Dr, Sugarloaf 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
• 

  

  /36

  Est $2,407,626 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  333 Indies Rd, Ramrod Key, FL 33042
• 

  

  /21

  $920,000

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

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
• 

  

  /51

  $1,100,000 Sold May 02, 2025

  27984 Barton Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1993

  Last Sold Summary

  • 8% Below List Price
  • $898/SF
  • 126 Days On Market

  Current Estimated Value $1,097,869

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  27984 Barton Ave, Little Torch Key, FL 33042
• 

  /2

  Est $1,575,854 Not Listed For Sale

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

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
• 

  

  /44

  $725,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  Priced to sell....Enjoy sweeping ocean views from this desirable 2-bed/2-bath residence, featuring a 35' dock on a pristine 60' wide canal, an exceptional setting for avid boaters with immediate access to both the Atlantic Ocean and the Gulf of Mexico. This charming home offers a wonderful canvas for personalized upgrades or serves perfectly as a serene vacation retreat. Additional highlights

  Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, 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 $1,410,325

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
• 

  /2

  Est $883,588 Not Listed For Sale

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

  22842 Buccaneer Ln, Summerland Key, FL 33042

  22842 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /57

  $1,650,000

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft

  25368 2nd St, Summerland Key, FL 33042

  Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

  Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, 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 $710,827

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
• 

  

  /24

  Est $953,778 Not Listed For Sale

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

  19453 Seminole St, Sugarloaf Key, FL 33042

  19453 Seminole St, Sugarloaf Key, FL 33042
• 

  

  /9

  $3,500,000

  • Land

  19657 Seminole St, Sugarloaf Key, FL 33042

  Unique Waterfront Property with Opportunity to Build Your Dream MansionWelcome to your once-in-a-lifetime opportunity to own a truly exceptional waterfront property in the Florida Keys. This expansive property boasts a total of 3 lots ensuring unparalleled potential for building your waterfront mansion.Property comes with build back letter. There's not another property like this south of

  Derek Epperly Engel & Volkers Key West

  19657 Seminole St, Sugarloaf 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 $1,349,457

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

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

  

  /55

  Est $1,334,208 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,108 Sq Ft

  350 W Shore Dr, Summerland Key, FL 33042

  350 W Shore Dr, Summerland Key, FL 33042
• 

  

  /60

  $2,700,000

  • 3 Beds
  • 3 Baths
  • 2,167 Sq Ft

  556 Caribbean Dr E, Summerland Key, FL 33042

  The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  556 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /36

  $1,215,000 Sold Apr 09, 2025

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $844/SF
  • 23 Days On Market

  Current Estimated Value $1,207,590

  Last Listing Agent Stephen Hachey

  17246 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /64

  Est $1,654,406 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  553 Indies Rd, Summerland Key, FL 33042

  553 Indies Rd, Summerland Key, FL 33042
• 

  

  /24

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  853 Indies Rd, Summerland Key, FL 33042

  Move right into this well-maintained 3-bedroom, 2-bath canal front home, built in 2006 and cared for with pride. The bright, open layout features a split floor plan that offers comfortable space for everyday living and entertaining.The primary bedroom includes an en-suite bath and a versatile bonus room -- ideal for a home office, nursery, or cozy retreat. Step outside to enjoy peaceful canal

  Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  853 Indies Rd, Summerland Key, FL 33042
• 

  

  /49

  $750,000 Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $766,572

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
• 

  

  /49

  Est $1,167,777 Not Listed For Sale

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

  403 Indies Rd, Ramrod Key, FL 33042

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /53

  $1,799,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  1481 Sugarloaf Blvd, Summerland Key, FL 33042

  Welcome to this spacious canal-front retreat set on an oversized half-acre lot with endless potential. This four-bedroom, 2,605 sq ft home offers a rare combination of water access, outdoor living, and privacy.Enjoy true Florida Keys living with a private concrete boat ramp, a dock, and direct canal access leading to mangrove-lined creeks and open water just minutes away. Whether you're exploring

  Jenna Stauffer Ocean Sotheby's International Realty

  1481 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /21

  $642,500 Sold Feb 10, 2025

  19518 Caloosa St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1992

  Last Sold Summary

  • 8% Below List Price
  • $562/SF
  • 159 Days On Market

  Current Estimated Value $661,881

  Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  19518 Caloosa St, Summerland Key, FL 33042
• 

  

  /16

  Est $939,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  273 Indies Rd, Summerland Key, FL 33042
• 

  

  /25

  $745,000

  • Land

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

  Barbara Eads Barbara Eads Realty

  28587 Peg Leg Rd Little Torch Aly, Little Torch Key, FL 33042
• 

  

  /100

  $3,300,000 Sold Dec 01, 2025

  815 E Shore Dr, Summerland Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,531 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $728/SF
  • 295 Days On Market

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
• 

  

  /62

  Est $4,726,764 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,421 Sq Ft

  1141 Ocean Dr, Summerland Key, FL 33042

  1141 Ocean Dr, Summerland Key, FL 33042
• 

  

  /49

  $329,000 Open House 1/03

  • 2 Beds
  • 1 Bath
  • 738 Sq Ft

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042

  BACK ON MARKET WITH UPDATES DONE on this charming 2 bedroom, 1 bathroom property in Venture Out. Take a look at this listing with all the updates to make this a cozy home or potential to become a profitable investment property or a relaxing weekend getaway in the highly coveted Venture Out Community in Cudjoe Key. This property boasts a great kitchen with newer appliances, plenty of counter

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 641, Cudjoe Key, FL 33042
• 

  

  /32

  $450,000 Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
• 

  

  /37

  Est $1,150,236 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  716 Caribbean Dr E, Summerland Key, FL 33042

  716 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /15

  $644,500

  • Land

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042

Showing Results 281 - 320, Page 8 of 18