Summerland Key, FL Homes

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  $749,000 Sold Sep 19, 2025

  28009 Gulf Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $743/SF
  • 88 Days On Market

  Current Estimated Value $746,796

  Last Listing Agent Ian Calderwood Bluescape Real Estate

  28009 Gulf Blvd, Big Pine Key, FL 33043
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  /2

  Est $1,683,903 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,140 Sq Ft

  247 La Fitte Rd, Summerland Key, FL 33042

  247 La Fitte Rd, Summerland Key, FL 33042
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  $2,650,000

  • 3 Beds
  • 4 Baths
  • 2,087 Sq Ft

  31473 Warner St, Big Pine Key, FL 33043

  Welcome to an exquisite open-water retreat in Big Pine Key, an unparalleled blend of modern luxury and authentic Keys lifestyle. This completely updated and remodeled 3BD/4BA pool home offers panoramic water views from every angle, setting the stage for endless sunrises, sunsets, and starry nights. Designed with sophistication and comfort in mind, each bedroom is an ensuite, ensuring privacy and

  Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  31473 Warner St, Big Pine Key, FL 33043
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  $52,000 Sold Jun 30, 2025

  State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042

  • Land
  • 0.27 Acre
  • $189,391 per Acre

  Last Sold Summary

  • 31% Below List Price
  • 218 Days On Market

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042
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  Est $1,523,889 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft

  390 Les Rohde Dr, Summerland Key, FL 33042

  390 Les Rohde Dr, Summerland Key, FL 33042
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  $19,750,000

  • 6 Beds
  • 7 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson The Agency Florida Keys

  15760 Old State Road 4a, Summerland Key, FL 33042
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  /2

  $55,000 Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
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  Est $2,764,028 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,958 Sq Ft

  27440 W Indies Dr, Summerland Key, FL 33042

  27440 W Indies Dr, Summerland Key, FL 33042
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  $925,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
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  $235,000 Sold Oct 31, 2025

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 76 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
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  Est $2,682,043 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,006 Sq Ft

  961 W Indies Dr, Summerland Key, FL 33042

  961 W Indies Dr, Summerland Key, FL 33042
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  $459,000

  • 2 Beds
  • 1 Bath
  • 754 Sq Ft

  31131 Avenue D, Big Pine Key, FL 33043

  Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Bedroom 1 bathroom with a bonus office/guest room opening to a large screened patio and spacious back yard. This Home is a true Conch home Constructed with Miami Dade Pine originally built in Key West then moved to Big Pine to join the first few homes built on. the Island. Impact doors, new shutters, new roof,

  Heather Mason Coastal Collection Real Estate Inc.

  31131 Avenue D, Big Pine Key, FL 33043
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  /2

  $495,000 Sold Feb 25, 2025

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 773 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Below List Price
  • $640/SF
  • 78 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042
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  Est $801,576 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft

  27378 Haiti Ln, Summerland Key, FL 33042

  27378 Haiti Ln, Summerland Key, FL 33042
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  /20

  $345,000

  • Land

  27453 Antigua Rd, Ramrod Key, FL 33042

  Building permit in-process for a 3 bedroom / 2 bath stilted single family residence. 1320 square feet. The plans are for an Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment, great for your insurance rates.There are plans in review for an 8'x40' dock with the Army Corp.

  Donna Pezzi Keller Williams Key West Compass Realty

  27453 Antigua Rd, Ramrod Key, FL 33042
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  $390,000 Sold May 28, 2025

  28131 Helen Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $456/SF
  • 91 Days On Market

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  28131 Helen Ave, Little Torch Key, FL 33042
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  Est $905,166 Not Listed For Sale

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

  27468 Haiti Ln, Summerland Key, FL 33042

  27468 Haiti Ln, Summerland Key, FL 33042
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  $549,000

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
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  $1,000,000 Sold Jun 20, 2025

  27330 Barbados Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1991

  Last Sold Summary

  • 16% Below List Price
  • $567/SF
  • 79 Days On Market

  Current Estimated Value $1,005,937

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
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  Est $736,271 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  433 Indies Rd, Summerland Key, FL 33042

  433 Indies Rd, Summerland Key, FL 33042

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