Key West, FL Homes

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  /3

  $750,000

  Sold Dec 12, 2025

  2111 Flagler Ave, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,514 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Below List Price
  • $495/SF
  • 23 Days On Market

  Current Estimated Value $760,307

  Last Listing Agent Behmke The Compass Realty (KW)

  2111 Flagler Ave, Key West, FL 33040
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  /27

  Est $573,178

  Not Listed For Sale

  3655 Seaside Dr Unit 427, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft
  • Built 2000

  3655 Seaside Dr Unit 427, Key West, FL 33040

  Last Sold Summary

  • $744/SF
  • 14 Days On Market

  • Last Sold Price $574,500
  • May 21, 2021

  Last Listing Agent Heather Mason Coastal Collection Real Estate Inc.
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  /26

  $625,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 204A, Key West, FL 33040

  Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright and airy condo designed to capture natural light and showcase the stunning beach and ocean scenery.The unit was upgraded through the 2018 Airport Noise Improvement Project and includes hurricane-impact, sound-insulated windows and

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  2601 S Roosevelt Blvd Unit 204A, Key West, FL 33040
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  /59

  $4,000,000

  Sold Oct 24, 2025

  37 Cannon Royal Dr, Key West, FL 33040

  • 4 Beds
  • 5 Baths
  • 3,750 Sq Ft
  • Built 1998

  Last Sold Summary

  • 15% Below List Price
  • $1,067/SF
  • 157 Days On Market

  Current Estimated Value $4,006,042

  Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

  37 Cannon Royal Dr, Key West, FL 33040
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  /26

  Est $464,644

  Not Listed For Sale

  1016 Howe St Unit 5, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 138 Sq Ft
  • Built 1938

  1016 Howe St Unit 5, Key West, FL 33040

  Last Sold Summary

  • 2% Below List Price
  • $3,442/SF
  • 49 Days On Market

  • Last Sold Price $475,000
  • Jun 12, 2023

  Last Listing Agent Richard Haskins Brightwild Real Estate
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  /33

  $1,949,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040

  Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income.The Signature

  The Spottswood Team Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040
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  /34

  $525,000

  Sold Sep 30, 2025

  161 Golf Club Dr, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1997

  Last Sold Summary

  • 11% Below List Price
  • $673/SF
  • 67 Days On Market

  Current Estimated Value $545,522

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  161 Golf Club Dr, Key West, FL 33040
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  /7

  Est $2,920,315

  Not Listed For Sale

  109 Front St Unit 113, Key West, FL 33040

  • 2 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 1991

  109 Front St Unit 113, Key West, FL 33040

  Last Sold Summary

  • 6% Below List Price
  • $2,080/SF
  • 1 Day On Market

  • Last Sold Price $3,120,000
  • Jan 05, 2024

  Last Listing Agent Behmke The Compass Realty (KW)
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  /90

  $5,950,000

  • 6 Beds
  • 8 Baths
  • 4,094 Sq Ft

  723 Eaton St, Key West, FL 33040

  Private Old Town property with built-in income and exceptional flexibility. Ideally located near the Historic Seaport and Fausto's, this three-residence property is currently configured with two leased units generating immediate income and a separate 3-bedroom owner's residence with pool. The rear owners unit offers 3 bedrooms and 3.5 baths with direct access to the tropical courtyard pool, while

  Kirksten Irick Preferred Properties (KW)

  723 Eaton St, Key West, FL 33040
• 

  

  /41

  $540,000

  Sold May 23, 2025

  30 Merganser Ln, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft
  • Built 1995

  Last Sold Summary

  • 22% Below List Price
  • $692/SF
  • 93 Days On Market

  Current Estimated Value $570,813

  Last Listing Agent Zachary Goodfellow Keller Williams Key West Compass Realty

  30 Merganser Ln, Key West, FL 33040
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  /6

  Est $276,005

  Not Listed For Sale

  3312 Northside Dr Unit 310, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • Built 1980

  3312 Northside Dr Unit 310, Key West, FL 33040

  Last Sold Summary

  • 20% Above List Price
  • $564/SF
  • 43 Days On Market

  • Last Sold Price $230,000
  • Jun 28, 2013

  Last Listing Agent Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty
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  /29

  $2,070,000

  Open Sat 12PM - 2PM $115K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,409 Sq Ft

  419 Simonton St Unit C, Key West, FL 33040

  Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined

  Team Kaufelt Truman & Co. (KW)

  419 Simonton St Unit C, Key West, FL 33040
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  /46

  $951,000

  Sold Sep 10, 2025

  76 Palm Dr, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,598 Sq Ft
  • Built 2016

  Last Sold Summary

  • 27% Below List Price
  • $595/SF
  • 194 Days On Market

  Current Estimated Value $965,402

  Last Listing Agent Margarita Villoch Island Group Realty (KW)

  76 Palm Dr, Key West, FL 33040
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  /3

  Est $1,684,694

  Not Listed For Sale

  1500 Atlantic Blvd Unit 107, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,531 Sq Ft
  • Built 1986

  1500 Atlantic Blvd Unit 107, Key West, FL 33040

  Last Sold Summary

  • 1% Below List Price
  • $1,110/SF
  • 64 Days On Market

  • Last Sold Price $1,700,000
  • Apr 30, 2025

  Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)
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  /9

  $825,000

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  3711 Eagle Ave, Key West, FL 33040

  Prime redevelopment opportunity in the coveted upper section of Eagle Avenue, now offered with owner financing. This legal duplex is situated on one of the most desirable blocks in Key West, within a well-established residential neighborhood, presenting a compelling opportunity for investors, builders, or end users looking to create value.The main house is ready for a full renovation, offering a

  Terri Spottswood Truman & Co. (KW)

  3711 Eagle Ave, Key West, FL 33040
• 

  /2

  $1,400,000

  Sold Jan 14, 2026

  514 Margaret St, Key West, FL 33040

  • 5 Beds
  • 4 Baths
  • 2,068 Sq Ft
  • Built 1933

  Last Sold Summary

  • 11% Below List Price
  • $677/SF
  • 0 Days On Market

  Current Estimated Value $1,445,231

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  514 Margaret St, Key West, FL 33040
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  /8

  Est $447,398

  Not Listed For Sale

  3255 Flagler Ave Unit 406, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Built 1997

  3255 Flagler Ave Unit 406, Key West, FL 33040

  Last Sold Summary

  • 5% Above List Price
  • $567/SF
  • 76 Days On Market

  • Last Sold Price $425,000
  • Feb 20, 2019

  Last Listing Agent Deborah Batty Location 3 Real Estate of KW Inc (KW)
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  /21

  $1,379,000

  • 6 Beds
  • 3 Baths
  • 2,434 Sq Ft

  1401 5th St, Key West, FL 33040

  Rare Opportunity: Three Charming Homes on Adjacent Lots - Unlimited Potential!Discover the perfect investment opportunity with these three vintage 2-bedroom, 1-bathroom homes, nestled on separate adjoining lots and being sold together as a single package. Situated in a desirable location, this unique offering provides incredible flexibility for visionary buyers.Each home offers cozy layouts that

  Stacy Stahl Realty ONE Group Destination

  1401 5th St, Key West, FL 33040
• 

  

  /15

  $501,500

  Sold Mar 12, 2026

  5030 5th Ave Unit 80, Key West, FL 33040

  • 2 Beds
  • 3 Baths
  • 1,162 Sq Ft
  • Built 2008

  Last Sold Summary

  • $432/SF
  • 8 Days On Market

  Current Estimated Value $506,618

  Last Listing Agent Deborah Batty Location 3 Real Estate of KW Inc (KW)

  5030 5th Ave Unit 80, Key West, FL 33040
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  /9

  Est $849,791

  Not Listed For Sale

  Unlisted Address

  • 2 Beds
  • 1 Bath
  • 726 Sq Ft
  • Built 1928

  Unlisted Address

  Last Sold Summary

  • 6% Above List Price
  • $1,251/SF
  • 278 Days On Market

  • Last Sold Price $908,000
  • May 18, 2015

  Last Listing Agent Bernadette Restivo Berkshire Hathaway HomeServices Knight & Gardner Realty

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