Old Town Homes

• 

  

  

  /57

  $59,900

  $9K PRICE DROP

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

  617 Front St Unit C41 Week 50, Key West, FL 33040

  Own a deeded 4th-floor Gulf and waterfront corner end unit at the highly desirable Galleon Resort in the heart of Old Town Key West! This beautifully maintained 2-bedroom, 2-bath condo sleeps six and features new 2026 furnishings, a king bed, two twins (convertible to a queen), sleeper sofa, two full baths, and a private balcony with marina, gulf, live-music, and sunset views. Everything you love

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit C41 Week 50, Key West, FL 33040
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• 

  

  

  /14

  $2,600 Per Month

  • 1 Bed
  • 1 Bath
  • 459 Sq Ft
  • 1 Bedroom 1 Bathroom Apartment No Pets

  1306 Eliza St, Key West, FL 33040

  Located few blocks off White Street by Bayview Park this 1 bedroom 1 bath is a must see . The left side of duplex with 1 designated graveled off street parking. Completely renovated concrete polished floors, new kitchen cabinets, quartz countertop, breakfast bar and stainless steel appliances. All new windows, doors, central air conditioning unit with heat, and insta hot tankless water heater.

  1306 Eliza St, Key West, FL 33040
• 

  

  

  /29

  $1,075,000

  Sold Oct 07, 2025

  1127 Packer St, Key West, FL 33040

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

  Last Sold Summary

  • 14% Below List Price
  • $1,280/SF
  • 108 Days On Market

  Current Estimated Value $1,101,678

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  1127 Packer St, Key West, FL 33040
• 

  

  

  /53

  Est $5,332,024

  Not Listed For Sale

  1006 & 1008 Fleming St, Key West, FL 33040

  • 4 Beds
  • 4.5 Baths
  • 3,404 Sq Ft
  • Built 1938

  1006 & 1008 Fleming St, Key West, FL 33040

  Last Sold Summary

  • 49 Days On Market
• 

  

  

  /33

  $1,150,000

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft

  709 Chapman Ln, Key West, FL 33040

  Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  709 Chapman Ln, Key West, FL 33040
• 

  /2

  $3,200 Per Month

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft
  • 717 Emma - B

  717 Emma St Unit 717-B Emma, Key West, FL 33040

  Super cute 2 bed, 1 bath available soon.

  717 Emma St Unit 717-B Emma, Key West, FL 33040
• 

  

  /23

  $850,000

  Sold Oct 31, 2025

  308 Peacon Ln, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft
  • Built 1923

  Last Sold Summary

  • 43% Below List Price
  • $656/SF
  • 299 Days On Market

  Current Estimated Value $876,089

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

  308 Peacon Ln, Key West, FL 33040
• 

  

  /14

  Est $562,063

  Not Listed For Sale

  712 Galveston Ln Unit 2, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 526 Sq Ft
  • Built 1981

  712 Galveston Ln Unit 2, Key West, FL 33040

  Last Sold Summary

  • 130 Days On Market
• 

  

  /44

  $1,475,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,284 Sq Ft

  1211 Knowles Ln, Key West, FL 33040

  Timeless Old Town Charm!Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades.1211 Knowles Lane features a versatile 300 sq. ft. loft currently

  

  Emily Lombard

  Ocean Sotheby's International Realty

  1211 Knowles Ln, Key West, FL 33040
• 

  

  /19

  $2,500 Per Month

  • Studio
  • 1 Bath
  • 587 Sq Ft
  • Furnished Studio Apartment in Old Town

  327 Margaret St, Key West, FL 33040

  Beautiful second floor studio for two on the second floor of the historic Sailmaker's House. - Incredible location in Historic Old Town!This property is located 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.The open floor plan maximizes the space in this airy tree top studio. Comfortable Queen size bed will inspire sweet dreams and the large built

  327 Margaret St, Key West, FL 33040
• 

  

  /30

  $1,300,000

  Sold Jun 24, 2026

  1202 Whitehead St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,051 Sq Ft
  • Built 1933

  Last Sold Summary

  • 16% Below List Price
  • $1,237/SF
  • 111 Days On Market

  Current Estimated Value $1,527,264

  Last Listing Agent Richard Haskins Buy The Keys

  1202 Whitehead St, Key West, FL 33040
• 

  

  /19

  Est $881,536

  Not Listed For Sale

  914-1/2 White St, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 974 Sq Ft
  • Built 1928

  914-1/2 White St, Key West, FL 33040

  Last Sold Summary

  • 13 Days On Market
• 

  

  /13

  $3,600

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  514 Margaret St Unit 2, Key West, FL 33040

  It doesn't get more Key West than this. Tucked behind a white picket fence on one of Old Town's most coveted streets, this 2BD/1BA condo is pure island charm -- about 900 sq ft with soaring vaulted ceilings, a skylight, and rich hardwood floors throughout. French doors open to a lush, private tropical patio with a deck and garden -- the kind of outdoor space you'll actually use every day. The

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  514 Margaret St Unit 2, Key West, FL 33040
• 

  

  /16

  $2,625 Per Month

  • 1 Bed
  • 1 Bath
  • Old Town Location - 1 bed / 1 bath Apartment

  725 Southard St, Key West, FL 33040

  Welcome to this great Old Town Location, a charming 1 bed / 1 bath apartment nestled in the heart of Key West. This cozy and well-maintained home offers a convenient and desirable location. Step inside and discover a thoughtfully designed living space that includes a stove, refrigerator, AC Mini Splits, washer/dryer, microwave, and a private deck. With its prime location, you'll have easy access

  725 Southard St, Key West, FL 33040
• 

  

  /44

  $2,595,000

  Sold Nov 13, 2025

  628 William St, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,524 Sq Ft
  • Built 1928

  Last Sold Summary

  • 12% Below List Price
  • $1,703/SF
  • 9 Days On Market

  Current Estimated Value $2,631,841

  Last Listing Agent Paige Bethel Island Home Realty Inc.

  628 William St, Key West, FL 33040
• 

  /2

  Not Listed For Sale

  311 Amelia St Unit B, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 1979

  311 Amelia St Unit B, Key West, FL 33040
• 

  

  /22

  $769,000

  $31K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,057 Sq Ft

  1102 Whitehead St, Key West, FL 33040

  Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden

  

  Margarita Villoch

  Island Group Realty (KW)

  1102 Whitehead St, Key West, FL 33040
• 

  

  /25

  $1,135,000

  Sold May 29, 2026

  1120 Stump Ln, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1933

  Last Sold Summary

  • 9% Below List Price
  • $1,192/SF
  • 52 Days On Market

  Current Estimated Value $1,204,074

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

  1120 Stump Ln, Key West, FL 33040
• 

  

  /20

  Not Listed For Sale

  311 Amelia St Unit A, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,305 Sq Ft
  • Built 1979

  311 Amelia St Unit A, Key West, FL 33040

  Last Sold Summary

  • 21 Days On Market
• 

  

  /41

  $59,000

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

  617 Front St Unit A52 Penthaus Week 32, Key West, FL 33040

  PENTHOUSE! Beautiful straight-on views of the Gulf, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. Stay or rent it

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit A52 Penthaus Week 32, Key West, FL 33040
• 

  

  /26

  $600,000

  Sold Oct 09, 2025

  1105 Watson St, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • Built 1943

  Last Sold Summary

  • 50% Below List Price
  • $377/SF
  • 237 Days On Market

  Current Estimated Value $722,785

  Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

  1105 Watson St, Key West, FL 33040
• 

  

  /12

  Not Listed For Sale

  908, 910 & 910 Rear Emma St, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,848 Sq Ft
  • Built 1943

  908, 910 & 910 Rear Emma St, Key West, FL 33040

  Last Sold Summary

  • 78 Days On Market
• 

  

  /37

  $1,249,999

  $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft

  524 White St, Key West, FL 33040

  Welcome to ParotHdHideaway! Located in the heart of the Historic District, just steps to world famous Duval Street, 5 minutes to Higgs Beach, and Garrison Bight Marina being literally around the corner, this location is UNBEATABLE. Featuring almost 1700 Square Feet of indoor living space, this Gem mixes Old Town Conch Charm with contemporary living and comfortably sleeps 6 adults. On the first

  

  Mike Kane

  Internet Realty of the Florida Keys

  524 White St, Key West, FL 33040
• 

  

  /29

  $710,000

  Sold Apr 30, 2026

  1115 Varela St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1948

  Last Sold Summary

  • 16% Below List Price
  • $550/SF
  • 158 Days On Market

  Current Estimated Value $725,433

  Last Listing Agent Terry Garcia Keller Williams Key West Compass Realty

  1115 Varela St, Key West, FL 33040
• 

  

  /6

  Est $774,563

  Not Listed For Sale

  612 Petronia St Unit Rear, Key West, FL 33040

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

  612 Petronia St Unit Rear, Key West, FL 33040

  Last Sold Summary

  • 35 Days On Market
• 

  

  /41

  $62,000

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

  617 Front St Unit A-52 Penthaus Week 5, Key West, FL 33040

  Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events.

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit A-52 Penthaus Week 5, Key West, FL 33040
• 

  

  /36

  $1,300,000

  Sold Aug 29, 2025

  1327 Duncan St, Key West, FL 33040

  • 4 Beds
  • 2 Baths
  • 2,019 Sq Ft
  • Built 1945

  Last Sold Summary

  • 41% Below List Price
  • $644/SF
  • 192 Days On Market

  Current Estimated Value $1,230,776

  Last Listing Agent Barbara Crespo Keller Williams Key West Compass Realty

  1327 Duncan St, Key West, FL 33040
• 

  /2

  Est $500,790

  Not Listed For Sale

  1010 Grinnell St Unit D, Key West, FL 33040

  • Studio
  • 1 Bath
  • 380 Sq Ft
  • Built 1943

  1010 Grinnell St Unit D, Key West, FL 33040
• 

  

  /12

  $735,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 745 Sq Ft

  906 Truman Ave Unit 1, Key West, FL 33040

  This performing vacation rental sold as shown is a beautiful property which exudes a sense of warmth and character from the moment you set eyes on it. As you approach the home, you are greeted by a picturesque facade that captures the essence of Key West architecture. The vibrant colors and tropical landscaping create a welcoming atmosphere that invites you to step inside and explore further.

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  906 Truman Ave Unit 1, Key West, FL 33040
• 

  

  /7

  $3,700

  Sold May 18, 2026

  311 Amelia St Unit 1, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $5/SF
  • 46 Days On Market

  Current Estimated Value $1,626,000

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  311 Amelia St Unit 1, Key West, FL 33040
• 

  /2

  Not Listed For Sale

  619 Front St Unit J North, Key West, FL 33040

  • Built 1985

  619 Front St Unit J North, Key West, FL 33040
• 

  

  /53

  $62,000

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

  617 Front St Unit A-52 Penthouse Week, Key West, FL 33040

  PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year (Week 52)--one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Eve celebrations, including live music, fireworks, and iconic Duval Street

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit A-52 Penthouse Week, Key West, FL 33040
• 

  

  /53

  $1,650,000

  Sold May 05, 2026

  1416 Catherine St, Key West, FL 33040

  • 4 Beds
  • 2 Baths
  • 2,242 Sq Ft
  • Built 1938

  Last Sold Summary

  • 13% Below List Price
  • $736/SF
  • 45 Days On Market

  Current Estimated Value $1,662,545

  Last Listing Agent Jody Clark Key West Luxury Real Estate Inc (KW)

  1416 Catherine St, Key West, FL 33040
• 

  

  /6

  Est $483,647

  Not Listed For Sale

  1209 William St Unit 6, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 486 Sq Ft
  • Built 1928

  1209 William St Unit 6, Key West, FL 33040

  Last Sold Summary

  • 16 Days On Market
• 

  

  /16

  $9,888,000

  • 3 Beds
  • 2 Baths
  • 2,071 Sq Ft

  1430 Vernon Ave, Key West, FL 33040

  Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing

  

  Irina Pytlik

  Keys Top Realty LLC

  1430 Vernon Ave, Key West, FL 33040
• 

  

  /3

  $1,500,000

  Sold Sep 29, 2025

  951 Caroline St Unit 34, Key West, FL 33040

  • Built 2003

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $1,566,616

  Last Listing Agent Joanne Allen Berkshire Hathaway HomeServices Knight & Gardner Realty

  951 Caroline St Unit 34, Key West, FL 33040
• 

  

  /13

  Est $608,646

  Not Listed For Sale

  712 Galveston Ln Unit 3, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 526 Sq Ft
  • Built 1981

  712 Galveston Ln Unit 3, Key West, FL 33040

  Last Sold Summary

  • 269 Days On Market
• 

  

  /41

  $42,000

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

  617 Front St Unit B41 Week 1, Key West, FL 33040

  Views of the famous Key West Sunset, Gulf of Mexico and pool await you when you arrive at this 4th-floor end- deeded timeshare unit. The live music from the Tiki bar saunters up to the balconies. This highly desirable winter week is magical enjoy the warm weather and Christmas boat parades while Key West is all dressed up for the holidays. Enjoy the private beach, pool, hot tub, sauna, outdoor

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit B41 Week 1, Key West, FL 33040
• 

  

  /5

  $3,250,000

  Sold May 27, 2026

  906 Southard St, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 2,188 Sq Ft
  • Built 1943

  Last Sold Summary

  • 18% Below List Price
  • $1,485/SF
  • 173 Days On Market

  Current Estimated Value $3,559,957

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

  906 Southard St, Key West, FL 33040
• 

  

  /4

  Est $1,304,617

  Not Listed For Sale

  1304 Elizabeth St, Key West, FL 33040

  • 6 Beds
  • 4 Baths
  • 2,050 Sq Ft
  • Built 1939

  1304 Elizabeth St, Key West, FL 33040

  Last Sold Summary

  • 401 Days On Market

Showing Results 41 - 80, Page 2 of 18