Old Town Homes

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  /41

  $59,000

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

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

  PENTHOUSE! Beautiful straight on views of the Gulf of Mexico, 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. In

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  (645) 225-2567

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

  

  

  /22

  $6,500 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • House for Rent

  816 Center St, Key West, FL 33040

  Historic Bahama Conch Home for rent during the off season. It's in the center of Old Town , walking distance to everything and I provide 4 bikes to use included in the rent. Two bedrooms, 1 with a king size bed , 1 with a queen size bed. Full Kitchen, and large bathroom with the original claw foot tub and shower and 1 outdoor private shower. Large backyard for eating or relaxing. A Hammock

  816 Center St, Key West, FL 33040
• 

  

  

  /10

  $749,000 Sold Mar 11, 2026

  304 Amelia St, Key West, FL 33040

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1938

  Last Sold Summary

  • $800/SF
  • 9 Days On Market

  Current Estimated Value $1,014,592

  Last Listing Agent Marilyn Wilbarger Berkshire Hathaway HomeServices Knight & Gardner Realty

  304 Amelia St, Key West, FL 33040
• 

  

  

  /53

  Est $5,285,097 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

  • 6% Above List Price
  • $1,469/SF
  • 49 Days On Market

  • Last Sold Price $5,000,000
  • Feb 23, 2024

  Last Listing Agent Chris Remmert CENTURY 21 EXECUTIVE TEAM
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  /53

  $2,899,000

  • 3 Beds
  • 4 Baths
  • 2,286 Sq Ft

  814 Ashe St, Key West, FL 33040

  Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (866) 972-3334

  814 Ashe St, Key West, FL 33040
• 

  

  /6

  $3,200 per month

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft
  • Condo for Rent

  717 Emma St Unit C, Key West, FL 33040

  717 Emma St Unit C, 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 $1,086,078

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  1127 Packer St, Key West, FL 33040
• 

  

  /19

  Est $859,235 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

  • 11% Above List Price
  • $796/SF
  • 13 Days On Market

  • Last Sold Price $775,000
  • Feb 07, 2024

  Last Listing Agent Diana Fiddes Coldwell Banker Schmitt Key Largo
• 

  

  /42

  $69,000

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

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

  On the Gulf of Mexico this 4th floor end unit Timeshare is on the water and overlooks the Key West Marina. 2 bed 2bath with sofa couch sleeps 6. Week 50 is a very sought after week which offers ideal winter weather, a relaxed island atmosphere and peak rental demand. Enjoy the decorative Christmas boat parades from your own personal view balconies and experience Key West all dressed up for the

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  (645) 300-5987

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

  

  /25

  $4,000 per month

  • 2 Beds
  • 2 Baths
  • Old Town Apt Steps From Duval

  415 Julia St, Key West, FL 33040

  Welcome to 415 Julia-Back. This 2br two story furnished unit is part of a 2 unit duplex. Unit is located in the back of the property. You are steps away from famous Duval Street but the unit is tucked back on a one way street that you don't get the hussle and bussle noise. The first floor consists of the living room, full kitchen, guest bedroom with ensuite bathroom and washer/dryer.

  415 Julia St, Key West, FL 33040
• 

  

  /23

  $850,000 Sold Oct 31, 2025

  308 Peacon Ln, Key West, FL 33040

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

  Last Sold Summary

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

  Current Estimated Value $864,482

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

  308 Peacon Ln, 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

  Last Sold Summary

  • $975/SF

  • Last Sold Price $780,000

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)
• 

  

  /16

  $9,888,000

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

  1430 Vernon Ave Unit 1-2, 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

  (786) 981-9652

  1430 Vernon Ave Unit 1-2, 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
  • 3 Baths
  • 1,524 Sq Ft
  • Built 1928

  Last Sold Summary

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

  Current Estimated Value $2,571,712

  Last Listing Agent Paige Bethel Island Home Realty Inc.

  628 William St, Key West, FL 33040
• 

  

  /20

  Not Listed For Sale

  311 Amelia St Unit A, Key West, FL 33040

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

  311 Amelia St Unit A, Key West, FL 33040

  Last Sold Summary

  • $1,015/SF
  • 21 Days On Market

  • Last Sold Price $1,325,000
  • Dec 28, 2023

  Last Listing Agent Joe Bracciale Select Properties of NWFL
• 

  

  /69

  $3,168,000

  • 3 Beds
  • 3 Baths
  • 2,262 Sq Ft

  524 Southard St, Key West, FL 33040

  Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14'

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (786) 396-7585

  524 Southard St, Key West, FL 33040
• 

  

  /22

  $14,000 per month

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Condo for Rent

  918 Southard St Unit 205, Unit 205, Key West, FL 33040

  Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, ParkingLarge art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms, one with a large shower and one with bathtub, high ceilings throughout, wrap around porch in lush

  918 Southard St Unit 205, Unit 205, 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 $676,278

  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

  • $758/SF
  • 78 Days On Market

  • Last Sold Price $1,400,000
  • Feb 26, 2024

  Last Listing Agent Bill Vaught (REO Vaught Realty LLC Vaught Realty
• 

  

  /37

  $1,375,000

  • 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 floor

  

  Mike Kane

  Internet Realty of the Florida Keys

  (305) 853-8613

  524 White St, 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 $1,581,338

  Last Listing Agent Barbara Crespo Keller Williams Key West Compass Realty

  1327 Duncan St, Key West, FL 33040
• 

  

  /6

  Est $776,720 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

  • 55% Above List Price
  • $689/SF
  • 35 Days On Market

  • Last Sold Price $500,000
  • Sep 20, 2024

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

  

  /40

  $62,000

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

  617 Front St Unit A-52 Week 52, 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

  (844) 967-2396

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

  

  /29

  $1,400,000 Sold May 29, 2025

  1117 Whitehead St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1923

  Last Sold Summary

  • 6% Below List Price
  • $1,273/SF
  • 94 Days On Market

  Current Estimated Value $1,418,739

  Last Listing Agent Robin Nilsson Keller Williams Key West Compass Realty

  1117 Whitehead St, Key West, FL 33040
• 

  /2

  Est $489,155 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

  Last Sold Summary

  • 4% Below List Price
  • $1,343/SF

  • Last Sold Price $510,500

  Last Listing Agent Jessica Prescott Coastal Collection Real Estate Inc.
• 

  

  /12

  $735,000

  • 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)

  (645) 238-6011

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

  

  /3

  $1,500,000 Sold Sep 29, 2025

  951 Caroline St Unit 34, Key West, FL 33040

  • Land

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $1,503,851

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

  951 Caroline St Unit 34, 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

  Last Sold Summary

  • Last Sold Price $2,350,000

  Last Listing Agent Jerry Hughes Old Town Realty
• 

  

  /41

  $23,999

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

  617 Front St Unit B-41 Week 28, Key West, FL 33040

  Views of famous Key West Sunset, & Sunset Island/Christmas Island, overlooking the pool, Tiki bar & beach, this is what you see when you arrive at this 4th floor unit. Enjoy the sounds of the live music from your balcony as it saunters your way from the Tiki bar. This week celebrates the 4th of July, the Key Lime Festival, featuring a 5K race, the 42nd Annual Hemingway Days & A Marlin tournament,

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  (786) 977-4254

  617 Front St Unit B-41 Week 28, Key West, FL 33040
• 

  

  /60

  $900,000 Sold May 20, 2025

  205 Julia St, Key West, FL 33040

  • 3 Beds
  • 4 Baths
  • 1,264 Sq Ft
  • Built 1923

  Last Sold Summary

  • 43% Below List Price
  • $712/SF
  • 194 Days On Market

  Current Estimated Value $1,002,080

  Last Listing Agent Edward Salazar Bascom Grooms Real Estate (KW)

  205 Julia St, Key West, FL 33040
• 

  /2

  Est $1,200,715 Not Listed For Sale

  1119 Varela St Unit A, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1921

  1119 Varela St Unit A, Key West, FL 33040

  Last Sold Summary

  • 5% Below List Price
  • $905/SF

  • Last Sold Price $1,140,000

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

  

  /70

  $4,995,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,026 Sq Ft

  1014 Southard St, Key West, FL 33040

  Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance. With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key West's

  Suzanne Moore Suzanne Moore Real Estate

  1014 Southard St, Key West, FL 33040
• 

  

  /18

  $900,000 Sold Dec 01, 2025

  314 Southard St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1901

  Last Sold Summary

  • 43% Below List Price
  • $620/SF
  • 156 Days On Market

  Current Estimated Value $1,089,709

  Last Listing Agent Terri Spottswood Truman & Co. (KW)

  314 Southard St, Key West, FL 33040
• 

  /2

  Est $1,687,936 Not Listed For Sale

  624 Fleming St Unit B, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,271 Sq Ft
  • Built 1980

  624 Fleming St Unit B, Key West, FL 33040

  Last Sold Summary

  • 6% Below List Price
  • $1,258/SF

  • Last Sold Price $1,599,000

  Last Listing Agent Wendy Zintsmaster Truman & Co. (KW)
• 

  

  /31

  $1,190,800

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

  709 Chapman Ln, Key West, FL 33040

  Refined Island Living with Authentic Key West Heritage.Nestled in the heart of Old Town Key West and located in the coveted X-flood zone, the highest elevation of the island, this impeccably renovated historic cottage combines timeless charm with modern elegance. Just three blocks from Duval St. and half a block from Truman Annex, this home is ideally situated in a quiet, highly walkable

  Suzanne Moore Suzanne Moore Real Estate

  709 Chapman Ln, Key West, FL 33040
• 

  

  /26

  $1,125,000 Sold Apr 28, 2025

  827 Baptist Ln Unit 1 and 2, Key West, FL 33040

  • 4 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1923

  Last Sold Summary

  • 20% Below List Price
  • $819/SF
  • 117 Days On Market

  Current Estimated Value $848,609

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  827 Baptist Ln Unit 1 and 2, Key West, FL 33040
• 

  

  /6

  Est $483,588 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

  • 12% Above List Price
  • $885/SF
  • 16 Days On Market

  • Last Sold Price $430,000
  • Nov 15, 2023

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

  

  /40

  $2,290,000

  • 3 Beds
  • 3 Baths
  • 1,536 Sq Ft

  413 Frances St, Key West, FL 33040

  Take advantage of this major price improvement - now $2,290,000.Extraordinary home in the historic district! Enjoy Key West living in the prized Old Town neighborhood with the perfect combination of all the top sought after attributes requested by buyers: walkable location, swimming pool, & private parking without compromise.Offered entirely furnished, the 3 bedroom and 3 bath home is absolutely

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

  413 Frances St, Key West, FL 33040
• 

  

  /34

  $700,000 Sold Jun 05, 2025

  811 United St Unit 3, Key West, FL 33040

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

  Last Sold Summary

  • 18% Below List Price
  • $1,125/SF
  • 76 Days On Market

  Current Estimated Value $693,591

  Last Listing Agent Jeffrey Dunaway Key West Realty, LLC (KW)

  811 United St Unit 3, Key West, FL 33040

Showing Results 41 - 80, Page 2 of 18