Old Town Homes for Sale

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  /55

  $2,859,000

  $40K PRICE DROP

  • 3 Beds
  • 3.5 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

  814 Ashe St, Key West, FL 33040
• Explore Old Town

• 

  

  

  /68

  $37,500

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

  617 Front St Unit B-24 Week 45, Key West, FL 33040

  Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit B-24 Week 45, Key West, FL 33040
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  /44

  $65,000

  $4K PRICE DROP

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

  617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

  Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040
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  /66

  $26,000

  $5K PRICE DROP

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

  617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040

  Penthouse, top floor, end unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit delivers a truly unforgettable Key West sunset experience, among the finest views in Key West. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit D-54 Week 37 Penthou, Key West, FL 33040
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  /70

  $49,900

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

  617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040

  Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lock door unit - where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café--everything you need for a

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit E-43 AB Week 46 Lock, Key West, FL 33040
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  /58

  $32,500

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

  617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040

  Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit B51 Week 36 Penthous, Key West, FL 33040
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  /68

  $65,000

  $4K PRICE DROP

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

  617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040

  Experience elevated waterfront ownership with this deeded timeshare in the highly desirable Building C at the Galleon Resort. This penthouse end-corner unit boasts one of the most sought-after spots in the resort, showcasing unobstructed, head-on views of the Gulf of Mexico.The residence features vaulted ceilings, extra windows for enhanced natural light, and multiple balconies designed to

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit C54 Penthouse Week 3, Key West, FL 33040
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  /58

  $49,900

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

  617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040

  Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove

  

  Stephanie Herrmann

  Truman & Co. Real Estate

  617 Front St Unit E43-Ab Lockout Week, Key West, FL 33040
• 

  

  /66

  $32,500

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

  617 Front St Unit B-51 Penthouse Week, Key West, FL 33040

  Top floor unit! Experience premium waterfront ownership with this deeded timeshare in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort.The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit B-51 Penthouse Week, Key West, FL 33040
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  /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
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  /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
• 

  

  /53

  $62,000

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

  617 Front St Unit A52 Penthouse WK 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 Eve celebrations, including live music, fireworks, and iconic Duval Street

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit A52 Penthouse WK 52, Key West, FL 33040
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  /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
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  /57

  $59,000

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

  617 Front St Unit A52 wk32, Key West, FL 33040

  PentHouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy this deeded week 32 and celebrate Lobster Week and the Rum Festival yearly with the rest of Key West. The Penthouse boasts expansive, straight-on views of the Gulf of Mexico, Pool and hot tub, the private beach, and the Tiki Bar, where a local guitarist performs nearly every day or night. There

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit A52 wk32, Key West, FL 33040
• 

  

  /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
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  /65

  $2,160,000

  Open Wed 10AM - 12PM $190K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,150 Sq Ft

  1209 Packer St, Key West, FL 33040

  Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  1209 Packer St, Key West, FL 33040
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  /43

  $2,695,000

  $130K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,902 Sq Ft

  525 Louisa St, Key West, FL 33040

  A fantastic renovation of a classic Old Town Key West property, blending timeless charm with modern upgrades. First Impressions are made with a wonderful front porch greeting you as you step from your two off street parking spots--or arrive by bicycle & use the separate entrance with dedicated bike storage.Outdoor Living -A complete irrigation system with landscape lighting transforms the

  

  J. Michael Caron

  Keller Williams Key West Compass Realty

  525 Louisa St, Key West, FL 33040
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  /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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  /22

  $765,000

  $35K 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
• 

  

  /45

  $3,999,000

  New Construction $601K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,421 Sq Ft

  1010 Olivia St, Key West, FL 33040

  Introducing The Twins on Olivia - a storied Key West treasure reborn. Once known locally as ''Olivia's Twins'' and documented on the 1892 Sanborn maps, this historic Old Town property has been meticulously reimagined and rebuilt to perfection after once being condemned by the City of Key West.Today, it stands proudly renewed - a testament to timeless design, craftsmanship and the enduring

  Suzanne Moore Suzanne Moore Real Estate

  1010 Olivia St, Key West, FL 33040
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  /40

  $2,240,000

  $160K PRICE DROP

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

  413 Frances St, Key West, FL 33040

  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 move-in ready, prepared for your immediate occupancy. With over

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

  413 Frances St, Key West, FL 33040
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  /57

  $2,199,999

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft

  1328 Duncan St, Key West, FL 33040

  A true Historic Gem, meticulously restored to its former glory with a complete, ground-up revitalization. Every detail has been thoughtfully preserved and reimagined, blending timeless character with modern craftsmanship to create a stunning masterpiece that honors the past while embracing the future. Experience the ease and elegance of one-level living in this Island Inspired Retreat. This

  Suzanne Moore Suzanne Moore Real Estate

  1328 Duncan St, Key West, FL 33040
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  /27

  $28,900

  $1K PRICE DROP

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

  617 Front St Unit B54/42, Key West, FL 33040

  DEEDED ANNUAL TIMESHARE! Enjoy 7 nights PER YEAR in a large 2bd, 2ba PENTHOUSE condo at the Galleon Resort in Key West! Sleeps up to 6 adults. This Penthouse SWING FLOAT week is deeded as B54/42. Choose from the following 18 Swing Floating weeks every year: 18-23, 36-50. (excludes Fantasy Fest (usually week 42 and Boat Race weeks) A Penthouse 5th Top floor unit also GUARENTEED each year! Make

  Mary Bradford LIST FOR LESS, LLC

  617 Front St Unit B54/42, Key West, FL 33040
• 

  

  /24

  $1,295,000

  Open Sat 12:30PM - 2:30PM

  • 2 Beds
  • 1 Bath
  • 1,099 Sq Ft

  1124 Watson St, Key West, FL 33040

  Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers the quintessential Key West lifestyle. Inside, natural light highlights the home's historic Dade County pine walls and original wood floors, blending timeless character with modern comfort. The updated kitchen and dining area create

  Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

  1124 Watson St, Key West, FL 33040
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  /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 Saltwater Real Estate Florida Keys, Inc

  1211 Knowles Ln, Key West, FL 33040
• 

  

  /25

  $1,349,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,020 Sq Ft

  912 James St Unit 2, Key West, FL 33040

  Tucked away in the Historic Seaport District, this unique three-bedroom, two-and-a-half-bath condo offers privacy, charm, and flexibility in an exceptional location. Set behind a gated rear entry, the property features a private pool, deck, and lush mature tropical landscaping. The main cottage includes a spacious primary suite with en suite bath, inviting living and dining spaces, a large

  Peter Batty ICAMCO Realty LLC, dba Cosgrove Realty

  912 James St Unit 2, Key West, FL 33040
• 

  

  /5

  $1,095,000

  • Land
  • 2,388 Sq Ft
  • $19,974,121 per Acre

  416 Applerouth Ln, Key West, FL 33040

  Prime Vacant Lot in Historic Old Town Key West - Rare Opportunity! Located in a vibrant community with rich history, this vacant lot offers endless possibilities for development.

  Jenny Perry Preferred Properties (KW)

  416 Applerouth Ln, Key West, FL 33040
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  /29

  $1,480,000

  $100K PRICE DROP

  • 2 Beds
  • 4 Baths
  • 1,092 Sq Ft

  709 Olivia St, Key West, FL 33040

  Legal duplex in the heart of Old Town Key West offering flexibility for investors or owner-occupants alike. Each residence features a private entrance, in-unit laundry, electric meter, and thoughtful renovations that make the property truly turn-key. Classic Key West character shines throughout with vaulted ceilings, exposed beams, skylights, and beautiful wood floors creating a bright and airy

  Corey Breingan RE Florida Homes

  709 Olivia St, Key West, FL 33040
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  /41

  $1,175,000

  $224K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  617 Fleming St Unit 4, Key West, FL 33040

  An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  617 Fleming St Unit 4, Key West, FL 33040
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  /8

  $839,000

  $20K PRICE DROP

  951 Caroline St Unit 20, Key West, FL 33040

  Located in the heart of downtown Key West's Historic Seaport, Conch Harbor Marina is one of the premier marina destinations in the Key West Bight. Slip 20 accommodates vessels up to 50' LOA and includes deeded bay bottom ownership. Enjoy the flexibility to live aboard, keep the slip for your own boating, fishing, and island lifestyle, or take advantage of the marina's rental program when you are

  Julia Besson Century 21 All Keys Inc (KW)

  951 Caroline St Unit 20, Key West, FL 33040
• 

  

  /30

  $2,150,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  810 Carey Ln, Key West, FL 33040

  Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the home features a spacious, light-filled kitchen with updated finishes--ideal for entertaining or relaxed island living. Step outside to your own tropical retreat, complete with a refreshing plunge pool surrounded by lush

  Mitzi Krabill Truman & Co. (KW)

  810 Carey Ln, Key West, FL 33040
• 

  

  /6

  $849,000

  $100K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,501 Sq Ft

  1432 Eliza St, Key West, FL 33040

  EXCELLENT OPPORTUNITY! EXCELLENT LOCATION! This duplex offers several terrific options for the buyer -- from building a brand new home in a prime location to a top to bottom renovation project. In either case, you could choose to make it your own, or make it an income producing investment by living in one side and renting out the other or even renovating it to sell. Additionally, this property

  Ralph Sanchez Century 21 All Keys Inc (KW)

  1432 Eliza St, Key West, FL 33040
• 

  

  /36

  $3,495,000

  $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,250 Sq Ft

  710 Caroline St, Key West, FL 33040

  Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is

  jesse friedman Real Broker, LLC

  710 Caroline St, Key West, FL 33040
• 

  /2

  $15,000

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  323 Whitehead St Unit 702 wks 12, Key West, FL 33040

  Own Week 12 at The Banyan Resort and enjoy one of the most sought-after times of year in Key West. Nestled in the heart of Old Town, this charming one-bedroom loft suite offers the perfect island getaway just steps from the energy of Duval Street. Unit 702 comfortably accommodates up to four guests and features a unique loft-style design with a spiral staircase leading to a semi-private bedroom

  Monika Rydzak eXp Realty LLC KW Branch

  323 Whitehead St Unit 702 wks 12, Key West, FL 33040
• 

  

  /39

  $2,550,000

  $125K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,962 Sq Ft

  1017 Angela St, Key West, FL 33040

  Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1017 Angela St, Key West, FL 33040
• 

  

  /47

  $2,999,999

  • 2 Beds
  • 4 Baths
  • 1,596 Sq Ft

  405 Petronia St, Key West, FL 33040

  Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

  Bobby Coe IV Coastal Collection Real Estate Inc.

  405 Petronia St, Key West, FL 33040
• 

  

  /11

  $799,900

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1014 Truman Ave Unit 202, Key West, FL 33040

  1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condominium has been masterfully remodeled with designer finishes, offering a home that's as stylish as it is functional. Step inside to a sunlit, open-concept living space where clean lines and bamboo

  Dominic Paolillo Jr. Truman & Co. (KW)

  1014 Truman Ave Unit 202, Key West, FL 33040
• 

  

  /33

  $1,100,000

  $150K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 767 Sq Ft

  738 Olivia St, Key West, FL 33040

  Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart of Old Town Key West. Thoughtfully updated with quartz countertops, custom wood cabinetry, and top-of-the-line stainless steel appliances, this home seamlessly blends modern comfort with historic charm. A cozy sleeping loft offers

  Jimmy Lane Island Life Realty Experts

  738 Olivia St, Key West, FL 33040
• 

  

  /17

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 958 Sq Ft

  1401 Simonton St Unit 11, Key West, FL 33040

  This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom

  Ralph Sanchez Century 21 All Keys Inc (KW)

  1401 Simonton St Unit 11, Key West, FL 33040
• 

  

  /37

  $985,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,580 Sq Ft

  1222 Florida St, Key West, FL 33040

  Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned in the highly sought-after White Street Gallery District. Just a short stroll from Higgs Beach, the White Street Pier, neighborhood parks, tennis and pickleball courts, and less than a mile from the restaurants, boutiques, galleries, and nightlife of iconic Duval Street, this location offers the perfect

  Kelsey Caputo Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  1222 Florida St, Key West, FL 33040

Showing Results 1 - 40, Page 1 of 3

Why Live in Old Town

Old Town in Key West is a historic neighborhood known for its distinctive conch-style homes, characterized by cozy front porches, wooden shutters, and intricate trim. Many of these homes, particularly in Bahama Village, date back to the 1800s and are built on raised platforms to improve air circulation and reduce mold and water damage. The area is in the X-flood zone, making it less flood-prone than other parts of Key West, though flood insurance and hurricane preparedness are recommended. Homeowners must maintain the original exterior of their properties, with renovations reviewed by the Historic Architectural Review Commission. Interiors, however, are often modernized with open floor plans and updated kitchens. The neighborhood is rich in cultural and culinary attractions, with numerous restaurants offering local specialties like conch fritters and Key lime pie. Notable dining spots include Old Town Tavern & Beer Garden, Blue Heaven, and Santiago’s Bodega. For things to do, residents can explore the Red Barn Theatre, Key West Theater, and Tropic Cinema, or visit the Key West Museum of Art & History. Fort Zachary Taylor Historic State Park and Truman Waterfront Park provide outdoor recreation options, including snorkeling, picnicking, and a weekly farmers market. Key West High School, which has a high rating, serves the area, and there are several private school options as well. The crime rate in Old Town is lower than the national average, contributing to its appeal for residents.

Learn more about living in Old Town

Old Town Home Prices vs. Nearby Key West, FL Neighborhoods

	Old Town	Mid Town	Truman Annex	The Meadows
Median Home Price	$1,590,000	$1,372,500	$1,395,000	$1,490,000
Median Sale Price	$1,400,000 +10% YoY	$1,150,000 +17% YoY	$1,232,500 +19% YoY	$1,500,000 -12% YoY
Median Single Family Price	$1,597,500	$1,354,000	$1,345,000	$1,650,000
Median Condo Price	$951,000	$889,000	$969,500	$699,000
Total Active Listings	74 listings	61 listings	7 listings	8 listings
Market Conditions	6 Months of Supply Buyer's Market	7 Months of Supply Buyer's Market	3 Months of Supply Seller's Market	9 Months of Supply Buyer's Market

Frequently Asked Questions

Is Old Town a good place to live?

Old Town is a good place to live. Old Town is considered fairly walkable and very bikeable with some transit options. Old Town is a neighborhood with a crime score of 4, on par with the average neighborhood in the U.S. Old Town has 7 parks for recreational activities. It is somewhat dense in population with 10.0 people per acre and a median age of 51. The average household income is $101,271 which is below the national average. College graduates make up 41.9% of residents. A majority of residents in Old Town are renters, with 59% of residents renting and 41% of residents owning their home. A local real estate agent serving Old Town can help you decide if this neighborhood is the right one for you. Learn more on our Old Town neighborhood guide.

Is Old Town, FL a safe neighborhood?

Old Town, FL is a safe neighborhood and is on par with the average neighborhood in the United States. It received a crime score of 4 out of 10.

How much do you need to make to afford a house in Old Town?

The median home price in Old Town is $1,590,000. If you put a 20% down payment of $318,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $8,200 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $351K a year to afford the median home price in Old Town. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Old Town is $101K.

What are the best public schools in Old Town?

The best public schools that serve Old Town are:

• Key West High School has a B+ Niche grade, a student teacher ratio of 17:1 and an average review score of 3.6.
• Gerald Adams Elementary School has a B Niche grade and a student teacher ratio of 16:1.
• Horace O'Bryant School has a B- Niche grade, a student teacher ratio of 15:1 and an average review score of 2.8.

What are the best private schools in Old Town?

The best private schools that serve Old Town are:

• The Basilica School of Saint Mary Star of the Sea has an A- Niche grade, a student teacher ratio of 40:1 and an average review score of 3.9.
• Grace Lutheran has a student teacher ratio of 18:1.
• Montessori Children's School of Key West has a student teacher ratio of 7:1.

What are the most popular zip codes in Old Town, Key West, FL?

The most popular zip codes in Old Town, Key West, FL include 33040 and 33042.

What are the most popular neighborhoods near Old Town, Key West, FL?

The most popular neighborhoods near Old Town, Key West, FL are Casa Marina, The Meadows, Truman Annex, Mid Town and New Town.