Old Town Homes for Sale

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  /45

  $2,250,000

  • 4 Beds
  • 8 Baths
  • 4,013 Sq Ft

  1028 Truman Ave, Key West, FL 33040

  Prime Mixed-Use Investment Opportunity in Key West!Built in 2021 to current building codes, this exceptional four-unit commercial and residential compound is a rare find in the heart of Key West. A perfect 1031 Exchange candidate, this versatile property includes two licensed townhouse residences and two licensed commercial units, offering excellent income potential and flexibility.The commercial

  Team Spottswood/Vazquez Truman & Co. (KW)

  1028 Truman Ave, Key West, FL 33040
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  /21

  $1,100,000

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  817 Terry Ln, Key West, FL 33040

  This idyllic Old Town Key West home offers an extraordinary location and super-coveted parking. Light, Bright and in move-in condition, this furnished, turn-key oasis works well as an exceptional rental property and/or second home. Your own Key West pied a terre. Outstanding features include vaulted wood ceilings, loft, wood floors, oak cabinets, and a private deck perfect for al fresco dining

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  817 Terry Ln, Key West, FL 33040
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  /44

  $1,595,000

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

  1211 Knowles Ln, Key West, FL 33040

  Discover the timeless charm of this beautifully remodeled historic home located in Old Town, Key West. This fully furnished 3 bedroom, 2.5 bath property boasts lovingly restored Dade County Pine, and combines classic craftsmanship with modern comforts. 1211 Knowles Ln features a 300 sq.ft. loft currently used as a 3rd bedroom, office and storage ! Both front and side porches invite you to relax

  Emily Lombard Ocean Sotheby's International Realty

  1211 Knowles Ln, Key West, FL 33040
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  /27

  $799,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  900 Thomas St, Key West, FL 33040

  Nestled in the ''X'' flood zone of Old Town Key West, this charming one level, two bedroom and one bathroom home offers the perfect blend of historic character and modern convenience. Featuring classic island architecture, the property boasts a spacious open floor plan, high ceilings, and beautiful hardwood floors throughout. Located mere steps from Key West's vibrant downtown, renowned

  Jimmy Lane Island Life Realty Experts

  900 Thomas St, Key West, FL 33040
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  /37

  $4,775,000

  • 4 Beds
  • 5 Baths
  • 2,716 Sq Ft

  709 Eaton St, Key West, FL 33040

  Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  709 Eaton St, Key West, FL 33040
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  /26

  $695,000

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

  1105 Watson St, Key West, FL 33040

  Located in Key West's Historic District, this two-story, 2-bedroom, 2-bathroom home sits on a manageable lot, offering a unique renovation opportunity. Large primary bedroom, bathroom and sitting area located upstairs. Second bedroom and bathroom on the main floor along with the living, dining and kitchen.Located in the X Flood zone, centrally located on the island, close to downtown and

  Francesca Santiago Keller Williams Realty Professionals (KW)

  1105 Watson St, Key West, FL 33040
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  /98

  $3,595,000

  • 5 Beds
  • 5 Baths
  • 2,721 Sq Ft

  1114 Packer St, Key West, FL 33040

  X FLOOD ZONE! Luxurious Old Town Key West Oasis with separate Guest House! Nestled in the heart of Key West's historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to discover a

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1114 Packer St, Key West, FL 33040
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  /46

  $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 RE/MAX Keys Connection (KW)

  405 Petronia St, Key West, FL 33040
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  /16

  $1,600,000

  • 8 Beds
  • 5 Baths
  • 1,830 Sq Ft

  928 Truman Ave Unit 101, Key West, FL 33040

  Old Town Multi-Use PropertyLocated on Truman Avenue, this distinctive property features five legal long-term rental apartments, making it ideal for steady income or employee housing.Unit 101, a CBS building, offers the potential for commercial conversion (buyer to verify), provided the residential units remain onsite, creating valuable flexibility.Highlights include:8 bedrooms and 5

  Allison Findlay Preferred Properties (KW)

  928 Truman Ave Unit 101, Key West, FL 33040
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  /47

  $2,195,000

  • 3 Beds
  • 4 Baths
  • 1,522 Sq Ft

  816 Ashe St, Key West, FL 33040

  This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance

  Bascom Grooms Bascom Grooms Real Estate (KW)

  816 Ashe St, Key West, FL 33040
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  /17

  $2,175,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1115 Fleming St, Key West, FL 33040

  This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone else's overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890

  Derek Epperly Keys Atlantic Realty

  1115 Fleming St, Key West, FL 33040
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  /23

  $990,000

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

  308 Peacon Ln, Key West, FL 33040

  Yes - not too good to be true or a misprint! Priced to sell for just $990,000 with this $400,000 price reduction. Rare 2 unit property in Old Town! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was

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

  308 Peacon Ln, Key West, FL 33040
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  /32

  $5,500,000

  • 8 Beds
  • 11 Baths
  • 8,472 Sq Ft

  314 Simonton St, Key West, FL 33040

  Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  314 Simonton St, Key West, FL 33040
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  /33

  $1,425,000

  • 3 Beds
  • 4 Baths
  • 1,464 Sq Ft

  415 Julia St, Key West, FL 33040

  At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24.

  Annica Pedersen Key West Luxury Real Estate Inc (KW)

  415 Julia St, Key West, FL 33040
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  /57

  $2,070,000

  • 3 Beds
  • 3 Baths
  • 1,473 Sq Ft

  1116 Packer St, Key West, FL 33040

  X FLOOD ZONE! Exquisite retreat in the heart of Old Town Key West--an ideal private sanctuary with rental income. This remarkable home offers refined style, privacy, and a proven rental history, appealing to buyers who value luxury and the allure of a tropical lifestyle. Behind an unassuming facade lies a sophisticated residence filled with high-end details. Restored in 2017, this home features

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  1116 Packer St, Key West, FL 33040
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  /33

  $2,000,000

  • 2 Beds
  • 2 Baths
  • 958 Sq Ft

  1401 Simonton St Unit 14, Key West, FL 33040

  This second-floor luxury condo is ideally situated just one block from the beach and the iconic Southernmost Point, offering the perfect balance of vacation living and income potential. As a high-demand rental property with an impressive occupancy rate, it presents an excellent opportunity for a 1031 exchange, especially with on-site management ensuring seamless service for guests.The property's

  Graciela Lozano KeysLifestyle Real Estate (KW)

  1401 Simonton St Unit 14, Key West, FL 33040
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  /34

  $3,799,000

  • 5 Beds
  • 4 Baths
  • 2,960 Sq Ft

  1214 White St, Key West, FL 33040

  Introducing ''Blu on White'' one of Key West's most stunning historic single level residences in desirable Old Town Key West. Exceptional location scoring a full 10 on the walkability scale with easy access to the beaches, White St. Pier, an array of galleries, restaurants and cafes.Taking full advantage of the generous 5800 sq ft. lot, this 5BD/4BA home offers so much space and versatility with

  Suzanne Moore Suzanne Moore Real Estate

  1214 White St, Key West, FL 33040
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  /19

  $2,095,000

  • 8 Beds
  • 4 Baths
  • 3,383 Sq Ft

  905 Grinnell St, Key West, FL 33040

  BIG TIME INVESTMENT OPPORTUNITY in the heart of the Historic District of Key West. Originally built as a former church, this 4 unit active rental property offers 3,383 square feet of living space, featuring 8 bedrooms and 4 bathrooms, and currently generates $10,908.50 in monthly rental income. (See below for a breakdown of beds and baths per unit) With versatile possibilities, it has the

  Team Kaufelt Truman & Co. (KW)

  905 Grinnell St, Key West, FL 33040
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  /49

  $2,100,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  1022 Fleming St, Key West, FL 33040

  Over 100k price reduction!Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is

  Ellen Gvili Ocean Sotheby's International Realty

  1022 Fleming St, Key West, FL 33040
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  /4

  $1,349,000

  • 3 Beds
  • 3 Baths
  • 1,520 Sq Ft

  818 Elizabeth St Unit Front, Key West, FL 33040

  Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 2623 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Seller financing possible. Please note that advanced notice is required to arrange showings.

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  818 Elizabeth St Unit Front, Key West, FL 33040
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  /22

  $799,999

  • 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
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  /36

  $1,850,000

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft

  1011 Simonton St Unit 1, Key West, FL 33040

  Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a

  Marc Ulanowski Equestrian Sotheby's International Realty

  1011 Simonton St Unit 1, Key West, FL 33040
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  /30

  $875,000

  • 2 Beds
  • 2 Baths
  • 548 Sq Ft

  1422 Catherine St, Key West, FL 33040

  Discover the perfect slice of paradise with this enchanting Key West cottage nestled in historic Old Town! This quaint property offers an unparalleled opportunity to own a single family residence and experience the essence of island living. With two structures on this lot, the potential is endless! Step inside the main home to discover a cozy living room/kitchen combination with bar top seating

  Bobby Coe RE/MAX Keys Connection (KW)

  1422 Catherine St, Key West, FL 33040
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  /5

  $1,049,000

  • Land

  416 Appelrouth 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 Appelrouth Ln, Key West, FL 33040
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  /19

  $60,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  617 Front St Unit A54/Week 49, Key West, FL 33040

  UNIT AVAILABLE TO SEE DEC. 7TH-14TH. THIS IS A ONE WEEK TIMESHARE PROPERTY DEEDED FOR LIFE - Enjoy the Best Sunset Views from the Rooftop of This Building. Relax on the Large Balcony Facing the Water Where You Can Watch the Boats Coming and Going From Beautiful Key West. Unit Includes Everything You Could Ever Need to Enjoy One of the Best Vacation Destinations! Tastefully Furnished, Spacious

  Angela Cichorz-Epstein EXIT Realty of Naples

  617 Front St Unit A54/Week 49, Key West, FL 33040

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