Old Town Homes for Sale

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  /46

  $5,395,000

  • 4 Beds
  • 5 Baths
  • 3,336 Sq Ft

  1006 Fleming St, Key West, FL 33040

  Exceptional Old Town compound with pool, gardens, and two guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths.

  Terri Spottswood Truman & Co. (KW)

  1006 Fleming St, Key West, FL 33040
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  /50

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 784 Sq Ft

  611 Grinnell St Unit 4, Key West, FL 33040

  Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do

  Daniel Cloud Water Vista Realty, Inc.

  611 Grinnell St Unit 4, Key West, FL 33040
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  /9

  $799,900

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

  1014 Truman Ave Unit 3, Key West, FL 33040

  1014 Truman Avenue - Modern Island Elegance in the Heart of Key WestWelcome 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 3, Key West, FL 33040
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  /31

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  414 Virginia St, Key West, FL 33040

  Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price.

  Bernard Isler Isler Realty & Investments LLC

  414 Virginia St, Key West, FL 33040
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  /58

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 1,943 Sq Ft

  408 William St, Key West, FL 33040

  Blending timeless character and modern comfort this home is nestled on one of Old Town's most coveted streets. Come discover this captivating home steeped in rich history. The kitchen has been thoughtfully redesigned with granite counters, new stainless-steel appliances & now has an open layout that enhances both function and flow. The Richard Roberts home, originally transported from Green

  Terri Spottswood Truman & Co. (KW)

  408 William St, Key West, FL 33040
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  /42

  $4,595,000

  • 4 Beds
  • 5 Baths
  • 2,985 Sq Ft

  1113 Stump Ln, Key West, FL 33040

  Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic.

  Terri Spottswood Truman & Co. (KW)

  1113 Stump Ln, Key West, FL 33040
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  /43

  $3,595,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 4 Baths
  • 1,968 Sq Ft

  510 Margaret St, Key West, FL 33040

  510 Margaret Street and 3 Scheppens Lane deliver an unparalleled island retreat. Ideally positioned on one of the most coveted streets in the heart of Old Town, this light-filled 4BD/4BA compound offers both comfort and privacy. The beautifully updated 3BD/3BA main residence features restored Dade County Pine walls, striking hardwood floors, Verde granite countertops, Thermador stainless

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  510 Margaret St, Key West, FL 33040
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  /55

  $3,999,000

  • 4 Beds
  • 3 Baths
  • 2,271 Sq Ft

  813 Thomas St, Key West, FL 33040

  Discover an extraordinary opportunity to own a luxurious sanctuary in the heart of Old Town Key West. Built in 2002 and a complete renovation in 2025, this impeccably 4BD/3BA home masterfully fuses island-contemporary style with timeless sophistication. Located on a rare double lot in the coveted X flood zone, the 3/2 main house welcomes you with wrap-around porches, soaring ceilings,

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  813 Thomas St, Key West, FL 33040
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  /49

  $1,999,990

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

  1022 Fleming St, Key West, FL 33040

  Invest in Key West with this Duplex which can be also easily used as a single family home! 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

  Ellen Gvili Ocean Sotheby's International Realty

  1022 Fleming St, Key West, FL 33040
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  /29

  $2,299,000

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  1116 Elgin Ln, Key West, FL 33040

  This quintessential two story, 3/2 Key West home is situated in the Historic Seaport District on a quiet lane with coveted off street parking.....The original structure can be traced back to the 1850s and has many beautiful historic features such as Dade County Pine walls and flooring. The home has a wonderful open design with the kitchen overlooking the large, vaulted living/dining area. A wall

  Rob Severin Rob Severin Real Estate Co

  1116 Elgin Ln, Key West, FL 33040
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  /47

  $1,895,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,205 Sq Ft

  421 United St, Key West, FL 33040

  This super cute historic Old Town Key West 2,205 sq. ft. Conch-style home is perfectly positioned just steps from famous Duval Street and one block from the ocean, South Beach, and the Southernmost Point. If you're seeking the best location in Key West--walkable, vibrant, and effortless--this property is unmatched. The sun-filled first floor showcases timeless Dade County pine, cherry floors, and

  Timothy Swanson The Agency Florida Keys

  421 United St, Key West, FL 33040
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  /84

  $2,975,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  529 Simonton St, Key West, FL 33040

  X Flood Zone 13ft above sea-level! Gorgeous CONCH home in the ultimate Old Town location - only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to

  Lisa Swanson The Agency Florida Keys

  529 Simonton St, Key West, FL 33040
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  /21

  $1,625,000

  • 2 Beds
  • 3 Baths
  • 1,959 Sq Ft

  1011 Truman Ave, Key West, FL 33040

  1011 Truman Avenue is a stylish mixed-use property located in the heart of Old Town, Key West. The building includes three legal units with one covered off street parking space and sits in the desirable X-Flood Zone. The ground floor features a 795 sq. ft. professional office space with an industrial feel and a half bath, along with a 416 sq. ft. one-bedroom unit that includes a full bathroom and

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  1011 Truman Ave, Key West, FL 33040
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  /24

  $1,249,000

  • 3 Beds
  • 3 Baths
  • 2,080 Sq Ft

  611 Simonton St, Key West, FL 33040

  NEW PRICE! Fantastic Key West location in the heart of Old Town Key West. Close to famous Duval Street, Historic Seaport, fine dining, galleries and more. Spacious two story home with 2,080 sq ft of living space. Three bedrooms and three full baths. Fenced yard. Patio Space. French Doors. Lanai area. Off street parking for one small vehicle. Seller financing possible with minimum 30% down!

  Bascom Grooms Bascom Grooms Real Estate (KW)

  611 Simonton St, Key West, FL 33040
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  /46

  $5,895,000

  • 6 Beds
  • 7 Baths
  • 3,443 Sq Ft

  1109 Fleming St, Key West, FL 33040

  Located in the heart of Old Town, this truly magical estate presents an opportunity to own a private compound of remarkable scale and architectural distinction. Set on an oversized lot with off-street parking for two, the property features two fully independent residences--each appointed with impact-rated windows and doors. Situated along iconic Millionaire's Row, the main residence is a

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1109 Fleming St, Key West, FL 33040
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  /44

  $2,949,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 5 Baths
  • 2,412 Sq Ft

  1223 Margaret St Unit 4, Key West, FL 33040

  Turnkey Old Town Key West Luxury - Pool, Guest Cottage & Parking Escape to paradise in this exquisite 2412sf 3 story home located in Old Town Key West not far from the Casa Marina area. A rare blend of historic charm and luxury, this fully furnished, turnkey property invites you to live the island dream or step into a ready-to-go monthly vacation rental opportunity. Inside, discover airy open

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  1223 Margaret St Unit 4, Key West, FL 33040
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  /87

  $3,795,000

  • 5 Beds
  • 6 Baths
  • 3,006 Sq Ft

  1022 Packer St, Key West, FL 33040

  Custom Bahamian Style Estate built in 2005! 3006 sq.ft. in Old Town X-Zone. 5 bedrooms and 5 and a half baths with generous front porches on both floors and a 2nd floor wrap around balcony in the back overlooking the pool and gardens. Spacious covered outdoor living area complements the large pool & spa. Luxurious chef's kitchen, top of the line appliances, open to great room/dining area with

  Dawn Thornburgh Beach Club Brokers (KW)

  1022 Packer St, Key West, FL 33040
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  /43

  $2,499,000

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  1119 Whitehead St, Key West, FL 33040

  This stunning Old Town residence offers the perfect blend of historic charm and modern elegance, just one block from Duval Street and three blocks from the world-famous Southernmost Point. This 3 bedroom, 2 bath home was fully renovated in 2018. and features a private gated courtyard, off-street parking, and high-end finishes throughout.Enjoy effortless indoor-outdoor living with a thoughtful

  Jenna Blackwell Berkshire Hathaway HomeServices Knight & Gardner Realty

  1119 Whitehead St, Key West, FL 33040
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  /40

  $2,880,000 Open Sun 12PM - 3PM

  • 2 Beds
  • 3 Baths
  • 2,940 Sq Ft

  626 Grinnell St, Key West, FL 33040

  Tucked away in the coveted flood X zone of Old Town, the elegant William H. Malone House offers an exceptional blend of historic character and refined modern living. This expansive 2,940 square foot residence features exquisite architectural details, off-street parking for two, a heated pool and spa, whole home generator, and spacious covered porches--offering a tranquil private retreat mere

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  626 Grinnell St, Key West, FL 33040
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  /32

  $1,099,000

  • 2 Beds
  • 2 Baths
  • 896 Sq Ft

  808 Virginia St Unit 4, Key West, FL 33040

  Private Pool, Parking and Proximity to it all!This is your perfect townhome in the heart of Old Town. Lock and Go is the key for this quintessential Key West property! With Very Low Monthly Expenses!Two (2) Bedrooms, One (1) Full bathroom and a (.5) half bathroom but don't forget the outdoor shower, which makes it a Key West full bathroom, and with a private pool just outside for you to enjoy

  Bobby Coe RE/MAX Keys Connection (KW)

  808 Virginia St Unit 4, Key West, FL 33040
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  /71

  $6,750,000

  • 5 Beds
  • 5 Baths
  • 3,663 Sq Ft

  411 Louisa St, Key West, FL 33040

  Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment.This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable

  Bobby Coe RE/MAX Keys Connection (KW)

  411 Louisa St, Key West, FL 33040
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  /39

  $2,745,000

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

  1017 Angela St, Key West, FL 33040

  The perfect embodiment of Key West located on a quiet lane in Old Town just a stroll from Duval Street and Historic Seaport. This cozy newly renovated, 3-bedroom, 3.5-bathroom home is the ultimate blend of calm island style inside and out. From the moment you arrive, 1017 Angela Street welcomes you with bold colors and playful design. The front porch offers an idyllic spot to start or end your

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1017 Angela St, Key West, FL 33040
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  /78

  $6,895,000

  • 6 Beds
  • 7 Baths
  • 3,340 Sq Ft

  317 Whitehead St, Key West, FL 33040

  Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual island elegance with modern sophistication. With a total of 6 bedrooms and 6.5 bathrooms, this home is an award winning architect-designed, custom-built luxurious property, complete with off-street parking, impact windows and doors, and

  Bobby Coe RE/MAX Keys Connection (KW)

  317 Whitehead St, Key West, FL 33040

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