Old Town Homes for Sale

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  /29

  $1,399,000

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  1111 Watson St Unit B, Key West, FL 33040

  Secret Garden Cigar Maker's Cottage in Old Town 🌴Tucked behind a private gate on a quiet section of Old Town in Key West, this enchanting 2-bedroom historic cottage invites you into a hidden world of tropical beauty, offering a rare blend of privacy, charm, and walkable island living--set in an X flood zone for added peace of mind.Follow a palm-lined path into a lush, private

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1111 Watson St Unit B, Key West, FL 33040
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  /34

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 885 Sq Ft

  1025 Elgin Ln, Key West, FL 33040

  Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay

  Jimmy Lane Island Life Realty Experts

  1025 Elgin Ln, Key West, FL 33040
• 

  

  

  /23

  $1,174,000

  • 3 Beds
  • 2 Baths
  • 1,395 Sq Ft

  1209 Pearl St, Key West, FL 33040

  Charming historic duplex ideally located within walking distance to the White Street Gallery District, Old Town, and Key West beaches. The ground-floor unit features a 2BD/1BA layout with a separate living room and updated kitchen, off-street parking, and good size yard with room to add a pool. A covered outdoor living area spans the length of the property and is surrounded by tropical

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  1209 Pearl St, Key West, FL 33040
• 

  

  

  /21

  $779,000

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft

  1012 Packer St Unit 7 A, Key West, FL 33040

  PRICE REDUCTION!! This secluded condo is close to all the fun Key West has to offer, including famous Duval St! Bike to local markets, theaters, restaurants, music venues, and the beach!! The home is tucked away among a lush garden of mature trees in desirable Truman Gardens. Take in the beauty by sitting on either one of two porches. Inside, a split layout offers privacy with each of the two

  Matthew Zelko Berkshire Hathaway HomeServices Knight & Gardner Realty

  1012 Packer St Unit 7 A, Key West, FL 33040
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  /50

  $3,300,000

  • 4 Beds
  • 4 Baths
  • 2,573 Sq Ft

  214 Eanes Ln, Key West, FL 33040

  Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market.This unique property is configured as two separate units, featuring a main two-story

  Jaime Caballero Century 21 Prestige Realty Group (KW)

  214 Eanes Ln, Key West, FL 33040
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  /36

  $1,799,000

  • 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 private

  Marc Ulanowski Equestrian Sotheby's International Realty

  1011 Simonton St Unit 1, Key West, FL 33040
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  /21

  $998,000

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  817 Terry Ln, Key West, FL 33040

  Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive.Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the

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

  817 Terry Ln, Key West, FL 33040
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  /38

  $5,850,000

  • 6 Beds
  • 8 Baths
  • 3,010 Sq Ft

  421-423 Simonton St, Key West, FL 33040

  Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  421-423 Simonton St, Key West, FL 33040
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  /13

  $1,899,000

  • 7 Beds
  • 6 Baths
  • 2,790 Sq Ft

  909 Grinnell St, Key West, FL 33040

  Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  909 Grinnell St, Key West, FL 33040
• 

  

  /23

  $844,000

  • 3 Beds
  • 1 Bath
  • 1,342 Sq Ft

  1425 Eliza St, Key West, FL 33040

  3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

  Sean Farrer, P.A. Coastline R.E. & Property Mgmt. (KW)

  1425 Eliza St, Key West, FL 33040
• 

  

  /23

  $845,000

  • 2 Beds
  • 2 Baths
  • 712 Sq Ft

  508 Louisa St Unit 3, Key West, FL 33040

  Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the

  Paul Brooks Compass Florida, LLC

  508 Louisa St Unit 3, Key West, FL 33040
• 

  

  /43

  $2,595,000

  • 3 Beds
  • 3 Baths
  • 2,049 Sq Ft

  508 Grinnell St, Key West, FL 33040

  Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

  Marc Ulanowski Equestrian Sotheby's International Realty

  508 Grinnell St, Key West, FL 33040
• 

  

  /15

  $1,199,000

  • 3 Beds
  • 1 Bath
  • 943 Sq Ft

  719 Elizabeth St, Key West, FL 33040

  Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof and main electrical panel replaced (w/ permits) in 2014.

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  719 Elizabeth St, Key West, FL 33040
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  /40

  $2,699,000

  • 3 Beds
  • 3 Baths
  • 2,002 Sq Ft

  410 Louisa St, Key West, FL 33040

  Experience the epitome of luxury in this exquisite 3BD/3BA residence nestled on a quiet Lane in the heart of Old Town Key West, just a stone's throw from the world famous Southernmost Point and 1 block from the iconic Duval Street. Indulge in the unparalleled convenience of having Key West's renowned restaurants, museums, and art galleries at your doorstep, with the beach a leisurely bike ride

  The Spottswood Team Truman & Co. (KW)

  410 Louisa St, Key West, FL 33040
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  /35

  $1,495,000

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

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040

  Charming Old Town Duplex located in the heart of old town. Ideally located on Simonton Street this charming duplex places you just steps from Duval Street, along with world-class dining, boutique shopping, beaches, and neighborhood parks.This versatile property is the perfect Key West residence, second home, or income-producing investment. Live in one side and rent the other, or maximize its

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040
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  /33

  $800,000

  • 2 Beds
  • 2 Baths
  • 648 Sq Ft

  906 Truman Ave Unit 2, Key West, FL 33040

  Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ride to Duval street. This wonderful 2 bedroom, 2 bath condo is one of 4 units and is located steps from the shared pool. Unique to this condo is an outside covered area with a Grill, wet-bar, and seating, exclusively for use with

  Elaine Coyle Keller Williams Key West Compass Realty

  906 Truman Ave Unit 2, Key West, FL 33040
• 

  

  /22

  $868,000

  • 2 Beds
  • 1 Bath
  • 568 Sq Ft

  1218 Packer St Unit Rear, Key West, FL 33040

  Nestled in an X flood zone in Old Town , this lovely conch cottage has been well cared for, meticulously maintained and lightly used as a seasonal getaway. The two-bedroom, one-bath residence is fully furnished and move-in ready, offering a perfect blend of charm, comfort, and thoughtful design. Behind the private gate, the home immediately feels welcoming and serene, creating a true island

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  1218 Packer St Unit Rear, Key West, FL 33040
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  /25

  $3,485,000

  • 7 Beds
  • 7 Baths
  • 3,956 Sq Ft

  709 Whitmarsh Ln, Key West, FL 33040

  This exceptional 6-dwelling unit redevelopment opportunity perched atop Solares Hill, the 18' highest point in Key West, is practically shovel-ready and includes top-level planning & design that resulted in an issued building permit in 2024. Substantial renovation is already complete on four of the 1-bedroom units; only the single family house renovation and condo conversion remain. The current

  Keith Bland Truman & Co. (KW)

  709 Whitmarsh Ln, Key West, FL 33040
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  /38

  $1,799,000

  • 7 Beds
  • 5 Baths
  • 2,349 Sq Ft

  800 Elizabeth St, Key West, FL 33040

  Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind

  Jenny Perry Preferred Properties (KW)

  800 Elizabeth St, Key West, FL 33040
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  /30

  $820,000 Open Wed 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  817 Eaton St Unit 1, Key West, FL 33040

  Old Town Condo Near Duval:Bright 1-bedroom, 1-bath condo located in the heart of Historic Old Town Key West. Featuring high ceilings and an open floor plan, this residence is filled with natural light. Just steps from Duval Street, dining, shopping, and entertainment. Ideal as a vacation rental, investment property, or personal island retreat.OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

  Letisia Powell Robert Slack LLC

  817 Eaton St Unit 1, Key West, FL 33040
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  /5

  $3,300

  • 2 Beds
  • 1 Bath

  1110 White St Unit 2, Key West, FL 33040

  2-bedroom,1-bath apartment in prime Key West location .Walking distance to Sandy's cafe ,Fausto's Food Palace ,and local shops ,and just minutes from the beach .Conveniently located near restaurants ,grocery stores ,and laundry facilities. Enjoy the convenience of having everything you need just steps away in one of Key West's most desirable areas

  Ernie Cruz Berkshire Hathaway HomeServices Knight & Gardner Realty

  1110 White St Unit 2, Key West, FL 33040
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  /37

  $4,695,000

  • 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
• 

  

  /17

  $715,000

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  1119 Simonton St Unit A1, Key West, FL 33040

  Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex is just steps from Duval Street and close to dining, shopping, beaches, and neighborhood parks. Perfect as a full-time island residence, second home, or investment property, this home offers the quintessential Key West lifestyle in one of the island's most desirable locations. The property features a welcoming

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A1, Key West, FL 33040
• 

  

  /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
• 

  

  /15

  $2,975

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  1318 Duncan St Unit 3, Key West, FL 33040

  AVAILABLE JULY 1st. Lease at $2975 per month for a yearly lease. Renovated detached pool view cottage with stainless range and fridge/freezer close to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared

  Rob Severin Rob Severin Real Estate Co

  1318 Duncan St Unit 3, Key West, FL 33040
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  /51

  $4,990,000

  • 4 Beds
  • 4 Baths
  • 2,441 Sq Ft

  720D Simonton St, Key West, FL 33040

  KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE

  The Spottswood Team Truman & Co. (KW)

  720D Simonton 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
• 

  

  /45

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 1,804 Sq Ft

  846 Olivia St, Key West, FL 33040

  Historic Old Town Key West home offering character, a prime location, and strong potential for a buyer looking to add value. Originally built in 1908 and positioned on a desirable corner lot, this 3-bedroom, 3-bath property is just moments from galleries, dining, the waterfront, and Key West's well-known sunsets. The interior features high ceilings, Dade County pine floors, and an open living and

  Thomas Mack SBX Real Estate, LLC (KW)

  846 Olivia St, Key West, FL 33040
• 

  

  /37

  $2,990,000

  • 4 Beds
  • 3 Baths
  • 1,787 Sq Ft

  1327 Whitehead St, Key West, FL 33040

  Modern luxury meets historic charm at this ultimate Key West sanctuary! Experience the pinnacle of island living in this stunning multi-story home built in 2018. Situated on the largest and most private parcel within an exclusive gated community, this home offers a rare combination of space and privacy in an unbeatable location. Tucked away off Whitehead Street, you'll be just steps from the

  Rodney Culiver Last Key Realty, Inc (KW)

  1327 Whitehead St, Key West, FL 33040
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  /33

  $799,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  616 Caroline St Unit 6, Key West, FL 33040

  Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living—and easy

  Jimmy Lane Island Life Realty Experts

  616 Caroline St Unit 6, Key West, FL 33040
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  /42

  $4,450,000

  • 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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  /82

  $2,799,000

  • 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 Berkshire Hathaway HomeServices Knight & Gardner Realty

  529 Simonton St, Key West, FL 33040
• 

  

  /45

  $2,799,000

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

  1223 Margaret St Unit 4, Key West, FL 33040

  GORGEOUS Old Town Key West Luxury EXCELLENT VACATION RENTAL! Large 3 Story Single Family Home with Pool, Guest Cottage & Off Street Parking! Sleeps 10 people! Escape to paradise in this exquisite 2412sf 3 story home located in Old Town Key West close to 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

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  1223 Margaret St Unit 4, Key West, FL 33040
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  /35

  $1,169,500

  • 3 Beds
  • 2.5 Baths
  • 1,017 Sq Ft

  609 Margaret St, Key West, FL 33040

  Charming remodeled 1929 Old Town Key West home on iconic Margaret Street, offering privacy, new impact windows & doors, flooring and timeless island feel. Set back from the street, this three-bedroom, two-bath residence feels like a peaceful retreat while remaining close to Duval Street and the historic seaport. The outdoor living space features a beautiful pool and spa area surrounded by a

  Sean Farrer Coldwell Banker Schmitt RE Co

  609 Margaret St, Key West, FL 33040
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  /36

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 1,748 Sq Ft

  4 Aronovitz Ln, Key West, FL 33040

  Experience an authentic island lifestyle at this classic conch cottage nestled in the heart of Old Town. Located on a quiet lane, just steps to Duval Street and The Green Parrot, this updated home provides a unbeatable location for walking to all of the best spots in Key West. Designed in the iconic ''conch cottage'' style, the interior features Dade County Pine walls, vaulted ceilings, and

  Rodney Culiver Last Key Realty, Inc (KW)

  4 Aronovitz Ln, Key West, FL 33040
• 

  

  /33

  $865,000

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  1124 Olivia St Unit 321, Key West, FL 33040

  *** BEST PRICED 2/2 CONDO IN OLD TOWN *** Located in the sought-after Lionsgate community in the heart of Old Town, this charming 2-bedroom, 2-bath condo offers a rare blend of serenity, connection, and island ease. From the second floor, gentle breezes and soft eastern light filter through the palms each morning--an everyday moment that makes this home feel instantly uplifting. Vaulted ceilings

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1124 Olivia St Unit 321, 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
• 

  

  /78

  $6,895,000

  • 6 Beds
  • 7 Baths
  • 3,425 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
• 

  

  /18

  $1,000,000

  • 3 Beds
  • 3 Baths
  • 1,152 Sq Ft

  844 Olivia St, Key West, FL 33040

  Charming Old Town Key West home blending historic island style with comfortable modern living. This well-maintained three-bedroom, two-bath residence features beautiful hardwood floors, abundant natural light, and inviting living spaces that create a relaxed Key West atmosphere. The functional layout works well for full-time living, a second home, or an income-producing investment property, with

  Rebecca Cobo Key West Vacation Properties & Realty, LLC (KW)

  844 Olivia St, Key West, FL 33040

Showing Results 81 - 119, Page 3 of 3