Old Town Homes for Sale

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  /48

  $2,300,000

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

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

  Bottled Paradise at Its Best!! Exceptional opportunity in the heart of Key West! This fully renovated and furnished duplex with an additional ADU offers flexibility, income potential, and prime location—three separate lots available to be sold together or individually.The duplex features two mirrored 1-bedroom units, each thoughtfully updated and move-in ready. Both units include full

  Rhea Jeffrey INVESTMENT FLORIDA REALTY LLC

  1119 Simonton St Unit A1, A2, C1, Key West, FL 33040
• Explore Old Town

• 

  

  

  /19

  $2,000,000

  • 3 Beds
  • 3 Baths
  • 1,256 Sq Ft

  1110 Elgin Ln, Key West, FL 33040

  Located in the heart of the Seaport Historic District, this charming Conch home features a 2-bedroom main residence and a separate 1-bedroom guest cottage. The property offers exceptional outdoor living, highlighted by a large L-shaped, recently resurfaced heated pool and spa, surrounded by brick and wood decking. Inside, painted Dade County Pine accent walls add authentic character, while the

  Key West Luxury Finders Preferred Properties (KW)

  1110 Elgin Ln, Key West, FL 33040
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  /36

  $2,750,000

  • 3 Beds
  • 3 Baths
  • 1,519 Sq Ft

  610 Griffin Ln, Key West, FL 33040

  Privacy. Seclusion. Serenity. Tucked away at the end of a quiet lane, 610 Griffin Lane is a rare Old Town retreat--an intimate, multi-structure compound that feels worlds away from the everyday.Set on an oversized lot nearly twice the size of most in the area, the property unfolds like a private estate. The beautifully renovated two-bedroom, two-bath main residence offers effortless comfort and

  

  Cardenas & Krug Team

  Coastal Collection Real Estate Inc.

  (786) 933-8828

  610 Griffin Ln, Key West, FL 33040
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  /36

  $1,390,000

  • 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
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  /11

  $549,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  1318 Duncan St Unit 3, Key West, FL 33040

  Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. This renovated one bedroom condo cottage overlooking the large communal pool is just one block 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

  Rob Severin Rob Severin Real Estate Co

  1318 Duncan St Unit 3, Key West, FL 33040
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  /28

  $850,000

  • 2 Beds
  • 2 Baths
  • 548 Sq Ft

  1422 Catherine St, Key West, FL 33040

  Welcome to 1422 Catherine Street in The Heart of Key West.Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally

  Bobby Coe RE/MAX Keys Connection (KW)

  1422 Catherine St, Key West, FL 33040
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  /20

  $839,000

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft

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

  Welcome home to your oasis in the heart of old town Key West. Located a short walk to famous Duval St, this home is close to all the fun, yet secluded by a gorgeous 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 bedrooms with their own bathrooms. Vaulted ceilings

  Matthew Zelko Berkshire Hathaway HomeServices Knight & Gardner Realty

  1012 Packer St Unit 7 A, Key West, FL 33040
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  /79

  $2,750,000

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

  808 Carey Ln, Key West, FL 33040

  Experience the captivating charm of Key West through this stunning Conch home, a genuine gem steeped in history. Dating back to the late 1800s, this property has undergone meticulous restoration, blending the historical allure of Old Town Key West with modern comforts. Recognized for its outstanding restoration efforts, the home has proudly won the Historic Florida Keys Preservation Award,

  Derek Epperly Engel & Volkers Key West

  808 Carey Ln, Key West, FL 33040
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  /29

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 958 Sq Ft

  1401 Simonton St Unit 16, Key West, FL 33040

  Luxury Condo Hotel with rare Transient Nightly Rental Rights - Exceptional Key West Value.Discover a rare opportunity to own a luxury condo-hotel residence in the heart of Key West with full transient nightly rental privileges - an increasingly scare asset class in the Florida Keys. This turnkey Investment generated almost $200,000 in actual gross rental revenue in 2005, offering strong income

  Suzanne Moore Suzanne Moore Real Estate

  1401 Simonton St Unit 16, Key West, FL 33040
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  /30

  $2,299,000

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

  1116 Elgin Ln, Key West, FL 33040

  There are streets in Old Town that everyone knows, and then there are streets like Elgin Lane that most people never even realize exist. Quiet, tucked away, and remarkably private, this hidden lane offers what buyers search for endlessly in Old Town privacy, off street parking, and a pool, all in one of the most desirable locations in Key West. 1116 Elgin Lane is a 3 bedroom, 2 bath home located

  The Spottswood Team Truman & Co. (KW)

  1116 Elgin Ln, Key West, FL 33040
• 

  

  /18

  $1,200,000

  • 3 Beds
  • 2 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 Berkshire Hathaway HomeServices Knight & Gardner Realty

  844 Olivia St, Key West, FL 33040
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  /33

  $850,000

  • 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
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  /24

  $799,000

  • 1 Bed
  • 1 Bath
  • 721 Sq Ft

  828 White St Unit 2, Key West, FL 33040

  Tucked into the heart of Old Town Key West's White Street Gallery District, this renovated 1-bedroom, 1-bath condo offers a rare blend of character, flexibility, and proven rental performance. With a strong history of seasonal and monthly rentals, it presents an appealing opportunity for both personal use and investment.One of the most unique features is the private first-floor entry, opening

  Michelle Blades Realty Executives Florida Keys Old Town

  828 White St Unit 2, Key West, FL 33040
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  /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
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  /29

  $2,185,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  419 Simonton St Unit C, Key West, FL 33040

  Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand-new, ground-up construction, this private 2BD/2.5BA residence delivers modern island luxury within a lush, secluded enclave, featuring soaring cathedral ceilings in the bedrooms, impact-rated windows and doors, and a streamlined

  Team Kaufelt Truman & Co. (KW)

  419 Simonton St Unit C, Key West, FL 33040
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  /28

  $1,485,000

  • 2 Beds
  • 3 Baths
  • 1,123 Sq Ft

  419 Simonton St Unit A, Key West, FL 33040

  The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West--authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction

  Team Kaufelt Truman & Co. (KW)

  419 Simonton St Unit A, Key West, FL 33040
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  /25

  $849,000

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  828 White St Unit 1, Key West, FL 33040

  Located in the heart of Old Town Key West's sought-after White Street Gallery District, this beautifully renovated 2-bedroom, 1-bath condo offers the perfect blend of island charm, outdoor living, and investment potential. A rare highlight is the expansive private outdoor space, featuring two distinct areas: an open-air sun deck ideal for relaxing and entertaining, and a screened lanai with

  Michelle Blades Realty Executives Florida Keys Old Town

  828 White St Unit 1, Key West, FL 33040
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  /36

  $2,717,000

  • 4 Beds
  • 3 Baths
  • 2,058 Sq Ft

  717 Southard St, Key West, FL 33040

  Meticulously renovated 1866 Conch Revival perched atop Solaris Hill in the heart of Old Town and Steps from Old Town's vibrant culture, dining, and entertainment. This historic gem blends rich heritage with contemporary comforts offering an open Floor plan, 2 primary bedroom options (one on first level), X Flood Zone, cocktail pool, hammock porch and more! Step into the foyer at the corner of

  Kimberley Haley Brenda Donnelly Real Estate LLC

  717 Southard St, Key West, FL 33040
• 

  

  /23

  $4,700,000

  • 5 Beds
  • 6 Baths
  • 3,434 Sq Ft

  515 Amelia St, Key West, FL 33040

  Discover the charm of 515 Amelia St., a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles.Designed for entertaining, 515 Amelia St. features an expansive open floor plan that seamlessly connects the spacious living room to the

  Jenny Perry Preferred Properties (KW)

  515 Amelia St, Key West, FL 33040
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  /32

  $2,175,000

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

  1115 Fleming St, Key West, FL 33040

  This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. The nearly 5,000-square-foot lot stretches from

  Derek Epperly Engel & Volkers Key West

  1115 Fleming St, Key West, FL 33040
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  /24

  $995,000

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  120 Angela St Unit 102, Key West, FL 33040

  Welcome to Old Key West luxury living in this beautifully appointed 2-bedroom, 2-bathroom condo, ideally located in an X flood zone. This residence features hardwood floors, high ceilings, crown molding, granite countertops, and stainless steel appliances, creating a refined yet relaxed island aesthetic. The open-concept layout flows effortlessly for everyday living and entertaining, while the

  

  The Wesley Group

  Bascom Grooms Real Estate (KW)

  (786) 933-6012

  120 Angela St Unit 102, Key West, FL 33040
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  /36

  $1,395,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 3 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 Real Estate Co. (KW)

  609 Margaret St, Key West, FL 33040
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  /57

  $2,350,000

  • 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

  (786) 461-1882

  1209 Packer St, Key West, FL 33040
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  /16

  $2,033,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  1 & 2 Aronovitz Ln, Key West, FL 33040

  Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers.The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction

  Alexa Morgan Buy The Keys

  1 & 2 Aronovitz Ln, Key West, FL 33040
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  /7

  $925,000

  • 1 Bed
  • 1 Bath
  • 468 Sq Ft

  3 Nassau Ln Unit A, Key West, FL 33040

  Charming Key West Cottage on Historic Nassau LaneNestled along the picturesque and historic Nassau Lane, this delightful one-bedroom cottage offers a perfect blend of Key West charm and modern comfort. Nassau Lane is a little gem in Old Town Key West, known for its quaint historic character and tucked-away feel, providing a peaceful retreat while still being close to all the vibrancy Key West has

  Dominic Paolillo Jr. Truman & Co. (KW)

  3 Nassau Ln Unit A, 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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  /55

  $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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  /25

  $1,350,000

  • 2 Beds
  • 2 Baths
  • 1,125 Sq Ft

  1107 Olivia St, Key West, FL 33040

  Located on the desirable 1100 block of Olivia Street near the cemetery, this updated two bedroom, two bathroom, two story Conch home offers a balanced blend of Old Town character, privacy and walkability. This property is in the X flood zone and includes a pool and off street golf cart parking.This 1,125 square foot layout includes one bedroom and full bath on the first floor. The upstairs

  Forrest Shearin Berkshire Hathaway HomeServices Knight & Gardner Realty

  1107 Olivia St, Key West, FL 33040
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  /37

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  621 Elizabeth St, Key West, FL 33040

  This gorgeous two-cottage property is located at the top of Solares Hill in the heart of Old Town Key West and offers exceptional flexibility along with strong rental and income potential. The lovely main house sits at the front of the property and features a main-floor primary bedroom and bath, an open living and dining area with vaulted ceilings, and central air. Stairs lead to a second bedroom

  

  Jennifer Newman

  Truman & Co. (KW)

  (786) 980-9176

  621 Elizabeth St, Key West, FL 33040
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  /24

  $974,000

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  1124 Olivia St Unit 321, Key West, FL 33040

  Located in the desirable Lionsgate community in Old Town, this updated 2-bedroom, 2-bath condo offers an excellent opportunity to own in Key West at an attractive price point. Thoughtfully improved, the home features new laminated floors, updated quartz countertops, and a fresh interior paint palette, making it truly move-in ready.Vaulted ceilings create an open and airy living space, while a

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1124 Olivia St Unit 321, Key West, FL 33040
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  /30

  $850,000 Open House 2/15

  • 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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  /10

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 684 Sq Ft

  708 Bakers Ln, Key West, FL 33040

  Positioned on a rare 5000 Sq Ft. lot at one of the highest natural elevations on the Island, this property represents an exceptional opportunity in the heart of Old Town Key West - where location is everything.Set beneath a canopy of established trees, the site offers shade, privacy and a sense of timeless Old Town Character that is increasingly hard to find.Currently improved with a livable

  Suzanne Moore Suzanne Moore Real Estate

  708 Bakers Ln, Key West, FL 33040
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  /21

  $800,000

  • 3 Beds
  • 3 Baths
  • 1,216 Sq Ft

  1207 William St Unit 3, Key West, FL 33040

  This spacious 3-bedroom, 3-bath home offers a layout you simply don't see often in Key West. Each LARGE bedroom has its own en-suite bath, giving everyone their own private space. What really makes this property stand out are the three separate entrances, including private exterior access to two of the bedrooms. A hallway door can be closed to fully separate the front and back of the home,

  Sarah Bixby eXp Realty LLC

  1207 William St Unit 3, Key West, FL 33040
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  /38

  $5,995,000

  • 5 Beds
  • 7 Baths
  • 4,387 Sq Ft

  910 Watson St, Key West, FL 33040

  More than a residence and rarer than legend, 910-914 Watson Street stands as one of the most iconic private estates in all of Key West--a once-in-a-generation offering where historic gravitas, tropical scale, and modern refinement converge behind gated walls in the heart of Old Town. Just moments from Truman Waterfront Park and beloved local favorites such as 5 Brothers Coffee and Cafe Sole, this

  Team Kaufelt Truman & Co. (KW)

  910 Watson St, Key West, FL 33040
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  /50

  $3,399,000

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

  1114 Grinnell St, Key West, FL 33040

  Exquisite Old Town residence just completed!Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. Luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street

  Wendy Zintsmaster Truman & Co. (KW)

  1114 Grinnell St, Key West, FL 33040
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  /30

  $1,550,000

  • 3 Beds
  • 2 Baths
  • 1,051 Sq Ft

  1202 Whitehead St, Key West, FL 33040

  This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental!Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub,

  Richard Haskins Buy The Keys

  1202 Whitehead St, Key West, FL 33040
• 

  

  /23

  $775,000 Open Fri 3PM - 5PM

  • 2 Beds
  • 2 Baths
  • 862 Sq Ft

  1004 Watson St Unit 2, Key West, FL 33040

  Centrally located in flood X zone of Old Town, this 2-bed, 2-bath townhouse is classic Key West charm at its best. The galley kitchen offers abundant cabinetry, granite countertops, and stainless-steel appliances. High ceilings with wood-finished crown molding add warmth and character throughout. The spacious primary suite showcases beautiful Dade County pine and a private en-suite bath. Central

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1004 Watson St Unit 2, Key West, FL 33040
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  /36

  $1,250,000

  • 1 Bed
  • 2 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
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  /29

  $1,249,000

  • 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
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  /48

  $4,699,000

  • 4 Beds
  • 5 Baths
  • 3,624 Sq Ft

  406 United St, Key West, FL 33040

  A Grand Historic Masterpiece! Few residences capture the true spirit of Old Town Key West quite like 406 United Street. Rooted in one of the island's most defining eras of growth and prosperity, this remarkable home is a celebration of historic craftsmanship, generous scale, and timeless value. Spanning 3,624 square feet, this 4bedroom, 4.5bath residence offers exceptional versatility, perfect

  Terri Spottswood Truman & Co. (KW)

  406 United St, Key West, FL 33040

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