Old Town Homes for Sale

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  /48

  $1,680,000

  • 3 Beds
  • 5 Baths
  • 1,442 Sq Ft

  1001 United St Unit B, Key West, FL 33040

  Enjoy your tropical retreat in the heart of Old Town Key West with this stunning, fully remodeled, three-story corner lot island oasis. The first floor of this expansive attached home welcomes you with soaring vaulted ceilings, an open floor plan drenched in natural light, and seamless indoor-outdoor living. Throw open the French doors and lounge on your poolside veranda, or take a dip in the

  Michael Sorah Truman & Co. (KW)

  1001 United St Unit B, 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

  Located in the heart of Key West's Historic District, 905 Grinnell Street is a distinctive multi-unit property that blends architectural character with strong investment performance. Originally built as a church, the structure has been thoughtfully converted into four residential units totaling 3,383 square feet. Each unit is individually metered and currently leased, offering a stable and

  Team Kaufelt Truman & Co. (KW)

  905 Grinnell St, Key West, FL 33040
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  /31

  $1,099,000

  • 3 Beds
  • 1 Bath
  • 1,580 Sq Ft

  1222 Florida St, Key West, FL 33040

  Picture living right in the heart of Key West where you can roll out of bed, grab a cafe con leche, and be on your way to Duval, the Historic Seaport, or the island's best local spots in minutes--welcome to 1222 Florida Street. This 3-bedroom, 1 bathroom single-family home with brand new flooring offers that classic Key West lifestyle with the comfort and simplicity buyers love: an easy, livable

  Jimmy Lane Island Life Realty Experts

  1222 Florida St, Key West, FL 33040
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  /20

  $1,450,000

  • 1 Bed
  • 1 Bath
  • 405 Sq Ft

  422 Amelia St Unit 6, Key West, FL 33040

  Don't miss this TRANSIENT licensed condo just steps away from the famous Duval Street. This second floor 1 bedroom 1 bath unit with 14ft high ceilings is being offered turnkey. Currently operating as a very successful short term vacation rental business. Experience all that Key West has to offer nearby with restaurants, shops, art galleries, beaches and more all in walking or biking distance!

  Tonya Cabanas Truman & Co. (KW)

  422 Amelia St Unit 6, Key West, FL 33040
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  /16

  $775,000 Open Sun 12PM - 3PM

  • 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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  /22

  $950,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 968 Sq Ft

  1022 Watson Ln, Key West, FL 33040

  Priced to Sell in Old Town! Tucked away on a quiet lane, this versatile Key West home offers unbeatable value and rare features including the only home in Old Town with a private pool under $1M.The main living space upstairs includes 1 bedroom, 1 bathroom, a full kitchen, dining room, and living room, all with a comfortable layout and great potential for easy modern updates to match your style.

  Nick Norman Island Life Realty Experts

  1022 Watson Ln, Key West, FL 33040
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  /5

  $1,095,000

  • Land

  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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  /67

  $7,495,000

  • 5 Beds
  • 7 Baths
  • 4,000 Sq Ft

  616 Eaton St, Key West, FL 33040

  Nestled in the heart of Key West's historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern

  Terri Spottswood Truman & Co. (KW)

  616 Eaton St, Key West, FL 33040
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  /31

  $1,580,000

  • 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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  /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
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  /21

  $799,900

  • 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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  /47

  $1,399,000

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

  617 Fleming St Unit 4, Key West, FL 33040

  Looking for a gorgeous, lock and go, 2-bedroom condo in a perfect downtown Key West location? Just 1 1/2 blocks from Duval, on iconic Fleming Street, sits your dream Key West escape in the historic Campbell Building. This condo is gorgeous and its location can't be beat! A stone's throw from the action and the historic Seaport District, unit 4 is fully remodeled and looks directly down onto

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  617 Fleming St Unit 4, Key West, FL 33040
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  /6

  $899,000

  • 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
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  /53

  $1,895,000

  • 4 Beds
  • 2 Baths
  • 2,242 Sq Ft

  1416 Catherine St, Key West, FL 33040

  Priced to Sell - Exceptional Value in Old Town Key West! Opportunity meets island charm in this recently updated 4-bedroom, 2-bath home located in Old Town -- just a short walk or bike ride to everything Key West has to offer. Listed below market value for a swift sale, this is your chance to own a true tropical retreat at an incredible price. A classic white picket fence welcomes you in, leading

  Jody Clark Key West Luxury Real Estate Inc (KW)

  1416 Catherine St, Key West, FL 33040
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  /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 RE/MAX Keys Connection (KW)

  405 Petronia St, Key West, FL 33040
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  /22

  $599,000

  • 2 Beds
  • 1 Bath
  • 677 Sq Ft

  1124 Catherine St Unit 202, Key West, FL 33040

  This bright and well-maintained condo offers the perfect blend of comfort and convenience in one of Key West's most desirable neighborhoods. Just a straight shot down the road to White Street Pier, you're also minutes from both Higgs Beach and Smathers Beach for swimming, sunbathing, and seaside strolls. Head the other direction and you'll reach Bayview Park, with tennis courts, green space, and

  The Spottswood Team Truman & Co. (KW)

  1124 Catherine St Unit 202, 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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  /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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  /88

  $5,950,000

  • 6 Beds
  • 8 Baths
  • 4,094 Sq Ft

  723 Eaton St, Key West, FL 33040

  This unique three residence property is ideally located just steps from the Historic Seaport and Fausto's grocery store in the heart of Old Town. A newly constructed building offers a spacious 3-bedroom, 3.5-bath main residence overlooking the pool, with a generous 2-bedroom, 2.5-bath apartment above. At the front of the property, a charming 1-bedroom, 1-bath home features a large garden with

  Kirksten Irick Preferred Properties (KW)

  723 Eaton St, Key West, FL 33040
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  /29

  $2,070,000

  • 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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  /25

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 1,260 Sq Ft

  626A Fleming St, Key West, FL 33040

  Beautifully renovated 3bd/2.5ba townhouse incredibly located just 1.5 blocks from Duval Street with off street parking. The first floor is dedicated to an open concept living room and kitchen with built in custom banquette for dining and extra storage. Off the kitchen you will find a covered screened in patio for outdoor living or dining. The second floor features 2 bedrooms , balcony and a newly

  Wendy Zintsmaster Truman & Co. (KW)

  626A Fleming St, Key West, FL 33040
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  /7

  $825,000

  • 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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  /32

  $2,985,000

  • 3 Beds
  • 3 Baths
  • 1,872 Sq Ft

  1405 United St, Key West, FL 33040

  Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground pool. In addition, there is a detached studio/cottage, with each separately fenced from one another. On the third lot is a garage.Come and explore these three (3) contiguous, separate lots that all have the City of Key West's,

  Bobby Coe RE/MAX Keys Connection (KW)

  1405 United St, Key West, FL 33040
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  /34

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 866 Sq Ft

  711 Galveston Ln, Key West, FL 33040

  Nestled down a private and picturesque lane, this charming conch-style cottage offers the perfect blend of island charm and comfort. Featuring 3 bedrooms and 2 full baths, the home is thoughtfully designed for relaxed living and effortless entertaining.Step into a beautifully landscaped backyard with a newly built pergola--ideal for dining and unwinding in the spa beneath the stars. Though

  Monique Thiel Sunshine State Realty Services

  711 Galveston Ln, Key West, FL 33040
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  /52

  $3,099,000

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

  512 Amelia St, Key West, FL 33040

  Experience classic Old Town Key West living at 512 Amelia Street, complete with a valuable Transient License and a new private pool. Tucked on a quiet street just steps from world-class dining, galleries, and the island's best beaches, this home offers the perfect blend of relaxation and convenience. Thoughtfully designed indoor and outdoor living spaces make it ideal for both personal use and

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  512 Amelia St, Key West, FL 33040
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  /90

  $4,799,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 6 Baths
  • 3,092 Sq Ft

  600 Elizabeth St, Key West, FL 33040

  Elegantly positioned beneath the sweeping canopy of its namesake tree, Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trimwork, and warm mahogany floors that recall a bygone era of island craftsmanship.Inside, the

  Lori Langton Berkshire Hathaway HomeServices Knight & Gardner Realty

  600 Elizabeth St, Key West, FL 33040
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  /16

  $575,000

  • 1 Bed
  • 1 Bath
  • 526 Sq Ft

  712 Galveston Ln Unit 1, Key West, FL 33040

  Perched atop Solares Hill, the highest point in Key West, this Old Town luxury CBS condo offers an exceptional blend of location and lifestyle. Ideally situated on Galveston Lane, you're just a short walk from everything Old Town has to offer--from the charm of Bill Butler Park to the area's renowned restaurants, galleries, and vibrant island culture.This fully renovated, upstairs unit features

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  712 Galveston Ln Unit 1, Key West, FL 33040
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  /24

  $1,089,000

  • 1 Bed
  • 1 Bath
  • 731 Sq Ft

  921 Center St Unit 12, Key West, FL 33040

  These properties rarely come on the market. Great opportunity to own an income producing Townhouse in the heart of Old Town Key West. This one bedroom Townhouse has a Transient License and is able to be rented on a nightly basis. Strong Rental History with many repeat clients. Just steps from Famous Duval Street. Located in a private gated community. Beautifully landscaped grounds with a fabulous

  Julia Besson Century 21 All Keys Inc (KW)

  921 Center St Unit 12, Key West, FL 33040
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  /20

  $900,000

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

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

  Ideally located on Simonton Street in the heart of Old Town, this charming half-duplex and lot 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

  Paige Bethel Island Home Realty Inc.

  1119 Simonton St Unit A2 & C1, 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
• 

  

  /4

  $1,095,000

  • 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. 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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  /41

  $1,449,000

  • 2 Beds
  • 2 Baths
  • 1,207 Sq Ft

  800 Fleming St Unit B-3, Key West, FL 33040

  Perfectly situated just three blocks from Duval Street and two from the grocery store, this one-of-a-kind, fully furnished penthouse has been meticulously renovated to deliver unmatched luxury living in the heart of Old Town Key West. Offering rare off-street parking, this light-filled residence is perched among the treetops and features a private balcony with serene pool and garden views.Inside,

  Solaris Gregory Expert Realty LLC (HQ)

  800 Fleming St Unit B-3, Key West, FL 33040
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  /54

  $4,850,000

  • 5 Beds
  • 6 Baths
  • 2,230 Sq Ft

  627 Caroline St, Key West, FL 33040

  5 Beds | 6 Baths | Pool & Spa | Prime Historic Location627 Caroline Street is a rare opportunity to own a turnkey masterpiece in one of Key West's most coveted neighborhoods. Just steps from vibrant Duval Street and the iconic Historic Seaport, this fully furnished home perfectly blends timeless island charm with modern luxury.Completely rebuilt from the studs, this residence has been

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  627 Caroline St, Key West, FL 33040
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  /32

  $5,250,000

  • 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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  /30

  $1,479,000

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1306 Virginia St, Key West, FL 33040

  LEGAL DUPLEX with INVESTMENT OPPORTUNITY.Located in the Old Town Key West neighborhood in the X Flood zone, this historic property presents many opportunities. Increase the square footage and/or covert to a single family home. Bring your creativity to this historic charmer.Currently set up as a Legal Duplex with 2 bedrooms/1 bath downstairs, and 1 bedroom/ 1 bath upstairs with separate electric

  Joyce Craul Expert Realty LLC (HQ)

  1306 Virginia St, 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
• 

  

  /91

  $3,895,000

  • 7 Beds
  • 7.5 Baths
  • 3,015 Sq Ft

  919 Thomas St, Key West, FL 33040

  Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character

  Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  919 Thomas St, Key West, FL 33040
• 

  

  /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 garden oasis

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1111 Watson St Unit B, Key West, FL 33040
• 

  

  /6

  $1,900,000

  • 3 Beds
  • 1 Bath
  • 1,368 Sq Ft

  511 Tabby Way, Key West, FL 33040

  Unmatched Old Town Opportunity!Location, Location, Location! This is your chance to own one of the most coveted properties in Old Town Key West--a truly unique home and lot that must be seen to be fully appreciated. Tucked away and completely hidden from view, this remarkably private property is the only single-family home currently on the market with direct pedestrian access to Duval Street via

  Paige Bethel Island Home Realty Inc.

  511 Tabby Way, Key West, FL 33040
• 

  

  /21

  $789,000 Open Sun 11AM - 1PM

  • 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

Showing Results 41 - 80, Page 2 of 3