Homes for Sale near Monroe County Detention Center

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  /85

  $1,489,000

  • 2 Beds
  • 2.5 Baths
  • 2,292 Sq Ft

  1616 Atlantic Blvd Unit 5, Key West, FL 33040

  Rare Luxurious Atlantic Oceanfront Concrete 3 story home. 2 Bedrooms 2 1/2 bathrooms located in a private gated community. Ocean views from your balconies. This exquisite home has stainless steel appliances, custom cabinetry, vaulted ceilings, tiled carport, oversized well-manicured, private back yard. Huge storage room with built in shelving. This rare unit has the largest backyard in the

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

  1616 Atlantic Blvd Unit 5, Key West, FL 33040
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  /18

  $1,170,000

  • Land

  619 Front St Unit 7, Key West, FL 33040

  LOCATION, LOCATION, LOCATION - Every boater's dream - to own at Key West downtown Historic Seaport boat slip and walk everywhere!Purchase 1 of only 15 or so privately owned liveaboard slips at the popular downtown harbor 91-slip Galleon Marina. LICENSED FOR COMMERCIAL USE TOO!Boat tour and fishing charters okay.Monthly HOA and Maintenance fee only $840 per month. Sunset views wet slip located

  Jerry Hughes Old Town Realty

  619 Front St Unit 7, Key West, FL 33040
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  /4

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  1018 Georgia St, Key West, FL 33040

  Investors Alert! Legal Duplex in Old Town Key West. This property just had an Extreme Makeover. new roof, new siding, new kitchens, new bathrooms., new sub flooring in the back apartment, new impact windows . An opportunity to own a rental Property in Kew West with great income flow. With all the upgrades the rent will be increased. Downstairs lock out units; the back unit will rent for $2500

  Diana Fiddes Coldwell Banker Schmitt Key Largo

  1018 Georgia St, Key West, FL 33040
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  /55

  $3,999,000 Open Sun 12PM - 3PM

  • 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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  /60

  $979,000

  • 5 Beds
  • 4 Baths
  • 1,634 Sq Ft

  1925 Fogarty Ave, Key West, FL 33040

  Start living the Key West lifestyle at 1925 Fogarty Ave--an ideal property for anyone who needs space, flexibility, and an income or guest option. The main house welcomes you with an open, easy-flow layout that makes everyday living simple. A comfortable living room connects to the dining area and kitchen, creating an open space for relaxing or entertaining. Large windows bring in great natural

  Jimmy Lane Island Life Realty Experts

  1925 Fogarty Ave, 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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  /65

  $1,099,000

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

  1519 4th St, Key West, FL 33040

  Discover the perfect blend of comfort & convenience at 1519 4th Street; a spacious 4-bedroom, 2-bathroom retreat perfectly situated in Midtown Key West. Set on a 5,000 sq. ft. lot, this beautifully refreshed home offers everything you need to enjoy the quintessential Florida Keys lifestyle.Step inside to an inviting open floor plan that flows effortlessly from the kitchen to the living and dining

  Krystal Thomas eXp Realty LLC

  1519 4th St, Key West, FL 33040
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  /52

  $1,675,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  115 Front St Unit 301, Key West, FL 33040

  Third floor Harbour Place condo in the historic Navy Administration building.Enter into a private foyer where you have a full bath and a guest bedroom. Large living and dining area overlook Truman's Little White House. The primary bedroom is just down the hall and has it's own private balcony overlooking the entrance to the building and the Little White House. One covered parking space #92.

  The Behmke Group Keller Williams Key West Compass Realty

  115 Front St Unit 301, Key West, FL 33040
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  /20

  $1,675,000

  • 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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  /9

  $850,000

  • Land

  1720 United St, Key West, FL 33040

  Welcome to 1720 United Street -- a rare opportunity to own a spacious, build-ready lot in one of Key West's most desirable residential neighborhoods. Surrounded by mature palms and tropical greenery, this cleared parcel offers the perfect blank canvas to design your island dream home. Enjoy the quiet charm of a well-established neighborhood while being just minutes from beaches, restaurants,

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  1720 United St, Key West, FL 33040
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  /25

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,135 Sq Ft

  E14 11th Ave, Key West, FL 33040

  Charming 3 Bedroom 2 Bathroom Home Near Dining, Shopping, and Boating. Welcome to your new oasis! This delightful three-bedroom, two-bathroom home is perfectly nestled in a vibrant neighborhood, just moments away from an array of restaurants, shopping centers, and fishing spots. Enjoy an open-concept layout that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining

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

  E14 11th Ave, Key West, FL 33040
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  /6

  $1,550,000

  • Land

  1513 Seminary St, Key West, FL 33040

  Owner Financing Available - Flexible Terms!Rare opportunity in Midtown Key West! This cleared and vacant 75x100 lot--a true rarity on the island--is ready for your dream home. The owner is offering financing with $600,000 down and flexible terms, making it easier than ever to own a piece of paradise.This property comes with a ROGO Exempt / Right-to-Build letter, saving you time and expense in the

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  1513 Seminary St, Key West, FL 33040
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  /28

  $645,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040

  Only steps away from our island's largest and most serene sandy beach, this top-floor unit offers an unbeatable location for swimming, snorkeling, bicycling and beach walks. Enjoy stunning ocean and pool views from your private balcony and soak in that coveted west-facing Key West sunset every day. The bright and airy open floor plan is move-in ready, featuring impact windows and doors, along

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

  2601 S Roosevelt Blvd Unit 608, Key West, FL 33040
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  /44

  $4,130,000

  • 3 Beds
  • 4 Baths
  • 2,744 Sq Ft

  3741 Eagle Ave, Key West, FL 33040

  Experience refined island living in this BRAND NEW residence perfectly situated on a generous 10,800 square foot lot and elevated at an impressive 10.5 feet. This 3 bedroom, 3.5 bath home is a testament to modern coastal luxury, where timeless design meets effortless functionality.Constructed entirely of concrete, the open concept layout is framed by soaring cathedral ceilings and expansive

  Jenny Perry Preferred Properties (KW)

  3741 Eagle Ave, Key West, FL 33040
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  /32

  $985,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  1014 17th Terrace, Key West, FL 33040

  Welcome to 1014 17th Terrace in the highly desired neighborhood of Perlman Heights in Key West. This charming home offers a warm and welcoming atmosphere in one of the most sought-after areas of new town. Owned by only one owner, this property is waiting for you to make it your own.Located just two blocks from the Gulf and conveniently close to all local shopping centers, this home provides

  Amber DeBevec LoKation Real Estate

  1014 17th Terrace, Key West, FL 33040
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  /14

  $1,200,000

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  418 Olivia St, Key West, FL 33040

  Transient receiver site - Truly a diamond in the rough. Great location, behind the Hemingway House between Duval and Whitehead Street. Lot backs up to Whalton Lane (off Duval) with room for parking and a pool. Bring your contractor and a transient license to the property and she will truly shine like the Hope Diamond with happiness and prosperity. Buyers should do their own due diligence to

  Everett Watkins Keller Williams Key West Compass Realty

  418 Olivia St, Key West, FL 33040
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  /45

  $5,595,000

  • 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 and gate, the estate includes a grand main residence and two fully equipped guest houses, offering four bedrooms and four-and-a-half baths. The main house

  Terri Spottswood Truman & Co. (KW)

  1006 Fleming St, Key West, FL 33040
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  /44

  $995,000

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

  208 Golf Club Dr, Key West, FL 33040

  Welcome to Splendor @ Key West Golf Club, an impeccably transformed courtyard spa home located within The Sanctuary -- the exclusive gated enclave of single-family homes inside this desirable community. Every detail of this residence has been thoughtfully enhanced to perfection, offering a seamless blend of island elegance and modern comfort. Step into your private tropical oasis, surrounded by

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  208 Golf Club Dr, Key West, FL 33040
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  /31

  $1,700,000

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  1800 Atlantic Blvd Unit 327C, Key West, FL 33040

  Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one of Key West's sought-after waterfront resorts, 1800 Atlantic Blvd. A completely remodeled, stylish 2-bedroom, 2-bathroom condo encompassing approximately 1,311 sq ft of luxurious living space. Transient license and established management make this a rare turnkey investment opportunity offering both a

  Tommy Mack Coastal Collection Real Estate Inc.

  1800 Atlantic Blvd Unit 327C, Key West, FL 33040
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  /39

  $2,188,000

  • 4 Beds
  • 3 Baths
  • 2,276 Sq Ft

  1719 Laird St, Key West, FL 33040

  Experience elevated island living at 1719 Laird Street--a redesigned Mid-Century CBS home offering 4 bedrooms, 3 bathrooms, and exceptional indoor-outdoor living on a rare double lot. This move-in-ready property delivers the ideal blend of modern updates, storm-ready features, and low-maintenance coastal living.Step inside to an open-concept floor plan with abundant natural light, enhanced by

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  1719 Laird St, Key West, FL 33040
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  /26

  $725,000

  • 1 Bed
  • 1 Bath
  • 513 Sq Ft

  106 Southard St Unit 9, Key West, FL 33040

  The iconic condo called Brucie's Ocean Peek is now available for sale. Currently an active vacation rental it is the perfect spot for a Key West pied a terre,, it also has a large demand for monthly rentals. Perfectly situated overlooking the tropically landscaped Shipyard Park, it is close to the heated salt water pool. A separate entrance leads you upstairs to a wonderfully furnished living and

  Mike Caron Keller Williams Key West Compass Realty

  106 Southard St Unit 9, Key West, FL 33040
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  /10

  $350,000

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 712, Key West, FL 33040

  Experience Key West sunsets and ocean breezes from this TOP-FLOOR unit! This one-bedroom, one-bathroom residence boasts a spacious and practical floor plan with private balcony. Recent enhancements include a NEW HVAC system, NEW electricalpanel, NEW impact-resistant windows and doors and kitchen appliances. Situated in an excellent location near shopping centers, cinema, schools & dining. This

  Haydee Stewart Bascom Grooms Real Estate (KW)

  3312 Northside Dr Unit 712, Key West, FL 33040
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  /39

  $2,249,000

  • 3 Beds
  • 3 Baths
  • 1,938 Sq Ft

  1706 Seminary St, Key West, FL 33040

  Tucked behind a new privacy fence, 1706 Seminary Street is a fully renovated home where thoughtful design meets laid-back Key West living. Set on a generous 7,480 square foot lot, this 3-bedroom, 3-bathroom (two en suite) home offers nearly 2,000 square feet of indoor space that has been completely reimagined to deliver easy, breezy island living with all the modern updates already done for you.

  Ted Stewart Truman & Co. (KW)

  1706 Seminary St, Key West, FL 33040
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  /58

  $1,224,000

  • 4 Beds
  • 3 Baths
  • 2,664 Sq Ft

  1409 4th St, Key West, FL 33040

  Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. There's also a garage, laundry room, and

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  1409 4th St, Key West, FL 33040
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  /99

  $5,800,000

  • 8 Beds
  • 9.5 Baths
  • 6,611 Sq Ft

  39 Evergreen Ave, Key West, FL 33040

  Tucked within an exclusive Key Haven cul-de-sac, Casa di Sempre is a European-inspired waterfront estate offering more than 260 linear feet of water frontage across two sides of the property, including 200 feet of concrete dockage for boating enthusiasts. Resting on over 15,000 square feet of land, this residence showcases superior craftsmanship and thoughtful design throughout more than 6,500

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  39 Evergreen Ave, Key West, FL 33040
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  /31

  $3,495,000 Open Sun 11:30AM - 2PM

  • 4 Beds
  • 5 Baths
  • 2,628 Sq Ft

  1610 South St, Key West, FL 33040

  This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between

  Rob Severin Rob Severin Real Estate Co

  1610 South St, Key West, FL 33040
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  /24

  $1,350,000

  • 3 Beds
  • 1 Bath
  • 1,231 Sq Ft

  705 Chapman Ln, Key West, FL 33040

  Charming Old Town gem with endless possibilitiesDiscover a rare opportunity in the heart of Old Town Key West! This property sits on an exceptionally large lot -- a true find in this historic neighborhood. With plenty of room to expand, you can create your own island oasis by adding a pool, enlarging the existing home, or even building a separate guest cottage.Just a short stroll to lively Duval

  Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty

  705 Chapman Ln, Key West, FL 33040
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  /42

  $959,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  2311 Patterson Ave, Key West, FL 33040

  Your private island retreat awaits. Discover the ultimate in low-maintenance living with this charming, turnkey 3-bedroom, 2-bath single-level home, perfectly positioned in Key West's desirable New Town neighborhood. A true rarity, this concrete block residence offers the best of both worlds: quiet seclusion and walkable access to the island's premier amenities.Just a short stroll from the

  Graciela Lozano KeysLifestyle Real Estate (KW)

  2311 Patterson Ave, Key West, FL 33040
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  /54

  $5,000,000

  • 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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  /38

  $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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  /82

  $5,395,000

  • 5 Beds
  • 6 Baths
  • 3,597 Sq Ft

  18 Hilton Haven Rd, Key West, FL 33040

  Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront

  The Behmke Group Keller Williams Key West Compass Realty

  18 Hilton Haven Rd, Key West, FL 33040
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  /49

  $1,875,000

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

  101 Front St Unit 23, Key West, FL 33040

  Completely renovated and move-in ready, The Foundry #23 in Key West's exclusive Truman Annex is a rare gem that blends historic charm with modern luxury. This beautifully updated townhome features custom Hansen & Bringle cabinetry throughout, quartz countertops, and brand-new appliances in the kitchen. The Primary Suite offers ample closet space and a redesigned bath with custom cabinetry and a

  Loren Rea Truman & Co. (KW)

  101 Front St Unit 23, Key West, FL 33040
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  /10

  $4,300,000

  • 4 Beds
  • 6 Baths
  • 3,400 Sq Ft

  1314 Johnson St, Key West, FL 33040

  Step into sophisticated, maintenance-free living with this pristine newly-constructed home, where luxury, comfort, and design converge in perfect harmony. Spanning 3,400 square feet of interior living space and 2,892 square feet of outdoor decking, this gated residence offers an exceptional indoor-outdoor lifestyle. This thoughtfully designed turnkey home features four spacious bedrooms, each

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1314 Johnson St, Key West, FL 33040
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  /38

  $599,000

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  2601 S Roosevelt Blvd Unit 307C, Key West, FL 33040

  Enjoy resort-style living at Key West by the Sea, a coveted community that provides a perfect blend of comfort, convenience, and island charm.This beautifully maintained top-floor condominium offers serene garden and pool views. Featuring two bedrooms and one bath, this bright and inviting residence showcases impact-resistant windows, ductless air conditioning, and an open living area that flows

  Lori Langton Berkshire Hathaway HomeServices Knight & Gardner Realty

  2601 S Roosevelt Blvd Unit 307C, Key West, FL 33040
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  /32

  $1,150,000

  • 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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  /27

  $485,000

  • 1 Bed
  • 1 Bath
  • 388 Sq Ft

  1830 Fogarty Ave Unit 4, Key West, FL 33040

  Your Key West Hideaway Awaits. Tucked away at the back of a well-kept building, this charming 1-bedroom, 1-bath condo offers the perfect blend of island comfort and modern convenience. Step inside to find a bright, airy space filled with natural light and refreshed with newer appliances that make everyday living effortless. Outside, unwind in your private oasis complete with an outdoor shower and

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  1830 Fogarty Ave Unit 4, Key West, FL 33040
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  /47

  $2,599,000 Open Sun 10AM - 1PM

  • 3 Beds
  • 3 Baths
  • 1,916 Sq Ft

  312 Margaret St, Key West, FL 33040

  Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful home is one you're sure to fall in love with. Featuring two off-street parking spaces and a private pool, it blends luxury, comfort, and convenience, perfect for both vacation getaways and year-round living. Inside, you'll find three spacious bedrooms and three modern bathrooms, designed to provide everything

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  312 Margaret St, Key West, FL 33040
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  /46

  $1,149,000

  • 2 Beds
  • 2 Baths
  • 898 Sq Ft

  1616 Bertha St Unit 2, Key West, FL 33040

  Secluded Oasis! Discover this hidden gem in Midtown Key West--an immaculate, move-in-ready 2-bedroom, 2-bathroom home just minutes from two beautiful beaches. Designed for seamless indoor-outdoor living, this home features a full-wall sliding glass door, vaulted ceilings, and an updated open kitchen with brand-new Viking appliances (4-burner gas range & dishwasher). Step outside to your heated

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1616 Bertha St Unit 2, Key West, FL 33040
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  /48

  $3,299,000

  • 5 Beds
  • 3 Baths
  • 2,608 Sq Ft

  1420 White St, Key West, FL 33040

  Stunning Grand Key West Historic Home Newly Renovated into a Gorgeous Single Family Home with High Ceilings, Architectural Moldings, and Imported Tiles . This Home has undergone a Massive Transformation with the current owners paying great attention to New Spaces and Natural Light. There are so many possibilities to enjoy this Classic European Inspired Home. There are two Primary Suites, one on

  Lisa Lennon Berkshire Hathaway HomeServices Knight & Gardner Realty

  1420 White St, Key West, FL 33040
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  /45

  $3,200,000 Open Sun 12PM - 3PM

  • 5 Beds
  • 6 Baths
  • 2,760 Sq Ft

  1224 Florida St, Key West, FL 33040

  Nestled in a quiet Old Town neighborhood, this elevated three-story home blends timeless craftsmanship with contemporary design. Thoughtfully constructed for style and strength, 1224 Florida features five spacious bedrooms--each with its own en-suite bath--and an open, light-filled layout that flows seamlessly from indoors to out. The recently renovated chef's kitchen is equipped with premium

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1224 Florida St, Key West, FL 33040

Showing Results 121 - 160, Page 4 of 10