Homes for Sale near Monroe County Detention Center

• 

  

  

  /60

  $7,995,000

  • 11 Beds
  • 11 Baths
  • 3,034 Sq Ft

  525 Simonton St, Key West, FL 33040

  A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom

  Paige Bethel Island Home Realty Inc.

  525 Simonton St, Key West, FL 33040
• 

  

  

  /46

  $4,350,000

  • 4 Beds
  • 4 Baths
  • 2,458 Sq Ft

  3 Evergreen Ave, Key West, FL 33040

  Experience the ultimate Key West lifestyle in this new construction (2025) waterfront home in the exclusive Key Haven community. Situated on the coveted final canal, this 4BR+office/4BA entertainer's paradise offers 2,458 sqft of luxury living and 2,400 sqft of covered outdoor space. This home features a completely private top-floor guest quarters offering ultimate flexibility--perfect as a

  Steven Koleno Beycome of Florida, LLC

  3 Evergreen Ave, Key West, FL 33040
• 

  

  

  /43

  $995,000

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  1608 Venetian Dr, Key West, FL 33040

  New Bathrooms. New Kitchen with all new appliances. New interior doors. Fresh paint inside and outside. Quiet neighborhood. Two mango trees, palm trees, other trees. Room for pool and hot tub. Large open floor plan living-dining area opens to the kitchen with view to the concrete patio in the rear. New V-Crimp metal roof completed December 2021. Larger than average lot in the neighborhood,

  Dave Lewis Key West Real Estate Sales & Rentals, LLC (KW)

  1608 Venetian Dr, Key West, FL 33040
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  /48

  $1,700,000

  • 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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  /36

  $879,000

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  620 Thomas St Unit 176, Key West, FL 33040

  Ground floor end unit! Two-bedroom, one bath Shipyard condo. Updated kitchen with stainless steel appliances. Updated bath with shower. New impact windows and doors. The Shipyard is in the Truman Annex in Old Town Key West. Great location with easy walking and biking to all the action and great restaurants, beaches and sunsets that Key West offers.

  The Behmke Group Keller Williams Key West Compass Realty

  620 Thomas St Unit 176, Key West, FL 33040
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  /35

  $159,000

  • Land
  • 0 Acre

  1801 N Roosevelt Blvd Unit Tarpon 15, Key West, FL 33040

  AFFORDABLE WATERFRONT LIVING IN KEY WEST !Very nice 32' Custom Built floating home moored in a live aboard slip on a state of the art floating dock in central Key West.Live safely ON the water in Key West without paying millions !Well maintained. one bedroom, one bath, kitchen/dining area, living room, bath & shower,. front a rear deck/landings. Sale contingent upon Leasehold Transfer approval.

  Randy Moss Coldwell Banker Schmitt RE Co

  1801 N Roosevelt Blvd Unit Tarpon 15, Key West, FL 33040
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  /18

  $489,000

  • Land

  5555 College Rd Unit 9, Key West, FL 33040

  Discover an extraordinary opportunity to embrace the live aboard lifestyle at Sunset Marina with this spacious 60 ft x 20 ft boat slip with he ability to dock a 65ft boat, located on the coveted Barracuda Pier. This slip not only provides a comfortable living space but also serves as a profitable income-generating asset, making it an ideal investment for boating enthusiasts and investors

  Justyn Ewald Expert Realty LLC (HQ)

  5555 College Rd Unit 9, Key West, FL 33040
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  /13

  $1,000,000

  • Land

  6810 Front St Unit S-LL-1C, Stock Island, FL 33040

  One of the largest slips in the Florida Keys.Perfect for large yachts and wide beam catamarans...Survey shows 100' long by 34' wide...but can accommodate up to 125' LOA boat.Safe Harbour Marina is a deep water (14' min.) protected port and recreational marina. Originally constructed in the late 1950's and located in the heart of the last vestiges of the commercial fishing and shrimping docks, it

  Jerry Hughes Old Town Realty

  6810 Front St Unit S-LL-1C, Stock Island, FL 33040
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  /12

  $299,000

  • Land

  5555 College Rd Unit 10, Key West, FL 33040

  Incredible chance to own a premier slip in the private/gated Sunset Marina. Located at the end of the Sailfish pier, this 50' by 20' slip allows stress free docking and direct open water access for a wide range of boats. The slip is equipped with its own metered water, electric, and a lockable dock box to store items. HOA fees cover access to parking, the heated pool, spa, and clubhouse. In the

  Mason Kelly Expert Realty LLC (HQ)

  5555 College Rd Unit 10, Key West, FL 33040
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  /41

  $2,378,000

  • 8 Beds
  • 8 Baths
  • 3,532 Sq Ft

  909 & 913 Thomas St, Key West, FL 33040

  Situated in the heart of Old Town Key West, this exceptional multi-family property offers four well-maintained 2-bedroom, 2-bathroom apartments--perfectly positioned for strong, consistent rental income. Just a short stroll to Duval Street, renowned restaurants, the Truman Waterfront, and local attractions, this property is ideally located for long-term or monthly rentals.Each unit features a

  Richard Haskins Buy The Keys

  909 & 913 Thomas St, Key West, FL 33040
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  /10

  $1,699,000

  • 8 Beds
  • 10 Baths
  • 2,432 Sq Ft

  720 Emma St, Key West, FL 33040

  Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops

  Wendy Zintsmaster Truman & Co. (KW)

  720 Emma St, Key West, FL 33040
• 

  

  /43

  $699,000

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  1901 S Roosevelt Blvd Unit 201W, Key West, FL 33040

  Enjoy the Key West lifestyle in this 2 bed, 2 bath end unit at La Brisa--just steps from Smathers Beach! Relax on your private balcony with peaceful Salt Pond views, or take a short stroll across the street to sink your toes in the sand. The spacious open-concept layout features a bright kitchen, dining, and living area, plus two generously sized bedrooms, each with its own bath and ample closet

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1901 S Roosevelt Blvd Unit 201W, Key West, FL 33040
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  /62

  $2,600,000

  • 3 Beds
  • 3 Baths
  • 1,514 Sq Ft

  215 Whitehead St, Key West, FL 33040

  Welcome to 215 Whitehead Street, a captivating Mediterranean Revival home that artfully blends historic charm with sophisticated updates in one of Old Town Key West's most iconic locations. Once the beloved residence of Burt and Hazel Burnett, the property carries a rich legacy. Burt Burnett, a renowned artist, actor, and passionate supporter of the local theatre scene, infused the home with a

  Tommy Mack Coastal Collection Real Estate Inc.

  215 Whitehead St, Key West, FL 33040
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  /31

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 1,480 Sq Ft

  263 Golf Club Dr, Key West, FL 33040

  Impact windows and doors are on order. Installation by November 30th. Key West Golf Club single family home is now available for sale and immediate occupancy. Located in the Sanctuary, this home features 3 bedrooms and 2.5 baths. Enjoy your own private pool or relax at the community's large lagoon pool and fitness center. Open floor plan opens to the large rear deck with pool. Upstairs is the

  The Behmke Group Keller Williams Key West Compass Realty

  263 Golf Club Dr, Key West, FL 33040
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  /34

  $1,250,000

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  212 Southard St, Key West, FL 33040

  Take a look at this picture perfect townhouse located in the prestigious Truman Annex . Nice end unit located just off Southard St is in excellent condition with many renovations throughout the house. Kitchen has been nicely updated with stainless steel appliances, custom cabinetry and granite countertops. Bamboo flooring throughout the first level leads to a cozy back brick patio and the

  Mike Caron Keller Williams Key West Compass Realty

  212 Southard St, Key West, FL 33040
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  /60

  $4,850,000

  • 5 Beds
  • 4 Baths
  • 3,148 Sq Ft

  202 Admirals Ln, Key West, FL 33040

  Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  202 Admirals Ln, Key West, FL 33040
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  /53

  $2,925,000

  • 4 Beds
  • 4 Baths
  • 3,656 Sq Ft

  1610 von Phister St, Key West, FL 33040

  Fully renovated and redefined mid-century home, perfectly tailored for modern island living. Located on one of the most desirable streets in Key West, this turnkey property sits on an oversized 9,500 square foot lot in the heart of the island. Offering over 3,600 square feet of thoughtfully designed living space, the home features four bedrooms, four full bathrooms and a bonus room ideal for

  Jenna Stauffer Ocean Sotheby's International Realty

  1610 von Phister St, Key West, FL 33040
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  /32

  $1,790,000

  • 2 Beds
  • 3 Baths
  • 1,420 Sq Ft

  212 Fleming St, Key West, FL 33040

  Nestled within the highly sought-after Truman Annex neighborhood, this exquisite 2 bedroom, 2.5 bathroom single-family home offers an unparalleled Key West living experience. Its prime location puts you within effortless walking distance to Old Town's most treasured restaurants, vibrant attractions, and historic sites. Upon entering, you'll be captivated by the inviting ambiance. The interior

  Rodney Culiver Last Key Realty, Inc (KW)

  212 Fleming St, Key West, FL 33040
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  /25

  $584,000

  • 3 Beds
  • 2 Baths
  • 1,075 Sq Ft

  3930 S 3930 Roosevelt Blvd Unit N302, Key West, FL 33040

  Welcome to Las Salinas, where island living meets investment potential. This 3-bedroom, 2-bath condo offers one of the best oversized, covered parking spots in the complex (fits 2 mid-sized cars)--a rare and valuable feature in Key West. Whether you're seeking a full-time residence, vacation getaway, or income-producing property, Unit N302 is priced to sell and boasts a strong rental history.

  Ted Stewart Truman & Co. (KW)

  3930 S 3930 Roosevelt Blvd Unit N302, Key West, FL 33040
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  /24

  $925,000

  • 4 Beds
  • 2 Baths
  • 1,755 Sq Ft

  3746 Paula Ave, Key West, FL 33040

  This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana.The home had the roof replaced in 2014 and has

  Rob Severin Rob Severin Real Estate Co

  3746 Paula Ave, Key West, FL 33040
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  /38

  $980,000

  • 4 Beds
  • 3 Baths
  • 1,606 Sq Ft

  6460 Sunshine St, Key West, FL 33040

  Spacious 4-Bedroom, 3-Bath Home on Expansive Lot with Fruit Trees!Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled on a generous 9,375 sq ft fully fenced lot. Perfect for families and entertainers alike, this property offers the ideal blend of space, comfort, and outdoor living. Inside, you'll find a thoughtfully designed layout with ample natural light, spacious

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  6460 Sunshine St, Key West, FL 33040
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  /22

  $665,000

  • 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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  /52

  $2,250,000

  • 3 Beds
  • 2 Baths
  • 2,001 Sq Ft

  1110 Johnson St, Key West, FL 33040

  Blending the elegance of Danish modern architecture with the laid-back charm of island life in Key West is 1110 Johnson Street. The spacious 2000 sq ft, three-bedroom, two-bathroom home which also boasts a den and breakfast nook sits on a large, private 7500 sq ft land parcel located in the prestigious Casa Marina district on the most coveted, quiet, one-way street. The property offers plenty of

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

  1110 Johnson St, Key West, FL 33040
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  /35

  $1,195,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 1 Bath
  • 723 Sq Ft

  729 Windsor Ln, Key West, FL 33040

  Charming Historic Gem in the Heart of Old Town Key West!Welcome to 729 Windsor Lane--a rare opportunity to own a piece of Key West history nestled in one of the island's most desirable residential neighborhoods. Set on an expansive nearly 3,000 sq.ft. lot, this classic home offers a generous footprint that's almost unheard of in Old Town, along with the luxury of coveted off-street parking.Step

  Amber DeBevec LoKation Real Estate

  729 Windsor Ln, Key West, FL 33040
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  /6

  $443,000

  • 2 Beds
  • 2 Baths
  • 696 Sq Ft

  3312 Northside Dr Unit 407, Key West, FL 33040

  First time on the market since 1982. Santa clara condo building has been totally renovated with its 40 year inspection completed with no assesments to worry about This 2 bedroom 2 bath has all the updates and has tenants until 12/31/2025 paying $ 3100 per month . The tenants would like to stay . Need at least 24 hrs to show . Owners are license realtors

  Louis Condos Berkshire Hathaway HomeServices Knight & Gardner Realty

  3312 Northside Dr Unit 407, Key West, FL 33040
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  /25

  $685,000

  • 1 Bed
  • 1 Bath
  • 427 Sq Ft

  1203 Newton St Unit 2, Key West, FL 33040

  Welcome to your 'Slice of Paradise' in Old Town Key West! 1203 Newton #2 is a well-appointed & well-maintained condo in the much desirable Meadows neighborhood with city managed greenspace out back. One bed, one bath condo is located in 2 building, 8-unit complex with a pool. This first-floor condo feels spacious with nearly 10 Ft ceilings & abundant natural light. Features fragrant blooming

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  1203 Newton St Unit 2, Key West, FL 33040
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  /17

  $565,000

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  1500 Seminary St Unit 5A, Key West, FL 33040

  Welcome to this charming 1-bedroom, 1-bathroom apartment nestled in the heart of Key West. Located on desirable Seminary Street, this cozy yet functional home offers a perfect mix of comfort, character, and convenience.Step inside to find an open living space with hard flooring throughout the living room, office nook, and bedroom, complemented by easy-to-clean tile in the kitchen and bath.

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

  1500 Seminary St Unit 5A, Key West, FL 33040
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  /63

  $1,150,000

  • 5 Beds
  • 4 Baths
  • 2,160 Sq Ft

  397 Balido St, Key West, FL 33040

  A MUST SEE! Stock Island Gem! Live the Key West life only 4 miles away from the famous Duval Street, with incredible income potential! This beautifully renovated (2020) home with off street parking and enough room for a RV. Is A must-see for those seeking both a dream home and a smart investment property, with space and income-earning possibilities. Don't miss this opportunity in Stock Island.

  Letisia Powell Robert Slack LLC

  397 Balido St, Key West, FL 33040
• 

  

  /56

  $5,454,400

  • 4 Beds
  • 5 Baths
  • 3,577 Sq Ft

  3300 Riviera Dr, Key West, FL 33040

  Welcome to 3300 Riviera Drive--an exceptional, turn-key, waterfront, residential estate featuring 4 bedrooms and 4.5 bathrooms. Nestled on three lots in a serene enclave just minutes from Old Town, this meticulously maintained property features 3,577 Sq. Ft. of living space and redefines Key West luxury, comfort and convenience. Step inside to discover an expansive open-concept living space

  Bobby Coe RE/MAX Keys Connection (KW)

  3300 Riviera Dr, Key West, FL 33040
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  /7

  $999,999

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  620 White St, Key West, FL 33040

  This legal duplex offers fantastic potential with two separate units. The front unit is a 2-bedroom, 1-bath home and a rear unit is a 1-bedroom, 1-bath unit. The property features an in-ground pool and is ideally laid out for investment or owner-occupancy with rental income. While some work has been done, the entire property is in need of finishing renovations-- perfect for a buyer ready to

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  620 White St, Key West, FL 33040
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  /51

  $1,290,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  5960 Peninsular Ave Unit 101, Key West, FL 33040

  Location Location Location! Oceanview Condo Only 22 units nestled on an ocean front peninsula. Breathtaking views of flats, Mangrove estuary, and the Atlantic Ocean. Compare this property with the competition and you can for yourself. Unit 101 is an end unit with additional windows in the living area letting in natural light making this unit feel open and delightful. Unit faces East and enjoys

  Zachary Bentley Coastal Collection Real Estate Inc.

  5960 Peninsular Ave Unit 101, Key West, FL 33040
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  /24

  $1,985,000

  • 5 Beds
  • 2 Baths
  • 2,196 Sq Ft

  522 William St, Key West, FL 33040

  Welcome to 522 William Street - a rare renovation opportunity nestled in the heart of Old Town Key West. This classic Conch - style home sits on a prized street just steps from the Historic Seaport, world-class dining, and the island's vibrant energy. With its original Dade County pine, soaring ceilings, and vintage architectural details, this diamond in the rough is ready for

  Barbara Crespo Keller Williams Key West Compass Realty

  522 William St, Key West, FL 33040
• 

  

  /13

  $149,900

  • Land
  • 0 Acre

  1801 N Roosevelt Blvd Unit 8, Key West, FL 33040

  Very nice well maintained 34' Trojan Houseboat located in Central Key West.All fiberglass, very dry. Very efficient design with plenty of storage. Walk around bed in master stateroom. Two twin size bunks in the lower berth for guests. Standard head with shower and vanity. Galley and Salon area. Front and rear decks at the main level with a nice sized mid-deck and a great upper deck for

  Randy Moss Coldwell Banker Schmitt RE Co

  1801 N Roosevelt Blvd Unit 8, Key West, FL 33040
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  /42

  $1,590,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  5960 Peninsular Ave Unit 111, Key West, FL 33040

  Lavender, purple, magenta, emerald, milky baby blue, gemlike aquamarine. These are a few of the breathtaking colors you will experience while slumbering on your balcony of this beautiful ocean front home. Fully furnished, turnkey 3 Bedroom 2 Bath one level condo on the Atlantic in a gated community. Designer kitchen with custom lighting, beautiful cabinetry and exquisite furnishings are just a

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

  5960 Peninsular Ave Unit 111, Key West, FL 33040
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  /42

  $2,400,000

  • 2 Beds
  • 3 Baths
  • 1,350 Sq Ft

  107 Front St Unit 215, Key West, FL 33040

  Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of

  The Behmke Group Keller Williams Key West Compass Realty

  107 Front St Unit 215, Key West, FL 33040
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  /29

  $3,295,000

  • 2 Beds
  • 3 Baths
  • 1,650 Sq Ft

  806 Southard St, Key West, FL 33040

  Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully

  Richard Patten Your Keys Real Estate, LLC

  806 Southard St, Key West, FL 33040
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  /6

  $11,888,000

  • 3 Beds
  • 2 Baths
  • 2,071 Sq Ft

  1430 Vernon Ave Unit 1-2, Key West, FL 33040

  Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing

  Irina Pytlik Keys Top Realty LLC

  1430 Vernon Ave Unit 1-2, 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
• 

  

  /8

  $139,900

  • Land
  • 0 Acre

  1801 N Roosevelt Blvd Unit Marlin 22, Key West, FL 33040

  Affordable waterfront living in Key West !Custom Made House Boat in a beautifully located liveaboard slip in City Marina in the center of Key West.Low slip fee of $ 679 per month covers free pump out ,2 parking passes, 2 clean laundry and bath facilities, patrolled security. Located on a state of the art floating dock. Call agent for details.

  Randy Moss Coldwell Banker Schmitt RE Co

  1801 N Roosevelt Blvd Unit Marlin 22, Key West, FL 33040
• 

  

  /24

  $875,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  2910 Fogarty Ave, Key West, FL 33040

  Here's a classic Key West bungalow with an oversize lot located on a quiet treelined street. Interior features include a renovated kitchen and Energy Star stainless appliances, newly installed composite flooring, 3 bedrooms and a remodeled bathroom. A wall of French doors opens from the main living/dining are to a 450 sq ft covered deck/patio complete with a lounging TV area, bar, outdoor

  Mike Caron Keller Williams Key West Compass Realty

  2910 Fogarty Ave, Key West, FL 33040

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