Homes for Sale near Monroe County School District Virtual Instruction Program

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  /47

  $6,495,000

  • 3 Beds
  • 4 Baths
  • 3,104 Sq Ft

  1014 Flagler Ave, Key West, FL 33040

  Some homes are built; others are authored. This is one of the latter--an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been

  Team Kaufelt Truman & Co. (KW)

  1014 Flagler Ave, Key West, FL 33040
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  /36

  $518,000

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3635 Seaside Dr Unit 213, Key West, FL 33040

  Welcome to 3635 Seaside Drive, Unit 213, an amazing two (2) bedroom and (2) two bathroom condo with a beautiful pool view.This is the one, if you're tired of paying rent, here it is! Time to own this unit and make this condo your very own piece of paradise!A perfectly designed condo with a split floor plan, with the kitchen and living room in the heart of this home. Wake up and enjoy that fresh

  Bobby Coe RE/MAX Keys Connection (KW)

  3635 Seaside Dr Unit 213, Key West, FL 33040
• 

  

  

  /13

  $499,000

  • 1 Bed
  • 1 Bath
  • 434 Sq Ft

  1411 Truman Ave Unit 1, Key West, FL 33040

  NEW LISTING! Beautiful 1 bedroom 1 bath condo in the heart of Key West near park, tennis courts, grocery, galleries, and dining. This first floor one bedroom condo offers Dade County Pine walls, NEW AC units, and outdoor space. The kitchen has stainless steel appliances and there is in unit laundry. Less than 1 mile to famous Duval St. This is the perfect pied-a-terre with front porch area for

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1411 Truman Ave Unit 1, Key West, FL 33040
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  /25

  $2,525,000

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

  1427 Washington St, Key West, FL 33040

  Located in a charming midtown neighborhood sits this beautifully renovated 4BD/2.5BA Key West home with just over 2,000sf of living space. Upon entering the home you will find a first floor bedroom or office, half bathroom and an all new kitchen with new stainless appliances, countertops, custom built in cabinetry and all new lightning. The open living room is surrounded by French doors that

  The Spottswood Team Truman & Co. (KW)

  1427 Washington St, Key West, FL 33040
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  /39

  $1,999,000

  • 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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  /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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  /39

  $965,000

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

  1901 S Roosevelt Blvd Unit 404S, Key West, FL 33040

  PERCHED on the coveted top floor of La Brisa, this 4th-story condo offers an unbeatable vantage point where the horizon seems to melt into the turquoise waters of the Atlantic. As you step inside, your eyes are immediately drawn through the open-concept living space to the expansive balcony--a private outdoor sanctuary that feels like it's floating above the sea. Whether you sip your morning

  Donna Pezzi Keller Williams Key West Compass Realty

  1901 S Roosevelt Blvd Unit 404S, Key West, FL 33040
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  /35

  $3,250,000

  • 4 Beds
  • 4 Baths
  • 2,772 Sq Ft

  1600 Patricia St, Key West, FL 33040

  New listing in Midtown West! Discover a unique property located in the heart of Key West, featuring a double corner lot of 12,400 square feet with two swimming pools and ample living space. Key features of this property include a stunning chef's kitchen equipped with a gas range, abundant cabinet space, a double oven, and sleek granite countertops. Ideal for entertaining, the formal living room

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1600 Patricia St, Key West, FL 33040
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  /54

  $649,000 Open Fri 3PM - 5PM

  • 2 Beds
  • 2 Baths
  • 871 Sq Ft

  1 Spoonbill Way, Key West, FL 33040

  Tucked along the edge of the enchanting Butterfly Garden, this charming townhouse offers the perfect blend of privacy, tropical beauty, and resort-style amenities. Located within the gated community surrounding the Rees-Jones 18-hole Championship Golf Course, this home is a serene slice of paradise.Inside, you'll find thoughtfully designed living space featuring two upstairs bedrooms and 1.5

  Stephanie Wise Keller Williams Key West Compass Realty

  1 Spoonbill Way, 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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  /2

  $249,000

  • Land
  • 2.39 Acres
  • $104,184 per Acre

  6810 Front St, Key West, FL 33040

  23x47 deep water slip minutes from Key West. Experience the old charm of the Florida Keys at Safe Harbour marina. The marina offers security, laundry and shower facilities as well as plenty of parking. The marina is adjacent to Hog Fish Bar and Grill.

  Marc Ulanowski Equestrian Sotheby's International Realty Inc.

  6810 Front St, Key West, FL 33040
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  /25

  $373,000

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 405, Key West, FL 33040

  Own in Key West under 400k. Excellent investment as primary residence, second home, or rental property. This one bed one bath condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West. You have ample parking, storage, pool, tennis courts, laundry, on site management, etc. The unit has new flooring, new AC unit, new

  Karen Angle Coldwell Banker Schmitt Real Estate Co.

  3312 Northside Dr Unit 405, 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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  /35

  $1,599,000

  • 2 Beds
  • 3 Baths
  • 1,940 Sq Ft

  1616 Atlantic Blvd Unit 3, Key West, FL 33040

  OFFERED FULLY FURNISHED and completely renovated, this is the townhome buyers wait for and almost never get. Every finish, every furnishing, and every detail has been thoughtfully curated to deliver a truly coastal lifestyle. Set within the exclusive, gated oceanfront enclave of Casa Caselles, this solid concrete home has been meticulously renovated with a focus on timeless materials and modern

  Ted Stewart Truman & Co. (KW)

  1616 Atlantic Blvd Unit 3, Key West, FL 33040
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  /22

  $349,000

  • Land

  5950 Peninsular Ave Unit 613, Key West, FL 33040

  This is a 40' wet slip available for sale (16' width). Welcome to Oceans Edge Marina & Resort home to some of the best & quickest offshore boating & fishing access in this area with no bridges where you can head out for daily fishing, boat to the Dry Tortugus, beaches/sandbars or just hang out at the dock and see who is bringing in the fresh seafood. Owners may live aboard. The marina offers dry

  Sylvia Werling Keller Williams Key West Compass Realty

  5950 Peninsular Ave Unit 613, 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
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  /23

  $899,995

  • 2 Beds
  • 2 Baths
  • 798 Sq Ft

  3625 Seaside Dr Unit 25304, Key West, FL 33040

  Enjoy the view of the Salt Ponds & catch sunset from the balcony of this 2 bedroom / 2 bath Transient Licensed condo. Good investment opportunity to have your own place in Key West and generate rental income when you are not here to offset carrying costs. The condo comes fully furnished (turnkey) and has been updated with LVP flooring throughout, renovated baths with tiled, glass enclosed walk-in

  Shad Knapp Beach Club Brokers (KW)

  3625 Seaside Dr Unit 25304, 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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  /37

  $1,099,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,211 Sq Ft

  1440 17th St, Key West, FL 33040

  DUPLEX! Discover the perfect blend of flexibility, privacy, and income potential in this beautifully updated Key West duplex--ideal for families, extended living, or savvy investors. The main residence is a spacious 2-bedroom, 1-bath home thoughtfully updated in 2026 with a brand-new kitchen featuring modern cabinetry, sleek quartz countertops, a tile backsplash, and new stainless appliances.

  Dawn McComish Lokation Real Estate

  1440 17th St, Key West, FL 33040
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  /20

  $535,000

  • 1 Bed
  • 1 Bath
  • 489 Sq Ft

  1500 Seminary St Unit 2D, Key West, FL 33040

  Close to Duval Street but away from the hubbub, this immaculately presented one bedroom condo is just a few blocks from Smathers Beach and vibrant White Street with its restaurants, cafes, gourmet food store, galleries and fitness studios and just a walkable, rideable, half mile from the Atlantic and a mile from the Historic Seaport District and Gulf.......The condo is part of a very well run and

  Rob Severin Rob Severin Real Estate Co

  1500 Seminary St Unit 2D, Key West, FL 33040
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  /17

  $199,900

  • Land

  5555 College Rd Unit 5, Key West, FL 33040

  Well-positioned 30' wet slip located at Sunset Marina on the gated side of the property. This floating concrete dock can accommodate a vessel up to 35' in length and offers deep water access with a 6' control depth -- perfect for easy navigation to both the Gulf and Atlantic waters.Sunset Marina is a full-service marina with on-site fuel, bait, and marina store. Owners enjoy access to secured

  Jimmy Lane Island Life Realty Experts

  5555 College Rd Unit 5, Key West, FL 33040
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  /15

  $839,000

  • Land

  1920 Patterson Ave, Key West, FL 33040

  Primed and Cleared Vacant lot ready for a New build - Excellent Midtown Location with easy access to downtown, excellent schools and New Town Shopping and Restaurants.Property used to have a structure so this has been approved by the city to build a single family and the Build Back letter is available upon request.Concrete wall surrounds entire property.Utility City Easement to the rear.Container

  Suzanne Moore Suzanne Moore Real Estate

  1920 Patterson Ave, Key West, FL 33040
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  /30

  $429,000

  • 2 Beds
  • 2 Baths
  • 696 Sq Ft

  3312 Northside Dr Unit 607, Key West, FL 33040

  2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

  Bigya Niroula (Rihanna) eXp Realty LLC KW Branch

  3312 Northside Dr Unit 607, Key West, FL 33040
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  /71

  $2,695,000 Open Sun 10AM - 12PM

  • 4 Beds
  • 3 Baths
  • 1,931 Sq Ft

  1501 Florida St, Key West, FL 33040

  Excellent opportunity to purchase a luxurious, modern, and refined single family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living spaceand situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact

  Jason Barroso Century 21 All Keys Inc (KW)

  1501 Florida St, Key West, FL 33040
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  /49

  $2,499,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 4 Baths
  • 1,854 Sq Ft

  1320 Eliza St, Key West, FL 33040

  Welcome to the School House on Eliza!1320 Eliza Street is a stunning corner-lot property that exudes old-world charm and proudly served as a historic schoolhouse in Key West.This four (4) bedroom with two (2) full bathrooms with two (2) half bathrooms home sits on a tropically landscaped corner lot with great outdoor living and a perfect heated pool. A brand new roof was just installed.The main

  Bobby Coe RE/MAX Keys Connection (KW)

  1320 Eliza St, Key West, FL 33040
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  /26

  $525,000

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3635 Seaside Dr Unit 104, Key West, FL 33040

  Experience stunning Key West sunsets from your private balcony. This quiet residence is tucked away from the pool area, offering peaceful living with no pool noise and beautiful sunset views over the lush salt ponds. Surrounded by mangroves and wildlife, enjoy daily encounters with herons, ospreys, and pelicans, all just minutes from the turquoise waters of Smathers Beach.Inside, the comfortable

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  3635 Seaside Dr Unit 104, Key West, FL 33040
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  /32

  $999,000

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  3841 N Roosevelt Blvd Unit 222, Key West, FL 33040

  Enjoy unparalleled flexibility and luxury with this transient-licensed 3-bedroom, 3-bathroom condo, an exceptional opportunity for a personal coastal escape or a versatile vacation rental. Fully furnished with modern decor, high-end appliances, and meticulous craftsmanship, this turnkey property is poised to impress from the moment you step in. Conveniently located at the entrance to the island

  The Spottswood Team Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 222, Key West, FL 33040
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  /39

  $1,895,900

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  1121 Whitehead St, Key West, FL 33040

  Step into the charm of this beautifully designed two-story Conch home, originally built in 1923 and thoughtfully expanded to offer the perfect amount of space.The historic character shines through with rare Dade County pine walls, while the open floor plan, Birch hardwood floors, and soaring 10-foot ceilings create a bright and inviting space. The kitchen is a chef's dream, featuring stainless

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

  1121 Whitehead 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

  $869,000

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  204 Southard St Unit 5, Key West, FL 33040

  Welcome to your perfect island retreat! This beautifully maintained 2-bedroom, 1-bathroom condo is ideally situated on the second floor, offering the best of Key West living. Step out onto one of the two private balconies--one in the front and one in the rear--which are perfect for enjoying the ocean breeze and tropical treetop views.Inside, you'll find an inviting layout, featuring a modern

  Stacy Stahl Realty ONE Group Destination

  204 Southard St Unit 5, Key West, FL 33040
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  /36

  $819,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 415, Key West, FL 33040

  Experience the pinnacle of island sophistication with these beautifully appointed courtyard residences at the sought-after Beachside Condominiums in Key West. With two TRANSIENT RENTAL LICENSES, this turnkey property offers exceptional flexibility as a personal retreat, full-time residence, or lucrative vacation rental. WITH 50% SELLER FINANCING OFFERED = AN EXCEPTIONAL OPPORTUNITY! Thoughtfully

  Michelle Blades Realty Executives Florida Keys Old Town

  3841 N Roosevelt Blvd Unit 415, Key West, FL 33040
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  /30

  $2,950,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 4 Baths
  • 3,019 Sq Ft

  27 Evergreen Ave, Key West, FL 33040

  OPEN HOUSE MARCH 7, 11AM-1PM Look no further! Beautiful Key Haven home! Spacious 4 bedroom, 3.5 bathroom canal front home located only 4 miles from Key West. This property offers a flexible floor plan, multiple gathering areas, and a comfortable layout for family living or entertaining. Enjoy direct boating access from your backyard canal and the convenience of a 60 ft dock. Recent updates

  Maria Wilson Berkshire Hathaway HomeServices Knight & Gardner Realty

  27 Evergreen Ave, Key West, FL 33040
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  /61

  $2,100,000

  • 5 Beds
  • 3 Baths
  • 2,146 Sq Ft

  530 White St, Key West, FL 33040

  Wonderful large tri-plex with a 7400 square foot yard!. Currently configured as 3 units, this property can be lived in as is or renovated for maximum potential. Located on the corner of White street and Stump lane, this property has beautiful grounds, room for a large pool, a workshop, decking, and off street parking. The First level features 2 units, each one has 2 bedrooms and 1 bath. Each unit

  Elaine Coyle Keller Williams Key West Compass Realty

  530 White St, Key West, FL 33040
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  /36

  $899,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 213, Key West, FL 33040

  Discover the ultimate fusion of luxury and part time usage with this transient-licensed, 2-bedroom, 2.5-bath condo in Key West. Perfectly suited for vacation rentals, it offers the flexibility of a personal coastal retreat and a robust source of passive income. Fully furnished with sleek, modern decor, high-end appliances, and refined details throughout, this turnkey property is ready to impress

  The Spottswood Team Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 213, Key West, FL 33040
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  /47

  $2,499,000 Open Sat 11AM - 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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  /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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  /64

  $2,050,000

  • 4 Beds
  • 3 Baths
  • 1,602 Sq Ft

  1220 Georgia St, Key West, FL 33040

  Close to Duval Street but situated in a very desirable quiet and peaceful neighborhood within Old Town, this immaculately presented 4 bedroom, 3 bathroom property is just a few blocks from Smathers Beach and one block from vibrant White Street with its restaurants, cafes, gourmet food store, galleries and fitness studios. It is also easily walkable or rideable to the heart of Old Town, the

  Rob Severin Rob Severin Real Estate Co

  1220 Georgia St, Key West, FL 33040
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  /8

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  C1 9th Ave, Stock Island, FL 33040

  This 4 Bedroom 2-bathroom doublewide sits on a corner fenced lot with ample parking. This home has a roof that is only a few years old as well as newer central A/C. Currently it is being used as a rental with good monthly income. And you own the land

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

  C1 9th Ave, Stock Island, FL 33040
• 

  

  /18

  $2,200,000

  • 2 Beds
  • 3 Baths
  • 1,210 Sq Ft

  105 Front St Unit 119, Key West, FL 33040

  SOLD TURN KEY! This beautiful two bedroom, 2.5 bath Harbour Place condominium is located on the desirable first level with one of the largest decks which includes plenty of room for entertaining, relaxing and watching the sunsets and boats coming in out of the Key West harbor. There are gorgeous views of the open water from the living and dining rooms as well as the kitchen. The spacious bedrooms

  The Behmke Group Keller Williams Key West Compass Realty

  105 Front St Unit 119, Key West, FL 33040
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  /38

  $1,499,000

  • 2 Beds
  • 3 Baths
  • 2,016 Sq Ft

  1616 Atlantic Blvd Unit 13, Key West, FL 33040

  Wake up to the Atlantic. In the gated oceanfront community of Casa Caselles, this renovated townhome delivers wide-open sunrise views from four covered balconies, plus the ease of lock-and-go living in the heart of Key West's Mid-Town.1616 Atlantic Blvd. #13 offers 2,016 sq. ft. of livable space across three levels, with a bright, airy feel and high ceilings on the main living floor.Ocean-view

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  1616 Atlantic Blvd Unit 13, Key West, FL 33040

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