Homes for Sale near Monroe County School District Virtual Instruction Program

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  /4

  $2,649,000

  New Construction

  • 4 Beds
  • 4 Baths
  • 2,410 Sq Ft

  3409 Eagle Ave, Key West, FL 33040

  Introducing 3409 Eagle Avenue, a stunning new home, currently under construction in Key West, FL, designed for modern luxury and comfort. Current plans call for 4-bedrooms, 4-bathrooms but could be altered by a Buyer. Also, opportunity for buyer to customize high-end finishes to their personal taste. The entire lot was raised almost two feet and the home will be built above flood elevation, this

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  3409 Eagle Ave, Key West, FL 33040
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  /39

  $1,899,000

  $96K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 3,197 Sq Ft

  1229 5th St, Key West, FL 33040

  Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and

  The Spottswood Team Truman & Co. (KW)

  1229 5th St, Key West, FL 33040
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  /34

  $2,445,000

  $50K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  800 Fleming St Unit C1, Key West, FL 33040

  Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely

  Elizabeth Chamberlain Truman & Co. (KW)

  800 Fleming St Unit C1, Key West, FL 33040
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  /38

  $5,995,000

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

  910 Watson St, Key West, FL 33040

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

  Team Kaufelt Truman & Co. (KW)

  910 Watson St, Key West, FL 33040
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  /35

  $1,099,000

  • 2 Beds
  • 3 Baths
  • 1,824 Sq Ft

  97 Seaside North Ct Unit 97, Key West, FL 33040

  One of the greatest luxuries in Key West isn't extravagance--it's finding a home where life feels a little quieter, a little easier, and a little more connected to the island around you. That's exactly what you'll find at 97 Seaside North Court. Tucked inside the often-overlooked gated Seaside Residences community, this light-filled townhome offers something increasingly difficult to find in Key

  Richard Patten Your Keys Real Estate, LLC

  97 Seaside North Ct Unit 97, Key West, FL 33040
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  /36

  $875,000

  $50K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft

  817 Pearl St, Key West, FL 33040

  Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom

  Elaine Coyle Keller Williams Key West Compass Realty

  817 Pearl St, Key West, FL 33040
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  $1,990,000

  $160K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  3801 Flagler Ave, Key West, FL 33040

  This modern and luxury property consist of 3 bedrooms, 3 full baths, plus an office and detached office. The private gated corner lot has a home and guest house, large yard and beautiful pool, outdoor shower, dining and conversation seating. The main residence offers a full kitchen with gas cooking and stainless steel appliances, a primary bedroom suite with bath, and a large loft. The loft is

  Joe Bracciale Select Properties of NWFL

  3801 Flagler Ave, Key West, FL 33040
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  /34

  $2,800,000

  • 2 Beds
  • 2 Baths
  • 809 Sq Ft

  1009 Whitehead St, Key West, FL 33040

  High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1009 Whitehead St, Key West, FL 33040
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  /79

  $2,300,000

  $549K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft

  16 Azalea Dr, Key West, FL 33040

  Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated

  Tommy Mack Coastal Collection Real Estate Inc.

  16 Azalea Dr, Key West, FL 33040
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  /33

  $564,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,071 Sq Ft

  3930 S Roosevelt Blvd Unit S205, Key West, FL 33040

  Best Priced 3 BR Property on Key West! Stop throwing away money on rent and step into Key West homeownership with this 3 BR and 2 BA value. Properties like this are rare in the Key West market when considering the value pricing and the affordable costs of ownership with low condo fees, insurance and taxes. Offering granite tile floors, an upgraded kitchen, and crown molding and trim details, the

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  3930 S Roosevelt Blvd Unit S205, Key West, FL 33040
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  /19

  $3,449,000

  $151K PRICE DROP

  • Land
  • 7,405 Sq Ft
  • $20,288,235 per Acre

  15 Driftwood Dr, Key Haven, FL 33040

  An exceptional opportunity to purchase this premier waterfront vacant lot with easy access to the Gulf and Atlantic. Ideally positioned to capture privacy, views, and natural beauty, this luxury vacant lot offers the perfect canvas. Surrounded by upscale muti-million-dollar properties and set within a highly desirable area. This lot combines exclusivity, tranquility, and convenience-an ideal

  Jason Barroso Century 21 All Keys Inc (KW)

  15 Driftwood Dr, Key Haven, FL 33040
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  /12

  $499,000

  5950 Peninsular Ave Unit 643, Key West, FL 33040

  Own not rent your very own 50 x 22 liveaboard boat slip in Key West/Stock Island. Not many opportunities like this so do not hesitate! Located at the prestigious Oceans Edge Resort & Marina. It is a premium deeded and 9' control draft deep water slip with direct access to the Atlantic Ocean. This Marina is the home to many Luxury Yachts and Larger Boats. Owners are able to enjoy the wonderful

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  5950 Peninsular Ave Unit 643, Key West, FL 33040
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  /43

  $2,900,000

  • 2 Beds
  • 2 Baths
  • 1,598 Sq Ft

  1701 Laird St, Key West, FL 33040

  Seclusion meets striking contemporary design in this elevated sanctuary, positioned just moments from Higgs Beach and White Street Pier. Behind a signature pivoting red gate and architectural peekaboo wall, the residence unfolds as a curated experience of light and geometry. The entry foyer--anchored by a sun-drenched desk nook and an open-tread staircase--leads to a living space defined by

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1701 Laird St, Key West, FL 33040
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  /22

  $975,000

  • 2 Beds
  • 1 Bath
  • 7,080 Sq Ft

  6810 Front St Unit B-13S & SNL 18, Stock Island, FL 33040

  Excellent opportunity . The condo is divided in to separate units, each having one bedroom and a bath. The property includes a 25x70 live aboard commercial deep water slip. Minutes from Key West. The area provides many choices for dinning , shopping ,nightlife, golf, beaches and a short ride to the Key West airport.

  Marc Ulanowski Equestrian Sotheby's International Realty Inc.

  6810 Front St Unit B-13S & SNL 18, Stock Island, FL 33040
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  /60

  $795,000

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  2005 Fogarty Ave, Key West, FL 33040

  Welcome to Your Own Slice of Paradise! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive.This beautifully updated 2 bedroom, 2 full bath cottage is bursting with Key West charm and curb

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  2005 Fogarty Ave, Key West, FL 33040
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  /19

  $1,700,000

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft

  1224 2nd St, Key West, FL 33040

  Strong value-add multi-family fourplex investment opportunity with major improvements already completed. The heavy lifting has been done, including a new roof, brand-new windows, and updated concrete throughout, setting the stage for the next owner to bring the project to completion. Once finished and delivered furnished, the property has the potential to generate over $200,000 in annual income

  Jenna Stauffer Ocean Sotheby's International Realty

  1224 2nd St, Key West, FL 33040
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  /22

  $434,999

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 792 Sq Ft

  3312 Northside Dr Unit 202, Key West, FL 33040

  Enjoy the largest floor plan in the Santa Clara building with this spacious 2-bedroom, 2-bath condo in the heart of New Town Key West! Welcome to easy island living in tropical Key West, FL! This spacious 2-bedroom, 2-bath condo features the largest floor plan in the building and is conveniently located on the second floor with elevator access. The residence offers tile and laminate flooring,

  DANICA WATKINS Keller Williams Key West Compass Realty

  3312 Northside Dr Unit 202, Key West, FL 33040
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  /28

  $5,000

  • 2 Beds
  • 2.5 Baths
  • 1,288 Sq Ft

  1124 Eaton St, Key West, FL 33040

  Welcome to your Key West paradise at 1124 Eaton Street! Located in the heart of Old Town, this charming 2-bedroom, 2.5-bath home offers the perfect launchpad for your Key West adventure. Enjoy the luxury of a private off-street patio ideal for entertaining or a quiet retreat. Forget the hassle of parking with your own private parking space. Just a short walk to the Seaport, you'll have easy

  Lisa Karp Cashel Properties

  1124 Eaton St, Key West, FL 33040
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  /12

  $215,000

  5555 College Rd Unit 6 (starfish), Key West, FL 33040

  Sunset Marina offers a range of amenities and attractions that make it a desirable destination for live aboard boaters and visitors alike. Starfish # 6 is a 30 ft boat slip that accommodates a max of 35 ft overall boat length. The marina features a variety of boat slips that can accommodate different sizes of vessels, providing easy access to the water. A convenient fuel dock is available for

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

  5555 College Rd Unit 6 (starfish), Key West, FL 33040
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  /10

  $285,000

  5555 College Rd Unit 9, Key West, FL 33040

  OWNER FINANCING AVAILABLE!! Dock in a safe place for you vessel or liveaboard this boat slip with an overall length of 45' and width of 16' 1'. This floating concrete deep water boat slip has a 6' draft and is located in Sunset Marina in Key West, a locals favorite for 2 decades. Immediate access to gulf and easy access to Atlantic. Showers, laundry, dog walk, bike racks, convenience store, fuel

  James Spreitzer RE/MAX Keys Connection (KW)

  5555 College Rd Unit 9, Key West, FL 33040
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  /4

  $649,500

  $130K PRICE DROP

  • Land
  • 4,791 Sq Ft
  • $5,904,545 per Acre

  1610-1612 Dennis St, Key West, FL 33040

  SELLER FINANCING AVAILABLE! Seller willing to negotiate terms for owner financing while you develop this parcel. Options are open as Seller wants to move this property. Development opportunity now even more affordable! This property includes the rights to build duplex or attached townhomes in prime midtown location. Live in one unit and collect rental income from the other. Great proximity to

  Mark MacLaughlin R.W.A. Realty Inc

  1610-1612 Dennis St, Key West, FL 33040
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  /25

  $5,000

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

  101 Front St Unit 4, Key West, FL 33040

  Annual Rental Available in the Truman Annex Foundry Building! Enjoy the best of Key West living from this fully furnished 2 bedroom, 2.5 bath, 3 story townhome located in the highly desirable Truman Annex Foundry Building at 101 Front Street, Unit #4.This spacious residence is offered fully furnished and features multiple levels of living space, a private fenced yard area, and access to the

  Terri Spottswood Truman & Co. (KW)

  101 Front St Unit 4, Key West, FL 33040
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  /27

  $9,499,000

  $3M PRICE DROP

  • Land
  • 77.46 Acres
  • $122,637 per Acre

  7000 5th St, Stock Island, FL 33040

  Nestled along the serene waterfront, these two picturesque parcels offer an unparalleled opportunity to indulge in the quintessential Florida Keys lifestyle. These two expansive plots of land incl. bay bottom present the perfect canvas for your dream waterfront retreat and /or commercial ventures.The Northern parcel consists of about 1,400 ft. of native shoreline, providing ample space for

  Ellen Gvili Ocean Sotheby's International Realty

  7000 5th St, Stock Island, FL 33040
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  /61

  $7,495,000

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

  616 Eaton St, Key West, FL 33040

  Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive

  Terri Spottswood Truman & Co. (KW)

  616 Eaton St, Key West, FL 33040
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  /24

  $939,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  620 Thomas St Unit 186, Key West, FL 33040

  Located in the desirable Truman Annex Shipyard community, this beautifully updated first-floor condominium offers 2 bedrooms, 1 bath.The newly renovated kitchen features stainless steel appliances, granite countertops, and modern finishes, while the updated bath includes a stylish walk-in shower. A redesigned laundry area includes a new washer and dryer for added convenience.Step outside

  Kelli Houze Berkshire Hathaway HomeServices Knight & Gardner Realty

  620 Thomas St Unit 186, Key West, FL 33040
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  /32

  $979,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  1500 5th St, Key West, FL 33040

  Substantial concrete 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and

  Epperly - Celli Epperly - Celli Engel & Voelkers Key West

  1500 5th St, Key West, FL 33040
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  /24

  $2,525,000

  $225K PRICE DROP

  • 4 Beds
  • 2.5 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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  /4

  $995,000

  $100K PRICE DROP

  • 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 3038 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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  /72

  $3,398,000

  • 3 Beds
  • 4 Baths
  • 2,386 Sq Ft

  3034 Riviera Dr, Key West, FL 33040

  Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58' of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout.

  Richard Haskins Buy The Keys

  3034 Riviera Dr, Key West, FL 33040
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  /48

  $1,279,000

  • 2 Beds
  • 3.5 Baths
  • 1,824 Sq Ft

  25 Seaside South Ct, Key West, FL 33040

  Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels.You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not

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

  25 Seaside South Ct, Key West, FL 33040
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  /40

  $1,899,000

  $101K PRICE DROP

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

  1220 Georgia St, Key West, FL 33040

  Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both.Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The

  The Spottswood Team Truman & Co. (KW)

  1220 Georgia St, Key West, FL 33040
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  /9

  $5,800

  • 3 Beds
  • 2 Baths

  14 Aster Terrace, Key West, FL 33040

  Available AUGUST 1st. NOT FURNISHED. This key haven home is on one of the nicest boating swimming canals in Key Haven, just a few houses from open water and less than a mile from Key West. Seawall and deck. There is a formal dining area, living room, kitchen and three bedrooms, the outdoor spaces ideal for entertaining or just relaxing. Large pergola and a partial in ground large hot tub with

  Daniel Coll Coll & Coll Inc

  14 Aster Terrace, Key West, FL 33040
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  /53

  $2,250,000

  • 10 Beds
  • 6 Baths
  • 3,876 Sq Ft

  912 Pohalski St, Key West, FL 33040

  Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available.There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy

  Bobby Coe RE/MAX Keys Connection (KW)

  912 Pohalski St, Key West, FL 33040
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  /61

  $1,049,000

  New Construction $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  49G Miriam St, Stock Island, FL 33040

  This newly built 2026 home on Stock Island delivers what buyers rarely find in the Florida Keys: true new construction, built to current code, with a fully legal guest suite and insurance costs designed to be as manageable as possible -- all priced under $1.1M.The main residence offers 3 bedrooms, 2 bathrooms, and over 1,500 square feet of thoughtfully designed living space elevated 18 feet

  Jimmy Lane Island Life Realty Experts

  49G Miriam St, Stock Island, FL 33040
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  /17

  $175,000

  $60K PRICE DROP

  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 of slips on the

  Jimmy Lane Island Life Realty Experts

  5555 College Rd Unit 5, Key West, FL 33040
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  /20

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft

  2116 Fogarty Ave, Key West, FL 33040

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker

  Jenna Blackwell Berkshire Hathaway HomeServices Knight & Gardner Realty

  2116 Fogarty Ave, Key West, FL 33040
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  /70

  $2,595,000

  $200K PRICE DROP

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

  1501 Florida St, Key West, FL 33040

  Price Reduction. 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

  Jason Barroso Century 21 All Keys Inc (KW)

  1501 Florida St, Key West, FL 33040
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  /36

  $950,000

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1800 Atlantic Blvd Unit 218B, Key West, FL 33040

  Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along

  Donna Pezzi Keller Williams Key West Compass Realty

  1800 Atlantic Blvd Unit 218B, 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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  /63

  $1,425,000

  $125K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,387 Sq Ft

  9 Mccoy Cir Unit 9, Key West, FL 33040

  Experience the quintessential island lifestyle in this stunning waterfront townhome at Flagler's Landing, where Gulf views meet the convenience of a central Key West location with private boat dockage. This elevated residence offers approximately 1,387 sq ft of living space with open Gulf views from the main living areas, private balcony, and both upstairs bedrooms.The main level is designed

  Karen Verri Ocean Sotheby's International Realty

  9 Mccoy Cir Unit 9, Key West, FL 33040

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