Homes for Sale near Key West High School

• 

  

  

  /51

  $3,199,000

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

  512 Amelia St, Key West, FL 33040

  Charming, colorful, and unmistakably Key West--512 Amelia Street is where island life unfolds with ease. Enjoy your own private pool and the flexibility of a Transient License, allowing nightly rentals. Nestled in a serene pocket of Old Town, this home is surrounded by swaying palms, historic streets, and the gentle breezes of the nearby ocean. A home to love and a place guests will never want to

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  512 Amelia St, Key West, FL 33040
• 

  

  

  /17

  $235,000

  • 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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  /83

  $1,400,000

  • 6 Beds
  • 7 Baths
  • 1,306 Sq Ft

  1824 Fogarty Ave, Key West, FL 33040

  Discover a rare investment opportunity in the heart of Key West! This 4-unit tropical compound spans nearly 9,500 sq. ft. and includes a spacious 3BD/3.5BA main home plus three charming 1BD/1BA cottages. Enjoy resort-style living with a pool, tiki bar, and lush outdoor space. Generating $75K+ in annual income (excluding the main home), this property offers flexibility for employee housing,

  Krystal Thomas eXp Realty LLC

  1824 Fogarty Ave, Key West, FL 33040
• 

  

  

  /71

  $6,750,000

  • 5 Beds
  • 5 Baths
  • 3,663 Sq Ft

  411 Louisa St, Key West, FL 33040

  Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment.This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable

  Bobby Coe RE/MAX Keys Connection (KW)

  411 Louisa St, Key West, FL 33040
• 

  

  

  /60

  $949,900

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

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

  Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /25

  $1,449,000

  • 4 Beds
  • 3 Baths
  • 1,767 Sq Ft

  1527 von Phister St, Key West, FL 33040

  Centrally located in the heart of Key West, this beautifully restored traditional Conch-style home offers two legal units and exceptional versatility.The first-floor residence features two bedrooms and two bathrooms, a charming covered front porch, and thoughtfully updated interiors that maintain authentic island character. Upstairs, a bright and airy two-bedroom, one-bath home enjoys its own

  Key West Luxury Finders Preferred Properties (KW)

  1527 von Phister St, Key West, FL 33040
• 

  

  /10

  $1,824,900

  • 9 Beds
  • 7 Baths
  • 3,687 Sq Ft

  1821 Harris Ave, Key West, FL 33040

  Triplex with Stunning Rent Roll ($172,800/year)- This income-producing triplex features three well-maintained units, each offering 3 bedrooms and 2 bathrooms. The front unit, originally larger than the rear units and spans one level--ideal for tenants seeking single-story living. The rear units are two-story layouts, with bedrooms and baths upstairs and kitchen/living areas on the main level.

  Kayley Arn Coldwell Banker Realty - Aventura

  1821 Harris Ave, Key West, FL 33040
• 

  

  /25

  $699,500

  • 2 Beds
  • 1 Bath
  • 612 Sq Ft

  1042 United St, Key West, FL 33040

  Discover your perfect Key West getaway at 1042 United Street -- a charming single-story cottage with two bedrooms, one bath, and all the island character you've been dreaming of. Relax on the inviting front porch with your morning coffee, then unwind on the private back patio after a day of sun and sea. Bright, open interiors and a seamless indoor-outdoor flow make this home ideal for easy

  Barbara Crespo Keller Williams Key West Compass Realty

  1042 United St, Key West, FL 33040
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  /5

  $1,068,000

  • 6 Beds
  • 2 Baths
  • 1,694 Sq Ft

  1916 Seidenberg Ave, Key West, FL 33040

  Duplex with Solid Rent Roll ($91,800/year) - This income-producing duplex features 2 well-maintained units, each offering 3 bedrooms and 1 bathrooms. Units are rented for $3,850 and $3,800 per month on long-term leases ($91,800/year). Perfectly positioned near the coast and only a short ride from the energy of downtown.

  Kayley Arn Coldwell Banker Realty - Aventura

  1916 Seidenberg Ave, Key West, FL 33040
• 

  

  /63

  $3,395,000

  • 4 Beds
  • 4 Baths
  • 2,488 Sq Ft

  102 Admirals Ln, Key West, FL 33040

  The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway without the upkeep of a large yard or pool, this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning Truman Annex, this is the largest townhouse in the community. The

  Lisa Swanson The Agency Florida LLC

  102 Admirals Ln, Key West, FL 33040
• 

  

  /26

  $625,000

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  10 Verde Dr, Key West, FL 33040

  Keys living at its best in this updated 2013 elevated waterfront home designed with all the comforts. Situated near the end of the canal, this property offers quick and easy boating access to the open waters of the Lower Florida Keys; ideal for fishing, diving, sandbar trips or just island-hopping adventures. Inside, you'll find cathedral ceilings, a bright open floor plan, and a modern kitchen

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

  10 Verde Dr, Key West, FL 33040
• 

  

  /16

  $593,500

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

  3930 S Roosevelt Blvd Unit N304, Key West, FL 33040

  Experience the easygoing charm of island life in this thoughtfully updated 3-bedroom, 2-bath condo, in the desirable resort-style living in Las Salinas. Light pours into the open-concept living space, creating a warm and inviting atmosphere that feels like home. The primary suite includes a private balcony that overlooks the pool and steps away from the newly updated fitness center. The modern

  Kayley Arn Coldwell Banker Realty - Aventura

  3930 S Roosevelt Blvd Unit N304, Key West, FL 33040
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  /12

  $1,100,000

  • Land

  619 Front St Unit 21, Key West, FL 33040

  BEST MARINA LOCATION IN KEY WEST!Coveted and rarely available slip at the Galleon Resort in Historic Key West Harbor is now available.At the Galleon Resort, enjoy stunning sunset vistas, viewings of lighted boat parades and a two-block walk to Duval Street! The Historic Key West Seaport district is a stone's throw away where you can dine, drink and listen to live music at a multitude of great

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  619 Front St Unit 21, Key West, FL 33040
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  /44

  $6,850,000

  • 3 Beds
  • 3 Baths
  • 4,200 Sq Ft

  103 Front St, Key West, FL 33040

  103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is

  Laura McChesney Preferred Properties (KW)

  103 Front St, Key West, FL 33040
• 

  

  /91

  $3,995,000

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

  919 Thomas St, Key West, FL 33040

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

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

  919 Thomas St, Key West, FL 33040
• 

  

  /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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  /41

  $560,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  114 Newfound Harbor Rd, Big Pine Key, FL 33043

  Welcome to your private tropical retreat in the heart of the Florida Keys! This charming 2-bedroom, 1-bath elevated home offers the perfect blend of island charm, comfort, and outdoor living.Perched among lush palms and mature tropical trees, this home truly feels like a tropical hideaway. Step inside to find bright, open living spaces and a kitchen that flows effortlessly to a welcoming

  Jennifer Hamill Coldwell Banker Schmitt Real Estate Co.

  114 Newfound Harbor Rd, Big Pine Key, FL 33043
• 

  

  /19

  $475,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
• 

  

  /11

  $650,000

  • Land

  775 Pirates Rd, Summerland Key, FL 33042

  Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

  Melissa Gibbins Expert Realty LLC (HQ)

  775 Pirates Rd, Summerland Key, FL 33042
• 

  

  /55

  $3,999,000 Open Sat 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
• 

  

  /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 Open Thu 4PM - 7PM

  • 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
• 

  

  /29

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  17245 Jamaica Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern

  Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /65

  $1,099,000 Open Thu 1PM - 4PM

  • 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

  $1,795,000

  • 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
• 

  

  /29

  $1,377,000

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  141 Arica Ln, Cudjoe Key, FL 33042

  Experience the best of Florida Keys living in this beautifully maintained & extensively updated waterfront home on a desirable corner lot. Featuring a new 60 ft. concrete dock & 14,000 lb. elevator-style boat lift, you'll enjoy quick access to the Atlantic Ocean & Gulf for world-class fishing, diving, & sandbar adventures- making this property a true boater's dream! Inside, the split floor plan

  Madeleine Lowe Expert Realty LLC (HQ)

  141 Arica Ln, Cudjoe Key, FL 33042
• 

  

  /18

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /18

  $470,000

  • Land

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

  Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
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  /94

  $445,000

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  7 Barcelona Dr, Key West, FL 33040

  Seller Financing Possible!! On the Water-Close to Key West - Adorable -1-Bedroom/1 Bath Plus Loft & Bonus room on a quite canal, the home provides ultimate privacy with a 60' concrete seawall, RV hookups, and a boat ramp and dock right down the road - a fully fenced tropical backyard featuring mature Gumbo Limbo trees, landscape lighting, artificial turf, and paver paths.Inside, enjoy a brand-new

  Tracey Petrusha Venture Realty Group

  7 Barcelona Dr, 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
• 

  

  /32

  $985,000

  • 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
• 

  

  /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
• 

  

  /45

  $5,595,000

  • 4 Beds
  • 5 Baths
  • 3,336 Sq Ft

  1008 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)

  1008 Fleming St, Key West, FL 33040
• 

  /2

  $56,000

  • Land
  • 0.26 Acre
  • $217,064 per Acre

  0 State Rd Unit 4A, Little Torch Key, FL 33042

  ROGO land dedication lot worth 2 points with paperwork completed and Monroe County letter of eligibility on file. No hidden expenses with this lot. Cost-effective way to get your permit faster! This lot is not buildable and is sold for land dedication purposes only.

  Nate Meyer Meyer and Boumerhi Realty LLC

  0 State Rd Unit 4A, Little Torch Key, FL 33042
• 

  

  /26

  $1,180,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  27350 Barbados Ln, Ramrod Key, FL 33042

  Welcome to your slice of paradise in the Lower Florida Keys! This beautifully maintained 3-bedroom, 2-bath canal-front home offers everything you need for island living -- whether you're looking for a full-time residence, vacation getaway, or investment property. Nestled on a spacious 6,000 sq ft lot, this home boasts: - Direct Canal Access - Ideal for boaters! Navigate easily to open water.

  Jonathan Minerick Homecoin.com

  27350 Barbados Ln, Ramrod Key, FL 33042

Showing Results 161 - 200, Page 5 of 18