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Homes for Sale near Key West High School

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  • /22

    $2,850,000

    • 4 Beds
    • 3 Baths
    • 2,880 Sq Ft

    1100 South St, Key West, FL 33040

    Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100 square feet, occupying a

    Key West Luxury Finders Preferred Properties (KW)

    1100 South St, Key West, FL 33040
  • /23

    $799,000

    • 2 Beds
    • 2 Baths
    • 862 Sq Ft

    1004 Watson St Unit 2, Key West, FL 33040

    Centrally located in flood X zone of Old Town, this 2-bed, 2-bath townhouse is classic Key West charm at its best. The galley kitchen offers abundant cabinetry, granite countertops, and stainless-steel appliances. High ceilings with wood-finished crown molding add warmth and character throughout. The spacious primary suite showcases beautiful Dade County pine and a private en-suite bath. Central

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    1004 Watson St Unit 2, Key West, FL 33040
  • /58

    $1,199,000

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

    1409 4th St, Key West, FL 33040

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

    Keys Team Bryant and Kat Expert Realty LLC (HQ)

    1409 4th St, Key West, FL 33040
  • /54

    $535,000

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    55 Boca Chica Rd Unit 132, Key West, FL 33040

    WATERFRONT & SUNSHINE!A rare opportunity with 50 feet of dockage--this waterfront mobile home is your perfect entry into the laid-back Keys lifestyle. Whether you're dreaming of a full-time coastal escape or a tropical vacation retreat, this charming home offers the ideal blend of comfort, convenience, and coastal charm.Located in a gated condominium community known for its relaxed atmosphere,

    Donna Pezzi Keller Williams Key West Compass Realty

    55 Boca Chica Rd Unit 132, Key West, FL 33040
  • /25

    $425,000

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft

    201 Coppitt Rd Unit 301, Key West, FL 33040

    This beautifully, completely remodeled 1-bedroom, 1-bath penthouse waterfront condo in Big Coppitt Key sits just 10 minutes from Key West. Located on the top corner of a solid concrete building, this rare end unit offers sweeping open-water views from every direction, exceptional privacy, and abundant natural light throughout.One of the largest floor plans in the community, this residence

    Madeleine Lowe Expert Realty LLC (HQ)

    201 Coppitt Rd Unit 301, Key West, FL 33040
  • /15

    $1,450,000

    • Land
    • 2.29 Acres
    • $633,190 per Acre

    1261 Avenue A, Big Pine Key, FL 33043

    An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

    Ally Kelley Ocean Sotheby's International

    1261 Avenue A, Big Pine Key, FL 33043
  • /11

    $249,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    231 Pelican Ln, Big Pine Key, FL 33043

    The price is for the lot AND permit. Pre-construction showing a picture of the modular that is permitted. Make your changes now before price increases with work conducted OR purchase the property with the permit and finish it on your own. *Approved ROGO Allocation and Active Building Permit as of February 25, 2025. Building permit is ready to be picked up. Permit number: SFDUP-2023-0113 is

    Donna Pezzi Keller Williams Key West Compass Realty

    231 Pelican Ln, Big Pine Key, FL 33043
  • /24

    $265,000

    • Land

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /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
  • /24

    $385,000

    • Land

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeyEscape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig and start relaxing

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • /55

    $2,300,000 New Construction

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    30995 Watson Blvd, Big Pine Key, FL 33043

    FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

    Banks Prevatt Coldwell Banker Schmitt RE Co.

    30995 Watson Blvd, Big Pine Key, FL 33043
  • /38

    $2,400,000

    • 3 Beds
    • 4 Baths
    • 1,724 Sq Ft

    1109 Stump Ln, Key West, FL 33040

    Nestled on a tranquil lane in Old Town Key West, this classic Conch home is designed for relaxed island living. The property offers multiple entertainment spaces both indoors and out, with the expansive living area and kitchen opening to a great covered patio . Enjoy a large pool surrounded by spacious decks and lush landscaping for lounging and privacy. Inside, you'll find 3 bedrooms 2.5 baths

    Terri Spottswood Truman & Co. (KW)

    1109 Stump Ln, Key West, FL 33040
  • /68

    $1,895,000

    • 3 Beds
    • 3.5 Baths
    • 2,295 Sq Ft

    1136 W Shore Dr, Big Pine Key, FL 33043

    Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking

    Beata Sharpe Coldwell Banker Vanguard Realty

    1136 W Shore Dr, Big Pine Key, FL 33043
  • /15

    $425,000

    • 2 Beds
    • 1 Bath
    • 798 Sq Ft

    69 Palm Dr, Key West, FL 33040

    ROGO exempt! Opportunity to easily replace existing mobile with a hurricane-rated modular, wood frame or Concrete home in a relaxed Lower Keys community just 15 minutes from Key West. Located on a 60+ ft wide deep-water canal with a solid seawall that spans the width of the property, 35 feet--ideal for boating or fishing right from your backyard. Enjoy neighborhood amenities like tennis and

    Natallie Liz Expert Realty LLC (HQ)

    69 Palm Dr, Key West, FL 33040
  • /31

    $1,100,000

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

    1800 Atlantic Blvd Unit 337C, Key West, FL 33040

    Unit 337C at 1800 Atlantic is a beautifully furnished, turn key, two bedroom, two bath unit in immaculate move in condition. The location in the building offers glorious views of the Atlantic ocean from the living room and the expansive balcony. The spacious primary bedroom has a beautiful en suite bath and lots of closet space. Both the main bedroom and the guest bedroom have sliding glass doors

    Laura McChesney Preferred Properties (KW)

    1800 Atlantic Blvd Unit 337C, Key West, FL 33040
  • /31

    $1,150,000

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

    263 Golf Club Dr, Key West, FL 33040

    New impact windows and doors! 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 primary bedroom ensuite, two guest bedrooms

    The Behmke Group Keller Williams Key West Compass Realty

    263 Golf Club Dr, Key West, FL 33040
  • /85

    $2,650,000

    • 2 Beds
    • 3 Baths
    • 1,681 Sq Ft

    68 Sunset Key Dr, Key West, FL 33040

    First Time on the Market! Surprising water views combined with maximum privacy are the signature advantages of this luxurious and well positioned Overlook home on the exclusive private island of Sunset Key. The original owners bought pre-construction and added many thoughtful upgrades and architectural improvements. This three story, 2 bedroom, 2 and a half bath home has been well maintained

    Dawn Thornburgh Beach Club Brokers (KW)

    68 Sunset Key Dr, Key West, FL 33040
  • /63

    $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
  • /40

    $2,450,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    1330 Sugarloaf Blvd, Summerland Key, FL 33042

    Luxury Waterfront Living on Sugarloaf KeyExperience the epitome of island elegance in this beautifully completely renovated waterfront retreat on desirable Sugarloaf Key. This three-bedroom, two-bath home evething is brand NEW home showcases high-end finishes throughout, blending modern luxury with laid-back coastal charm. The open-concept living area flows seamlessly onto an expansive outdoor

    Brenda Donnelly Brenda Donnelly Real Estate LLC

    1330 Sugarloaf Blvd, Summerland Key, FL 33042
  • /24

    $580,175

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

    Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

    Sarah Dolson Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
  • /79

    $875,000

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    19512 Aztec St, Summerland Key, FL 33042

    Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    19512 Aztec St, Summerland Key, FL 33042
  • /20

    $360,000

    • 1 Bed
    • 1 Bath
    • 536 Sq Ft

    201 Coppitt Rd Unit 201, Key West, FL 33040

    Enjoy gorgeous sunset views from this unique waterfront end-unit condo on Big Coppitt Key, just 10 minutes from downtown Key West. Perfectly positioned, this residence offers exceptional water views and an abundance of natural light thanks to its extra windows and desirable end unit location.Recently renovated, the condo features 1 bedroom and 1 bath with modern upgrades throughout. Improvements

    Terri Spottswood Truman & Co. (KW)

    201 Coppitt Rd Unit 201, Key West, FL 33040
  • /10

    $335,000

    • Land

    Indies Indies Rd, Ramrod Key, FL 33042

    Waterfront vacant lot located on Ramrod Key in an established canal community on the oceanside of the Lower Keys. This property offers boating access to the Atlantic with connectivity to Florida Bay. No building permit is currently in place; buyers may pursue development through ROGO or obtain a separate building right. Conveniently situated between Marathon and Key West, offering easy access to

    Jenifer Hirsch Bluescape Real Estate

    Indies Indies Rd, Ramrod Key, FL 33042
  • /35

    $710,000

    • 3 Beds
    • 1.5 Baths
    • 1,247 Sq Ft

    29283 Coconut Palm Dr, Big Pine Key, FL 33043

    Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3-bedroom, 1.5-bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless

    Stephany Duvall Engel & Volkers Marathon

    29283 Coconut Palm Dr, Big Pine Key, FL 33043
  • /70

    $3,979,000

    • 3 Beds
    • 3 Baths
    • 2,188 Sq Ft

    906 Southard St, Key West, FL 33040

    Situated in the prestigious heart of Old Town, 906 Southard Street is an impeccably restored Historic Key West eyebrow house filled with timeless architectural character. This Home has off street parking, pool and all that Key West Charm you are looking for. A large ipe wood front porch adorned with classic gingerbread trim and iconic gas lanterns welcomes you to the refined residence.This home

    Bobby Coe RE/MAX Keys Connection (KW)

    906 Southard St, Key West, FL 33040
  • /2

    $379,000

    • Land

    27463 Antigua Rd, Ramrod Key, FL 33042

    Exceptional Opportunity to develop this 6200-sf canal front Ramrod Key Lot with Plans in the super relaxed Breezeswept Beach Estates community! Ideal Tier 3 Canal. Currently has 38 Rogo points and plans for an exceptional home, dock, and lift. Building Permit application is finalized and approved. 3/2 elevated home that is a certified green build. Just need Rogo award. Great Open water ocean

    Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

    27463 Antigua Rd, Ramrod Key, FL 33042
  • /43

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft

    30461 Poinciana Rd, Big Pine Key, FL 33043

    Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features a vaulted ceiling, brand new mini split air condition units and plenty of windows and French doors that allow light to fill the home. The large primary bedroom has a screened in porch off the back perfect for relaxing. Also, in the rear of the home is an attached, private

    Francesca Santiago Keller Williams Realty Professionals (KW)

    30461 Poinciana Rd, Big Pine Key, FL 33043
  • /12

    $599,000

    • Land
    • 0.27 Acre
    • $2,183,468 per Acre

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042

    **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

    Daiane Sardinas Carvalho Centennial Realty Group, LLC

    16841 Driftwood Ln, Sugarloaf Shores, FL 33042
  • /20

    $205,000

    • Land

    5555 College Rd Unit KF7, Key West, FL 33040

    Sunset Marina KINGFISH PIER 7 Deeded Slip, Title to the boat slip is Fee Simple. Verified commercial and residential use. Rare opportunity Prime location on the Marina Side directly beside the ship store. This Wet boat slip has a state of the art concrete floating dock on the live aboard side, this slip will accommodate up to a 35' boat which is 30' x 15'8'' with 6' controlled depth. Being that

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

    5555 College Rd Unit KF7, Key West, FL 33040
  • /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
  • /28

    $1,950,000

    • 3 Beds
    • 3 Baths
    • 1,797 Sq Ft

    860 Lagoon Dr, Summerland Key, FL 33042

    This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

    Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

    860 Lagoon Dr, Summerland Key, FL 33042
  • /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
  • /45

    $4,250,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,103 Sq Ft

    231 E Shore Dr Unit 1, Key West, FL 33040

    Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5

    Stephanie Muzzillo Serhant

    231 E Shore Dr Unit 1, Key West, FL 33040
  • /45

    $1,849,000

    • 3 Beds
    • 2 Baths
    • 1,309 Sq Ft

    1613 Rose St, Key West, FL 33040

    Welcome to your beachside paradise! Situated on Rose Street, in the desirable Beachside district of Key West, just a couple blocks from both Smathers Beach & Higgs Beach, this recently renovated one-story home provides a magical setting for those looking to live on the island in style! Designed with ultimate comfort and privacy in mind, this home features two spacious living areas, a desirable

    Rodney Culiver Last Key Realty, Inc (KW)

    1613 Rose St, Key West, FL 33040
  • /65

    $1,099,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
  • /47

    $2,999,999

    • 2 Beds
    • 4 Baths
    • 1,596 Sq Ft

    405 Petronia St, Key West, FL 33040

    Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

    Bobby Coe RE/MAX Keys Connection (KW)

    405 Petronia St, Key West, FL 33040
  • /25

    $699,000

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

    317 Cross St, Key West, FL 33040

    This 3 bedroom, 2 bathroom home is a great family home or investment opportunity; situated on a large 5625 sf corner lot within walking distance of the neighborhood park. It is currently configured with the main section having 2 bedrooms, living area, kitchen and a full bathroom plus an adjoining guest section that has it's own living area, kitchen, bedroom, full bathroom and it's own separate

    Rob Severin Rob Severin Real Estate Co

    317 Cross St, Key West, FL 33040
  • /22

    $659,000

    • 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
  • /18

    $119,000

    • 1 Bed
    • 1 Bath
    • 357 Sq Ft

    38801 Overseas Hwy Unit 153, Big Pine Key, FL 33043

    This is your chance to own your very own vacation cottage at a top rated Florida Keys RV resort. This cottage is fully set-up onsite and comes fully furnished. The Island Cottage features a fully equipped kitchenette, LED SmartTVs, central air conditioning, and a full bath. Enjoy your island view of paradise from your covered porch. You'll have access to top notch amenities and activities: Scuba

    Michael Weber

    38801 Overseas Hwy Unit 153, Big Pine Key, FL 33043
  • /36

    $1,189,000

    • 4 Beds
    • 3 Baths
    • 1,896 Sq Ft

    31569 Avenue D, Big Pine Key, FL 33043

    Welcome to your Florida Keys fortress! This newly constructed 4-bedroom, 3-bath concrete home offers unmatched durability, modern finishes, and gorgeous open water views from porches on both levels. Just a few hundred feet from deep water boating, this property provides the closest boat access to the world-famous Bahia Honda Bridge of any neighborhood in the Lower Keys, navigating to the ocean or

    Austin Kimbler Expert Realty LLC (HQ)

    31569 Avenue D, Big Pine Key, FL 33043

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