Ahoy, dreamers and visionaries! Step into the pages of Key West history with this captivating waterfront property, whispering tales of Old Town charm from its perch on the edge of paradise.Built prior to 1912, and lovingly held by the same family for over a century, this sprawling 15,609 square foot lot, zoned General Commercial, awaits your masterpiece. Picture a bustling restaurant serving up fresh seafood and island vibes, a charming boutique hotel nestled amidst tropical gardens, or a tranquil marina where sailboats sway in the gentle breeze. The possibilities are as endless as the ocean views.This unique property boasts a legal five-unit multi-family configuration, including a historic main house and a separate cottage. The main house features four units with a total of 5 bedrooms and 4 bathrooms, perfect for accommodating guests or creating a vibrant community. Meanwhile, the charming cottage, with its 2 bedrooms and 1 bathroom, offers a private oasis for rest and relaxation.Nestled beside Garrison Bight, a stones throw from Bayview Park and Tennis Courts, and just a bike ride away from some of the islands most stunning beaches and attractions, this location is a true Key West treasure.Now, for the fine print: the property is currently tenant-occupied, so please allow 48 hours notice for viewings (and you might not be able to see all units in one go). Savvy investors should verify restoration and development rights to unlock the full potential of this historic gem.Ready to set sail on a new adventure? This once-in-a-lifetime Key West investment is calling your name. Dont miss out on the chance to turn your dreams into reality!

Here is the perfect Sunset Key island getaway home with stunning panoramic Key West Harbor and Gulf views. Lounge by your pool and spa or on your four covered porches with IPE decking while you enjoy the sites of open water where the Gulf meets the Atlantic. This home is in absolute mint condition with an open flow throughout. This 3 bedroom, 3 bath quality home needs nothing more. Elegant and comfortable finishes throughout, hardwood and tile flooring, whole house sound system, central alarm, impact windows and doors, luxurious built in cabinets and plantation shutters provide luxury, security and safety. Bonus features include a detached garage AND an electric cart. Accessible by a 24 hour dedicated ferry this island retreat has it all including a fabulous restaurant in Latitudes, relaxing Spa, private beaches, tennis courts and a fitness center.

Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. A recently sold $3.5M, 4000 sq. ft. home was torn down just to obtain a buildable lot on Hilton Haven. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock while overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75 by 300 bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living rooms custom hand built beamed wood cathedral ceiling and a majestic staircase. The current sunroom, converted into a dining room, features French doors that open to views of the pool and harbor. The expansive deck leads down to the lower entertaining level. The chefs kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to the rear private deck and dock. Completing the first floor are the laundry room, a half-bath, a full bath, and a charming guest bedroom. The sunroom with a wet bar and bathroom provides access to the one car garage, and second staircase leading to the second-floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. https://show.tours/e/4vNFpvG

Experience unparalleled island living on Sunset Key, an exclusive island community located in the heart of Key West Harbor. Accessible 24 hours a day via a dedicated island ferry, this extraordinary home offers the ultimate blend of privacy, luxury, and convenience. All this just a four minute boat ride from the vibrant streets of Key West.This bright and airy 4-bedroom residence is designed to capture breathtaking open ocean views. Large windows bathe the home in natural light, creating an inviting and serene atmosphere. The heart of the home is a fabulous chefs kitchen equipped with top-of-the-line appliances, perfect for creating culinary masterpieces while taking in the views of the sparkling water.Step outside to your beach-front oasis, where you can unwind and enjoy the gentle sea breeze or take in a spectacular sunset over the Gulf of Mexico. On the island, a wealth of world-class amenities awaits, including a gourmet restaurant, a rejuvenating spa, tennis courts, and more, ensuring your every need is met in this tropical paradise.With unparalleled luxury, exceptional views, and exclusive island living, this property offers the perfect retreat in one of the most sought-after destinations in the world.

LUXURY PROPERTY AUCTION: BID 21-31 MARCH. Listed for $18.5M. Starting Bids Expected Between $5M-$8M.Experience unparalleled luxury at 400 South Street, the true Southernmost private residence in the Continental United States. This iconic Key West estate, winter home to esteemed American artist, the late Seward Johnson and his wife, seamlessly blends timeless elegance with modern amenities. The expansive 4,008-square-foot concrete home, situated on a generous lot plus almost one acre of bay bottom, offers five bedrooms and five and a half bathrooms. Upon entering, the formal living room evokes the charm of the Hemingway era, leading to a sunlit Florida room with sliding glass doors that open to a vast outdoor oasis. The primary suite and two guest bedrooms are accessible via an elevator, each opening to a large balcony that provides panoramic views of the Atlantic Ocean. The property boasts a magnificent 50 x 20-foot pool and ample lounging areas, perfect for enjoying ocean breezes and observing local birdlife. With its unique location adjacent to the iconic Southernmost Point buoy and proximity to Key Wests vibrant attractions, this estate offers an unparalleled living experience. Additionally, a coveted transient license allows for nightly rentals, presenting a prime investment opportunity or the option for a lavish private or corporate compound. Designated Multifamily (could accommodate up to 8 residential units) and located in the historic commercial tourist district, the possibilities are vast for a savvy investor. THE Southernmost House is a rare gem in the United States!