Lower Keys Real Estate for Sale, Homes and Condos in the Florida Keys

With its special transient license, The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. Whats interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in Truman Annex and is being offered as the ultimate turnkey property. There are a total of 5 bedrooms and 4 bathrooms: 3 bedrooms and 2 bathrooms in the main house and two 1 bedroom, 1 bathroom private cottages. This expansive property includes a covered seating and dining area under the gazebo, which overlooks the resort-style heated pool and outdoor kitchen. The value of this home is not only its privacy with exotic landscaping, but its ability to generate income when you are away. Schedule your private showing of The Royal Compound to appreciate the uniqueness of this one-of-a-kind property!

Nestled in the heart of Key Wests historic district, 616 Eaton Street is a testament to quality, timeless beauty, and refined living. This single-family residence was constructed in 1911 and painstakingly renovated and reimagined over the last few years culminating in 2024 with the spectacular like new home. Most hidden from the Street, it exudes classic Key West architecture blended with modern elegant designs. With 5 bedrooms, 5 full baths & 2 half baths, the home spans 4,000sf on a large 12,478sf lot. The 2-story primary home contains the living room, dining room, kitchen, 2 office spaces/dens, one of which could be a bedroom if desired, 2 half baths on the living level & a spectacular 2nd floor primary suite with office/ laundry & an enormous outside covered deck for private lounging. Thoughtful renovations include a stunning glass wall that opens between the outdoor dining pavilion & the top of the line kitchen w/ functional pass-through windows from the kitchen to the pool area. Reclaimed hardwood floors & tall ceilings ensure a perfect balance of historical character & contemporary functionality. The substantial living area, accented by natural light, offers a warm & inviting atmosphere & the gorgeous central pool w/ a water feature creates a stunning outdoor oasis & is perfect for entertaining. Surrounding the pool & outdoor dining pavilion are 2 phenomenal guest houses, housing a total of 4BD/4BA plus a full 1,512sf attic w/ staircase that is built for storage. Lots of off-street parking is offered along w/ a carport & small garage. Everything is new, from the hard wood floors & bathrooms to the salt generated heated pool & generator. This property is a rare offering that combines historical significance, luxurious living & an unbeatable location in one of Key Wests most coveted neighborhoods. Located in the X flood zone just 2 blocks from both Duval St. & the Historic Seaport, it is walkable to all the wonderful restaurants, galleries & shops.

Exclusive opportunity to own one of the largest TRANSIENTLY licensed properties in Old Town Key West. 11 Br, 11Ba, 2 pools, 2 transient licenses, and off street parking for 4+ vehicles. The Watson House is Located centrally on Key Wests most iconic street and only 1 block off Duval street. The Grand Estate is comprised of a 7 Bedroom Mansion and a 4 bedroom Villa. Each home offering a private pool.The mansion was refitted by a local designer in July 2022, including fresh paint and new furniture. Upon entering the mansion you will be greeted with 12 foot soaring ceilings, 2 first floor guest rooms with bath, parlor, living room, dining room and kitchen. The kitchen opens up to a private pool with decking and lounge chairs. A large family style outdoor table is provided for dining al fresco. Heading back inside you will take the Victorian staircase to the second floor. On the second floor you will find 4 bedrooms with en suite baths. The front primary suite offers a private balcony overlooking Simonton Street. A secondary balcony is provided for the rear primary suite overlooking the pool. Take the spiral staircase to the third floor and you will discover a large third floor private suite. Bright and airy the suite provides a living room, wet bar and balcony overlooking the pool. All three floors can also be accessed by exterior and interior staircases. Going back into the parking area, you will take a side entrance to the villa. The villa was renovated to the studs in 2014 with modern and sleek finishes. The villa offers 4 bedrooms and 4 baths, full kitchen, living room, private pool and outdoor bar. The 2 transient licenses give versatility for the property to be rented as an 11 bedroom and 11 bath estate or rented separately as a 7br main house and 4br villa. There are few large estates in Key West, which gives way to its popularity and advance bookings.

Welcome to Cypress Point, an exceptional and highly private oceanfront estate on almost 1 acre on Cudjoe Key, where luxury and coastal beauty seamlessly blend. Behind a private electric gate, this 7-Bedroom, 6-Bath home, designed by Design Source, boasts the finest finishes and a wealth of amenities, including an oceanfront Pool, outdoor Theater, 6-hole Golf Green, Bocci Ball and a 7-car Garage--each detail crafted for ultimate enjoyment. Upon entering, youre greeted by rough-cut coral flooring, 8-foot doors, and an expansive Great Room that offers sweeping ocean views. The gourmet Kitchen is perfect for entertaining, featuring a Viking stove and microwave, refrigerator drawers, two farm sinks, quartz countertops, an ice maker, wine cooler, wet bar, and beverage cooler with Subzero refrigerator & freezer in the adjacent Butlers Pantry. A pop-up TV allows for both Kitchen and Living Room viewing. The dining area is enhanced with wide water views and summer kitchen for table side gilling. Also on the main level youll find 3 ensuite Guest Suites, 2 with gorgeous ocean views plus a 2 Bedroom Family Suite with Bath and veranda. The third floor showcases the luxurious Primary Suite, complete with endless ocean views, a private balcony, drop-down screen projector, morning kitchen, walk-in closet, and a spa-like ensuite with a massive shower, linen closet, and a drop down mirror with TV offering stunning ocean views or your favorite morning show. A 5th Guest Suite with a private balcony completes this level.For boating enthusiasts, the estate offers deep draft dockage with a 40K and 17K boat lift, two davits, and a 6K lb swim platform. Enjoy breathtaking views of the sunrise and sunset over the open ocean, channel, and canal. This stunning retreat is equipped with impact doors and windows, electric blinds, a whole-house generator, two 1,000-gallon propane tanks and laundry chutes. Built-in speakers throughout the property ensure an unforgettable ambiance.

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

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 9 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!