Mile Marker 0 - 10 homes for Sale in the Florida Keys Real Estate

Perched on the prestigious Millionaires Row and enveloped by lush tropical greenery, this extraordinary estate boasts two spectacular homes on one expansive lot, offering a rare blend of luxury and exclusivity in Old Town Key West. With six lavish ensuite bedrooms and a serene pool, this property is a true masterpiece.The main residence, meticulously restored, exudes timeless charm while seamlessly integrating modern opulence. Off-street parking for two and a newly constructed guest house elevate this homes grandeur. Upon entry, youll be greeted by an airy living space featuring rich Dade County pine walls that lead to a 12-person dining room, perfect for hosting elegant gatherings.The kitchen is a chefs delight, adorned with bespoke cabinetry, sculpted marble countertops, and state-of-the-art Sub-Zero & Wolf appliances, including a wine cooler and coffee center. Elegant French doors open to a wrap-around porch that blends indoor and outdoor living.On the main floor, a versatile ensuite bedroom can double as a welcoming den. Upstairs, three additional ensuite bedrooms offer breathtaking views of the lush foliage, each adorned with vaulted ceilings and luxurious finishes. The primary suite is a haven of comfort, featuring a retractable window, custom closets, and a lavish bath with timeless marble, dual sinks, and a walk-in shower.The guest house is a marvel of design, with soaring vaulted ceilings, exposed cross beams, and a charming sleeping loft. It includes two ensuite bedrooms, a full kitchen fitted with Miele appliances, custom tiling, and a stylish island for casual dining. Every detail, from the reclaimed river wood floors to the impact windows and doors, exudes luxury. Separating the two homes is a Craig Reynolds-designed tropical paradise, complete with a saline pool and cascading waterfall. The outdoor space is thoughtfully finished with an outdoor shower and private half bath. 1109 Fleming Street is the epitome of refined island living.

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!

Set against the backdrop of one of Key Wests most prestigious streets, this extraordinary estate is a masterpiece of luxury and refinement, offering an unmatched blend of Palm Beach elegance and Key West historical charm. Moments away from waterfront dining, beaches and tennis and pickleball courts, 1101 Casa Marina Court is a home like no other. With a deeply rooted rich history, this rare property spans half a city block, commanding attention with its vast landscaped grounds,sweeping open spaces, and a stunning pool surrounded by an elaborate courtyard with a meditation garden--ideal for grand entertaining or peaceful relaxation.This estate built was by A. Maitland Adams in the early 1930s, who was said to be a partner of Charles Thomas, Ernest Hemingways fishing companion.If the walls could talk at this iconic residence, it would tell you that this is the very home where renowned author Philip Caputo penned Indian Country and where Gregory Peck and Harry Truman played cards in the dining room. The home features five bedrooms and four and a half bathrooms, including a second-story guest apartment that offers privacy and versatility. Recent updates to the home include travertine marble floors, new roof (2025), high-impact windows and doors, a chefs kitchen, and a welcoming fireplace. Located in the coveted and exclusive Casa Marina neighborhood, this home radiates a sense of timeless elegance and modern luxury. Set on nearly half an acre, this corner estate is the finest of its kind in Key West, offering a lifestyle that is nothing short of spectacular.With every detail thoughtfully curated, this property is a rare opportunity to own a piece of island history, sophistication, and unparalleled beauty.

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.