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.

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.

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.

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!

Located on iconic Millionaires Row in the heart of Old Town Key West, this extraordinary estate offers a rare combination of timeless charm, modern luxury, and unmatched privacy. With two stunning homes both with impact rated windows and doors on one oversized lot, this tropical compound is an exceptional opportunity to own one of the most unique properties in Key West.The main residence, a beautifully restored historic home, features four ensuite bedrooms, including a flexible downstairs suite that doubles as a den or office. Classic Dade County pine walls, high ceilings, and an abundance of natural light create a warm yet sophisticated atmosphere. The gourmet kitchen is outfitted with custom cabinetry, sculpted marble countertops, Sub-Zero and Wolf appliances, and complete with a built-in wine cooler and coffee center. A spacious 12-person dining room and wraparound porch invite relaxed island entertaining with elegant flair.The newly built guest house offers two additional ensuite bedrooms, soaring vaulted ceilings, exposed beams, a cozy loft, and a fully equipped kitchen with Miele appliances and stunning artisan tile. Ideal for hosting guests or enjoying extended family stays in total comfort and style.At the center of the estate lies a tropical paradise, designed by renowned landscape architect Craig Reynolds. A sparkling saline pool, cascading waterfall, outdoor shower, and private half bath make this backyard feel like your own private resort.With reclaimed river wood floors, rare off-street parking for two, every inch of this property has been crafted for beauty, durability, and ease of island living.1109 Fleming Street isnt just a home--its a rare slice of paradise in the best location Key West has to offer.

Property is being sold with MLS #614840This waterfront home on a canal in Key West is ready for your creative touch! With 3 bedrooms, 2 bathrooms, a large 9794 sqft lot and there is plenty of room for the boating enthusiasts. It has a large in ground pool and outdoor fire pit area. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.**

Property is being sold with MLS #614841This 3 bedroom 3 bathroom home is located on Riviera canal in Key West. It sits on a 10,000+sqft lot, has a newer pool, outdoor kitchen, 24,000lb boat lift, and outdoor shower. There is plenty of parking, air-conditioned storage and large patio for outdoor entertainment. With its original cuban tile and vaulted ceilings if offers a charming old Key West vibe. **You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase of both homes located at 3608 & 3612 Sunrise Drive.Make this a large family compound or reconfigure to one large estate. The possibilities are endless.**

3608 Sunrise Drive & 3612 Sunrise Drive are located next door to each on Riviera canal in Key West. You have the opportunity to own over 20,000sqft of canal frontage in Key West with the purchase or both homes. Make this a large family compound or reconfigure to one large estate. The possibilities are endless.See MLS#s 614840 & 614841 for more photos and property details.

Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12 ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chefs dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views perfect for outdoor lounging. Two charming, detached guest houses each with full baths and one offering a living room and kitchenette allows secluded spaces for all to enjoy. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill that provides the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear ocean, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Dont miss the opportunity to be able to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent.

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

Welcome to 3300 Riviera Drive--an exceptional, turn-key, waterfront, residential estate featuring 4 bedrooms and 4.5 bathrooms. Nestled on three lots in a serene enclave just minutes from Old Town, this meticulously maintained property features 3,577 Sq. Ft. of living space and redefines Key West luxury, comfort and convenience. Step inside to discover an expansive open-concept living space bathed in natural light, with elegant finishes that include custom cabinetry, granite counters and hardwood floors. The gourmet remodeled kitchen, complete with high-end appliances including two dishwashers and a generous island, flows effortlessly into a spacious great room--ideal for entertaining. Wall to wall impact-rated sliders lend to an indoor/outdoor feel throughout the space, and lead to an expansive outdoor living area that overlooks the pristinely landscaped, resort-like grounds. Retreat to the primary suite, a private sanctuary featuring serene water views, wrap-around balcony, a spa-inspired bath with a steam shower and ample, two walk-in, closet space. Additional bedrooms, all with ensuite bathrooms, offer flexibility for guests, home office, or fitness needs. A gracious guest house, one bedroom and one bathroom, is located above the two car garage which gives your guests total privacy.Outdoors, lush tropical landscaping surrounds a stunning pool and patio, creating a peaceful ambiance with sunset views over the canal. A private sea-wall with boat lift offers direct access to open water -- perfect for boating enthusiasts. Additionally, an electric gate leads to a climate-controlled two-car garage, ideal for storing vehicles. A two car carport is also located just out side of the garage, you can park four vehicles that will be covered from the elements, you just cant find this in Key West.Built with security and peace of mind in mind, the concrete property is elevated and includes impact-rated windows and doors throughout. Call today!

Nestled in the storied heart of Old Town Key West, this grand estate is a masterpiece of luxury & history. Spanning a majestic 8,397 sq. ft. lot, the property at 1014 Southard St. Invites you into a world where classic charm meets modern elegance.With 4 bedrooms and 3.5 Baths and over 3,000 sq. ft. of interior space across two separate structures, enjoy an unparalleled gem in one of Key Wests most coveted neighborhoods. Constructed in 1899 by renowned William Cash, this estate radiates a colonial grandeur, enriched with a cranberry cut -glass transom sophisticated dark green shutters & classic french doors.The current owners have meticulously restored the property using only the finest selection of materials, from river reclaimed old growth hardwood floors in living room and hallways, to stunning Blue Castle Limestone in master suite and kitchen and continued through the magnificent garden and pool to the separate guest quarters. Smarthome features have been introduced, including Zigbee Lights integrated with Home assistant, sensor mixs, Ecobee Thermostats, 6 Node Eero Mesh Network, Abode Alarm Systems & Nest protect Sensors.The master suite located on the ground level is a peaceful sanctuary with private library & den, exceptional ensuite, three sets of French doors and opens out to the magnificent saltwater pool and tropical landscaped garden. Two additional bedrooms on second floor in main house share a bath and private veranda.Separate cottage provides exceptional guest quarters and can be accessed from Roberts Lane for additional convenience. Stunning post & beam cathedral ceilings, Limestone floor, built-in bar and kitchenette and spacious living room offers excellent space for entertaining with deck and pool access.Additional features include, One off-street parking spot, equipped with Tesla charging station & new 2023 generator powered by dual propane tanks.Welcome to Key West Living at its finest.

Discover the charm of Casa Grande, a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles.Designed for entertaining, Casa Grande features an expansive open floor plan that seamlessly connects the spacious living room to the kitchen, creating the perfect setting for gatherings. Step outside to enjoy one of the largest private pools on the island, surrounded by a beautifully landscaped backyard that includes a half bath and outdoor shower--ideal for lounging, dining, or barbecuing in complete privacy.This remarkable home boasts five well-appointed bedrooms and six bathrooms. One suite includes a kitchenette and separate living area. You can walk or bike to local attractions, dining, shopping, and beaches.Dont miss out on this incredible opportunity to own a transient rental property in Key West!

Discover the epitome of island elegance with this stunning Spanish Mediterranean-style home situated on an expansive 10,000+ sq. ft. corner lot in the heart of Key West. This exceptional property offers over 3,100 sq. ft. of living space, featuring 4 spacious bedrooms and 3 full bathrooms. Step inside to find a light-filled living and dining area that seamlessly opens to a lush tropical oasis, complete with mature landscaping and an oversized heated saltwater pool--an entertainers dream. The chef-inspired kitchen is designed for those who love to cook, offering ample space and functionality. The first-floor primary suite is a true retreat, boasting an ensuite bathroom and charming French doors that lead to the expansive garden and pool area. Upstairs, youll find 3 additional generously-sized bedrooms and a full bath, perfect for family and guests. Adding to the homes appeal is a carport providing off-street parking for 2, a whole-home generator for peace of mind, and an ambiance that perfectly balances indoor and outdoor living. Experience the ultimate Key West lifestyle in this one-of-a-kind Key West residence!

Discover the perfect blend of historic charm and modern elegance in this fully renovated and expanded Key West home, tucked away on a picturesque lane. Offering 4 bedrooms, 4.5 bathrooms, and 2,985 square feet of thoughtfully designed living space, this property is a rare find. The light-filled interiors feature soaring cathedral ceilings and walls adorned with rich Dade County pine, seamlessly blending classic character with contemporary upgrades. Engineered wood floors flow throughout, while the downstairs master suite boasts a spa-like bathroom with marble floors and travertine walls. Entertain effortlessly with high-end Miele appliances in the gourmet kitchen and a custom bar complete with an icemaker. The home opens to a private outdoor oasis, where an ipe deck surrounds a heated and chilled saltwater pool. Two outdoor showers complete the tropical lifestyle experience. This 4,616-square-foot lot also includes two off-street parking spaces, 2 custom stair cases, Cummins diesel generator, impact glass windows for peace of mind, and a durable metal shingle roof. Additional features include two central A/C systems and the finest materials throughout, making this home as functional as it is beautiful. Whether relaxing in the elegance of your home or enjoying the vibrant lifestyle in Old Town Key West, this property is the best location for it all. Home is expected to be completed in the next 4-5 weeks. ***Images are renderings and are approximations of the finished product, not representations. ***

Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a wonderful, covered porch.Discover the timeless elegance of its living room, dining room, and a fantastic den with an open kitchen floorplan complete with Viking appliances. Step outside to enjoy your covered patio, private pool, and inviting outdoor living areas surrounded by lush tropical foliage. Driveway for two cars with one covered parking space.Perfectly situated for exploring Key Wests vibrant attractions, this home offers a rare opportunity to own a piece of island history while indulging in the ultimate Key West luxury lifestyle.

Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and vacationers alike. Situated nearby the iconic Duval Street and the tranquil expanse of Fort Zachary Taylor State Park, this home epitomizes the quintessential Key West lifestyle. Upon entering, youre greeted by an inviting main living area, adorned with French doors that effortlessly blur the lines between indoor and outdoor living. A sun-drenched sunroom, encased in glass doors, is the perfect setting for relaxation or entertainment year-round. Additional living spaces abound, including a bright and airy sitting room. The main floor is thoughtfully appointed with a convenient full bathroom, ensuring comfort and convenience for guests. The 2nd level offers 4 bedrooms and 3 full baths and the ensuite 3rd floor is great for guest . Included is a Truman Annex transient rental license allowing for weekly rentals, 202 Admirals Lane presents a lucrative investment opportunity as a successful vacation rental. Rare for Key West, this home features a coveted 2-car garage, providing secure parking and storage, a coveted amenity for sure. Offered turnkey, the residence comes complete with all furnishings and future reservations, promising a seamless transition for discerning buyers or investors seeking the ultimate Key West retreat.

3741 Eagle Avenue - A Masterpiece of Coastal Luxury This stunning 3 bedroom, 3.5 bath fully furnished residence on a generous 10,800 SF lot offers unparalleled coastal elegance at an impressive elevation of 10.5ft. The new concrete construction features an open concept with cathedral ceilings and large impact sliding doors throughout. Premium materials, high-end appliances, and thoughtful layout create both functionality and sophistication.Two en-suite primary bedrooms, both upstairs and downstairs, open to the outdoors. The property includes a fully equipped guest cottage featuring sliding doors that offer stunning views. The grounds, masterfully designed by Craig Reynolds, showcase lush tropical landscaping, covered patios all surrounding a heated/chilled pool with shelf seating and a distinctive coral rock outdoor shower which adds a luxurious touch. The garage provides 481 square foot for parking and ample storage.Security and comfort are ensured with a whole-house Generac generator, standing seam metal roof, impact windows and doors. Every detail of this turnkey residence has been executed to perfection, creating an extraordinary Keys retreat.

Built in 1943, and Originally owned within the Singleton Estate, 1319 Olivia St. is more than just a home, its a legacy, embodying beauty, elegance and history at every turn.Ideally located within the heart of the meadows, this Historic Grand Dame is one of the most impressive homes in Key West today, known for its stunning architecture and superb craftsmanship.Both kitchen and living rooms flow out to an abundant outdoor area, featuring a large covered Gazebo, saltwater pool, deck and impressive garden allowing a wonderful setting for large scale entertaining or intimate gatherings. Meandering gardens with mature fruit trees and dozens of blooming orchids with wrap around porches and roof-top decks offer many ways to enjoy the home.With 5 bedrooms and three full Bathrooms, three floors and a new master suite with stunning marble bathroom, Olivia has room for a large family with 3300 Sq Ft. interior space and situated on an enviable sizable 7800 sq ft. lot.Dade County Pine floors and walls throughout, wrap-around porches, french doors, marble bathrooms, elevated and built to last, this home is sure to leave a lasting impression with a longing for more.Permanent carport offers covered off street parking with additional street parking available. A must see for any buyer looking for the ultimate Key West home.

This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and opens up into the great room showcasing living, dining and kitchen space with soaring 20 foot ceiling and skylights. The hallway, kitchen and dining room walls are finished with Shiplap and all the floors throughout the home are a stunning custom stained Heart Pine reminiscent of the historic floors of Key West homes. The kitchen boasts a large island with sink & electrical connections as well as seating for 6; a wet bar, two pantries and a full Viking professional package round out the space. There is also a laundry room with a 1/2 bath that opens onto the back deck right next to the 15X8 pool with water feature. The Shiplap continues up the stairs to the interior balcony overlooking the great room and there are 2 additional bedrooms each with their own private baths and walk-in closets as well as a massive storage area that wraps an entire half of the second floor and is a finished and fully air conditioned space. All exterior doors are Mahogany impact with impact transoms and all windows are impact as well. Also, a 250 gallon propane tank is buried, hooked up to the gas stove & on demand water heater and is generator ready. There is 1 off street parking spot with electric gate. The home has been professionally landscaped and professionally furnished.