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$18,500,000
Key West
Filer Boyle Subdivision   - MM: 1.00
5 Bed, 5 Baths, 4,008 SqFt Days Listed: 231
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

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!

$7,999,000
Key West
Old Town Unrecord   - MM: 1.00
11 Bed, 11 Baths, 4,295 SqFt Days Listed: 265
-5.89% ($501,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$7,950,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,998 SqFt Days Listed: 361
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$6,995,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,173 SqFt Days Listed: 114
-3.50% ($254,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$6,995,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 4,279 SqFt Days Listed: 66
-6.73% ($505,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Prime Old Town Key West Gem - 326 Caroline St. Welcome to 326 Caroline Street, a historic estate in the heart of Old Town Key West. Located in the prestigious Truman Annex and directly across the street from the Truman Little White House, this property offers a rare blend of history, privacy, and tranquility just steps from Duval Street. Set on over 13,000 square feet of lush tropical landscaping, the estate includes a three-bedroom, three-bathroom main house and a two-story guesthouse connected by a covered deck. Enjoy hardwood floors, crown moldings, and an updated kitchen with custom cabinetry and KitchenAid appliances, top of the line Mitsubishi Central HVAC system and many other luxurious custom finishes. The property features a large garage for two vehicles, plus gated parking for two more--an exceptional find in Old Town. Originally located across the street, the main home was moved to its corner location in 1990, adding a unique historical touch.With spacious decks, sunshine on your pool and lush landscaping, this serene retreat is perfect for relaxing or entertaining. Dont miss this opportunity to own a piece of Key West paradise--schedule your private showing today!

$6,895,000
Key West
Sunset Key   - MM: 0.00
4 Bed, 4 Baths, 2,558 SqFt Days Listed: 66
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

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.

$6,700,000
Key West
Old Town Unrecord   - MM: 1.00
6 Bed, 6 Baths, 3,443 SqFt Days Listed: 37
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$6,500,000
Key West
The Foundry   - MM: 1.00
3 Bed, 3 Baths, 4,200 SqFt Days Listed: 342
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This distinguished estate, erected in 1904, proudly stands as the revered historic landmark known as Building 11, The Smithery within the esteemed confines of the Truman Annex--an exclusive gated community formerly part of the United States Naval Station, Key West. This exceptional offering epitomizes expert restoration, boasting lofty ceilings, majestic 22 brick exterior walls, and imposing wooden beams that seamlessly marry historic allure with contemporary finesse upon an expansive, idyllic plot. A quintet of majestic arched French doors adorns the facade, beckoning vistas of the verdant tropical surroundings. The ground level unfolds with sweeping travertine floors adorned with artisanal fixtures, housing a gracious great room with a bespoke bar, a gourmet kitchen, an elegant dining area, and additional living space. Nestled on this level, a guest suite seamlessly extends to the inviting poolside retreat, graced with a cascading waterfall and tranquil stone deck. Ascending to the upper level reveals an enchanting realm, where the primary and guest suites are interconnected by a captivating gallery bridge, each enveloped in luxurious amenities and adorned with custom built-ins, sumptuous hardwood flooring, and exquisite lighting fixtures. Lavish bathrooms, featuring opulent upgrades, adorn both wings, ensuring unparalleled comfort and refinement. Exquisitely maintained, this abode has garnered the admiration of a select few, its architectural brilliance cherished by those fortunate enough to experience its splendor. The expansive carport, a newly fashioned storage enclave echoing the original architectural charm--further enhances the allure of this hidden treasure. Nestled amidst illustrious neighbors, including Trumans Little White House this jewel epitomizes one of the most coveted addresses within the Florida Keys, offering a lifestyle of unrivaled sophistication and allure.

$6,150,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,342 SqFt Days Listed: 114
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Historic Luxury Meets Modern Elegance in Old Town Key West!Step into a piece of Key West history with this remarkable home built in 1869 by Robert Watson, now completely reimagined as a luxury retreat while preserving its historic charm. Located on iconic lower Simonton Street, X Flood, this 6,608 sq ft sanctuary boasts 3,342 sq ft of living space with 5 en-suite bedrooms, including two primary suites, each with its own unique luxuries. The 1st-floor suite offers a jetted shower with chromotherapy lighting, while the 2nd-floor suite includes a private porch and soaking tub.This estate blends old-world craftsmanship with modern amenities, featuring a gourmet chefs kitchen with Viking, KitchenAid, and Bosch appliances, plus a separate dining room with a private porch--perfect for morning coffee. The spacious great room, with 20-foot retractable doors, opens directly to the outdoor oasis where youll find an 18,000-gallon saltwater pool with swim-up bar, waterfall, and color LED lighting, plus a separate spa for ultimate relaxation.The detached guest house with kitchenette is ideal for visitors or extended family. Entertain outdoors with the fully equipped outdoor kitchen and al-fresco dining areas surrounded by lush tropical landscaping for complete privacy.Historic touches, including restored windows, doors, and custom woodwork, blend seamlessly with modern upgrades like a whole-house Generac generator, hurricane shutters, and advanced smart-home technology--control everything from pool settings to security from your phone.With gated parking for 3 cars, EV charging station, and just steps from the best dining and entertainment in Key West, this estate offers the rare opportunity to own a piece of history while enjoying unparalleled luxury. Dont miss out on a home that offers everything youve been searching for, and more! Step into Luxury! For the Discerning Few: Arrange Your Exclusive Private Showing Today!Video Tour https://tinyurl.com/522Simon

$5,850,000
Key West
Old Town Unlisted   - MM: 1.00
6 Bed, 6 Baths, 3,209 SqFt Days Listed: 153
-2.50% ($149,999) 2 Price Changes : Last Change 8 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Introducing 522 Elizabeth Street, a fully reimagined Key West masterpiece offering 6 bedrooms, 6.5 bathrooms, and over 3,000 sq ft of luxurious living space. Just 2 blocks from vibrant Duval Street, this rare gem combines historic charm with modern sophistication. The home has been meticulously rebuilt with all-new concrete footings, structural lumber, impact windows, copper gutters, a brand-new roof, two 5-ton A/C units, dual washers/dryers, and much more. Inside, the layout has been entirely redesigned with award-winning David L. Smith Interiors curating a stunning decor.Upon entering the home, youre greeted by elegant three-piece base and crown molding- setting the tone for the homes attention to detail. The first floor features a spacious primary ensuite bedroom with a custom walk-in closet, Italian glass tile accents, a floating double vanity, a walk-in shower, and a fully automated Kohler toilet. A beautifully appointed living room leads to an additional ensuite bedroom and the show-stopping gourmet kitchen. This culinary space boasts Viking appliances, quartz counters, and a massive waterfall island perfect for entertaining.Step outside to your private oasis, featuring a new Gunite pool with a large sun ledge and 4 custom waterfalls cascading from a glass mosaic wall. The professionally landscaped yard is complete with mature trees and a 6-zone irrigation system. The expansive IPE deck with a covered outdoor dining area is the ideal backdrop for island living and entertaining. Upstairs, the home offers another primary ensuite bedroom with spiral stairs that lead to loft storage. The 3 additional ensuite bedrooms each offer their own unique charm- some with treetop views, Italian porcelain, or private balcony.This residence epitomizes luxurious island living with two off-street parking spaces and a carport for added convenience.Dont miss the opportunity to make it yours- schedule a private showing today!

$5,750,000
Key West
Hilton Haven Sec 2 A   - MM: 2.00
5 Bed, 5 Baths, 3,597 SqFt Days Listed: 125
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

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

$5,695,000
Key West
W C Maloney Diagram   - MM: 2.00
6 Bed, 6 Baths, 4,182 SqFt Days Listed: 68
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to the Majesty of the Meadows. This exquisite estate is truly an historic masterpiece that blends timeless charm with modern luxury in one of Key Wests most coveted neighborhoods. Nestled on a rare 11,200 sq. ft. lot, the property offers over 4,180 sq. ft. of living space, including a detached one-bedroom guest quarters, creating the ideal balance of comfort, style, and functionality.The grounds are a serene tropical oasis surrounded by meticulously designed landscape featuring mature native foliage and aromatic tropical plants, all irrigated by natural well water. At the heart of the backyard lies an expansive saltwater pool and spa with a cascading waterfall, framed by historic Key West curbstones. Ipe wood decking and a spacious patio enhance the estates natural beauty and functionality. A lighted gazebo with a built-in grill and cabinetry provides the perfect setting for outdoor dining and entertaining.Inside, the homes historic elegance is unmistakable. Soaring 14-foot coffered ceilings, intricate crown molding, and wide plank wood floors reflect masterful craftsmanship. The gourmet kitchen is a chefs dream, overlooking the pool and outdoor spaces. It features a six-burner Viking stove, dual ovens, and a 1,000-bottle wine cellar--ideal for both intimate gatherings and formal entertaining.Privacy and tranquility abound throughout the estate. The separate guest quarters offers a secluded retreat for visitors, while a luxurious steam room elevates relaxation. Every detail has been thoughtfully curated to preserve the homes historic character while enhancing modern comfort.Ideally located in a prime historic neighborhood, the estate is within walking distance of the vibrant Historic Seaport, Key West Bight Marina, the Atlantic beaches, and Duval Street. This legacy property is more than a home--its a true piece of Key Wests history in a setting that simply cannot be duplicated

$5,399,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 3,026 SqFt Days Listed: 451
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$5,250,000
Key West
Old Town Unlisted   - MM: 1.00
5 Bed, 5 Baths, 3,434 SqFt Days Listed: 66
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$5,150,000
Key West
Kamien Plat #2   - MM: 2.00
4 Bed, 4 Baths, 3,154 SqFt Days Listed: 6
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$4,995,000
Key West
Martello Towers   - MM: 1.00
4 Bed, 4 Baths, 2,064 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This Casa Marina estate home was built for the Edward Strunk family and has had only two owners. The current owners restored and upgraded the home using the finest materials and incredible attention to detail. The four bedroom, two and a half home sits on an expansive 12,000+ sq. ft. corner lot in the most desirable Casa Marina area. One of the four bedrooms is now a den that opens to a large sun porch with panoramic island views. One enters the home through the sun room which, like the rest of the first floor has 14 ft. ceilings. Upstairs the ceilings are 12. The Mahogany interior doors and millwork are all custom by Hansen & Bringle. The exterior windows and doors are also custom Mahagony and are hurricane rated. The first floor includes a living room with a fireplace, an office with powder room, a spacious dining room and a top-of-the-line gourmet kitchen with incredible appliances and details. The restoration included new wiring, plumbing, a new hurricane rated roof on the main house and the garage, a whole house generator with buried propane tank, new hardware, refurbished Cuban tile floors, and a 7,000 gallon cistern connected to the copper gutter system for irrigation Theres also Cat 5 & 6 wiring, and a McIntosh audio system throughout the house. The amazing grounds are completely fenced and surrounded by lush native landscaping. A large outbuilding is presently used for storage. An electronic gate opens to the two-car garage and parking area. This incredible property is a rare find.

$4,995,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 3,015 SqFt Days Listed: 261
-3.94% ($205,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to 524 Frances Street, where sophisticated style meets Old Town charm. Rarely does an architectural gem such as this property become available for purchase. This iconic home has been completely and professionally updated, including impact windows and doors. Enter the property through a white picket fence and ascend the front porch steps with views of Frances Street. Just beyond the historic, glass-etched front door is a welcoming foyer; prepare to be awestruck by the style and craftsmanship of the home. Situated on a double lot, this 4 bedroom/3.5 bathroom property is the ultimate Key West escape, with Brazilian Cherry wood floors, crown moulding and top of the line finishes. The first floor offers three bedrooms. Two spacious guest bedrooms, each with Queen-sized bed and custom closets, are adjoined by a shared bathroom with standup shower. Opposite side of these guest bedrooms is a formal living room with double sliding pocket doors leading into a formal dining room with access to a side porch. Beyond the dining room is a gourmet kitchen that overlooks an additional living room with wall-to-wall glass doors. A hallway leads to a separate wing inviting you to one of two Primary Suites at this property (the second Primary Suite is upstairs). With a King-sized four-posted bed, and ensuite bathroom with dual headed shower and soaking tub. Upstairs is the second Primary Suite with open-concept layout, no need to ever leave this room, as the second floor is only for this room. A beautiful soaking tub to just let all your trouble slip away, with a double stand-up shower. A wet bar with wine fridge serves as the perfect coffee bar for your morning cup, or an evening drink on your private sundeck overlooking the backyard. The private backyard offers a huge in-ground lap pool, outdoor shower, Ipe wood decking, & outdoor dining gazebo with built-in Wolf grill. This home comes with two brick-paved, gated driveways. Offered turn key with a very small exclusion list.

$4,950,000
Key West
Old Town Unlisted   - MM: 1.00
4 Bed, 4 Baths, 2,985 SqFt Days Listed: 31
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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. ***

$4,900,000
Key West
Old Town Unrecord   - MM: 1.00
4 Bed, 4 Baths, 2,716 SqFt Days Listed: 13
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$4,850,000
Key West
Old Town Unrecord   - MM: 1.00
5 Bed, 5 Baths, 3,148 SqFt Days Listed: 82
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

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.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 02-22-2025.
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