Old Town ~ Unrecord Properties For Sale - Homes and Condos in Old Town ~ Unrecord Key West, Florida

400 Aronovitz Lane is a contemporary island estate that redefines luxury and sophistication right in the heart of Old Town, Key West. Step through the grand entryway into a lounge that greets you with soaring 18 cathedral ceilings, a chic wet bar, elegant granite countertops, and top-notch amenities like a beverage cooler and ice maker. The open-concept living and dining areas are designed for seamless indoor-outdoor living, flowing effortlessly to multiple outdoor spaces. Imagine uninterrupted sight lines through expansive sliding glass doors, revealing a tropical poolside patio. This outdoor oasis features a Craig Reynolds-designed heated pool with a water feature, lush landscaping, ambient lighting, and a refreshing outdoor shower. The first-floor primary bedroom is a haven of relaxation, featuring a stunning en suite bathroom with luxurious marble finishes and an enclosed steam shower. The Chefs Kitchen boasts a large granite island, custom lighting, ample cabinetry, and high-end Sub-Zero and Thermador appliances. Upstairs, the second primary bedroom offers an en suite bathroom, wide plank hardwood floors, and sliding glass doors that open to a covered porch and outdoor shower. A cozy guest bedroom includes a beautiful bathroom with a soaking tub and access to a covered patio. Two additional downstairs guest suites, located just off the kitchen, each feature a sitting room, kitchen, washer/dryer, finished loft space, and a charming porch surrounded by lush landscaping for added privacy. This property is zoned for live-work (Historic Residential Office) and includes an ADA-compliant entrance. Located on a 5,891SF lot in the X-Flood Zone, and just a short walk or bike ride to the world-famous Duval Street, the islands finest restaurants and shopping, Truman Waterfront Park, and Fort Zachary Taylor Beach. 3+ off-street parking spaces! Dont miss out--schedule your private viewing today.

Exquisite Key West Retreat in Truman Annex! Experience the best of Key West with this luxurious retreat in the exclusive gated community of Truman Annex. This Caribbean and British Colonial-inspired home blends sophistication and comfort, making it ideal as an upscale vacation home or investment with rental potential. The transient license allows weekly rentals. The residence spans three levels with 4 bedrooms, 3.5 baths, and high-end features, offering an oasis of elegance in the heart of Key WestStep inside and be in awe with the light-filled open floor plan where tall ceilings and plantation shutters highlight the living, dining and updated kitchen with quartz countertops, a breakfast bar, and premium finishes. The dining area features a stunning shell chandelier, and French doors open to a private back patio with lush landscaping, perfect for entertaining or unwinding under the stars. On the second floor, the primary suite exudes luxury with reeded wallpaper, seagrass wall-to-wall carpet, and a spa-like ensuite bath with gold fixtures, double vanities, and abundant natural light. A second bedroom offers style and comfort, with a picturesque window in the separate bath. A stacked washer and dryer are located on the 2nd floor. The upper level provides privacy for guests with two additional bedrooms and a full shared bath. Throughout, the home showcases coastal sophistication with wood plank vinyl flooring, seagrass carpet in the bedrooms, reeded colonial-style wallpaper, and tasteful touches like gold bathroom fixtures and glass shower doors, embodying refined Key West charm. Enjoy a shared community pool, assigned covered parking, and walkable access to Duval Street, Mallory Squares sunset celebrations, Fort Zachary Taylor State Park, Truman Waterfront Park and an array of dining and entertainment options. Whether a personal retreat or a smart investment, this property combines historic allure with modern luxury, providing an unparalleled Key West lifestyle.

This Old Town Villas luxury townhome is within a gated community, built in 2017 and located in the heart of Old Town. A private elevator takes you to each of the 4 floors from the 2+ car garage to the rooftop terrace. Enjoy 3 private bedrooms, 3.5 baths and a 41x14 (574 sq.ft.) garage on the ground level. Just under 2,600 SF of solid concrete construction, a large shared pool & cabana area, high end appliances, quality decor and sold turn key.

Welcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. With six luxurious bedrooms, each boasting en suite bathrooms and kitchen facilities, this historic gem offers unparalleled convenience and privacy. Whether you seek a tranquil retreat or an investment opportunity, the Seaport Inn beckons with its unique features. Prime Location: Situated just one block from the iconic Historic Seaport boardwalk and a mere three blocks from the vibrant energy of Duval Street. Flexible Rental Options: With two transient rental licenses and four non-transient rental licenses, this property presents a myriad of rental possibilities. Excellent opportunity for vacation rentals or consider the long term and/or employee rental possibilities. Expansive Lot & Outdoor Oasis: Spanning over 5000 square feet, the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping. Historic Charm: Steeped in history and architectural beauty, the Seaport Inn exudes timeless charm and character. Immerse yourself in the rich heritage of Key West while enjoying modern amenities and comforts.Perfect for savvy investors, hospitality entrepreneurs, or those seeking a slice of paradise to call their own, the Seaport Inn offers a rare opportunity to own a piece of Key Wests storied past while embracing its vibrant present. Dont miss your chance to experience the quintessential island lifestyle at the Seaport Inn.

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.

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.

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.