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

Charmingly restored and updated historic home on a quiet street in the heart of Old Town, one of the best neighborhoods. This island oasis is spacious with plenty of storage and ample off street parking. The master bedroom with ensuite bath is on the first floor. There is plenty of room to entertain around the pool or relax on the front porch. The property is very private with a lush tropical landscape, visible from the open kitchen which has accordion hurricane impact windows and a full size hurricane impact pocket door that transforms the inside to outside.

Discover your dream home at the prestigious Truman Annex Community, situated on the serene Admirals Lane. This two-story detached single-family residence offers a perfect blend of comfort and elegance with 3 bedrooms and 3 full bathrooms. Enhanced by impact windows and doors, the house also features a private carport for added convenience.Adjacent to the property lies a shared community pool, ideal for relaxation and enjoyment. Inside, the main living area boasts exquisite travertine floors, creating a luxurious ambiance. Open the French doors to the composite wood back deck, where outdoor dining, barbecues, and lounging become a daily indulgence.The fully equipped kitchen is a culinary haven, catering to every chefs desires. With one bedroom on the first floor and two bedrooms on the second floor, each with a private bathroom, this home is designed for utmost comfort and privacy.Emphasizing its prime location, this property is just a stones throw from Duval Street, the Key West White House, and the Key West Harbor, all while being nestled within the security of a gated community. Live out your Key West dreams in this exceptional property that epitomizes the essence of island living.

Welcome to 610 Griffin Lane, a charming Key West style compound perfectly blending modern elegance with island character. Tucked away on a quiet lane in the coveted Old Town area, this unique property offers a rare opportunity for privacy, relaxation, and easy access to the vibrant lifestyle of Key West.This sweet compound features three separate dwellings, all surrounding a serene, brick-paved courtyard. The main home is a beautifully updated 2-bedroom, 2-bath retreat with French doors that open to spacious porches--perfect for morning coffee or evening libations. The open-concept living space includes a stylish kitchen with quartz countertops, stainless steel appliances, and an island with seating. The natural flow from the indoors to the outdoors makes entertaining a breeze.The light-filled first bedroom includes an en-suite bath with a solid-surface vanity, glass walk-in shower, and a private outdoor shower for that true island vibe. The second bedroom boasts vaulted ceilings with transom-style windows and direct access to the cocktail pool and patio through French doors. The second bath is conveniently located just steps away from the pool.The guest cottage, a charming 1-bedroom, 1-bath space, offers a private retreat for guests or the potential for rental income. A third versatile structure provides additional living space, perfect for an art studio, home office, or extra bedroom.Lush and abundant tropical landscaping surrounds the private heated cocktail pool, creating a peaceful oasis. Additional amenities include hardwood floors, vaulted ceilings, a generator, and the rare luxury of off-street parking in Old Town. The entire property is fenced, ensuring complete privacy in your personal haven.Situated just a short walk from Key Wests finest restaurants, the best shops, and attractions, these cozy cottages offer a welcoming slice of paradise in one of the most sought-after areas of Key West. Dont miss the chance to call this island retreat yours!

Historic charm meets modern living in this unique Key West home! 1017 Angela Street is a beautifully restored 3 bedroom, 3.5 bathroom home with a vibrant personality, nestled on one of the quietest streets in Old Town, just steps from Duval Street and the Historic Seaport. Enjoy the convenience of modern amenities that this home offers, alongside playful, eclectic touches throughout. Relax and unwind in the private backyard oasis shaded by majestic mango trees, and featuring a heated pool and jacuzzi spa. The entire property is fenced and surrounded by lush tropical landscaping. Additional benefits include first floor primary bedroom, off-street parking in the driveway, and an outdoor shower. This is Key West living at its finest!

Historic Classic Revival Home in the Heart of Old Town Key WestNestled in the charming heart of Old Town, this stunning Classic Revival home, built in 1890 by the esteemed ship captain Benjamin Saunders, has been beautifully restored in the past two years, blending historic elegance with modern comforts. Situated just two blocks from the vibrant Duval Street and within close proximity to the historic seaport, renowned restaurants, and local attractions, this home offers the perfect combination of privacy and convenience.Spanning two lots, this remarkable property boasts a brand-new 40-foot pool surrounded by mature landscaping, providing an oasis of complete privacy. With over 2,450 square feet of living space, the home features three spacious bedrooms and three full bathrooms, offering ample room for both relaxation and entertainment.Multiple verandas and porches invite you to enjoy the gentle tropical breeze and views of the lush surroundings, while maintaining the essence of old-world charm. This Key West treasure offers a rare opportunity to own a piece of local history, complete with modern updates that cater to todays lifestyle.Dont miss your chance to make this captivating home your very own slice of paradise in the heart of Key West!

Rare opportunity to own your Key West dream home designed to satisfy both peace of mind and self-indulging luxuries. Exquisite Old Town residence in the making with a completion date of late 2024. Builder is willing to allow for substitutions as construction phases permit. If you are seeking an opportunity to personalize a home to suit your specific desires, look no further! This historic structure has been rebuilt from the foundation up to create the perfect harmony of historic restoration, structural integrity and custom design. The builder has teamed up with well-known local designer, Ben Teague, for the selection of all custom finishes, fittings, fixtures and optional furniture package. The result is a luxurious 5 bed/ 4 bath including a detached poolside cabana and off-street parking. An exceptional floor plan perfectly combines open concept living and defined spaces with attention to both function and elegance. Practice your culinary skills in the state of the art kitchen with high end appliance package to include Viking and Subzero or your personal selections. Delight in the perfect combination of indoor/outdoor living with custom door wall and sliders off bedrooms that lead to vast covered porches both up and down that cater to space for both dining and lounging Relax around the custom pool with sun shelf and waterfall or on the sunny poolside patio surrounded with tropical vegetation. Located in the X flood zone plus new roof and new impact windows/doors throughout lend itself to energy saving sound proofing, insurance discounts and ease of ownership. This a rare opportunity to customize a like new home that enjoys an ideal combination of historic character, modern floor plan, space and designer finishes.

This newly built, exquisitely designed home, located in a prime location offers comfort and style to the highest standard.The architecture and gardens are designed by Key Wests renowned designers. This 4 bedroom, 3.5 bath home embodies the pinnacle of luxury living. The open floor plan, introduces you to beautiful hand-finished walnut flooring, featuring 10-foot ceilings, an elegant half bath, a gourmet kitchen equipped with a Thermador appliance package, a wet bar, 58-bottle wine column beverage refrigerator, and built-in ice maker. The first floor primary suite with access to the backyard, features dramatic, cathedral ceilings, a wall of custom cabinetry, and a spectacular bathroom with double vanities, back lit mirrors and a skylight in the shower. The second story has 9-foot ceilings, 3 guest bedrooms, one of which is en-suite. For added convenience, there is an additional wet bar on this level, equipped with a beverage refrigerator. Other indoor features include marble tile, quartz counters, Samsung Frame TVs, impacted rated windows and doors, spray foam insulation, dual zone HVAC, and smart home controls. The outdoor experience presents IPE decking, a lush and private backyard with a stunning outdoor shower, sparkling saltwater, heated/chilled pool with a water feature, and off-street parking behind a motorized gate.

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.

Located in the Heart of Old Town, this Rare Home has It all. 3 Bedrooms with 3.5 Baths in the Main House plus a Guest Cottage with Bedroom & Bath and Outdoor Shower. Completed in 2021 to the Highest Standards with Design by Matthew Stratton Architecture, Landscape and Pool Design by Craig Reynolds Landscape Architecture, and Custom Cabinetry by Hansen and Bringle. No Expense was Spared. All Impact Doors and Windows throughout with Soaring Ceilings, 8 Ft. Doors, Sub- Zero and Wolf Appliances including Built-in Wine Refrigerator and Ice maker, 4-Zone HVAC, Restored Dade County Pine, and Marble-Tiled Baths. Furnished by Ben Teague Design, Off Street Parking for 2 Cars. This house is located in a transient receiver zone.

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 2nd 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, and Truman Waterfront Park. Whether a personal retreat or a smart investment, this property combines historic allure with modern luxury, providing an unparalleled Key West lifestyle. Video tour https://tinyurl.com/102-Admirals

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.

Situated directly across from the iconic Ernest Hemingway House, this exceptional family compound combines the rich history of Old Town Key West with modern luxury and island charm. From the famous six-toed cats that roam next door to the vibrant energy of Duval Street just steps away, this location is as legendary as it is convenient. Spanning two addresses at 407 and 415 Olivia Street, this versatile property is situated in the X flood zone and offers four off-street parking spaces. The main house, a meticulously renovated mid-century modern gem, welcomes you with a grand entrance foyer that flows into a spacious living, dining, and media area. Perfect for entertaining, the space features a working fireplace and a 76-inch TV. The gourmet kitchen boasts solid wood cabinetry, Bosch and Thermador appliances, an induction cooktop, column fridge/freezer, wine cooler, and an impressive 13-foot quartz waterfall island. Impact sliding doors open to a stunning saltwater pool complete with a sun ledge, slide, and waterfall. Surrounded by tropical landscaping, this backyard oasis also features an outdoor shower, fully equipped kitchen, and plenty of space for entertaining. The main house offers four bedrooms, each with generous closet space and outdoor access. The primary bedroom includes a new custom walk-in closet with solid maple built-ins. Another ensuite bedroom has been transformed into a stylish home office with a built-in Murphy bed. The two additional bedrooms share an elegant bathroom featuring a luxurious soaking tub and shower. Adjacent to the main house is a charming two bedroom, two bath Conch-style cottage that provides the perfect guest retreat or mother-in-law suite. This home features a fully equipped kitchen, Dade County pine accent walls, and a tranquil outdoor space to relax under the shade of swaying palm trees. Dont miss the chance to see this unique compound that provides the perfect blend of history, luxury, and the ultimate Key West 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.

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.

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!

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!

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.