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

Discover this hidden gem in Key Wests vibrant Historic Seaport area. This beautiful and rare home stretches from Eaton Street to Thompson Lane, offering multiple off-street parking spots through the large gates on the Lane. As you step inside, the very high ceilings immediately catch your eye--a unique feature in these traditional homes. Large custom barn doors provide privacy and add a touch of design to the front receiving room.The chefs kitchen boasts all the comforts within arms reach, with an open layout perfect for social meals and gatherings. Upstairs, three bedrooms (two en suite) offer ample space for family or guests. The ground floor features a charming one-bedroom attached studio--ideal for guests or a home office. An additional air-conditioned work/craft room adds to the homes uniqueness.French doors open from both the main house and the studio to a spacious backyard. Theres even room to add a pool, if desired, near the roomy back deck (the seller has already provided a quote). The wrap-around porches (1500 sq. ft.) are a dream, surrounded by lush landscaping in a serene setting. Impact windows and doors provide peace of mind and energy efficiency.This thoughtfully updated traditional Key West home combines comfort with old-town charm. Plus, its just steps away from great restaurants, shops, and amenities. A must-see!

Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether youre looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool--perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!

Tucked away on a hidden lane just a half of block off of Duval Street, 1 and 2 Aronovitz Lane is a true diamond in the rough! A one of a kind opportunity that is being offered for the first time ever. This listing consists of two platted lots with a total of three development rights and 5,614 sq. ft. of land. The existing well maintained house at 2 Aronovitz Lane is a two bedroom/one bathroom Conch style cottage that is considered a non contributing structure according to HARC. This expands the available options for the redevelopment opportunities with the combined properties. The vacant lot at 1 Aronovitz Lane was once a legal duplex. The build back letter from the City of Key West is included in the documents section along with the surveys for each parcel being offered. The owner will only sell both parcels together. The time is now to make this unique property your very own island destination!

Experience the quintessential Key West lifestyle in this beautifully transformed gem in the heart of Old Towns Solaris Hill. Restored and reimagined in 2022, this unique home seamlessly blends modern comfort with the historic charm of an 1889 cigar makers factory, as noted in Key West Sanborn maps. Enter through an inviting white picket fence to a spacious front porch, perfect for enjoying lazy afternoons with a cool drink or chatting with neighbors under swaying palms.Inside, a refreshing breeze welcomes you into an airy foyer with exquisite hickory hardwood floors, custom lighting, and a stunning locally crafted floating staircase that serves as a stylish focal point. The chef-inspired kitchen is the heart of the home, equipped with top-of-the-line Wolf appliances and a Sub-Zero refrigerator, all nestled in custom cabinetry with gorgeous soapstone countertops. An eye-catching iron and marble island takes center stage, surrounded by a handcrafted Cle tile wall that sets the scene for culinary adventures.Bright and inviting, the spacious living area features two sets of impact-rated French doors, enhancing the essence of indoor-outdoor living, where you can bask in the gentle sea breeze. Original Dade County pine adds warmth and character throughout. The retreat-like primary bedroom and two thoughtfully designed guest bedrooms offer ample relaxation space, each with beautifully upgraded bathrooms featuring custom tiles and Kohler fixtures.Step outside to your personal oasis, complete with a brand-new saltwater pool surrounded by tropical landscaping and a travertine deck, ideal for sun-soaked gatherings or starlit evenings. An outdoor shower adds a refreshing touch, while a custom-built privacy fence ensures your sanctuary from the outside world.Enjoy the convenience of private off-street parking and proximity to the vibrant culture, dining, and entertainment that Key West offers. Duval Street is just two blocks away, with nightlife and fabulous restaurants.

BIG TIME INVESTMENT OPPORTUNITY in the heart of the Historic District of Key West. Originally built as a former church, this 4 unit active rental property offers 3,383 square feet of living space, featuring 8 bedrooms and 4 bathrooms, and currently generates $10,908.50 in monthly rental income. (See below for a breakdown of beds and baths per unit) With versatile possibilities, it has the potential for improvement and the possibility of condominium conversion. Each unit is large and spacious by Key West standards and includes high ceilings. The building is of concrete block construction and is currently undergoing exterior repairs to address some concrete spalling. Off street parking for three cars, a rarity for Old Town, Key West. This property is located in one of the most desirable neighborhoods and is just a short walk to World famous Duval street, the islands best restaurants, shopping and more! Unit breakdown: (A) 3BD/1BA leased for $3,039.50 per month (B) STUDIO/1BA leased for $2,369 per month (C) 2BD/1BA leased for $2,700 per month (D) 2BD/1BA leased for $2,800 per month

Nestled in the heart of the Old Town district, just two blocks from the Historic Seaport, this endearing building has a stylish 1BR/1BA apartment on the upper level and a charming commercial space at street level. With tile floors, sky lights, stainless-steel appliances & washer/dryer, as a pied-a-terre or full time residence this space is perfect! Outside enjoy a spacious second-floor deck overlooking a tree-lined rear patio, offering a perfect retreat for relaxation. Fully fenced, the rare parcel offers a deep lot and generous backyard to be used in conjunction with a commercial or residential use. The storefront commercial unit has rare, covered street frontage & includes a half bath. HNC-2 Historical Neighborhood Commercial District Zoning allows for many uses, including single-family, business & professional offices, commercial retail low intensity, restaurants with limited seating etc. The property is beer/wine license eligible and for many years was the neighborhood landmark Binas grocery store. The property has undergone many upgrades in recent years. Live/Work properties are rare in Old-Town and this one has a wonderful mix of attributes. It would certainly be the ultimate Key West solution for a creative professional offering a studio, gallery & home all under one roof in the X flood zone.

Welcome to this character-filled, 3 bedroom, 2.5 bathroom home, built in 1918, which is situated in a much sought-after neighborhood found within the X-zone. As you enter the home, the charming foyer features rich wood floors, crisp white walls, and a convenient half bath. A staircase leads to a bright and spacious bedroom/sitting area, ideal for hosting guests. While the main floor corridor guides you to what the rest of the Old Town home has to showcase. A guest bedroom offers a versatile space, easily accommodating twin beds or a king, his-and-hers closets, and a private en suite bathroom with a relaxing tub. The living room is bathed in abundant natural light, thanks to french doors that offer a view of the inviting backyard. The kitchen features granite countertops, stainless steel appliances, and a designated island with ample workspace and bar stool seating. A master bedroom is strategically located on the far end of the house. One of its standout features being French doors layered with ouver exterior shutters that open directly to the pool. This room also boasts his and hers closets and an ensuite bathroom, including a sleek marble and glass block shower. The backyard is the ultimate entertainment space, with a spacious covered lanai for relaxation. The washer and dryer are housed in a designated outdoor shed. The backyard also offers direct access to and from two bricked off-street parking spaces.

Located in the heart of Key Wests sought-after Old Town, 711 Olivia Street is a stunning fusion of historic charm and modern luxury. This meticulously crafted residence sits on a double private lot surrounded by lush tropical landscaping, showcasing classic Key West architecture with contemporary elegance. Step inside to discover an open layout with high ceilings, premium flooring, and abundant natural light. The spacious living and dining areas flow seamlessly into the outdoors, creating a harmonious indoor-outdoor living experience. At the heart of the home is a gourmet kitchen equipped with high-end appliances, expansive counter space and custom cabinetry--perfect for entertaining. Outside, a private oasis awaits. The backyard features a custom-designed saltwater pool with a waterfall, a spacious deck for lounging and an outdoor kitchen for alfresco dining, making it an ideal space for relaxation or hosting gatherings under the sun or moon. Each bedroom serves as a tranquil retreat. Modern amenities such as a security system, climate control, and smart home technology enhance comfort and convenience. Off-street parking adds to the convenience, a valuable perk in Old Town. Living here means more than owning a home; its about embracing the vibrant lifestyle of Key West. With fine dining, art galleries, and Duval Streets nightlife just a short stroll away, youll enjoy the best of the islands culture and entertainment. For outdoor enthusiasts, the surrounding waters provide endless opportunities for boating, fishing, and more. With its blend of historic elegance, luxurious amenities, and prime location, 711 Olivia Street offers a rare opportunity to own a piece of paradise in one of Key Wests most desirable neighborhoods--a timeless investment in both lifestyle and legacy.

Unlock the potential of this exceptional multifamily complex nestled in the heart of Old Town Key West. With a total of six units offering a diverse mix of layouts, including three 1-bedroom/1-bathroom units, two 2-bedroom/1-bathroom units, and one 3-bedroom/1-bathroom unit, this property presents an unparalleled investment opportunity in one of the most coveted destinations in the Florida Keys. Dont miss your chance to seize this investment gem in the heart of Old Town Key West. Schedule a viewing today and make your mark on the vibrant landscape of Key West real estate!

Welcome to The Chavez House, a beautiful 3-bedroom, 2 bath Allen Law transient rental home proudly listed on the National Register of Historic Places. With a solid rental history, this property is a fantastic investment opportunity in the heart of the historic seaport neighborhood.Upon entering, youre greeted by a bright and inviting family room bathed in natural light--an ideal space for intimate conversations and gatherings. The main floor features a spacious primary en-suite bedroom with king-size accommodations, accentuated by Dade County pine walls and a thoughtfully designed bath with dual sinks, a tub/shower combination, and a separate pedestal sink room.The inviting dining area comfortably seats six and offers an option for outdoor dining on the lanai, creating an authentic island experience. The lanai, complete with a vaulted ceiling and tropical fan, serves as an excellent gathering spot for family and friends. The kitchen features a convenient breakfast bar for four, stainless steel appliances, white quartz countertops, and a vaulted shiplap-style ceiling. French doors lead to a private pool area where you can relax in the heated pool, surrounded by lush tropical landscaping.Ascend the beautiful wrap-around staircase to discover two additional queen bedrooms on the second floor, each featuring unique elements such as barn doors, vaulted ceilings, and ceiling fans. The shared bathroom includes a vanity sink and tub/shower combination, ensuring comfort for all guests.Located in vibrant Old Town, The Chavez House, is just a short stroll from the allure of Duval Street, the Key West Cemetery, and the Historic Seaport district. With its proven rental history, this Allen Law Transient ensures the potential for lucrative income and offers a serene escape.Dont miss your chance to own The Chavez House--where historic charm meets modern living. Schedule your showing today!

Indulge in the pinnacle of luxury at this stunning three-story Old Town Key West residence, a property that simply must be seen. Located directly across from the historic Key West Lighthouse and just steps from the renowned Duval Street, this home offers unparalleled access to Key Wests finest attractions. A leisurely stroll takes you to the Southernmost Point and the Atlantic Ocean, mere minutes away. Located in the coveted X Flood Zone, one of Key Wests highest elevation points and boasting over 3,000 square feet of meticulously designed living space, including four bedrooms and four bathrooms featuring two master suites, this home effortlessly blends sophistication with contemporary comfort. The first floor showcases a generous eat-in kitchen, a versatile guest bedroom or sitting room, and two full bathrooms, while the expansive great room provides an ideal retreat for relaxation or entertainment. French doors open to reveal a spacious in-ground pool, perfect for enjoying refreshing breezes and ample outdoor space. The second and third floors house two additional master suites, each offering privacy and opulence. Embrace a lifestyle of refinement and coastal allure in this exclusive Key West haven. Ideally situated for walking or biking to renowned restaurants, enjoying live music, exploring galleries, spending the day at Fort Zachary Taylor State Park or savoring the vibrant energy of Duval Street.

First time on the market in over 50 years! This property is a plant lovers paradise. The owner spent his entire life collecting plants and seeds from all over the world and created a quiet serene and private oasis in the middle of Old Town Key West, on a huge oversized lot. Some of the rare plants and palms are found nowhere else in the continental United States. The main house has many structural upgrades, but the best thing is that the existing carport has HARC approved plans to turn it into a large guest cottage or studio. This is an artist/musicians dream. Quiet solitude in the middle of Key West to stimulate creative juices, or just to chill out in paradise.

Welcome to this newly reimagined architectural gem in Old Town Key West. This historic home has been meticulously renovated to blend timeless charm with modern sophistication. The main house offers three bedrooms, 3.5 luxurious baths, all illuminated by natural light pouring through impact-resistant doors and windows. Throughout, the warmth of oak floors complements the clean, contemporary lines of the space. The gourmet kitchen, fitted with Bosch stainless steel appliances, is a dream for culinary enthusiasts, while the open-concept design makes it perfect for entertaining. Step outside to your private oasis, where a stunning waterfall pool is the centerpiece of a lushly landscaped garden. The outdoor kitchen and spacious dining area are perfect for hosting al fresco dinners, making the most of the tropical Key West climate. For guests, a separate one-bedroom, one-bath guest house ensures privacy and comfort. Additional features include off-street parking and an electric vehicle charging station. Just two blocks away, the iconic Duval Street invites you to explore world-class dining, art galleries, and nightlife, with historic stops like Sloppy Joes. A two-block stroll west brings you to the literary haven of the Ernest Hemingway Home and Museum, while the Key West Lighthouse, just one block farther, offers panoramic island views.For beachgoers, the tranquil shores of Fort Zachary Taylor Historic State Park await, only five blocks away. History lovers will appreciate being just*five blocks from the Truman Little White House, a symbol of presidential retreat. Each evening, Mallory Square, also five block away, offers a festive sunset celebration, a must-see experience. For waterfront dining and sailing excursions, the Key West Historic Seaport is within the same easy reach. 907 Whitehead Street isnt just a home--its a luxurious retreat in the heart of Key Wests most coveted neighborhood, offering a blend of history, elegance, and walkable island living.

**BREATHTAKING RENOVATION** Nestled in the heart of Old Town, this century-old gem has been lovingly renovated and is waiting for you to call it home. This historic residence perfectly balances convenience and tranquility, offering a true slice of paradise just waiting for you.Every inch of this home has been thoughtfully updated and perfected--from the floors to the air ducts to the attic. The kitchen boasts luxurious black leather granite countertops, new Bosch appliances, and a beautifully modified centuries-old cabinet from England surrounding the sink. New flooring and high-impact resistant windows and doors have been installed throughout the entire home. The third bedroom, currently used as an office, features a large, bold window with a view of the pool.Upstairs, youll find two master en suites, each with a fully renovated bathroom and ample storage space. A new Miele washer and dryer and a bonus media room that doubles as a fourth bedroom for guests.This stunning residence offers an incredible outdoor living space with a refreshing pool, a beautiful outdoor kitchen, and a covered lanai, creating a serene oasis just blocks from Duval Street. Plus, a cedar-lined shed offers something truly rare in Key West: space for storage! This meticulously cared for home is situated on one of the most coveted streets in Old Town, youll be steps from groceries, restaurants, the beach, and the vibrant historic district. If youve been searching for your piece of Key West, this historic home offers everything youve dreamed of.*** Check under documents for a complete renovations list ***

Your DREAM home awaits.. Located in Truman Annex, where luxury meets island living. This stunning 5-bedroom, 5-bathroom residence boasts over 3000 sq ft of living space offering unparalleled comfort and elegance.As you step inside you are greeted by an expansive and open floor plan, featuring 11ft high ceilings and abundant natural light that illuminates the interior. The kitchen and dining area are open and spacious perfect for entertaining guests. The lavish master suite is a sanctuary of relaxation. Open and full of natural light streaming in from the glass doors that lead to your covered balcony. The en suite bath is completely updated, open and spacious with dual sinks. Featuring fully enclosed steam shower!Each additional bedroom is generously sized and appointed. Two of the bedrooms are adjoined by a remodeled Jack and Jill bathroom and one with a beautiful en suite bath. Outside, the tropical Oasis awaits, with sparkling resurfaced and new tile pool with brand new waterfall surrounded by beautiful landscaping. Lounge poolside or beat the heat in your pool house.Additional features include tube elevator, covered parking, and balconies on the front and back of the home. Numerous updates from bathrooms to new ac units, resurfaced pool, new waterfall and fresh paint throughout

This magnificent TRANSIENT rental property with two homes and a heated pool blends privacy with convenience. Nestled in historic Old Town and just steps from Duval Street, this 3 bedroom/3.5 bath complex has a strong rental history. Once home to iconic fashion designers, this gated haven will astonish you. To your right is the main single-story building which includes a king bedroom and large, sleek ensuite bath. Vaulted ceilings, skylights, exposed beams, and French doors surround the expansive open concept living room and dining room. The space is bathed in sunlight and perfect for entertaining. At the far end of the main building, you will find a spectacular stainless steel commercial kitchen with a vaulted ceiling and outdoor views. Equipped with prep areas, an island, cabinetry, a double sink, and an oversized gas range with hood, you have everything you need to prepare meals or parties for large groups. A personal Chef would be delighted to cook in this kitchen. As you move out onto the covered porch, you will enjoy indoor-outdoor living at its finest. With easy access to the pool, you can spend your afternoon relaxing outdoors. The porch provides a respite from the sun and an area for al fresco dining. The two-story home at the rear of the property stacks two spacious bedrooms with ensuite baths and seating areas. Each is complemented with either a balcony or covered porch overlooking the pool. Guests or extended family can mingle around the gorgeous outdoor area or retreat to their own private spaces. Both homes surround the large pool with the convenience of an outdoor shower. The complexs stunning tropical lush landscaping and privacy fencing offers a tranquil oasis including off-street parking, a rare amenity in Key West. From here you can walk to Higgs Beach, the Southernmost Point and the shops and restaurants on Duval Street. This opportunity to own a transient rental property in an ideal location wont last long. Call today for a private showing!

Available for sale with owner financing options: $3 million down and $2 million seller-financed at 5% interest, with negotiable terms. The building, made from rare coral limestone, features Gothic architecture, including arched stained glass windows, a bell tower, and exposed beams.ROCKHOUSE consists of three units: two vacation rentals and a mixed-use gallery with modern renovations, offering 5 bathrooms and 5 sleeping quarters across the units. The property is in the higher X-Flood Zone, offering safer flood conditions. It has flexible zoning for residential or mixed-use purposes, making it a unique luxury investment with historical significance.Located just steps from popular Key West landmarks like Duval Street and, the Hemingway House, the property offers proximity to cultural and entertainment amenities in Old Town. Ideal for buyers seeking luxury, flexibility, and a piece of Key West history, this is the largest residential flex property in the area.

This spacious 5 bedroom and 5 1/2 bath two story home was beautifully restored and finished in 2019. Stepping through the inviting main floor porch the entryway opens to a large open floor plan on the right with a living room that will seat 8-10 comfortably then flows into the custom kitchen. To the left of the entry is a first floor master with king and and an ensuite bath and walk-in closet. Up the stairs is a customized wall of restored Dade County Pine from the original home which beautifully showcases the custom cut heart pine floors throughout the entire home. The second floor holds 4 additional bedrooms - 1 guest room with queen bed and ensuite bath and another guest room with an ensuite bath and a queen murphy bed that could also be used as an office. There are two additional master bedrooms with kings, both ensuite with walk-in closets. Between the two masters is the exit to the second floor balcony with porch swing and rocking chairs overlooking the beautiful front yard. The custom kitchen has french doors spread out across one wall, a wet bar and a large kitchen island with counter seating for 7. The 1/2 bath is accessible to all on main floor and just steps to the french doors opening to the large covered deck with seating for 6 and an additional large open air back deck with table and seating for 8 and showcasing the 12X24 pool with waterfall. A few steps down from the back porch is the parking with an electric gate and stepping stones winding through the exquisitely landscaped yard. A full house generator with large buried propane tank are installed on the far side of the yard along with some storage bins for pool toys and furniture covers. Property being sold turnkey with just a few exclusions.

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 Fines

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!

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!

Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Dont miss the chance to own a piece of Key Wests past while shaping its future with this truly one-of-a-kind property.