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

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Total Listings 56
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$1,995,900
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 61
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Step into the charm of this beautifully designed two-story Conch home, originally built in 1923 and thoughtfully expanded to offer the perfect amount of space.The historic character shines through with rare Dade County pine walls, while the open floor plan, Birch hardwood floors, and soaring 10-foot ceilings create a bright and inviting space. The kitchen is a chefs dream, featuring stainless steel appliances and an oversized split farmhouse sink. This home offers three ensuite bedrooms, each providing comfort and privacy.Step outside to enjoy the stunning Ipe wood decking, perfect for relaxing or entertaining. The newer heated and chilled pool is ideal for year-round enjoyment, whether youre cooling off in the summer or warming up on cooler nights.And you cant beat the location! Just one block from world-famous Duval Street and a few blocks from the Southernmost Point, this home puts you right in the heart of Key West. Stroll to galleries, dine at amazing restaurants, and enjoy some of the best local music in town--all just a short walk from your front door.Not only is this home perfect for personal use, but its also in a fantastic area for an investment property. With its prime location and desirable features, it has great potential for rental income.This home blends history with modern comfort--dont miss the chance to make it yours!

$2,150,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 2,016 SqFt Days Listed: 262
-10.38% ($249,000) 2 Price Changes : Last Change 37 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Over 100k price reduction!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!

$2,150,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 2,016 SqFt Days Listed: 87
-5.91% ($135,000) 1 Price Change : Last Change 37 Days Ago
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$2,195,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,522 SqFt Days Listed: 162
-8.35% ($200,000) 4 Price Changes : Last Change 43 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance of restaurants, art galleries, and Duval Street, the location is ideal. A spacious porch with classic painted Cuban tiles provides a relaxing outdoor retreat, while reclaimed heart pine flooring extends throughout the interior. The open floor plan offers a seamless view from the living room to the pool deck, making it perfect for both relaxation and entertaining. The original tongue-and-groove Dade County Pine has been carefully removed, refinished, and reinstalled, creating a warm and inviting atmosphere.The L-shaped kitchen overlooks the heated dip pool and features custom craftsman shaker cabinets and quartz countertops. The master suite is conveniently located on the first floor, complete with an en-suite bathroom and walk-in shower. Two guest bedrooms, each with en-suite baths and vaulted ceilings, are located on the second floor.This home has been completely rewired, replumbed, and foam-insulated, ensuring compliance with modern building codes. A new foundation and a reinforced metal shingle roof have been added, along with fabric hurricane shutters for protection and insurance benefits. Smart switches, appliances, locks, and wired ethernet connectivity allow for remote home management via phone.The property is located in the X Flood Zone! The propertys historic charm makes it a remarkable piece of Key West history. Owner is a Lic. FL Real Estate Agent.

$2,200,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,445 SqFt Days Listed: 111
-10.20% ($250,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

A Rare Opportunity in Key Wests Historic Heart - 719 Bakers LaneNestled in the tranquil charm of Old Town Key West, 719 Bakers Lane offers an exceptional chance to craft your dream home in the islands most coveted location. This nearly finished 3-bedroom, 3.5-bath residence presents the rare opportunity to pick your own finishes, fixtures, appliances and landscaping and skip the endless waiting for permits and architectural drawings and contractors. Featuring impact door and windows and rated for 190MPH winds.Located just 3.5 blocks from the Historic Seaport and 2.5 blocks from Duval Street, youre moments from world-class dining, entertainment, and Key Wests vibrant culture. Walk to the islands best shops, restaurants, and bars, all while enjoying the peaceful privacy of a lane home surrounded by historic architecture.This home sits on Solares Hill, the highest and most desirable flood zone (X500), offering the ultimate peace of mind. Featuring impact-resistant doors and windows, its designed for both security and style. This beautiful new construction blends modern convenience with Old Town charm.Embrace the opportunity to own a piece of paradise, where history, privacy, and luxury come together in perfect harmony. Live in the heart of Key West--steps from everything the island has to offer.

$2,300,000
Key West
Old Town Unlisted - MM: 1.00
8 Bed, 8 Baths, 3,383 SqFt Days Listed: 231
-8.00% ($200,000) 1 Price Change : Last Change 30 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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 currently had all concrete spalling issues resolved and painted. 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

$2,375,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,600 SqFt Days Listed: 207
-8.65% ($225,000) 6 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

711 Olivia Street is a rare gem that fuses timeless Conch-style architecture with sophisticated, modern upgrades. This 3-bed, 3-bath home has been meticulously remodeled, creating a private sanctuary that honors its historic heritage while offering all the comforts of -contemporary living. The open-concept layout welcomes you with premium flooring & abundant natural light, all designed to enhance the seamless flow between indoor and outdoor spaces. At the center of the home is a beautifully appointed gourmet kitchen equipped with high-end appliances, a gas range, expansive counters, and custom cabinetry.Significant enhancements have been made with no detail overlooked. All windows, French doors, and sliders have been upgraded to hurricane-rated impact glass, while the original HARC-protected front windows remain beautifully preserved with hurricane shutters for protection. The roof is securely tied to the structure and treated with a specialized coating that reflects heat and seals out humidity. The outdoor space is a lush tropical retreat, surrounded by professionally designed landscaping featuring mature palms & vibrant orchids supported by an irrigation system. A heated pool with updated plumbing and a new pump invites you to relax in style, complete with a spacious deck and an outdoor kitchen. Further upgrades include spray foam insulation beneath the main home and throughout the pool house to enhance energy efficiency & guard against moisture. New AC units provide reliable comfort year-round. Smart home technology, a security system, and ductless climate control elevate the living experience with comfort & peace of mind. Situated on a 3,350 sq. ft. lot in the highly desirable X flood zone, this home also offers the rare advantage of off-street parking. More than just a home--its a refined blend of historic charm and luxury living in one of Key Wests most coveted neighborhoods.

$2,449,000
Key West
Old Town Unlisted - MM: 1.00
2 Bed, 2 Baths, 888 SqFt Days Listed: 266
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$2,495,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,391 SqFt Days Listed: 121
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Dona Calabash - Located just a half a block from the upper end of Duval Street this charming Old Town beauty has it all! Three bedrooms including a luxurious master suite with spa bath, two guest bedrooms and two full baths. The gourmet kitchen features commercial grade stainless appliances, granite countertops and plenty of storage. Rear French doors open to a covered deck and the refreshing pool and surrounding lush gardens. The adjacent cabana house has a beautifully appointed bath and cozy sleeping/sitting area. Features here also include high ceilings, hardwood Brazilian cherry floors, Dade County pine feature walls, gorgeous grounds and a convenient electric gate for the off street parking for multiple vehicles. This property has been meticulously designed and maintained for the discerning new owners! Walking distance to the ocean, restaurants, shops and nightlife and still have privacy & quiet, this special fully appointed property is a must see.! Very easy to show!

$2,495,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 1,967 SqFt Days Listed: 39
-7.56% ($204,000) 1 Price Change : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

If you are looking for location and a historic home, this triplex is tucked away on one of Old Town Key Wests most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character, and enduring appeal.The main house features generously sized rooms, high ceilings, and Dade County pine walls, all beautifully restored by local craftsmen.Attached to the main house is a versatile studio apartment, originally part of the homes original footprint and easily convertible back into a grand primary suite. In addition, there is a detached studio cottage perfect for guests or additional income.Part of the historic preservation focused on the large wraparound front porch with delicate gingerbread trim. The original water cistern was turned into a pool. This residence is a living piece of Key Wests vibrant history. Jimmy Buffett used to live next door for some time writing his book and songs.Now available as part of an estate sale, dont miss your opportunity to be the next steward of this extraordinary legacy.

$2,495,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 1,967 SqFt Days Listed: 10
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

If you are looking for location and a historic home, this wonderful home is tucked away on one of Old Town Key Wests most peaceful lanes. This charming Conch home won the distinguished Historic Florida Keys Preservation Star in 1988 and has been in the same family for over 40 years--a true testament to its warmth, character, and enduring appeal. The main house features generously sized rooms, high ceilings, and Dade County pine walls, all beautifully restored by local craftsmen. Attached to the main house is a versatile studio apartment, originally part of the homes original footprint and easily convertible back into a grand primary suite. In addition, there is a detached studio cottage perfect for guests or additional income. Part of the historic preservation focused on the large wraparound front porch with delicate gingerbread trim. The original water cistern was turned into a pool. This residence is a living piece of Key Wests vibrant history. Jimmy Buffett used to live next door for some time writing his book and songs. Now available as part of an estate sale, dont miss your opportunity to be the next steward of this extraordinary legacy.

$2,500,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 3,009 SqFt Days Listed: 322
-19.22% ($595,000) 2 Price Changes : Last Change 108 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

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.

$2,500,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,724 SqFt Days Listed: 68
-7.39% ($199,500) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Nestled on a tranquil lane in Old Town Key West, this classic Conch home offers an ideal blend of historic charm and modern amenities. The property features multiple entertainment spaces both indoors and outdoors, seamlessly connecting the expansive living area & kitchen to a covered patio & spacious pool deck. This home includes 3 bedrooms plus a poolside cottage. The gourmet kitchen is equipped with stainless steel appliances and custom cabinetry, flowing effortlessly into the island-style dining room. The main floor primary suite exudes a calming energy with its vaulted ceilings and glass doors opening onto the pool. Features include Dade County Pine walls, wood floors, open floor plan, and tall ceilings. The poolside cottage enhances the outdoor experience with an outdoor shower and an additional bathroom, providing ultimate convenience. Experience the casual yet elegant island lifestyle, where every detail has been thoughtfully designed for comfort and style.

$2,788,000
Key West
Old Town Unlisted - MM: 1.00
6 Bed, 6 Baths, 3,876 SqFt Days Listed: 80
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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!

$2,799,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 1,223 SqFt Days Listed: 424
-19.91% ($696,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$2,999,999
Key West
Old Town Unlisted - MM: 1.00
2 Bed, 2 Baths, 1,596 SqFt Days Listed: 144
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

$3,495,000
Key West
Old Town Unlisted - MM: 1.00
2 Bed, 2 Baths, 1,650 SqFt Days Listed: 34
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Welcome to your private oasis in the heart of Old Town Key West, where modern luxury meets historic charm. This beautifully renovated home perfectly blends timeless island architecture with sleek, contemporary comforts, offering an unparalleled living experience just steps from the Seaport and world-renowned Duval Street. Behind its classic facade, an airy, open floor plan awaits, thoughtfully designed for effortless indoor-outdoor living. Soaring vaulted ceilings crown the expansive living, dining, and kitchen space, where folding glass doors dissolve the boundaries between inside and out. The gourmet chefs kitchen features a premium Sub-Zero and Wolf appliance package, ideal for preparing island-inspired meals at home. Step outside to a lush backyard retreat anchored by a stunning saltwater pool--heated and chilled for year-round enjoyment--with a relaxing sun shelf, tranquil waterfall, and optional scupper cascades. A fully equipped poolside gazebo with a built-in grill, refrigerator, and ice maker invites unforgettable alfresco gatherings under the stars. The flexible layout includes two elegant bedroom suites and a versatile den with an adjacent full bath, perfect for guests or a home office. The first-floor primary suite offers a serene escape with a luxurious king bed and spa-inspired bath, while upstairs, a second bedroom shares a full bath and a convenient laundry area. Additional features enhance both comfort and value, including hurricane-rated windows and panels, roof certification, and a coveted X-flood zone location--offering significant savings on insurance costs. A private off-street parking space adds to the ease of island living. Tucked away on a quiet residential street yet just moments from the best of Key West, this exceptional home offers the rare opportunity to own a fully updated historic property in one of the islands most sought-after neighborhoods--where every day feels like a vacation, and every evening invites you to savor the sunset.

$3,675,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 2,438 SqFt Days Listed: 90
-2.00% ($75,000) 1 Price Change : Last Change 3 Days Ago
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This stunning Gingerbread-style home seamlessly blends historic charm with modern luxury right in the heart of Old Town . A covered wraparound porch welcomes you into a bright, window-lined foyer, leading to an elegant living and dining area. Throughout, gorgeous pine floors and walls highlight the homes timeless character.The open gourmet kitchen, featuring high-end appliances, flows into the living room and out to the covered loggia through vanishing pocket doors, creating seamless indoor-outdoor living. With 3 or 4 bedrooms, the main floor offers two en-suite bedrooms + a custom office, while upstairs, a spacious sitting room with a breakfast bar leads to the primary suite, complete with dual closets and a private balcony overlooking the heated pool and lush backyard.Designed for relaxation and entertaining, the large covered back porch offers serene views of the tropical landscaping and tranquil pool waterfall. A gazebo-style outdoor living space expands your backyard retreat and could easily convert back into a guest cottage as it once was.A rolling front gate, off-street parking, and a charming front porch perfect for people-watching complete this exceptional property.

$3,999,000
Key West
Old Town Unlisted - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 152
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

$3,999,000
Key West
Old Town Unlisted - MM: 1.00
3 Bed, 3 Baths, 2,532 SqFt Days Listed: 3
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Located in the heart of Old Town Key West, 316 Southard Street is a meticulously renovated single-family home that pairs modern comfort with classic Conch-style architecture. Originally built in 1938, the home has undergone a comprehensive renovation, blending timeless character with thoughtful, high-quality upgrades. Offering over 2,500 square feet of finished living space on a 6,165-square-foot lot, the residence features three bedrooms and three and a half bathrooms--well-proportioned for relaxed daily living and effortless entertaining. The ground-up renovation includes a new metal roof, all impact windows and doors, sound proofing in the walls, upgraded plumbing and electrical systems, a premium two zone HVAC installation, integrated indoor and outdoor sound system, and the addition of a custom-designed pool with integrated lighting and heating. The jaw dropping kitchen has a blend of the very best, from Wolf there is a gas stove, induction stove, steam oven, convection oven & microwave. Bertazzoni integrated refrigerator, freezer and wine fridge. Finally a top of the line Miele dishwasher rounds out the appliances. A thoughtfully designed rear addition, approved by the HARC, enhances both the function and flow of the home. Inside, historic elements are complemented by premium finishes, while outside, a partial wraparound porch, ample off-street parking, and color-adjustable smart lighting add both charm and convenience. The 12 x 24 pool and private yard create a quiet retreat, just steps from the vibrant energy of town. Positioned just blocks from the waterfront, restaurants, and cultural landmarks, this turnkey residence offers a rare opportunity to own a refined island home in one of Key Wests most coveted locations. *Seller is a licensed Florida realtor.

$3,999,000
Key West
Old Town Unlisted - MM: 1.00
7 Bed, 7 Baths, 3,015 SqFt Days Listed: 147
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

This property has a glamourous three bedroom, three and a half bath owners unit with private pool and hot tub, plus three lucrative long-term rentals. It is the entire Lighthouse View Condominium Association, currently inactive. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence with its heated pool and hot tub is secluded in the rear with a pretty garden and brick terrace. A free-standing two story building contains a great room, splendid kitchen and half bath downstairs. Above is a bright and breezy master suite with cathedral ceilings and skylight. In addition, there are two guest cottages, each with one bedroom, one bath and a pretty front porch. On the deck between the cottages is an outdoor wet bar and there is an outdoor shower by the pool. The other apartments are in a building at the front of the property. Downstairs are two one bedroom-one bath units. Upstairs is a glamorous two bedroom-one bath with a big, wonderful deck under the trees.

$4,950,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 2,985 SqFt Days Listed: 130
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. ***

$4,999,000
Key West
Old Town Unlisted - MM: 1.00
5 Bed, 5 Baths, 3,434 SqFt Days Listed: 165
-4.78% ($251,000) 1 Price Change : Last Change 81 Days Ago
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!

$5,399,000
Key West
Old Town Unlisted - MM: 1.00
4 Bed, 4 Baths, 3,026 SqFt Days Listed: 550
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.

$5,900,000
Key West
Old Town Unlisted - MM: 1.00
8 Bed, 8 Baths, 8,472 SqFt Days Listed: 200
-14.49% ($1,000,000) 2 Price Changes : Last Change 2 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Median - Dockage: None

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.

$6,500,000
Key West
Old Town Unlisted - MM: 1.00
6 Bed, 6 Baths, 3,010 SqFt Days Listed: 55
Duplex - Active - Waterfront No
Side of Island: Median - Dockage: None

Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool--perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms.Whether youre looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.

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 06-01-2025.
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