Old Town ~ Unlisted Properties for Sale in Key West, FL

Motivated Seller! This is the lowest priced, residential listing within a block of Duval St in the Key West MLS! Convenient - Quiet - Comfortable. Located just a 1/2 block off Duval & priced under $480K! One bedroom, one bath condo in a serene building nestled in the heart of Old Town Key West and within walking distance to many popular attractions. Prime spot to enjoy Fantasy Fest, Goombay, New Years, multiple parades and more. Just steps away from the iconic Bahama Village Arch, Rainbow Cross Walks & the Hemingway House. Looking for the ease of condo living with NO yard work and NO exterior maintenance, this one is it! Ground level unit (no stairs) in the X - Flood Zone with NO one above you. This is one of six condo units in a building that is only two stories high. Condo boasts its own interior washer / dryer, NEW AC, and NEW on demand water heater. The last condo to sale in this building was smaller & went for $560K. For a comfortable condo in a choice location, look no further than 416 Petronia St #4!

Transiently licensed vacation rental unit ideally located in the heart of Old Town Key West! The complex comprises 13 units with amenities including a shared pool, deck, and onsite laundry facilities. Situated on the first floor, this unit offers convenience and privacy. Just steps away are Key Wests top attractions such as the Ernest Hemingway Home and Museum, vibrant Duval Street, iconic Mallory Square, and the picturesque Fort Zachary Taylor Beach and Park. Perfect for those looking to invest in a prime income producing vacation rental.

Discover a rare opportunity to bring your vision to life with this single-family home nestled in the heart of Old Town Key West. Steeped in history, this typical Conch cottage offers a historical charm, making it an ideal canvas for creating your dream residence. Embrace the rich heritage of Key West with this exceptional home, a true testament to the islands storied past. Originally part of the Cigar Cottages build around the old Pohalski Cigar Factory, where the Chevron gas station currently sits.Youll enjoy convenient off-street parking for multiple vehicles, a rare find in Key West, and peace of mind knowing this home is located in the X Flood Zone. Tucked away on a quiet lane, the property offers a serene escape from the hustle and bustle of daily life, yet it is conveniently close to the lively Duval Street. This single-family home presents endless potential for customization and renovation, allowing you to craft a home that perfectly reflects your style and personality. Dont miss out on this extraordinary opportunity to own a piece of Key West history. Contact me today to schedule a showing and take the first step towards making this historic house your new home in Paradise.

Fully renovated Old Town CBS luxury condo on Solares Hill, the citys highest point. Nestled on Galveston Lane, it provides serenity along with central location allowing you to walk to everything in Old Town. Bill Butler Park is a mere stroll away, complemented by the finest Old Town restaurants and galleries at your doorstep. This first floor unit is complete with impact windows, off-street parking, and elegant porcelain tile floors. Whether youre envisioning it as your permanent Key West residence or an upscale vacation rental, this unit seamlessly combines style, comfort, and convenience with low Condo Fees! Good rental income on the books for season ahead, call for details.

Fully renovated Old Town luxury condo on Solares Hill, the citys highest point. Nestled on Galveston Lane, it provides serenity along with central location allowing you to walk to everything in Old Town. Bill Butler Park is a mere stroll away, complemented by the finest Old Town restaurants and galleries at your doorstep. Boasting impact windows, off-street parking, and elegant porcelain tile floors, this turnkey upstairs unit is offered fully furnished. Whether youre envisioning it as your permanent Key West residence or an upscale vacation rental, this unit seamlessly combines style, comfort, and convenience with low Condo Fees!!

Location, location, location! 306 Truman Avenue is nestled in the heart of Old Town Key West and offers a fantastic opportunity for a renovation project. This 3 bedroom/1 bath home has a nice sized rear yard with room for a pool. The roof was done in August of 2021. A fixer upper for re-sale or to hold for long term use.

This stunning two-bedroom, two-bath condominium has just hit the market and is ready to wow you with its luxurious features and unbeatable location in the heart of Key West.Step inside to discover a beautifully remodeled interior boasting designer-grade finishes throughout. The spacious layout offers two full baths for added convenience, ensuring comfort and privacy for you and your guests.Enjoy the convenience of in-unit laundry, making chores a breeze, and indulge in the epitome of coastal living with your very own small outdoor seating space. Perfect for savoring your morning coffee or unwinding with a cocktail as you soak in the tropical vibes.Located in a prime spot, this condo puts you just moments away from Key Wests vibrant attractions, world-class dining, and pristine beaches. Whether youre seeking a full-time residence or a vacation getaway, this condo checks all the boxes for luxury living in paradise.Dont miss out on the opportunity to make this Key West gem your own. Schedule a showing today and experience the epitome of island living!NEW IMPACT DOORS & WINDOWS COMING SOON! --will cut the monthly HOA roughly in half!

Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience.Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key Wests South Beach, where sun-soaked days and breathtaking sunrises await.The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors.Whether youre lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Dont miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location.Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

Welcome to your dream getaway! This enchanting conch cottage is just two blocks from Duval Street, featuring a delightful pool house that enhances its charm and a desirable off street parking space. A Slice of Paradise featuring High ceilings with exposed beams and trapezoid transom windows create an airy, open atmosphere. Modern Upgrades include a beautifully updated kitchen and baths, complete with stainless steel appliances, including a gas stove, composite counters, and stylish cabinetry.A cozy loft area serves as extra sleeping space for kids or guests and offers incredible climate-controlled storage.Outdoor Oasis**: The fabulous outdoor space under canvas extends your living area and is prepped for an outdoor TV, perfect for entertaining. Gorgeous Shared Pool with a stunning pool adorned with distinctive mosaic tiles that reflect the colors of the sand and sea. The pool house includes a full-size futon, half bath, and a private outdoor shower ideal for guests who appreciate their own space. A rear shed and brick pavers provide extra storage options alongside the house.Low monthly HOA fees, an X-zone flood designation, and insurance mitigations like hurricane-rated storm shutters make this a smart choice for Old Town living. Located just steps from the iconic Hemingway House, Blue Heaven, and Truman Annex, this cottage offers the perfect blend of comfort and convenience. Dont miss out on this exceptional opportunity!

MOTIVATED SELLERS A must see this desirable beautiful bright condo located in the heart of historic Old Town area. This charming 1 bedroom 1 bath home offers high ceilings, with open spacious floor plan. The perfect spot within walking distance of great restaurants and a few blocks to the Historic Seaport and the famous Duval Street.

NEW LISTING! TRANSIENT LICENSED 2BR CONDO! One of the most luxurious condominiums in Key West. This transient licensed condominium with contemporary design and decor offers two level living and three balconies. The main level features a gourmet kitchen, balconies, powder room, and living room with pool views. Upper level has two bedrooms with designer en suite baths. Santa Maria amenities include stunning heated pool and grounds, bellman, 24 Hour full-service concierge, parking, & gym.

Uncover the possibilities of this classic Old Town Key West conch cottage! Beneath the shade of a mature mango tree, the front porch welcomes you to a 2-bedroom, 1-bath renovation project providing the ideal canvas to make it your own. With coveted gated off-street parking and an expansive backyard with space for a pool and outdoor living, this property has room to create the ultimate island retreat.Located in the highly desirable X Flood Zone and Transient License Receivership Zone, this property is just a half block from Duval Street, offering easy access to all of the amenities of Old Town. HNC-1 zoning allows this property to become a transient license receiver property (it currently does not include a transient license).

Step into this bright and airy two-story single-family move in ready home nestled in the heart of Historic Old Town Key West. Boasting 3 inviting bedrooms, 2 baths, and an open floor plan with a spacious kitchen and dining or bonus room, this residence offers the perfect blend of comfort and entertainment space. With the added convenience of off-street parking and its prime location within walking distance to an array of restaurants, clubs, and the waterfront, this home presents a wealth of flexibility for your ideal living experience.

This residence is a beautifully appointed 2-bedroom, 2-bath exuding timeless charm & modern elegance in one of the most sought-after neighborhoods on the island. From the moment you enter through the private entrance, youll be enchanted by the serene patio, a perfect spot for sipping your morning coffee or evening cocktail. This outdoor oasis provides is an ideal setting for intimate gatherings or peaceful solitude.Step inside to discover the open-floor plan, where high ceilings & large windows fill the living, dining, & kitchen areas with light, creating an airy, welcoming ambiance. French doors seamlessly connect the indoor & outdoor living areas, making this home perfect for entertaining. This kitchen is a stunning blend of modern elegance & functional design. Marble countertops & stainless steel appliances provide the backdrop for any culinary endeavor. Open shelving adds a touch of airy sophistication.The large first-floor bedroom serves as a luxurious retreat, featuring an en-suite bath for convenience. The room is beautifully accented by a striking arched entrance.High ceilings enhance the spacious feel, creating an airy & inviting atmosphere. With ample closet space, youll have plenty of room for all your belongings. The bedroom offers direct access to the front porch--a perfect spot to unwind & enjoy the lively sights of the neighborhood. The upstairs master suite is a true haven. This spacious upstairs bedroom is a charming sanctuary, defined by its unique dormer ceilings that add character & a cozy ambiance to the space. The room features a comfortable sitting area, perfect for unwinding with a book or enjoying a quiet moment. Two closets provide ample storage. The en-suite bathroom is a private retreat featuring a dual walk-in shower, just steps from your bed. Located just a short walk from Key Wests most iconic landmarks.Whether youre searching for a new full-time residence, a vacation retreat, or investment property, this is the ideal home

Multi-family 2 buildings nestled in one of the most sought-after locations in historic Key West just a block from world famous Duval Street, this charming Old Town property offers the perfect blend of historic character and future potential. Just a short stroll from world-renowned dining, vibrant nightlife, and picturesque parks, this two-unit property is a true island gem. Rich with the classic charm of Old Key West, this property is a blank canvas waiting for your personal touch. Whether youre looking for a primary residence with a detached guest wing, or a versatile income-producing property, this home offers endless possibilities. The first of two units features two spacious bedrooms, a bonus den that can easily function as an additional bedroom or office, a full bathroom, and separate living and kitchen areas. A private courtyard separates the first unit from the detached second unit, which includes a kitchenette, living area, two additional bedrooms and 1.5 bathrooms, ideal for guests or rental income. A covered carport provides shaded parking for one vehicle, with additional off-street parking available. Located just a short walk from iconic Duval Street, the Ernest Hemingway House, the historic Key West Lighthouse, Truman Waterfront Park, and the tranquil shores of Fort Zachary Taylor State Park, this Old Town retreat offers an unparalleled Key West lifestyle nestled in a prime location. With endless dining, entertainment, and cultural attractions nearby, this property is the perfect blend of convenience and charm. Dont miss this rare opportunity to own a piece of Old Town Key West; properties like this dont last long!

Its Love at first sight! Experience all the extraordinary charm of historic Old Town Key West in your own super-private oasis. Just 3 blocks from Duval St ... but an entire world away, resides this breathtaking, gated, tropical treasure thats tucked away on a quiet, idyllic little lane. Love Lane. You will never want to leave! This home is timeless and stunning. A taste of the tropics coupled with modern comfort. Two very large split bedrooms offer exceptional guest privacy, and the elegant living room, with its sky-high exposed wood beam ceilings and gleaming wood floors, make for extremely comfortable living. Large kitchen ready for your gourmet touch with center cooking island, icemaker, and wine fridge. Enjoy year-round, alfresco dining on the back deck and relax in the wonderfully private lanai featuring a super refreshing dip pool. A major bonus is the attached one car garage! When youre ready, head out and enjoy all that Key West has to offer from the Duval Crawl with its bars and phenomenal live music to all the quaint charming streets and restaurants throughout Old Town. This Home is the perfect sanctuary to channel your inner Hemingway, Tennessee Williams, and Buffett. Relax, youre living on Key West time and youre on Love Lane. How perfect is that??

Welcome Home! Turnkey, Recently Remodeled and Ready to move in! This three (3) bedroom and two (2) bathroom property has been fully upgraded throughout. Including a brand new central A/C system, all new plumbing and updated electric system! The brand new kitchen is filled with natural light and welcomes you into the heart of the home, with new stainless steel appliances, a Farmhouse Sink, granite countertops and a walk-in pantry. Just beyond the kitchen island is a dining area and large sliding glass doors leading to the spacious backyard which comes complete with a brand new in-ground pool, with a new heater/chiller, outdoor backyard living and dining space, and a private outdoor shower. The Primary bedroom has its own brand new ensuite bathroom. The two additional bedrooms offer plenty of room for visiting houseguests or family members. Great Bahama Village location, close to Truman Waterfront, Coffee Butler Amphitheater, Ft Zachary Taylor State Park ( Locals favorite beach ) and walking distance to Duval Street! Completely furnished with modern furniture and furnishings included in sale and strong rental numbers on this excellent vacation rental property. Call today for your private showing! *Rented February 2025 $19k

Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 2623 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

Income producing opportunity close to Duval Street, Truman Waterfront Park, Hemingway Home and the Southernmost Point! If you are looking for a single family home or multi-family that is like no other, youve found it in this charming and eclectic, restored, Conch home. The restoration brought out the best blend of history, island flavor, comfort and useful design. Move right in. Everything is up to current code with new impact-rated windows and doors, new metal roof, and re-built foundations. The 2 bedroom, 2 bath main house with extra rooms has new, wood flooring, closets in every bedroom, lofts for extra sleeping or storage and a large, eat-in kitchen with lots of cabinetry. The main house has a welcoming and covered front porch plus 2 more porches off either end of the kitchen. The detached 1 bedroom, 1 bath cottage in the rear of the property is also beautifully renovated and furnished and has 2 porches. It is a legal rental allowing minimum 28-day rental periods. The third building is an historic structure that was once a beloved neighborhood variety store. It has also been restored and includes a half bath and studio/creative space with a beautiful cedar ceiling. Theres an outdoor shower attached to this building.Drive right in to your off-street parking spot that will double as a patio for a party. Youll find rain barrels at the downspouts of the new gutter system. Theres a mature mango tree, an egg fruit tree, a papaya plant, a hog plum tree and several banana palms. An herb garden is located outside of the kitchen next to the barbecue patio. The landscaping evokes a beach feeling with rock and seashells, a hammock and of course tropical plants making it ideal for beautiful, garden gatherings.

Income producing opportunity close to Duval Street, Truman Waterfront Park, Hemingway Home and the Southernmost Point! If you are looking for a single family home or multi-family that is like no other, youve found it in this charming and eclectic, restored, Conch home The restoration brought out the best blend of history, island flavor, comfort and useful design. Move right in. Everything is up to current code with new impact-rated windows and doors, new metal roof, and re-built foundations. The 2 bedroom, 2 bath main house with extra rooms has new, wood flooring, closets in every bedroom, lofts for extra sleeping or storage and a large, eat-in kitchen with lots of cabinetry. The main house has a welcoming and covered front porch plus 2 more porches off either end of the kitchen. The detached 1 bedroom, 1 bath cottage in the rear of the property is also beautifully renovated and furnished and has 2 porches. It is a legal rental allowing minimum 28-day rental periods. The third building is an historic structure that was once a beloved neighborhood variety store. It has also been restored and includes a half bath and studio/creative space with a beautiful cedar ceiling. Theres an outdoor shower attached to this building.Drive right in to your off-street parking spot that will double as a patio for a party. Youll find rain barrels at the downspouts of the new gutter system. Theres a mature mango tree, an egg fruit tree, a papaya plant, a hog plum tree and several banana palms. An herb garden is located outside of the kitchen next to the barbecue patio. The landscaping evokes a beach feeling with rock and seashells, a hammock and of course tropical plants making it ideal for beautiful, garden gatherings.

At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24. When you are sitting on your front porch its hard to believe that you are in between the two busiest streets as Julia street is a really quiet and cute street! Dont miss out on this great opportunity!

This is a classic Conch cottage located on a quiet Old Town lane. Beautiful Dade County pine throughout from walls and ceilings to hardwood floors. Updated open kitchen with quartz countertops and stainless steel appliances. French doors open to the landscaped backyard with saltwater pool, deck, outdoor shower and privacy fence. This home is just a short walk or bike ride to all of Key Wests best restaurants, galleries & shops.

Welcome to this turn of the century conch house. This home has been in the same family since 1913 and is now available for a new owner who can appreciate its classic architectural style and expansive yard. The wrap around porch provides a wonderful place to relax in the shade and enjoy the Old Town neighborhood. There is a large living room, separate dining room and 3 bedrooms and 2 baths. The home has high ceilings and there is an attached carport for off street parking. This home is a rare find for a buyer looking to preserve the charm of our building heritage with such a sizeable yard.

Price Reduced, Owners motivated! This triplex is situated in a prime area of Old Town, just three blocks away from Duval Street. It presents an attractive investment opportunity with its three separate units, offering potential for rental income, extended family stays, or versatile usage. Constructed from concrete blocks in 1979, this propertys main unit is currently occupied by the owners, who benefit from consistent rental earnings from the other two units, frequented by repeat monthly guests. Unit A comprises two bedrooms and one bath, spanning 768 sq. ft., while Units B and C are one-bedroom, one-bath units with 528 and 564 sq. ft. each. Each unit features its own laundry facilities and a private outdoor patio area perfect for relaxation. Additional conveniences include on-site parking and storage. The propertys strategic location, mere minutes from Duval Street, restaurants, bars, beaches, historical landmarks and waterfront attractions, enhances its appeal as a multi-unit investment. Take the opportunity to explore this property today and envision its myriad possibilities!

DEVELOPER ALERT !!!!!PERMIT IS READY TO BE PICKED UP**Historic Old Town Home Ready for Rehabilitation**This charming property is located in a highly desirable X flood zone and offers 5,470 sq ft of land. HARC has already approved the rehabilitation of this historic home, increasing the current square footage from 2,020 to 2,575. The finished product will include 4 bedrooms, 4.5 bathrooms, a pool, and plenty of off-street parking--a prime need in Old Town. This home also offers a large open attic that could add living space.Situated just steps from the world-famous Duval Street, youll enjoy the convenience of nearby attractions while being far enough to avoid the noise. This is a rare opportunity to own and restore a piece of Key West history.Manager of LLC is a License Florida Real Estate Agent.

This charming three-unit property at 808 Fleming Street represents an exceptional investment in one of Key Wests most desirable neighborhoods. Located in the historic Old Town district, this versatile building offers multiple revenue streams and tremendous potential for savvy investors.This property is ideal for investors or multi-family living. With separate electric and water meters for each unit, management is effortless and efficient.Property Features:Downstairs Unit: A spacious 984 sq. ft. living area, perfect for an owners residence or premium rental unit. Its open layout offers flexibility and comfort.Upstairs Units: Two additional units occupy 1,019 sq. ft. of living space, providing privacy, comfort, and excellent rental potential.Outdoor Living:Island living comes alive with this propertys inviting front porch and expansive front balcony, perfect for enjoying the tropical breezes. The private backyard includes a 22 x 18 wooden deck and an additional 22 x 23-yard area, offering endless possibilities for entertaining, relaxation, or further enhancements. An unused 11 x 6 cistern adds a touch of Key West history and utility to this unique property.Prime Location:Centrally located, this property provides easy access to Key Wests vibrant dining, shopping, and world-famous nightlife. Tenants and residents will enjoy the best of island life, with the perfect balance of convenience and tranquility in a sought-after neighborhood.Endless Potential:This multi-unit property offers endless possibilities--generate strong rental income, create a multi-generational living arrangement, or craft your dream Key West retreat. With its combination of private utilities, multiple spaces, and outdoor amenities, this property is ready to fulfill your vision.Call today

Experience the charm of Old Town living at 923 Eaton St, a beautifully updated historic home featuring three bedrooms and two baths, ideally situated just steps from the Historic Seaport and a short stroll to Duval Street. Offered turn-key, this property combines classic Key West architecture with modern enhancements, making it perfect for enjoying the local lifestyle.Inside, youll find Dade County Pine walls, hardwood floors, and renovated kitchen and bathrooms. The second floor boasts two inviting bedrooms, while the first floor offers a charming bunk room. Step outside to discover a spacious 10x20 ft heated pool and a private tropical backyard oasis, perfect for outdoor relaxation. Additional features include a newer metal roof, an impact-rated sliding glass door leading to the rear deck, and efficient ductless AC units.This charming home is fully furnished and ready for you to move right in or to generate a reliable income as an investment property, allowing you to enjoy all that Key West living has to offer!

Excellent opportunity whether looking for a private residence or an investment. This condo will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless.

Beautiful 3 bedroom 2.5 bath home being offered Turn-key, perfect walking location to restaurants, historic waterfront, shopping and all the nightlife on Duval St . Spacious open floor plan for easy living and entertaining friends and family includes the ever important first floor bedroom, half bath and laundry room. Just off the kitchen/ dining area sneak out to the hot tub to relax, or outdoor patio for dining with plenty of shade and privacy. Back inside, make your way up the gorgeous staircase to the second level to find an oversized master bedroom with walk in closet and ensuite bath. The second floor also includes the third bedroom and second full bathroom! 400 White St is a home you wont want to leave ! Call today to schedule your private tour.

This charming two-story Old Town cottage in Key West is ideally located just a half block off of Duval Street. The interior was beautifully renovated throughout with new floors, updated kitchen and impact windows & doors. The first floor includes a master bedroom with French doors leading out to an in-ground swimming pool. Upstairs, a loft provides a spacious guest bedroom. Overlooking the large pool and guest cottage which features vaulted ceilings and tiled flooring. A spacious wood deck covered by a large tiki hut connects the main house and guest cottage, creating a seamless indoor-outdoor living experience.The private pool, surrounded by lush landscaping, offers a tranquil retreat characteristic of Key West living. Additional amenities include an outdoor shower and covered off-street parking.