Key West Old Town Real Estate

This is a rare and elegant home that's rich in history and gracious in its architectural details. Stately and elegant, this historic home has five bedrooms, seven and one-half baths. The current owners have carefully combined an impeccable restoration with state of the art amenities to create comfort along with the splendor of a historic residence. There are large rooms, expansive covered porches, a custom designed wine room, outdoor living and dining pavilions, a heated pool, new guesthouse, gym and pool cabana built to withstand a category 5 hurricane, including a generator. This special home has 6888 SF and the lot is 14,702 SF. More information on this property

Incredible Old Town location totaling 6 bedrooms, 5 full & 2 half bathrooms in two brand new state of art structures each with private pool, 2 transient licenses, offered tunrkey furnished. Totaling nearly 4500 SqFt of a/c space complimented by fabulous outdoor living with covered dining, brick patios, huge roof top terrace overlooking famous Duval Street and spacious garden and pool view balconies. High-end fixtures & finishes throughout both homes include heart pine floors, granite countertops, Smart House Technology, gourmet kitchens with Viking appliances, high-impact windows & doors & excellent sound proofing. Off street parking for 4-cars including 2-car garage. Brand new & beautiful with huge earning potential! More information on this property

This stunning property is absolutely Captivating. In the heart of Old Town just one block from the Historic Seaport Harbor enjoy true relaxed elegance. Totaling 6 bedrooms and 6 bathrooms throughout 2 wonderful structures this property is laid out with careful attention to every detail & privacy. A tasteful combination of an historic home and new one, enjoy the whimsical timeless character of this gem. Spread over a huge corner lot, this dazzling property even has a water view. Endless porches & decks, rooftop patios, balconies and wonderful breezeways all surrounding your beautiful heated & chilled pool. This significant property will amaze you. Every bathroom is a work of art, lush landscaping, 2 gated off St parking spaces. More information on this property

Traditional yet stylish with careful attention to classic detail. Timeless elements throughout including 10ft ceilings finished in oversized moldings, marble and stone bathrooms and counters, wood floors and plenty of indoor and outdoor covered entertaining area including a beautiful 2nd story porch. Totaling 5 ensuite bedrooms including guesthouse, there is plenty of room to spread out both inside and out with a spacious pool area finished in rich Epay decking. The finest amenities complete the well appointed kitchen including Miele, Subzero and Viking professional appliances, a pass through window and walk in pantry. More information on this property

Luxurious 4 level waterfront townhome custom designed by architect, Michael Ingram. This is the opportunity of a lifetime to own a gorgeous home in Old Town Key West with a private boat slip. Features include private waterfront pool, private elevator, covered parking, maple and slate floors, Viking stainless steel appliances and breathtaking views from most rooms. More information on this property

This wonderful family home is beautifully sited on a huge double lot on a peaceful cul-de-sac in Truman Annex. The three story main house has 4BR/4.5BA, double porches front and back, and spectacular ocean views from an amazing widow's walk. The glorious gardens surround a spacious veranda, an artist's studio, gardener's gazebo, adorable guest cottage and an inviting pool.More information on this property

Spectacular and dramatic 18' peaked ceilings and multiple glass doors lead to the heated pool, tropical gardens, outdoor bar, an entertaining area, and poolside bath and dressing room. Brick and hard wood floors, fireplace, dining room and enormous new gourmet kitchen with stainless appliances and granite countertops. French doors in the kitchen open to a wraparound porch and patio beyond. The master includes a sitting room, dressing room, and opens to a large sun deck. A second bedroom and bath is on the ground floor. Off street parking for two cars, 2 fresh water wells supply water for the gardens and pool. Extensive brick walkways and lush gardens surround the property, and fencing and plantings provide complete privacy. More information on this property

Built in 1897 and formerly owned by both Calvin Klein and interior designer Angelo Donghia this is one of Key West's premier signature homes. The architecturally beautiful southernmost octagon house is one of only 2 octagon homes in Key West. Soaring ceiling heights, Dade County Pine walls & floors, spacious rooms and huge porches everywhere make this property truly remarkable. This comfortable & casual home offers three or four bedrooms, three baths & meandering brick pathways throughout a lushly landscaped enormous lot. Relax & entertain by your oversized pool & Jacuzzi. Off street parking for 3 cars. All in the heart of Old Town! More information on this property

One of Key West's finest tucked away down an Old Town lane in a most enchanted setting. An arched wood bridge over cascading waterfalls that spill into a koi pond welcome you to a total of 3 structures joined by breezeway, balconies, wood decks, and open air living room all over looking a huge pool, gorgeous tropical gardens and a canopy of mature trees. Spanning a total of 7500 sq ft with 2500 sq ft of a/c living space including 4 bedrooms, 3 baths plus a den. A combination of an addition and a stunning restoration with careful attention to historical detail including antique leaded glass accent windows, exposed original wood shake roof and original wood flooring to name a few. Truly a hidden gem not to be missed.
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Distinguished Old Town 2-story Conch Home beautifully renovated in 2005 to be a very spacious 5 br, 5.5 ba including a detached guest house, pool & 2 off street parking spaces. Grand curb appeal with 88ft of street frontage privatized with a custom sliding Cedar louver wall. Gourmet kitchen with Thermodaore appliances, Meile coffee station, wine chiller, ice machine, triple sinks & granite counters. Ensuite bathrooms for each of the 5 bedrooms with private porches off 3. Open floor plan & telescoping door system off great room to a covered Ipe breezeway/patio to guesthouse. Outdoor grill finished in granite & teak cabinetry. Custom pool with waterfall feature & bench seating. Every amenity & detail you would expect in a luxury home. More information on this property

Exquisite designer Old Town Home with state of the art amenities. Dramatic great room welcomes you with coffered ceilings, wood walls, sophisticated gourmet kitchen, wet bar & beautifully appointed living & dining area. Indoor/outdoor living room finished in Ipe, pool, waterfall & new guest house. Unsurpassed craftsmanship & custom designer materials grace this home including walnut countertops, marble selections, bamboo & seagrass treatments, plantation shutters, generator to name a few. A Truly impeccable work of art to be appreciated by the most discerning buyer. More information on this property

Designed by award winning architect Tom Pope and constructed by Erik DeBoer in 2000 is this outstandingly built large home located in the highly desirable Meadows area. This well proportioned 4 bedroom/4 bathroom home has over 2500sf of living area incorporating luxurious touches such as Brazilian cherry floors, gourmet kitchen and living area overlooking the pool and beautifully landscaped yard, a large master suite with walk-in closet and a covered deck for relaxing in the shade by the pool. There is also off-street parking for 2 cars. More information on this property

Prime Historic District location and newly built with master craftsmanship throughout. 4 bedrooms and 4 luxury baths, including a master bedroom ensuite on the ground floor and another on the second. Hand rubbed Brazilian cherry flooring, beautiful crown moldings, gourmet kitchen with marble countertops and a hand forged copper hood and a honey onyx back splash, gorgeous. All windows and doors have impact glass (qualifies for insurance credits) and the exterior has hardy board siding for easy maintenance. French doors open to the beautiful pool, spa and waterfall all surrounded by tumbled marble and tropical palms and plants for privacy. This home is exceptional and a must see! More information on this property

Customize your own new home in Old town just a block away from the Historic Seaport. Currently under construction with plenty of time to choose your finishes this 6BR/6BA home will include a 2BR/2BA guesthouse with full kitchen. Upon entering your new home your will be greeted with an elegant stairway, mahogany & Travertine floors & a wonderful great room with glass doors to the large back yard & heated pool. Additional amenities include an eat-in gourmet kitchen with granite counter tops, wet bar with wine cooler, Boston Acoustic surround sound, Dublin Embassy lamps, Italian hand crafted Rohl fixtures, Hardie Plank Siding, storm rated Hurd windows, PGT doors, Timber Tech decking & off-street parking. Photos are of the sister home next door. More information on this property

One of a kind! Fabulous two-story Duval Street penthouse with transient license features 3 bedrooms, all with private porches, & 2.5 baths. An enormous roof deck overlooks Duval St., while the back porches enjoy views of the private garden with swimming pool and spectacular waterfall. High-end fixtures and finishes throughout include heart pine floors, granite countertops, smart house'' technology, gourmet kitchen with Viking appliances, high-impact windows and doors and excellent sound proofing. Brand new and absolutely stunning, this penthouse is ideal for entertaining. Fabulous earning potential! More information on this property

An imposing Victorian styled home that has been beautifully and totally restored and remodeled in a way that combines classic details with the convenience of modern amenities and luxuries. The high ceilings and large windows give the home a bright, tropical feel that is enhanced by the lush vegetation, Brazilian decking and pool which is overlooked by the gourmet kitchen and large living area. This home is perfect for entertaining guests or the large family with it's two master suites plus two additional bedrooms. Located in the highly sought-after Old Town area close to the harbor, boutiques and fine restaurants. Off-street parking for 1 full size auto (or 2 little cars). Awarded a coveted 'Ceramic Star' for historic preservation. More information on this property

Rare, spacious lot in the Casa Marina area. Total of 12700 SF fronting Washington and Whalton Streets. More information on this property

Location! Charming 3bd/3.5ba house with transient license offered turnkey furnished. Tucked away on quiet Bahama St., but just steps from the fabulous restaurants and nightlife of Duval, this lovely new home captures the charms of Old Town'' Key West. On the main floor, a wall of French doors opens onto your private garden with heated pool and spectacular waterfall. On the second floor, the master suite enjoys a private porch and the two guest rooms on the third floor each have their own baths. Dark walnut floors, wood paneled ceilings, a gourmet kitchen with Viking appliances, high-impact windows and doors, off-street parking for two cars, and top of the line finishes through out make this house a true gem. Fabulous earning potential! More information on this property

This beautiful historic 2-story home has been completely renovated including a new 2 story addition. Craftsmanship and attention to detail are evident throughout this home with hand sanded Dade Co. pine walls, pine floors, crown molding and intricate tile work. The entrance foyer leads to a showplace kitchen and great room with multiple sets of French doors to the backyard with pool. Also on the first floor is a large guest bedroom with ensuite bath and a powder room. The second floor has a generous sized guest bedroom with ensuite bath and a large master suite with beamed cathedral ceiling, French doors to a small balcony, and master bath with double sinks, tub and separate shower. Best location - walk to the historic seaport, Duval Street, restaurants and shops. More information on this property

This 8 unit apartment building is located on a prime corner - Truman Avenue and Georgia Street in the Meadows/Old Town neighborhood. The building is in very good condition and includes 4 efficiency units and 4 one bedroom units. Recent electrical service upgrade - all units are separately metered for electric. Property is 1.5 lots with great outdoor space including a 15' x 30' pool with water service to pool provided by well. More information on this property

A perfect primary residence or second home, currently being used as a vacation rental, situated on a quiet Old Town lane. The spacious floor plan includes a main level bedroom and bath, large galley style kitchen with new appliances and a great room with French doors opening to a large covered porch. Upstairs are two enormous master suites with vaulted ceilings, wood floors and French doors to a canopied balcony overlooking the landscaped yard and heated pool. The home is being sold furnished and includes a transient license which allows the owner to rent the property on a nightly basis. More information on this property

This extraordinary home was custom designed and built with master craftsmanship in 2002 by an award-winning architect. Situated on a beautiful block of the Casa Marina area, the property has 3 bedrooms plus an office, 4 bathrooms, a gourmet kitchen, large windows for lots of light, and off street parking for 2 cars. An outdoor shower on the second floor master bedroom porch has wonderful privacy and serene views of the pool and gardens. More information on this property

Delightful Old Town cottage boasting 3bd/2.5ba, two off street parking spaces and pool. An outstanding use of space brings the outdoors in with living room nestled between spacious covered decks, lush landscape, generous pool with waterfall and private spa. Enjoy charming Dade County pine walls and ceilings, renovated kitchen & baths, cathedral ceilings and lots of glass doors, windows and skylights. Impeccably cared for both inside and out and designer finished available turn key with optional furniture package negotiable. More information on this property

This house has been beautifully renovated with easy island living in mind. The first floor is open with living/dining and outstanding cook's kitchen and custom burled maple cabinetry, granite countertops and Viking and Bosch appliances and Brazilian cherry floors throughout. Upstairs are two bedrooms, a beautiful bath and an enormous walk-in attic space that easily could be finished for a third bedroom, studio, etc. Ipe decks surround the heated swimming pool and separate spa. There's outdoor dining through French doors and large tropical plantings all around. Old Chicago bricks cover the off street parking area. More information on this property

Just completed, this newly constructed gem has it all. Features include 3 bedrooms, 3.5 baths, a wonderful great room that opens to pool & water fall, granite counters, impact resistant windows and doors, GE Smarthouse capabilities and crown molding all located on a quiet, private lane in Old Town. More information on this property

This is THE perfect Key West house designed for easy living. A wall of sliding glass doors in the living room disappear into the walls and opens to a large covered porch overlooking the beautiful pool and gardens. A divine kitchen with outstanding appliances and storage is a cooks dream plus there's an outdoor kitchen preferable on those warm and balmy nights. Two bedrooms 1 1/2 baths in the main house plus a separate guest room and bath adjacent to the pool area. Unbelievable as it may seem, there's a full basement under the house for storage. Glorious gardens, off street parking and its all on a beautiful block. More information on this property

This recently renovated home on a corner lot in the Meadows has 3 bedrooms and 2.5 baths. There is a separate office in the main house, and a detached guest house with half bath and outdoor shower. The cheerful home has many top of the line features and appointments as well as a heated pool, deck, outdoor kitchen and off street parking. The fenced garden is full of colorful flowers and maturing trees. More information on this property

Old Town Gem! Everything is new and top of the line! A truly beautiful renovation almost complete featuring four bedrooms & 4 bathrooms, new pepperwood floors, new kitchen with granite countertops & Viking appliances, all new bathrooms and a pool. More information on this property

Hidden away on a quiet, private lane this brand new home is just waiting for you. Featuring 3 bedrooms, 3.5 baths, a wonderful great room opens to a pool and waterfall, granite counters, impact resistant windows & doors, GE Smarthouse capabilities & crown molding. Built by one of Key West's best contractors you will see the quality craftsmanship throughout. More information on this property

A transient licensed vacation rental in super location one half block off Duval Street on a quiet dead end street. This two story home has a flexible floor plan that will accommodate up to 12 guests. The main level opens through sliding glass doors to a large rear yard with a heated pool. Also on the first floor are two bedrooms, two baths, wood and tile floors and high ceilings. The second floor is accessed through a private outdoor stair case and has a very large bedroom/living area and full bath.
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Attractive three-story home located in the Heart of Old Town. The upstairs floor plan has 3bd/3ba, downstairs has two 1BD/1BA apartments. Gorgeous hardwood floors throughout, plenty of porches, private pool & deck area, tall ceilings and a third-story terrace with amazing 360 views of Key West Historic Seaport. More information on this property

This totally renovated Old Town cottage is in the most desirable location atop Solares Hill. An absolutely stunning 2 bedroom, 2 bath home with a large family room with 3 walls of sliding glass doors opening onto the tropically landscaped yard, large deck and in-ground jacuzzi/dip pool. The gourmet kitchen has granite countertops, Bosch stainless steel appliances, vaulted ceiling and a dining area with a wall of glass. The bright and airy interior features crown molding, designer lighting and beautiful heart of pine floors throughout making this one of the most appealing homes available. More information on this property

What a value for 3 bedrooms, 2 1/2 bathrooms, pool, spa and off street parking for 2. With some TLC this property could be fabulous boasting high ceilings finished in natural wood, large open spaces, eat-in kitchen, French doors off of virtually every room to porches and decks that wrap around practically the whole house. A fantastic project just waiting for someone to unveil its full potential.  More information on this property

Located on a beautiful block of Washington Street is this single level concrete block house with a great floor plan. There are tile floors, a large living room that opens to the patio and pool area as does the dining room. The master bedroom has a large dressing area and a private spa and outdoor shower off the bathroom. In addition there's an office area off of the master bedroom. The second bedroom has it's own bathroom and there's an outdoor building with the washer and dryer. More information on this property

Incredible value awaits the smart buyer for this recently built quality home. Top of the line finishes are used throughout including stone and wood floors, granite countertops in the kitchen and baths and wind impact windows and doors. The home has an up-to-date floor plan with an open living/dining and kitchen opening to a covered porch and stunning pool with water feature. Also on the main level is a guest bedroom and bath. Upstairs are two oversized master suites both with walk-in closet, and bath with separate tub and shower. One of the master suites includes a large loft area with stairs to a rooftop widows walk with spectacular panoramic views of Key West and the waterfront. More information on this property

This very attractive cigar maker's cottage is located in the Conch Grove Compound. The tastefully renovated home features pine floors, new kitchen appliances, vaulted ceiling and an open, airy floor plan that opens through French doors to a large private landscaped garden. Note the large lot. Walk through the private L-shaped lot to a beautifully landscaped yard with heated pool and sundeck. Also note that the upstairs loft (26 ft. x 11 ft) is not included in the square footage. More information on this property