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

This stately home sits on a 16,632 sq. ft. beautifully landscaped lot. The meticulous resurrection of the historic Jefferson Brown home (circa 1889) was completed approximately 2 years ago. The attention to every custom detail and quality of construction make this one of the most outstanding residences in Key West. There are 4 bedrooms 3.5 baths, classic living room complete with fire place, elegant dining room, expansive master suite, and a private state of the art theatre room. The back of the home opens to the spectacular private garden with a pool side pavilion. 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

Finally. . . . A Fantastic Old Town Beauty that has it all. A magnificent lot , large heated pool , 2 guest houses & a fabulous home totaling 5 BR, 4.5 BA all on one of the best streets in Key West. An enormous great room opens out to a huge covered porch & full service bar. It's an entertainers dream. Enjoy a spacious Master suite with large his & her closets to die for and a lounging balcony overlooking the pool & lush landscaped grounds. A 600 bottle air conditioned wine room, generator, irrigation system, outdoor lighting, storage galore & 2 gated, off-street parking spaces are just a few of the luxurious amenities this home has to offer.  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

Formally the movie set for the James Bond film License to Kill,'' now a tropical oasis with a License to Chill.'' Low key casual setting on rare sprawling 14,351 sq ft parcel just 2 blocks from famous Duval Street. 3 structures & 2 pools total 6 bedrooms with a historic 3 or 4 bedroom home boasting light filled rooms with high ceilings, original wood floors, open spaces and French doors to fabulous covered porches. Relaxed floor plan laid out for private guest spaces with exterior entrances, private ipe decks, 2 detached guest homes and plenty of off-street parking with access from either Villa Mill Alley or South Street. A casual Key West compound perfectly suited for family comfort, entertainment paradise & an occasional movie set. More information on this property

An Elegant historic house on a large corner lot in the Casa Marina area. Built in 1900 of concrete block the house has been beautifully renovated with fine reclaimed pine floors, windows custom built with impact glass, 11 foot ceilings, handsome crown moldings and large rooms with lots of light. The outstanding kitchen is equipped with all modern and gourmet appliances, a pantry, custom solid cherry cabinetry and limestone flooring. Three bedrooms, four baths plus a study or fourth bedroom with a private balcony. The house has wrap around porches on two floors, a large outdoor sitting and dining patio plus an in-ground pool, serene tropical gardens, off street parking for two cars. The property is walled for 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

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

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

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

Hidden away at the end of a quiet lane in the heart of the historic district is this recently built home in the style of Key West Conch Architecture. The shady front porch features the classic three bays and opens into a wide gallery entry flanked on one side by an open custom designed staircase with cable railing. At the rear of the home is an expansive great room with a beamed 22 foot ceiling, beautiful maple floors, custom cabinetry and a well designed kitchen. This spectacular room opens through multiple tall sliding glass doors to the tropically landscaped yard with pool and spa. The master suite is on the main level while two guest rooms with ensuite baths occupy the second. Both levels are clean, crisp and light-filled. This contemporary take on a classic has been designed for low maintenance, carefree living with GE Smart Sense wiring and wind resistant doors and windows. More information on this property

Desirable Love Lane: Complete renovation just completed from New piers to new roof. Home taken down to the studs and rebuilt! Vaulted ceiling in Living room, private office. Beautiful Kitchen dining area. Large covered patio off Kitchen. Laundry room and storage room off patio. Landscaped and ready to move in immediately. Most desired location in Old Town, walk to Restaurants, Seaport, Theatre and Duval St or enjoy quiet private setting at the end of Love Lane. 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

Bank owned & Drastically reduced! Designer Old Town Home with 4 bedrooms plus an office and 4 full bathrooms & 2 half baths. State of the art amenities include beautiful coffered ceilings, wood walls, sophisticated gourmet kitchen, wet bar, detached pool house/office & a full finished attic . Wonderful Enjoy your pool & waterfall from your Indoor/outdoor living room finished in rich Ipe wood . Unsurpassed craftsmanship & custom designer materials grace this home including walnut countertops, built ins galore, bamboo & sea grass treatments, plantation shutters & wired for a generator. Home is currently vacant, not as photographed. 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

Just completed renovation from top to bottom: This beautiful transient licensed home situated at the end of a quiet dead end lane in the heart of the historic district is currently being used as a vacation rental. The spacious floor plan includes a main level bedroom and bath, large galley style kitchen and great room with French doors that open to a large covered porch. Upstairs are two enormous master suites with French doors to a partially canopied balcony overlooking the landscaped yard and pool. Features include high ceilings, wood and tile floors and heated pool. The property is being sold beautifully furnished. More information on this property

Privacy Abounds: 3BR/2.5BA family home with tile flooring, lots of custom built-ins, a large kitchen with a pass through to the outdoor wetbar and fridge poolside. Overlooking the pool is the 1BR/1BA guest house with living room, bedroom, bath and loft - ideal for Mother In Law or office. Heated pool and spa, lush private gardens with off street parking and a koi pond. 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

Just completed renovation of this transient licensed home in a super location one half block from Duval Street on a quiet dead end street. Two story home with large living/dining room, eat-in kitchen, office, 2 bedrooms, 2 baths on the first floor. The upstairs is accessed via an exterior staircase and is a large studio suite with private bath. There is a very large, pretty landscaped rear yard with porch for outdoor entertaining and decked large heated pool with waterfall. Home is being sold furnished (turnkey) including large entry mural painted by Rick Worth. 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

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

Previously a single family home with a separate cottage this property has recently been converted into a 2 unit condominium with the 2 story home one unit (Front) and the cottage at the rear of the property the second unit (Rear). Classic Key West architecture with an up-to-date interior makes this perfectly located three bedroom, two bath Old Town home a smart choice. The floor plan is ideal for entertaining with the kitchen/dining and living room opening onto a rear covered porch and private large yard with spa pool. In addition there is off-street covered parking for one car. This is the perfect property to enjoy the privacy of a single family home with the carefree life style of a condominium. More information on this property

Located in The Meadows on a lovely block of Newton St. This is a classic two story conch house originally built in 1929 with two levels offering over 1100 SF of wrap around porches and approx. 4000 SF of interior spaces. Currently configured as multi family income property, it has the potential of a handsome single family conversion or maintained as income property. Current gross income is over $50,000. per year. Off street parking for 1 car. 24 hours notice to show. More information on this property

Wonderful Key West Charisma! This sweet remodeled cottage is located on an enchanted Old Town Lane with a pool and off street parking. 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

2010 Certificate of Excellence Star: Award winning preservation home. Quiet street in Old Town with dedicated walking lane to Whitehead St. All new interior. 2 bedroom , 1 and 1/2 bath and a study. Covered porches, front and back. Seperate laundry shed. No detail overlooked! More information on this property

Transient licensed Old Town Conch home complete with lovely front porch and secluded dipping pool. Enjoy an open , airy floor plan with cathedral ceilings totaling 2 bedrooms & 2 baths. Walk to Duval Street attractions , the Southernmost Point and beaches. 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

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

A beautiful and total renovation in 2003, this is the perfect 2BR/2BA home in the Heart of Old Town that’s been meticulously maintained, and is being offered fully and wonderfully furnished. Wild pecan floors, stainless steel appliances including a wine cooler, French doors to a rear deck and cocktail pool, lush landscaping, irrigation and off street parking to boot. Driving by won’t do. 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

Private Home tucked away on quiet lane. 1/2 Block to Whitehead St. Recently renovated Kitchen and Baths. New deck installed. Vaulted ceilings. French doors opening to private deck area. Walking distance to shops, restaurants, Fort Zachary Taylor. Great Location! More information on this property

This is a magical cottage with an open floor plan, saltillo tile floors, wonderful screened porch overlooking the 10 X 20 foot pool and gardens. In addition, two sets of French doors from the living area opens to a beautifully designed side porch which also opens from the kitchen and has access to the pool and gardens. There are two bedrooms upstairs each with private half baths and a full bathroom on the ground floor. Off street parking. More information on this property

Newer home in the heart of Old Town with great view of Lighthouse from upstairs balcony. Front Two Story home with cottage in rear. Pool between the two. Off street parking for 2 cars. More information on this property

A beautiful Key West cottage located in the heart of old town and just a short stroll to the Harbor and Duval Street. The first floor features 2 generous sized bedrooms, 2 baths and an open living/dining/kitchen with two sets of French doors opening to the pretty backyard with spacious deck for outdoor entertaining and heated pool with water feature. In addition there is a spiral staircase to a large loft (235 sq. ft) that is not included in the square footage. The loft is finished to the same quality as the downstairs with hardwood floors and ample ceiling height. Lots of features today's buyer wants are included: Wood floors throughout, Dade County pine walls, granite countertops, stainless steel appliances, central air and outdoor shower. More information on this property

Great corner lot. Adorable house with room for pool. Mahogany Flooring. Stainless Steel Appl. Off Street parking.  More information on this property

This is an original turn of the Century Conch House in good condition with great bones, Dade Co. Pine walls, 4 bedrooms, 2 baths, double porches, and gingerbread trims. The home has been well maintained , has updated wiring, a newer v-crimp metal roof, and it is located in the popular Meadows neighborhood with room in the back yard for a small pool. More information on this property

Unique duplex in The Meadows. This historic property was originally built in 1934. All on one level, each unit has 2BR/1BA, a covered front porch and a screened in patio at the rear. Live in one and rent out the other. May be purchased with adjacent property MLS#111282. One owner is a licensed Florida Realtor. More information on this property

This is a nice home with off street parking and a master bedroom up the spiral staircase. Currently configured as a one bedroom. Nice space in the back yard for your enjoyment. This property is adjacent to Jose's Cantina. This is a short sale transaction requiring 3rd party approval. More information on this property

This adorable shotgun style cottage is located on a quiet lane in the heart of Old Town. The two bedroom one bath home has a wide entry hall and kitchen opening to a small living room on the rear of the house. French doors lead from the living room to a large porch, free form heated pool and recently rebuilt guest cottage. The guest cottage is an additional 100 square feet of living space plus a loft not included in the listed 735 square feet and is almost complete. Behind the cottage is a nice size yard. The house has off-street parking for 2 cars. More information on this property