Key West real estate and luxury estates for sale from Truman & Co. Real estate in the keys of florida is a great investment for a vacation home or residential purchase. Truman & Company hosts some of the finest Key West estates, waterfront condos, residential and commercial Key West real estate for sale. Stop in and see us or call our Florida Keys real estate number at 305-292-2244
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Key West real estate in Old Town Old Town Key West FL homes
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Key West Old Town Real Estate

Key West real estate listing photo
1006-1008 Fleming Street


Exquisitely restored & renovated, this captivating Old Town home on a rare large lot is truly perfect & in mint condition. Enjoy a fabulous great room w/soaring ceilings & a new Heart of Pine wall that completely opens up to pool & lush private gardens. Totaling 4 bdrms/4.5 baths including 2 guest houses. Since these owners purchased this compound they have done nothing but refine every detail of this fabulous property. Upgrades include a generator, privacy wall & gate, sprinkler system, pool retiled & refinished, day kitchen in pool house, & off st pkg for 2, hurricane shutters, security, sound & camera system throughout, new doors, landscaping, window treatments & much more! More information on this property
Key West Waterfront Real Estate
626 William Street

A Historic Masterpiece. Come revel in this homage to the art filled mansions of long ago. Sitting in the heart of Old Town with 5BR/4.5BA, including a 1BR/1BA guest cottage, you can relax by one of the largest pools in Key West or indulge in your artistic endeavors in the detached studio/office. A massive great room & flowing design elements incorporated by previous owner Jerry Herman make entertaining a delight. The master bedroom has soaring ceilings & a pair of his & her closets bigger than most Manhattan apartments! Balconies, access to Baker's Ln via an electronically locked gate, Dynasty & SubZero appliances, storage for over 3000 bottles of wine, 25KW whole home generator, video security system, intercom system, off street parking for 8 SMART cars, 18 feet above sea level, even a well to water the extensive grounds! This is one of the rare properties that can truly say it has it all! More information on this property

Key West Waterfront Real Estate
717 White Street

Subtropical Modernist Architecture. Preconstruction offering for an upscale home to be built at the corner of White and Newton Streets. This thoughtfully designed home has high end finishes throughout with a spacious open living area and 3 bedrooms, 3.5 baths. The home has two light filled structures separated by a courtyard with pool, covered dining, outdoor kitchen, fireplace and projection cinema. The main living area and master suite are on one side while the 2 guest rooms are in the other. Storage has been carefully designed to maximize space and create a place for everything. There are outdoor spaces, off-street parking for 2 cars, native landscaping and evening lighting. Minimalist modern style with careful attention to every detail. More information on this property

Key West real estate Old Town
415 Margaret Street

This is one of those very special homes where all of the elements come together to create an incredible setting for the perfect Key West lifestyle. The home is a beautiful combination of historic restoration and superior renovation with a wonderful floor plan that includes three ensuite bedrooms including the master suite which is located in a private wing overlooking the landscaped gardens and 40 foot pool. At the rear of the property is a spacious guest cottage complete with living room, kitchen, bedroom and secluded hot tub. Thoughtful details include large shady porches, Chicago brick patios and pathways that meander through the tropically landscaped gardens. Very private with off-street parking. More information on this property

Key West real estate Old Town
920 Fleming Street

Pure Classic Conch home in the heart of Old Town with a fully detached 1 bedroom, 1 bath guest home on Hibiscus Lane in the rear. With off street parking, a large deep lot and a wonderful pool, this home has it all! Immaculate and award winning, totaling 4 bedrooms and 3.5 baths with hardwood floors & Dade county pine throughout. A great family room sits right off the new gourmet kitchen and covered porches are everywhere for you to relax and enjoy! Truly an entertainers delight! A rare find, walk to everything!. More information on this property

Florida Keys real estate

727 Love Lane

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

Key West Real Estate
1319 Eliza Street


The renovation of this beautiful property is now complete and the 3 bedroom, 3 bath home is ready for its proud new owner. The spacious floor plan has open living and dining areas and a magazine quality kitchen all with French doors opening to the rear yard with a large deck and stunning pool. The high vaulted ceilings and numerous windows create a light and airy interior that is accentuated with sanded Dade Pine walls and light hardwood floors. Finishes include top quality stainless steel appliances, custom tile work in the baths and designer lighting throughout. This superb home is located on a large corner lot providing lots of sunlight and privacy and is move-in ready! More information on this property
Key West Real Estate
530 William Street


Elegant Historic Home located in the most desirable area of Old Town. Large spacious rooms in main house. Downstairs has Formal living dining, eat-in kitchen, 2 bedrooms 1 bath. Upstairs also full kitchen 2 bedrooms and 1 bath. Two meters with separate heating and cooling units. Easily converted back to a grand single family home. Also, included 725 and 727 Southard Street cottage. Each is Living room, 1 bedroom 1 bath and kitchen. total of 4 units. Grand home in great condition. Well maintained. Must see to appreciate. More information on this property
Key West Real Estate
415 Frances Street


This beautiful example of a classic Bahamian eyebrow style home has been totally renovated from top to bottom. The first floor of the main house includes a formal living room with exposed Dade Pine walls, study/den which could possibly be a 4th bedroom, full bath and gorgeous great room. The great room features a vaulted ceiling, built-in cabinetry, recessed lighting and granite countertops and stainless appliances in the kitchen. Upstairs are two large, sunny guest bedrooms. The separate cottage is a private master suite with vaulted ceiling and multiple sets of French doors opening onto the large deck and access through the bath to a private deck with outdoor shower. There is an inground pool, off-street parking and lots of outdoor space. More information on this property

Key West Real Estate

717 Southard Street

Elegance and Luxury is what you will experience as you enter the foyer of this magnificent Old Town Beauty. Built in 1866 and located atop of Solares Hill, this home underwent a complete renovation, introducing all the modern amenities while maintaining the historic integrity of the property. 3 bedrooms all ensuite, including a spacious master suite with third floor library and separate office. Gourmet kitchen overlooking the open floor plan of dining and living room. Luscious tropical landscaping, cozy patio and cocktail pool offer ideal outdoor space, while one off street parking spot will accommodate your vehicle. Make an appointment to see this showcase today! More information on this property

Key West Real Estate

1175 William Street

Ground floor living at its best. This completely updated home in the Historic district and high in the X flood zone, has made access, flow and usage a main priority. The living room, dining room with wet bar and well appointed kitchen with teak cabinetry plus two bedrooms that share a bath are all on the ground floor. There's loads of light through walls of glass that opens to the lovely heated pool and expansive outdoor dining and sun deck. A stairway leads up to a second floor with two bedrooms that share a full bathroom with shower. Closet space and room sizes throughout will please even the biggest clothes or furniture collector. The gardens create a tranquil zone for you and your guests. Off street parking for 3 cars. More information on this property

Key West Real Estate

2 Fletchers Lane

Wonderful, turn-key, 2 story Old Town home with beautiful Brazilian cherry floors, custom kitchen cabinets & Dade County pine walls. Obviously built by a ship builder, you can feel the custom woodwork quality throughout. Each bedroom enjoys lots of privacy with a split floor plan plus a guest cottage. Totaling 3 bedrooms & 3.5 baths with a great room that opens completely to the outdoors. Tropical landscaping and new Trex decking surround the heated pool & spa. The third bedroom cottage can double as guest quarters or a bar entertaining area with according style windows that open it up completely. Fully fenced for privacy & located between Grinnell & Margaret Streets, you can walk to everything from this unique property More information on this property

1514 Von Phister

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

Key West Real Estate

702 Catherine Street

This is a freestanding house located in a beautiful compound of just 9 homes in a convenient Old Town location. Designed by Tom Pope and built in 1990, the house is in immaculate condition. The excellent floor plan has an open kitchen/dining area that opens to a screened porch, and on the other side of the entry is the living room that opens thru French doors to the rear porch and shared pool beyond. Upstairs are 2 BRís each with ensuite baths and a porch ideal for sitting and reading. Low maintenance hardy plank, the roof has been repinned to the new code, new windows and screens, new AC, an off street parking space and the house is fully shuttered, all in the X zone. Perfect! More information on this property

Key West Real Estate

1122 Whitehead Street

Historically significant property built in the 1880's originally as a cigar factory. The current owner has carefully rehabilitated the property with an eye to preserving its historic architecture and was awarded a certificate of excellence in historic preservation from the Historic Florida Keys Foundation. Sited beautifully near the Southernmost Point the property is currently a legal duplex with the first floor being a 1 bedroom and 1 bath apartment and the second floor a 1 bedroom and 1 bath apartment. Additionally there is a finished third floor. Plans have been completed by a local architect to convert the property to a single family home with room in the rear yard for a pool. This is a beautiful property with many options. More information on this property

Key West Real Estate
421 Catherine Street

Charming and meticulously renovated 2 bedroom 2.5 bath home in Old town Key West. The home has a breezy front porch for relaxing and watching the interesting neighborhood stroll past. The interior is impeccable with Brazilian Cherry Floors, and vaulted ceilings. There is a bedroom and bath on the first floor, a top of the line kitchen, half bath, surround sound system, wet bar with wine cooler, and living room which opens through French doors to the private back yard. There is a master bedroom and bath with walk-in closet and a balcony on the second floor. New roof and hurricane shutters. More information on this property

Key West Real Estate
218 Olivia Street

Amazing 3 story Old Town hidden retreat. This home features beautiful Mexican tiles and wood floors, high ceilings, European style open kitchen with stainless steel appliances, 3 bedroom ensuite baths. A wonderful loft master bedroom with views into the treetops. There is also a big porch perfect for entertaining, family dinners and just relaxing. An outdoor shower and a bathtub are an extra bonus. This home is located a few blocks off busy Duval St. and a short walk away from the Truman waterfront and Fort Zachary Taylor park and beach. Here you don't need more than a bike to get around. More information on this property

903 Grinnell Street

A beautiful Old Town Conch house conveniently located near the White Street corridor and a quick stroll to Duval Street. The 3 bedroom, 2.5 bath home has an open floor plan on the main level with a spacious living/dining, kitchen/den, half bath and third bedroom or office. Upstairs has a split floor plan for privacy with a good sized guest bedroom with ensuite bath and a master bedroom suite with French doors to a private balcony. The home has been totally renovated with hardwood floors throughout, kitchen with granite countertops and stainless steel appliances and multiple sets of French doors opening onto the rear deck which is large enough to accommodate a pool. In addition there is a rocking chair front porch and outdoor shower. More information on this property

612 Mickens

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

1004 Watson Street

Old Town Duplex: Renovated and move in condition. Left side is 2 bedroom, 2 baths. Right side 3 bedrooms 1 bath with extra loft. Wonderful Old Town location in X500 Zone. New roof being installed. New windows and A/C. More information on this property

615 Mickens Lane

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

Key West Real Estate
1009 Simonton Street, #3

This beautiful office condominium is located near the intersection of Truman Avenue and Simonton Street. This commercial space comprises the second and third floors of the free standing building and consists of a reception area, two large offices, storage and bath on main level with the upper level being an open floor plan with full bath. Also included are two reserved parking spaces. More information on this property

Key West Real Estate
1110 Olivia Street

Short Sale: Adorable cottage in Old town. Walking distance to Duval St. Desirable X Zone. Potential short sale transaction subject to lender approval which may require a commission adjustment between the listing agent and selling agent regardless of the MLS offer of compensation. More information on this property


Truman & Co. Real Estate Services - Key West, FL
1205 Truman Avenue . Key West . Florida . 33040
Telephone: 305.292.2244 :: Fax: 305.292.2202 :: Email:

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