Key West Old Town Real Estate

Featured in magazines this is an outstanding example of Queen Anne architecture. This award winning house sits on an enormous lot and is within easy walking distance all that Key West has to offer.
Fully renovated and restored in 2005, the main house features 3 bedrooms and 2 ½ luxury bathrooms, wraparound porches on both floors, living room, dining room, library and an outstanding kitchen equipped with all modern and gourmet appliances. Across the back of the house is a glorious covered porch that spans 34’ X 16’ with ample seating and dining space and views of the pool, outdoor kitchen and gardens. Beyond the pool is a cottage currently used as a study and is kitchen ready and has sleeping loft and separate access from Sawyer Lane. There are also approved plans to double the size of the cottage.
Great care was taken to replicate historical detail while installing all new mechanical systems including, plumbing, electrical, air conditioning and irrigation. The house is wired throughout for audio /visual, telephone and cable needs and runs with great efficiency. This is a one of a kind house that accommodates a garden party for 200 just as intimately as it welcomes a couple or family for a quiet evening on the porch. More information on this property

Truman Annex Beauty--Stunning Estate on one of the largest parcels in the Annex. This historic commanding officer's home features 6BD,7½BA + an office or in-laws quarters & detached studio. Exquisite tropical grounds surround a huge pool & entertaining gazebo with sauna & bath. A wonderful 3rd floor bonus room for play or hobbies, 2-car garage, basement, hardwood floors, 2 fireplaces, storage galore & relaxing porches everywhere. 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! One of the largest properties in historic Old Town Key West! Dramatic 18' peaked ceilings and multiple sliding glass doors lead to the huge heated pool and tropical gardens, outdoor bar and entertaining area, poolside bath and dressing room. The main house has brick and hard wood floors, fireplace, dining room and enormous new gourmet eat in kitchen with cathedral ceiling that boasts stainless steel appliances and granite countertops. Custom French doors open to a wraparound porch and patio beyond. The master suite is upstairs which includes a sitting room/office, and large dressing room, and opens to a large sun deck. A second bedroom and bath is on the ground floor. The guest house has 18' cathedral ceilings in the open living dining kitchen area that opens through French doors to a private heated swimming pool. There are 2 bedrooms, each with full baths and a finished attic that is ready for expansion for a third bedroom and bath. Off street parking for two cars, 3 working fresh water wells supply water for all gardens and pools.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

Exquisite designer Old Town Home just completed, offered turnkey, stunning furnishings & state of the art amenities included. 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. This gem comes fully furnished with 9 flat screen T.V.'s, all accessories, most of the art & linens. A Truly impeccable work of art to be appreciated by the most discerning buyer. More information on this property

Luxurious 4 level waterfront townhome custom designed by architect, Michael Ingram nearing completion. 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

Stellar new home boasting a modern & innovative 4000 sqft. Totaling 4 generous ensuite bedrooms & outstanding display of luxury amenities including state of the art kitchen w/ pantry & pass thru. Exceptional entertainment set-up with 2 bars including sunken pool side swim up bar. Unique 3rd floor deck w/ great tree top view of the elegant Casa Marina neighborhood. Thoughtful extras throughout include 2nd laundry room + morning kitchen & 2nd living room. Exceptional detail w/ distinctive trim, molded ceilings & dramatic lighting. Finished in fine materials including granite, marble, wood, ipe decking & impact doors/windows. Situated on a 7480 sqft corner parcel, surrounded by a privacy wall, this is a rare combination not to be missed. More information on this property

Outstanding Architecture and Gardens
Spectacular views from the widows walk of this elegant four bedroom home. Marble floored entry, 25’ living room, 10’ ceilings, and connecting dining/living porch that overlooks tropical gardens, flagstone terraces, pool and waterfall. State of the art kitchen including wine cooler and walk in pantry. There is a charming dormered space suitable for another bedroom/bath, office or gym. The master suite has 12’ vaulted ceilings, walk in closet and glorious master bath. Car parking for two. More information on this property

Magnificent mansion built in 1888 represents fine architecture and outstanding details. Located in the prime historic district and high on a beautiful corner of Fleming and Elizabeth St., this jewel has high ceilings, beautifully scaled rooms , Dade pine floors, large rooms and incredible woodwork throughout. 5 bedrooms, 6 baths (4 full and 2 half) open kitchen, formal dining room, family room, glorious wrap around porches on two floors and much more. 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. May be combined with MLS#108052 to crate a magical compound for $3,490,000. More information on this property

A beautiful custom built home located in the gated community of Truman Annex. Located on a quiet side street this home has a wonderful street presence with classic Key West architecture including front porches on the first and second floor and a rear entry drive with 2 car covered parking. This is a special home, in perfect condition and a must see for any buyer looking quality and location. More information on this property

A spectacular renovation has just been completed in one of the most sought after locations in Old Town Key West. Located on William Street between Eaton and Fleming Streets this historic home has been renewed from top to bottom. This gracious 4 bedroom, 4.5 bath home has luxurious features throughout including hardwood floors, exposed Dade Pine walls, 10 ft. ceilings, crown molding, spectacular gourmet kitchen and multiple areas for entertaining including a formal living room, dining room, great room and well designed outdoor space with pool. The master suite is breathtaking - vaulted ceiling, French doors to a private deck and a beautiful master bath. This is truly a wonderful classic Key West home that features everything today’s buyer desires. More information on this property

Just completed superior renovation of a beautiful 3 bedroom, 2 bath home in one of Key West's most desirable old town locations, this stunning home features Brazilian cherry floors, high ceilings, crown molding and custom built French doors throughout. The gourmet kitchen is equipped with soapstone countertops and professional stainless steel Viking appliances. The bathrooms are spectacular with large walk-in showers, marble slab floors and Waterworks fixtures. Outdoors is off street parking, a covered loggia and heated pool. More information on this property

A rare opportunity to own a freestanding single family waterfront home in Key West in the gated community of Truman Annex: This recently built two story home has classic Key West style architecture, 3 or 4 bedrooms, 3 baths, private heated pool with spa/waterfall and spectacular unobstructed views of the Gulf of Mexico and those famous Key West sunsets. More information on this property

Brand new & beautifully constructed home situated on a quiet street in the historic district. Classic architecture boasting many outdoor living areas w/ generous balconies & wrap porches. Impressive proportions best describe this 5bd/5ba + den w/ open spaces & 12ft ceilings. Every amenity you would expect in a fine home w/ laundry room, pool, Jacuzzi, impact windows, picket fence, covered parking & lush landscape. Top of the line materials w/ wood floors, crown molding, gourmet kitchen, 8ft. doors, epay decking, tumbled brick & more. Well appointment floor plan for guests with enuite baths, private entrances & optional lock out. A must see if you are looking for a large home, in the historic area, walking distance to Duval Street. . More information on this property

Old Town 3bd/2ba classic beauty built in 1890, lovingly restored & renovated, formerly the home of Phillip Burton. New Brazilian wood floors, Dade County Pine walls, 12-ft ceilings, brand new kitchen with stainless steel Viking appliances, lovely spacious porch, master suite with French doors opening onto the heated pool and brick off-street parking. More information on this property

This special Old Town home has beautiful architectural details, wonderful street appeal and is located on one of the most desirable streets in Key West's historic district. The one level home is landscaped for total privacy and has a wraparound front porch, tall ceilings, wood and antique tile floors and Dade pine walls. It has a spacious and open floor plan with multiple sets of French doors opening from most rooms to the outdoor space which includes a beautiful heated pool, guest cottage, covered rear porch and large sunning area. There also is a recently built master suite addition. Other features include off street parking and an outdoor shower. 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

This renovated home has 3 bedroom 2.5 baths and provides that magnificent Key West indoor - outdoor living. The back of the home opens through 3 sets of French doors to a wonderful 8' x 35' covered porch and stunning black pool. Ipe decking is used extensively around the entire outdoor area The interior is in exception condition with many unique architectural details. There is a grand master bedroom and bath on the first floor with separate office space. This is a wonderful private location with easy parking for owners and guests. More information on this property

This elegantly renovated cottage is located on a quiet hidden lane in the heart of Old Town, and near the Key West Seaport. The home, dating back to 1885, now has a wonderful open feel with high ceilings, and French doors opening to a covered porch, tropical garden, and heated pool. There is also a private bricked driveway.

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Fantastic investment property! This Transient licensed three bedroom, three bath money maker is located on a quiet lane off Duval Street. A perfect second home that can be rented on a nightly basis as a vacation rental when not occupied by owner, sleeps 12. The two story conch home is being sold furnished and has a spacious outdoor area with a brand new large heated pool. This is a must see! More information on this property

This top-notch renovation was awarded The Historic Keys Foundation Award of Excellence in 2006. A beautiful yet comfortable 3BR/3.5BA home with front and rear porches, gated entry, covered parking and a wonderful poolside lounging/entertaining area. The house is state-of-the-art and beautifully finished with stainless steel appliances, Dade pine, wood and stone floors and every amenity for easy island living. 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

Great Old Town multi-unit property located on the corner of Eaton Street and Fletchers Lane. This large property is comprised of a 3 bedroom, 2 bath home, (3) one bedroom units plus an in-law suite. The owner uses the main house as a second home and rents the remainder. Rents currently on the 4 units are: $875, $825, $1025, $1025. All tenants are on month to month. More information on this property

This is a wonderful Key West cottage, 3BR/2BA, on a quiet lane in the historic district. Loads of Dade County pine, spacious rooms, a gorgeous kitchen with stainless steel Jenn-Air appliances including wine cooler and gas range with handsome granite countertops. The kitchen opens to a large living area with a double set of wind resistant French doors that leads to a large covered porch and a 24 x 10 pool and gardens beyond. The very private master bedroom is upstairs with two large closets and an en suite bath. Two bedrooms and another full bath are downstairs and the home is centrally air conditioned. Brick paved off street parking makes this an ideal Key West hideaway. More information on this property

Beautiful one level home located in the Meadows neighborhood of Old Town Key West. Recently renovated, this large 3 bedroom and 3 bath home has everything today’s buyer wants - classic Key West architecture, gourmet kitchen, hardwood floors, luxurious baths and high ceilings all on an oversized lot. The open floor plan is perfect for entertaining with 10 ft ceilings in all rooms except for the wonderful family room/kitchen which has vaulted 13 ft ceiling with three sets of French doors that open to a lovely covered porch overlooking the large back yard with room for a generous sized pool. Great attention to detail and quality workmanship is evident throughout this very special home. More information on this property

Built in 1918 with a wonderful front porch that still has the original Cuban tiles, set with flair, the house was totally renovated in 2005. There’s an open living/dining area that leads to a beautiful kitchen with excellent workspace and top stainless appliances and granite countertops. 3 bedrooms, 3 baths in the main house with travertine flooring, new windows and the house is wired for sound, cable, and security (GE Smart Home). Beyond the kitchen are a covered porch and enormous swimming pool (14 x 28) that has spa jets and is heated. There’s even a small rental unit upsta irs. Everything is in tip top shape and ready for a new owner. More information on this property

This home offers a tremendous location in the Historic Seaport District of Old Town Key West and a large lot. It is in the middle of everything Key West offers. The concrete constructed home is in good shape. It may be torn down because it is non-contributing. In the back yard is a covered and enclosed garage for parking or storage. The main house has 2 bedrooms and 1 full bath. More information on this property

Beautiful single family home located in the quiet Meadows of Old Town. 2 bedrooms and 2 full baths plus a pool house, new concrete pool and off-street parking. Freshly renovated and updated including resurfaced wood floors, new bathrooms, central a/c, Chicago brick patio, new decking around pool, newly painted both inside and out and much more. Enjoy covered outdoor dining, laundry room/ pantry off kitchen and a very open floor plan. A must see turnkey home. 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 historic home, built in 1873, has been carefully renovated into a two bedroom, two bath cottage. The large open kitchen and living/dining area has an 18 foot peaked ceiling, and there is room to add a third bedroom and bath in the finished windowed attic. There is a freshwater well on the property providing water to the gardens and pool. This property is surrounded by brick pathways and lush gardens, and has a private heated pool in the rear garden. May be combined with MLS#108054 to create a magical compound for $3,490,000. More information on this property

This property makes extremely good use of the space and has excellent storage areas in the carport, garage and shed. It has been renovated and remodeled throughout to a high standard and has a beautiful new kitchen and bathrooms and gorgeous new tile floors in every room. There is a great outdoor area with large pool. This is a short sale. More information on this property

Here's a wonderful 3BR/2.5BA family home with tile flooring, lots of custom built-ins, a large kitchen with a pass through to the outdoor wet bar and fridge poolside. Overlooking the pool is the 1BR/1BA plus living room and loft that's an ideal office and/or Mother In Law. Heated pool and spa, lush private gardens with covered off street parking and a koi pond. More information on this property

A wonderful historic home in fantastic shape located in the highly desirable Meadows neighborhood of Old Town Key West. Exquisite details follow: rich Dade County pine walls and floors in the living areas and bedrooms, an open and recently constructed kitchen flowing right out to a relaxing outdoor eating/lounging/pool area with tile and Brazilian hardwood Ipe decking accented by natural foliage. Further benefits include a large finished loft area, dual zone AC, custom Ipe window shutters and fresh paint throughout. Large front porches give the home great style and ample space for outdoor enjoyment both up and downstairs. This home is well worth a visit. More information on this property

A really great opportunity to own a larger Key West classic location. On the corner of Southard and William Streets, this home is currently 3 legal units but lends itself to conversion back to single family. The single family home is a 3/2/2 and each of the two cottages have 1 bedroom and 1 bath. Over 3800 square feet of living space (per tax rolls) and enough lot space for your pool and outdoor living space. A+ location and priced very competitively. Currently leased for $4800 per month. More information on this property

Beautiful Classic Revival home in the heart of the historic district. Walking distance to restaurants, boating and more. The house is in fabulous condition with all newsystems, Dade pine walls and wood floors, 2 zone central air and heat, new granite countertops in the kitchen with great appliances. Upstairs are two bedrooms, two baths and cathedral ceilings plus each bedroom has it’s own covered porch. There’s also a beautiful heated pool. More information on this property

Located in the Casa Marina neighborhood, you'll fall in love with this distinctive 3BD, 2.5BA two-story home with a wonderful floor plan. Open and inviting great room, custom built-in shelving, Gourment kitchen with stainless appliances including a warming drawer, Mexican tile floors and a wall of glass doors that open onto the sparkling heated pool and spacious covered patio. The 2nd floor master suite features vaulted ceilings, hardwood floors & glass doors that lead to a private balcony overlooking the pool. Many extras include attic storage, irrigation system, storm shutters, outdoor shower and a carport plus off-street parking. More information on this property

The home at 520 Grinnell is a wonderful opportunity for a great Old Town location near everything Key West offers. The lot is perfectly located on the corner of Hibiscus Lane and Grinnell Street. Built in 1953, this concrete and stucco home is in wonderful shape. Because it is a non-contributing structure it may also be torn down. It has 2 bedrooms and 2 full baths, off-street parking with a sun deck above and a jacuzzi spa in the back deck. More information on this property

Absolutely perfect story book cottage in one of the most desirable locations in Old Town. Step onto the rocking chair front porch and open the front door to the open floor plan with a large living/dining room and beautiful kitchen with custom cabinetry, granite countertops and stainless steel appliances.  More information on this property