1006 -1008 Fleming Street - Old Town - Key West

1006 Fleming Street in 1965 sat right on Fleming Street

1008 Fleming Street sat further back and anchored a huge undeveloped lot

1006 Fleming Street (2010)

I remember showing the two house assemblage at 1006-1008 Fleming Street when it was offered for sale in 2001 at $899,000. I remember one particular couple who loved the property and appreciated the rarity of having two houses located on such a large lot on one of the best blocks in Old Town Key West. The were lookers-not quite ready to buy. More about them later.

The house at 1008 Fleming Street had been redone. The renovation was less than professional in my opinion. Let's just say the place had its faults. I remember urging buyers to look beyond the mistakes of that existing renovation and instead to consider buying the property because of its great location and upside potential.

1008 Fleming Street in 2001

The front door of the second home at 1006 Fleming Street was located almost on the front sidewalk. That place was then used as a long term rental. I urged buyers to consider that building as a good spot for a guest house. Although the front is only 50 feet wide, the lot is deceptively large for Old Town. (It is 150 feet deep and includes a back parcel for a second Guest Cottage. The total lot is 9108 sq ft.) But the lot did not have a coherent flow between the houses or the pool at the rear. The pool was quite large. Palm trees sheltered the pool from the adjoining properties on the east, south, and west. The rest of the garden was pea rock and a few straggler plants. The large pool and yard had the potential to become a great Key West garden.

Fast foword ten years and a couple of intervening renovations. The house at 1006 Fleming Street is now the guest house I envisioned except it is totally fabulous. Treat your guests to a stay in this place and they will not want to leave. A front door still opens onto Fleming Street, but the real entrance is located at the rear where the guest house and The Great House meet at a common elevated deck. The front facade of 1006 Fleming Street has been dramatically altered. The front porch is more gentile and refined. The facade fits the character of the compound as a whole and blends with the other homes in the area.

1006 Fleming Street in 2010 as The Guest House

The guest house living room (or library) is a large rectangular room with vaulted ceiling and bookcases on three walls. Window seats have been added as delightful perches where you can read or contemplate the art of living well. The bedroom is another delight. Large pocket doors create the illusion that the two spaces blend together as opposed to a typical door that closes one space off from the next.

The Guest House Living Room or Library

Built in window seat

The guest house bath is extra large. The walls are covered with incredible Czechoslovakian iridescent green glass tiles made in the 1950's. These tiles catapult an otherwise common space into another dimension. The glass tiles, bath fixtures, and lights make this space truly one of kind. In a town where so many styles are repeated and re-created, this is a space that will be forever unique. A Pullman kitchen rounds out the guesthouse which has a rear door that actually opens onto the welcoming raised courtyard which marks the entrance to the Great House.

The Guest House Bath
Czechoslovakian iridescent green glass tiles made in the 1950's

Recall my criticism of the original renovation and how there was no cohesive flow between the houses. That problem has been resolved by the creation of an elevated courtyard that brings the two original houses onto a common platform where residents can go from Point A to Point B without walking on ground. Moreover, the buildings now share the same simple geometric design and work in harmony with either as a compound instead of as dysfunctional seemingly unrelated buildings sitting next to each other. The lines of the original house at 1006 Fleming were totally different from 1008. The new master bedroom addition mimicked the lines of 1008 and 1006 was changed to look compatible with 1008. The Guest Cottage at the very rear adopted the architectural look. The result is a unified design made simple by geometry. Moreover, even though the houses are old, they look totally modern even from the outside. It is as if time doesn't matter when you are creating something eternal.

New Master Suite addition

The Great House was featured in Metropolitan Home Magazine a few years ago after the current owner renovated the property the first time. I mention this because the property just went through a new upgrading to make it more special and more fresh. So if you saw this home before, you must see it now.

You enter the Great House though large French doors into a very formal entry hall with a one-of-a-kind chandelier that attracts your eyes ever so briefly, that is until you look down toward the living room and then though the wall of French doors that open onto the large pool and garden beyond. A second guest cottage is secluded away at the far end of the garden.


The freshly renovated kitchen is located to the left. The kitchen is bright and modern and is almost too pretty to cook in. (Why cook when you can walk for a few minutes and get great food and won't have to clean up after yourself later?)


A custom fireplace and entertainment cabinet anchor one end of the living room. A wall of French doors frame the pool and garden area but also help to create the special feeling you get being "inside" this incredible living space. Huge architectural columns are almost dwarfed by the soaring height of the fifteen foot ceiling in this truly great room.



The main house has two bedrooms. The master bedroom is quite large and has traditional Key West six over six paneled windows framed with bright white trim and crown molding. The master bath is larger than many master bedrooms in other homes. A second bedroom(with en-suite bath) is located in the front portion of the original 1008 Fleming Street house. This space has a subtle opulence.

The Master Bedroom

A second smaller Guest Cottage is located at the back end of the property. A private porch provides sitting space where you can watch the people in the pool or the goings-on in the main house. But sitting there, you are away from the to do up front. This is a private space for the lucky duo who get to use this special space. The extra bedroom has a sitting area and dining area plus high vaulted ceiling. This cottage has another special bathroom and an outdoor shower. In my opinion, it is the view out onto the garden and pool that make this little retreat so neat.

The Guest Cottage adopted the same lines as the Great House and the Guest House

View from the secluded Guest Cottage toward the pool and the Great House

This incredible Key West home is offered for sale at $2,999,999. CLICK HERE to view the mls datasheet and to view listing photos.

If you read my blog often you know that I like to remind readers about the importance of location in Key West. This property is within a few minute walk to the Historic Key West Seaport or Duval Street. There are neigbhorood eateries like Azur and Cafe Sole. Michael's is a Key West favorite and it is located just around the corner. The A&B Lobster House is a few minutes walk. The new Old Town Bakery is down on the corner of Eaton and Grinell. The Monroe County Library is only three blocks away. The Tropic Cinema, The Red Barn Theatre, the San Carlos Institute, and The Waterfront Theatre are less than a ten minute walk. Various pubs and watering holes are nearby. Music is free most nights in many Old Town venues. And you can walk to almost every place you really need to go.

I took photos of this property that you may want to view. CLICK HERE to see more photos of this incredible Key West Property. Better yet, please call me, Gary Thomas, 305-766-2642 to schedule your private showing. This home is listed by Preferred Properties Coastal Realty, Inc. in Key West, Florida. Our office is the Exclusive Lower Florida Keys affiliate of Christie's Great Estates. Remember the couple that I showed this home to ten years ago. I run into them from time to time. Their kids are almost out of college. Maybe they've sold that investment property in Connecticut and now have the money to buy their Key West dream house. This place will cost them more today than it would have ten years ago. But it was worth the wait, and it is well worth the price.