812 Simonton Street - Old Town - Key West - Transient Licensed Investment

Just Listed 812 Simonton Street in Old Town Key West. This new listing is offered as either a single, stand alone one bedroom cottage in the rear with a valuable transient rental license or as two building investment property with a total of four units, two of which have transient rental licenses.

I found a couple of old photos taken fifty years ago that show the front house and rear cottage that make up this property. Even back then it appears the original wood front porch was removed and a cinder block addition added to provide a bit more living space. If you look at the top photo you will see a typical cigar maker cottage type building with a sawtooth attachment. In the far rear you will see the outline of the rear cottage which appears clearly as a distinct unit the lower photo. The backside of St. Peter's Episcopal Church is seen to the far rear. Today the buildings appear to me to be pretty much the same. The exteriors are in much better shape and the interiors have been renovated for daily rental purposes.

The house next door to the south at 814 Simonton Street is pretty much identical to 812 Simonton Street with a couple of exceptions that might work for the available properties. The front porch offers a perfect place to sit and watch the world go by. 812 Simonton would have to be restored, but it could be done. The front house has a similar sawtooth addition located midway. The cottage in the rear has been expanded to two stories. The space between the front house and rear cottage is shorter than next door at 812 Simonton and that allowed for the addition of a pool. Finally, the neighboring property has parking whereas 812 Simonton does not have parking.

812 Simonton Street (rear) is offered at $525,000. It is a legal stand alone cottage with a transient rental license. The house is located at the rear of the lot and is accessed via a deeded walkway that flanks the north side of the property. The front house has an easement that provides access for the front one bedroom unit and the separate efficiency unit. The third unit in the main house has access off the front entry. The rear unit is gated and totally private.

The rear cottage is a fully contained one bedroom house with living room, dining area, kitchen with adjacent (outdoor) covered laundry, bedroom, and rear deck. The living space has all been updated and ready for rentals. The deck area is very attractive and very private. There is room for a hot tub or maybe even a plunge pool. The building at the rear is the backside of St. Peter's Episcopal Church. 

 I was not able to take get inside the front unit. The photos shown of the interiors are from the mls listing. The above photos show the living room which is accessed off the side easement. Note the vaulted ceiling where the sawtooth addition attaches to the original front cottage. The kitchen is located to the rear. (I believe this same space was taken away from the house next door which permitted the construction of a pool there.) The front room is the bedroom in this unit. This unit is rented as a transient rental unit.

An efficiency unit is located at the rear of the front house. It is also accessed off the side walking easement. It has a small kitchen, bath, and living/sleeping space. This unit could be legally rented as a monthly vacation rental or as a long term rental. Alternatively, a new owner might buy a transient rental license that could be transferred to this location. A transient rental license just sold for $90,000. That may help prospective buyers value either of the current listings as well.  Alternatively, a new owner might want to restore the front porch, redo the front house, perhaps expand the back cottage to add a second floor and add a pool in the middle. A good architect or designer might help a new owner come up with a nifty plan for using the two current transient licenses to create a healthy revenue stream.  I have more ideas which I will share with interested buyers.

Neither a pool nor parking is necessary to have a successful rental.  Both are helpful but not mandatory. This property has a very good location that is within easy walking distance to most Old Town attractions. The shops, restaurants, and nightlife on Duval is just one block away. You can't get much closer than that.

CLICK HERE to view the Key West mls datasheet on 812 Simonton Street as total investment package with two transient units priced at $1,300,000. CLICK HERE to view the rear cottage as a stand alone property offered at $525,000. The two properties must close in a simultaneous closing but may be sold to separate buyers. Please call me, Gary Thomas, 305-766-2642 to schedule a showing of these properties. I am a buyers agent and a full time Realtor at Preferred Properties Key West.

Key West Waterfront Condo - 833 Eisenhower Drive #203

If you have not noticed it yet, prices are on the rise and the number of available properties available for sale are on the wane.  Old Town is still the area most in demand. Cute little cigar maker cottages, would-be fixers, and even Grand Conch houses are the properties potential buyers seek the most often. Shipyard Condominiums is most popular property for first time home buyers in Key West because of the price, location, and ability to rent on a limited transient basis.

Today I am writing once again about a property that is priced similarly to what you might pay for a much smaller unit at Shipyard Condominiums.  833 Eisenhower Drive #203 which is a lovely two bedroom two bath 1351 sq ft condominium that overlooks the Garrison Bight.  This unit also comes with a boat slip. The asking price has been reduced to $599,000 or $443 per sq ft.

The listing agent at Preferred Properties (that's where I work but this is not my listing) describes this unit like this:

"Take advantage of this major Price Reduction! This pristine 2/2 Harbor Lodge condominium comes with a boat slip! You'll love this bright end unit with extra windows, designer kitchen, high ceilings and covered deck overlooking the pool and the sparkling water. This beautifully maintained unit also has assigned covered parking and an extra large workshop/storage area. Harbor Lodge is a well maintained and managed property overlooking the boats and activity at Garrison Bight and is within walking/biking distance to Key West's main attractions. This is a great opportunity to own a beautiful unit in an A+ building on the water. Easy to see!"

Harbor Lodge Condominiums was built in 1990. There are just three units per floor and there are only three floors. All units have assigned covered parking and an extra large storage room. The storage room is large enough to store motor scooters, bikes, kayaks, and other outdoor sports equipment. Transient rentals are not permitted at this property. Owners may rent on a month to month basis or annual basis, however.

Daytime or nighttime, there is always something interesting to watch when you own a waterfront home.

Unit 203 has an updated kitchen, plantation shutters, and is in pristine condition. The owners have maintained this home and a new owner will need only bring a toothbrush. CLICK HERE to view a slide show of photos of this wonderful waterfront condo. And CLICK HERE to see the Key West Association of Realtors mls datasheet.

Please contact me, Gary Thomas, 304-766-2642 or send me an email at kw1101v@aol.com if you would like to see this unit or any other property available for purchase in Key West. I am a buyers agent and a full time Realtor at Preferred Properties Key West.

204 - 1 Southard Street - Shipyard Condos - Truman Annex - Key West

A lot of potential buyers of second homes in Key West have a wish list of items they desire which typically includes two bedrooms, two baths, off street parking, a pool, and an ability to rent the place from time to time in order to help make the purchase more affordable. Almost everybody wants a convenient location close to all of the fun things to do in Old Town. Unfortunately for most buyers, there are more buyers than properties and prices are for available properties are priced beyond the comfort level of many.


Every once in a while a property becomes available that has the key features that attracts a large universe of potential buyers. The Shipyard Condo at 204-1 Southard Street is just such a property. The listing Realtor describes this unit as follows:

"One of only three Cottages on the Shipyard Park, this end unit, two story condominium is loaded. It features a huge rear courtyard w/ awning and new entertaining deck. It is located across from the swimming pool and is only a short walk to its parking space. The home has a brand new kitchen with granite counter tops, there are storm shutters on all openings, plantation shutters inside, tile floors down and carpeting up. There is a bedroom on the main level with full bath and two bedrooms (one is small) with one more bath on the second. Shipyard is a condominium assoc. in the Truman Annex Gated Community which is located just beyond MM 0 in Oldtown and at the entry to Ft. Zach Taylor Beach. This unit comes with Transient Rental License."

204-1 Southard Street viewed from afar - but not too far

This two story unit has 1100 sq ft of living space, three bedrooms, two baths, a large indoor living area, and a pleasant rear deck. The place is so inviting from the outside that your friends and potential vacation renters will fall for it at first sight. You cannot beat the location on Shipyard Park. The views are just capitivating. The setting is picture perfect. Guests will dream of the cute little house and quiet location and probably plan to return again just to stay in this special little house. And that means you should keep this transient rental licensed unit rented throughout the year when you or your family are not using it (subject to licensing restrictions).

The unit is laid out with the dining and kitchen located at front left and a bedroom at front right. The living room is at the rear which has two sets of French doors that open onto the rear deck. The master bedroom and a third bedroom are located on the second floor. The rear deck provides additional outdoor living space where one can wine and dine in style. The pool is across the park within a 90 second walk.

The dining area and kitchen are located up front

Living area opens out to the deck

Master bedroom is on the second floor

204-1 Southard Street is offered at $795,000. CLICK HERE to view the Key West mls datasheet on this property. And CLICK HERE to view a slide show of photos I took of this property. The monthly condo fees on this unit are $505 and include exterior building maintenance, building insurance, common area and pool maintenance, security, cable tv, and management.

The Pool is just a 90 second walk from the house across the park

Ft. Zach Taylor State Park and Beach is around the corner - a ten minute walk

Please contact me, Gary Thomas, 305-766-2642 to arrange to see this unit or any other active listing in Key West. I am a buyers agent and a full time Realtor at Preferred Properties Coastal Realty, Inc. in Key West.

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1116 Stump Lane "Little Paradise" - Old Town - Key West

Little Paradise in Key West is now offered for sale. Just listed by Preferred Properties (that's where I work) is 1116 Stump Lane in Old Town Key West. Stump Lane is a one-way lane that is entered from White Street and exits onto Frances. It is situated between Fleming Street to the north and Southard Street to the south. CLICK HERE to see an aerial Google Map photo of the area. In his book The Streets of Key West: a History Through Street Names, J. Willis Burke says "Running parallel to Curry is Stump Lane, once called Garrison due to its location near the Army barracks. Stump Lane is named for the Charles Stump family." (Go back and look at the Google map. That big area east of White is the former Army base.)

The listing Realtor describes 1116 Stump Lane this way:

" Artist cottage on quiet lane in the heart of Old Town Key West. Well maintained home with large outdoor area with hot tub. Transient license to convey for the buyer looking for an investment. Hurry! Won't last long!"

Did you notice the words "Transient license"? Our office also manages this property and you may find the description there more helpful:

"The perfect place to relax in your own little paradise, located on a quiet historic Old Town lane. This unique Conch Cottage is pet friendly and features front and side covered porches, vaulted ceilings, an open floor plan, and also offers a fully equipped kitchen with easy access to the outside deck. You can access the spacious and shady deck which provides lots of privacy where you can grill, dine outside, and soak in the hot tub. The master bedroom has a queen bed, and the second bedroom offers 2 twin beds and opens to the cozy living room. Tucked away from the living area, is a spacious and bright bathroom with a tub/shower which also houses the washer/dryer. Sliding glass doors open from the living room to another small side deck where you can relax and read a book, or have your morning coffee. "

The cottage is just 858 sq ft and it sits on a 50' x 40' (2000 sq ft) lot. There are two bedrooms and one bath. The asking price is $615,000. CLICK HERE to checkout the mls datasheet and to view listing photos. (By the way the listing sheet is in error as to date of construction. The Monroe County Tax Appraiser says this house was built in 1906. I even have an old time photo taken in 1965 CLICK HERE.

A Transient license permits an owner to rent a home every day of the year to somebody different. We have lots of "different" people here. Boy, do we. Places like this typically are rented either weekly or monthly and sometimes for the season. It is the ability to rent a home to different tenants more than one time per month that separates a place with a Transient license apart from a place where an owner is limited to just one rental per month. The difference can mean a substantial increase in income over the course of a year.

I sold a neighboring cottage on Stump Lane last year. The new owners love it. The location is so Key Westy. Here are a couple of photos of neighboring homes.


If you are looking for your place in Paradise, please call me, Gary Thomas, 305.766.2642, to see Little Paradise. I am a full time Realtor at Preferred Properties Coastal Realty,Inc. in Key West, Florida. Our office is the Exclusive Lower Florida Keys affiliate of Christie's Great Estates.