Posted: Jul 03, 2022
Old Town Key West Six Neighborhood Sales Report 1st Half 2022
90 miles to Cuba

There are six neighborhoods in Old Town Key West; The Meadows, Old Town - North, Truman Annex, Bahama Village, Casa Marina and Old Town - South.  Here is a map.  Despite the close and seamless proximity of these neighborhoods to one another, each is different.  Whether the neighborhood is the original Old Town, was pre-planned or just evolved over time, each neighborhood offers Buyers an opportunity to own a home specifically suited to their style and character.  Each neighborhood has different price points and cost factors. Let's take a look at the individual sales figures for each of these neighborhoods for the 1st Half of 2022.

The Meadows

Until the early 1900's, The Meadows was very sparsely populated, there was a small cigar manufacturer or two, a few cottages and a couple general stores.  The area was mostly open terrain with rough roads and coarse grass.  History tells us there was a small dairy or two.


Not until Henry Flagler brought his Overseas Railroad to Key West in the 1920's was The Meadows (Sheets 23 & 24) built up at all.  As the railroad came closer to downtown, the workers needed homes close by in which to live - but there were none.  The Meadows was ideal.  It was close to the work area, level and mostly uninhabited.  Workers built simple, sturdy and enduring one story houses on small plots of land.


Today The Meadows is approximately 300 single family frame homes, single and two story with even a few Sears "kit" homes still standing.  The style is mostly "cigar" or "shotgun" homes with homey porches, pocket pools and a real sense of neighborhood. Zero drive through traffic and a total absence of commercial structures makes for quiet and genteel living.


As you can see from the chart below, 10 homes sold in The Meadows in the 1st Half 2022 at an average sale price of $2.35M and an average of $1105 per square feet. (2021 ended at 29 sales, average sold price $1.59 and $907 per sqft.)


Due to three sales over $3M and two sales over $2M, The Meadows had the second highest average sales price in the 1st Half 2022.

Old Town - North

Old Town - North is the original Old Town, Key West. For many people this is the most desirable neighborhood in Key West; hence, it leads all neighborhoods with 47 sales and total sales volume of $84.8M (2021 finished with 107 sales and volume of $179M).


Many of the homes in this area are on the National Registry of Historic Homes.  Some homes were originally built in the Bahamas, de-constructed, boated to Key West and re-constructed.  Old Town - North contains the grand homes of former political, artistic, military and social dignitaries. Also, there are beautifully renovated eyebrows, shotgun homes, craftsman bungalows and cottages that adorn the many hideaway alleys and byways. Some of the older, grander homes have been expanded and converted into lovely Guesthouses and Bed & Breakfast's.


Sprinkled through the area are a variety of beautiful boutiques, artisan galleries and delicious hideaway eateries and cafes. Continuing to the waterfront one can both imagine and see restored remains of the warehouses that once made Key West one of the richest cities in the US.


The average sold price in this area is approximately $1.8M with an average of $1176 per square foot (2021 ended at $1.7M and $954 per square foot).

Truman Annex

Truman Annex traces its roots to the mid 1800's when it was an Army base, that became a Navy base, that then housed the winter White House for President Truman and to this day retains a military presence.


As a residential community, Truman Annex is a Homeowner's Association, governed by the Truman Annex Property Owners Association (TAMPOA).


Truman Annex is a "new' community with frame-built townhomes and single family homes specifically designed and constructed to reflect the historic Key West architecture.  Additionally, upscale condos are located in restored concrete buildings that date to the 1940's which were used by the US Navy when "The Annex" was all Navy property.


A key component of home ownership in Truman Annex is a transient license specific to properties in The Annex.  This transient license allows property owners to rent their property on a weekly basis.  This income producing element is a key factor in the sale price of Truman Annex properties. (Note: Not every property in The Annex has such a license).


As you can see, 10 properties sold in the 1st Half of 2022. The Annex average sold price is $2.06M and because of the transient license, the Annex once again had the highest average sale price per square foot at $1422. (2021 ended at 30 sales, average sold price $1.85M and $1102 per sqft).

Bahama Village

Bahama Village is the Greenwich Village of Key West.  It is the most vibrant, coolest and colorful neighborhood in Key West.  Bahama Village traces its roots to when some of the oldest families in Key West immigrated to the US from the Bahamas and other Caribbean island nations.


The area is a patchwork of predominantly frame constructed homes alongside numerous tasty Caribbean eateries, eclectic galleries and locally owned eco-boutiques.  Everything in Bahama Village has its own signature, nothing corporate or cookie-cutter.


For the 1st Half 2021, 16 homes have sold in Bahama Village.These 16 sales had an average sold price of $1.31M at an average of $1031 per square foot.  Bargains are rapidly disappearing in the Bahama Village. (2021 ended with 22 sales, an average sold price of $1.24M and $815 per sqft).

Casa Marina

The Casa Marina neighborhood owes its name to the hotel there of the same name - Casa Marina.  The hotel was another of Henry Flagler's contributions to Key West.  It began as a grand hotel, was then purchased for use as officer quarters by the US Navy and then sold and bought multiple times by numerous hotel corporations (currently Waldorf-Astoria).


The Casa Marina neighborhood was in fact the first "suburb" of Key West as prominent home owners in the original Old Town relocated to "the other side of the island" for a little more elbow room.  Hence the lots and homes themselves tend to be larger than the other neighborhoods.  Additionally, most of the homes are made of concrete or concrete block and tend to be a 50/50 mix of ranch and two story.


Casa Marina homes tend to be very stylish and more "modern" in design.  There are some very unique homes including one on South St. that contains much of the 1900's La Brisa Dance Hall.  The La Brisa was located at the end of the line for the Overseas Railroad. It was mostly destroyed by the 1910 Cuba Huricane with sections of the roof towed to its present site.


The Casa Marina had 15 sales in the 1st Half of 2022. As usual, Casa Marina had the highest average sold price at $2.58M.  The average size of these 15 Solds was 2273 square feet with an average sale price per square foot at $1139. (2021 ended with 28 sales at an average sold price of $1.97M and $812 per sqft).

Old Town - South

For many, Old Town - South is identified as the old Cuban neighborhood.  This no doubt is in reference to the cigar manufacturers who populated the area in the very late 1800's and early 1900's, some of which were the most prosperous cigar manufacturers in the United States, and the managers and workers who lived close to the cigar factories. This neighborhood has many homes that still retain elements of Cuban architecture, most notably wrought iron adornments and Cuban tile.  Of the several cigar manufacturers once in the neighborhood, none was more prestigious than the Ferdinand Hirsch Cigar Manufacturing Co.


Most of the homes in this neighborhood were enlarged as families grew by birth or marriage; hence many of the homes here are an assembly of additions. This makes for excellent opportunities to buy, renovate into larger single family homes and hold or resell.  Old Town - South is a vibrant neighborhood with many young familes, couples and singles.


Old Town - South had 20 sales in the 1st Half of 2022  The average sold price is $1.72M. This neighborhood had shortest period of time to sell at 29 days. (2021 ended with 38 sales at an average sold price of $1.37M and $926 per sqft).



I have not met a homeowner/seller who did not believe their property deserved a premium because of their neighborhood.  Such is the degree of pride and belonging that each neighborhood provides to its residents.


Therefore, please do not limit yourself or allow yourself to be limited, to a particular neighborhood because you think or have been told that one neighborhood is better than another.  Search all of Key West for that property that fits your style and comfort.  It's here - Welcome to the Neighborhood.


If you have any comments or questions, please contact me here.


Good luck!


Additional Sources: