Posted: Apr 16, 2018
Are there any Good Deals in Old Town Key West?
58 Front St. Truman Annex

As of April 15, 2018, there were 115 single family homes for sale in the Old Town area of Key West. Inventory is about normal for this time of year.  Sale prices range from $475,000 to $15,580,000; Median sale price of $1,495,000 and Average of $2,146,000. And so, if you were looking for "a deal", does such a thing exist in Old Town?  True enough, number of sales continue to slide from their peak in 2015; but still, there have to be a few properties out there that really do merit your scrutiny and investment.  So I looked through all 115 properties on the market and came up with 5 candidates. 

First - there ain't no cheap sales

Hold on to your breath - out of 115 single family homes for sale - only two homes are under $500,000, four homes are between $500 and $599,000 and seven homes are between $600 and $699,000.  There are eight over $5M and two over $13M.


In addition to the Median For Sale price of $1,495,000, the Median For Sale price per square feet of living area is $852.  The Average For Sale price of $2,146,000 comes with an Average For Sale price per square feet of living area of $889.


By comparison, at the end of the 1st Quarter 2018, the Average Sold price per square feet of living space for all the homes sold (27) in the Old Town area in the 1st Qtr was $750. (For the entire year of 2017 (121 sales) it was $724).



1112 Varela St. Old Town - South


1112 Varela St. is a single level, frame home dating to 1938.  Inside throughout, the architecture is cool and clean with a soft pallet accentuated with hardwood floors and multiple 6 over 6 double hung sash windows. Both bedrooms are good size with modern ensuite bathrooms. Furnishings are included. Neat as a pin.


The efficient, all-electric galley kitchen sits mid-house. To the rear of the kitchen sits the dining area; then, sliding glass doors to a nicely covered and spacious sitting area, beautifully landscaped rear yard, wood deck and heated pool with brick coping.



From the front door, thru to kitchen and rear.


Today, this area is called Old Town - South.  Historically the area was well known as the Cuban neighborhood.  In the late 1800's and early 1900's many extended families associated with the thriving cigar industry of Key West lived in the Cuban neighborhood. Homes were/are solidly constructed with efficient use of space and have an airy, light-filled design.


In 2017, 26 homes sold in Old Town - South at an average sale price of $840,000 and $645 per square foot.


1112 Varela St. is offered at $899,000.

409 Frances St. Old Town - North


409 Frances St. dates to the early 1950's.  The 1st floor great room runs the length of the house and provides open and unimpeded "run and jump" into the large pool and deck area.  (I like a pool you can actually swim in).


Each of the three bedrooms and two full bathrooms are on the 2nd floor (a half bath is on the 1st floor).  Access to the 2nd floor is only from the inside. The 2nd floor balcony runs the length of the 2nd floor, giving each bedroom access to the balcony for a view to the pool below, to the stars above and over Old Town in between.

The glass doors face South and the pool.


409 Frances St. sits towards the NW corner of Old Town - North, the original "Old Town" of Key West. It shares the corner with Elgin Lane, a quiet lane with minimal drive through traffic. 


In 2017, 53 homes sold in Old Town - North at an average sales price of $1,169,000 and average sale price per square foot of $733.


409 Frances St. is offered at a sale price of $999,000. This sale price calculates to a 14% discount to the 2017 average sale price per square foot for Old Town - North.

626 Margaret St. Old Town - North


626 Margaret St. dates to before 1892 and features a Craftsman-style Architecture, modernized and updated to optimize indoor/outdoor living. The interior is rich with exotic hardwoods and a personalized, contemporary design. The "L" shaped kitchen has a pantry, wainscoated eating nook and is efficient, airy and naturally lit. Very ship-shape. To the rear is a royal blue-tiled dip pool and spacious cabana and wet bar.  Private and discreet.


In each room of the house you will see some of the most beautiful and exotic woods you can find; mahogany, teak, curly maple and African rosewood. Both bedrooms are on the 2nd floor.  The oversized master bedroom has a cathedral ceiling of mahogany, abundant natural light and polished rosewood.

Beautiful hardwoods in every room.


626 Margaret St. is very much in the middle of Old Town.  The uncrowded area is open for steady easterly breezes and has minimum drive through traffic.


Through March 2018, five 2bed/1bath homes have sold in the entire Old Town area at an average of $793 per square foot.


626 Margaret St. is offered for sale at $1,189,000.

1309 Villa Mill Alley - Casa Marina


1309 Villa Mill Alley is a large, exotic oasis; 3500+ square feet, 5 bedrooms, 4 full bathrooms, soaring ceilings, fireplace, heated pool and lush tropical gardens. And yet a homey ambiance prevails, encouraged through polished hardwoods, natural light and the comfort of privacy and security.


This property sits in an X-Flood Zone - flood insurance not required for a mortgage. I recommend everyone carry at least nominal coverage, especially since new Flood maps in 2019/20 will likely shrink the X Zone. I am told that if you are in an X-Flood Zone and are carrying at least minimum coverage but then must carry flood insurance because your X-Zone became an AE Zone, the premiums will be less than if you are starting coverage from scratch.

A real foyer.


Homes sold in the Casa Marina area have historically commanded the highest average sales price.  For 2017, 19 homes sold in the Casa Marina area at an average sale price of $1,949,000 and average sale price per square foot of $797.


1309 Villa Mill Alley is offered for sale at $2,224,000. This sale price equates to a 21% discount to the 2017 average sale price per square foot for the Casa Marina area.

58 Front St., Truman Annex


Can a property listed for sale at $4,950,000 really be "a deal"? It is if you have $5M to spend. 


Conch Casa Grande is the largest single family home in Truman Annex. Large, symmetric rooms feel even larger under 11' ceilings.  Each of the six bedrooms are ensuite bathroom. Mahogany floors and detailed craftsmanship accentuates each of the spacious and airy rooms. An X-Flood zone house with big shoulders. To the rear, five 1st floor sets of french doors open to a large heated pool that begs for year-round lap times.

Grand living room w/ french doors to the pool


58 Front St. comes with a Truman Annex transient license and presently yields $260,000 in gross annual rents.  A Truman Annex license allows up to 25 weekly rentals and 6 monthly rentals.  There are no controls on who manages the rental program for your home.


Historically, and because of the transient license, Truman Annex homes have sold at the highest average sale price per square foot in the Old Town area.  For 2017, thirteen homes, townhomes and condos (excluding Shipyard) sold for an average sale price per square foot of $964.


58 Front St. is offered for sale at $4,950,000.


626 Margaret St. Master Bedroom


Make no mistake about it, there are a Bunch of beautiful homes for sale in the Old Town area of Key West. My first screening of the original 115 homes yielded 48 candidates. From the 48 came these 5.  Twenty of the forty-eight were between $1M and $2M.  Why so many $1M+ list prices?


Remember, for the most part sellers are not compelled to sell. Additionally, I would say that often the List Price is more of a desire; but, they are not wedded to it. Therefore, if you see something you like, make an offer (Cash can sometimes give a Buyer more leverage) and see what happens.


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


Good luck!


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