400 Simonton Street - Key West Investment Property

400 Simonton Street as it appeared in 1965

400 Simonton Street as it appears in August 2011

Just listed, but not be me, 400 Simonton Street in Old Town Key West. According to the Monroe County Appraiser this landmark building was built circa 1889. See the black and white photo which shows how this property looked back in 1965. That's nearly half a century ago. My God, I graduated from high school that year. Compare it to the color photo below. The property has had various uses over the years. And now it is offered for sale. The listing broker describes this property like this:

"High curb appeal, landmark architecture located on the prominent and convenient corner of Simonton and Eaton Streets in downtown Key West, FL (only 1 block from Duval St.) 1920's design, 3 stories with commanding porches, Dade County Pine, 12 ft ceilings, grand interior staircase, fire monitoring system, balconies, lovely bricked courtyard, iron entry gate, fountain & tropical landscaping. 6 residential, non-transient units, 6 electric meters with onsite manager. Zoned Mixed Use. Formerly Meyer's Place of Key West and also a restaurant. See MLS supplement for unit configurations, rental amounts, and other pertinent information. This historic Old Town Key West investment property has much to offer and has been well maintained."

I considered buying this property and The Artist House (located next door at 534 Eaton Street) when the owner at that time was tinkering with the idea of selling both. That owner had been renting rooms at 400 Simonton Street as part of the guest house. I don't know if he ever got caught because that is not permitted. That owner sold both properties to different people and The Artist House has sold at least twice since then. Today the property at 400 Simonton Street is licensed to rent six non-transient long term rentals.

I took a couple of not-so-good photos of the bricked courtyard and was reminded that the area was previously used as a small cafe. I think that space is quite lovely but very under utilized today.

The bricked courtyard

I did a Google search which resulted in an ad in The New Yorker in 1982. A real estate company had its office at that location back then.

Commanding presence at a key location

The building itself looks to be in very good shape. Compare the way the building looked in 1965 to its appearance in 2011. It is virtually the same. Even the exterior stairs between the floors is visible. According to the mls listing this building has 4078 sq ft of living space located on a 4200 sq ft lot (42'x100') at the corner of Eaton Street and Simonton Street


400 Simonton Street is offered at $1,699,000 or $417 per sq ft. CLICK HERE to view the Key West mls datasheet and to view listing photos. This property is zoned HNC-1 which is short for Historic Neighborhood Commercial-1. Uses for this zoning include include residential (including single family, duplex, and multi-family) and limited commercial including professional offices, banking and financial services, personal service shops, specialty shops, limited retail, transient accommodations and guest cottages. Rather than rely on what I write, do your own investigation to determine suitability for the use you intend. CLICK HERE to read the City of Key West zoning ordinances and consult with your own attorney. Just because some use may be permissible does not mean you will necessarily be able to do what you want.

If you would like to see 400 Simonton Street or any other property in Key West, please contact me, Gary Thomas, 305-766-2642. I am a buyer's agent and a full time Realtor at Preferred Properties Coastal Realty, Inc. in Key West.

GLEE Club - Key West

Do you watch GLEE? If you do you know it is okay to be whoever you want to be. You can be the boss of you. You can sing and dance and wear strange clothes. You can be a boy and like other boys. You can be fat and pretty and gifted all at the same time.


There is a lot of GLEE in Key West. It was here before the TV show first aired. It will be here after the show goes off the air. If you have dreamed of owning a small nightspot in Key West where you can let your inner-glee out, you may want to take a look at the new listing at 1114 Duval Street. The listing Realtor describes the property this way:

"The Keys, a Piano Bar, now available. Currently operated as a piano bar with light food service. 5COP liquor license with lease hold to convey. All equipment included, business sold turn key. Continue operations as is or develop into full service restaurant. Lease to convey expires July, 2013 with 5 year option to renew. Extensive improvements made to property within past year. Please do not disturb business. Leasehold and liquor license only, no real estate to convey."

Some readers may remember the space when it was Alice's on Duval. If you have been there under any of its incarnations you will recall that the corner building has large windows that open onto Duval Street to let the music out and the fresh air in. Patrons can watch thousands parade by each evening. The world famous La Te Da is right across the street.

CLICK HERE to see the mls listing info and agent provided interior photos. I took some street shots. You can see those pics if you follow me on TWITTER.

Seriously, if you have been thinking about fulfilling a lifelong dream of opening a small place in Key West that is either food or food and beverage oriented, you may want to consider taking a look at this business opportunity that includes ownership of a very valuable 5 COP Liquor License. This is a listing of Preferred Properties Coastal Realty, Inc. (That's where I work.)

If you would like more info on this property please call me, Gary Thomas, 305-766-2642 or send me an email at kw1101v@aol.com. I am a full time Realtor at Preferred Properties Coastal Realty, Inc. in Key West, Florida. Let your inner GLEE out!