64 Front Street - Truman Annex - Key West

64 Front Street - Key West, Florida

If you are looking for that special Key West home with lots of space for you and your family and friends to enjoy, you may want to consider the 3213 sq ft five bedroom home located at 64 Front Street in the exclusive Truman Annex area in Old Town Key West. The listing Realtor describes this extraordinary property in an understated manner:

"Located in the gated community of Truman Annex, this 5 Bedroom/5 Bath home is the perfect Key West retreat. Designed by local architect for entertaining; blending indoor living with the tropical Key West outdoor life style. All rooms have French doors opening to covered porches. The 5th bedroom is located in the pool-side guest cottage. Opportunity exists for a 6th bedroom on the main level - adjacent to a full bath. Perfectly located for complete poolside privacy. Easy walking distance to restaurants, galleries, sunset celebration and Fort Zach."

Presidential Gates to the Truman Annex circa 1938

The house has 3213 sq ft of living space on two floors. The facade faces Front Street which winds its way from the famous Presidential Gates up to Southard Street which then exits westerly to the oceanfront or easterly past the guard booth at Thomas Street. Almost all of the large single family homes in the area were built after the City of Key West annexed the property a couple of decades ago. A few historic homes became part of the development for good measure. The private streets provide a street scape that is near breathtaking. While some potential buyers may fret about a derelict little house on an otherwise historic block in Old Town, you won't find any reason to fret about the neighboring homes on Front Street. The views from the first and second floor front balconies are priceless.

Front porch first floor

Second floor balcony overlooks the old Weather Station

Front Street

Once inside you will find large and inviting rooms throughout this spacious home. The formal entry is gracious and inviting. The extra large living room is on the left. The space is so large that the grand piano barely stands out.

The study is located opposite the living room. The kitchen is located at the rear. A center hallway provides good separation between these spaces as is no longer typical in many properties these days.

Multiple French doors open from dining room to balcony overlooking pool

Large eat-in kitchen

A grand staircase provides access to the second floor. The master bedroom with en-suite bath is located over the same octagon shaped room where the dining room is located below. The bedroom also had French doors that open out to the rear second floor balcony that overlooks the pool below. There is even a rear staircase that provides access for a midnight skinny dip in the pool.


The master bathroom is immense. It is seductive in its simplicity and design. You just gotta see it! And there is an adjacent extra large walk-in closet that will sate any clothes hound.

Just off the pool is the guest cottage which has Murphy bed on one wall, a sofa on another, and a mini-kitchen for making toast and coffee. The problem with having such a great set-up like this is that your free-loading brother in law will never leave. Of course there is the pool and the house even has covered off street parking at the rear. CLICK HERE to view a slideshow of photos I took of 64 Front Street. Take the time to take a look. You will appreciate the quality of this home and the value of this location.


64 Front Street is offered at $2,195,000. CLICK HERE to view the Key West Association of Realtors mls datasheet and to view listing photos of this beautiful home. If you are shopping for a home at this price point, please contact me, Gary Thomas, 305-766-2642. I am a buyers agent and a full time Realtor at Preferred Properties Coastal Realty, Inc. in Key West, Florida. Like I said, there is nothing to fret about if you buy this home.

64 Front Street - Key West, Florida

This is how the listing agent describes the grand house located at 64 Front Street in Truman Annex: "Elegant 5BR/5BA home located on beautiful Front St. in Truman Annex. Open and airy design is perfect for Key West-style entertaining. Every room boasts one or more French doors opening onto covered porches. An abundance of walk-in closets and storage are among the many bonuses found throughout this home. The very private pool-side space makes this home just the best for tropical outdoor living. The 5th bedroom is located in the guest cottage (poolside). The large very unique pool with artisan mosaic tile is 6.5 feet at its deepest (pool newly resurfaced). All windows are protected with high impact-resistant Lexan 10, meeting existing hurricane standards. Pristine, well maintained, move-in condition".

I've been in a lot of the big homes in Truman Annex and 64 Front Street is one of the most memorable. When you enter the home you know you have arrived at someplace important. The ceilings are 12' tall on the main level and feature crown molding. The living room is extra large (there's a baby grand that is barely noticeable) and extends into an octagon shaped dining alcove that overlooks the pool. But it's the use of space planning, paint treatments, and design that makes you feel "at home" in each of the rooms. And that's the difference between a big house that tries to be "important" and a thoughtfully designed house that makes you feel comfortable.

The hand painted tiles in the kitchen make you feel at home and not in a designer kitchen showroom.

The master bedroom and bath are located on the second floor and overlook the pool below. There is a spiral stairway that leads down to the pool for a quick midnight dip before bed.

64 Front Street has 3213 sq ft of living space and sits on a 5005 sq ft lot. There is also covered off street parking. The home is offered at $2,295,000 or $714 per sq ft. CLICK HERE for more photos and detailed information on this elegant but livable Truman Annex home.

64 Front Street is a listing for Preferred Properties Christies Great Estates. Please call Gary Thomas, 305-766-2642 to schedule a showing.

By the way, today is the Second Anniversary of my little blog. Thank you to all of you readers and the buyers who found me over this great information highway that Al Gore created. And a special thanks to Jim from Nutley, New Jersey for suggesting that I write a blog about Key West real estate.