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Old Town North

Everything you desire in island living.

Technically Old Town has always been the area South of White Street and West of Casa Marina. However, due to its size, Realtors have begun differentiating between what is North and South of Truman Ave. Old Town North encompasses every street from The Gulf of Mexico south of White Street to Truman Ave. The gated community of Truman Annex is not used in this area, although it also technically falls within this area.

Old Town Key West is what you see advertised the most. It has it all: shops, restaurants, bars, theatre, culture and of course the beautiful Conch architecture. The walking and biking accessibility to everything from the Gulf to the Atlantic makes this location extremely desirable. The fact that the coveted X flood zone also falls within certain areas of Old Town lends to the allure.

Old Town North is host to The Key West Historic Seaport District which is the Caroline Street corridor that surrounds the Key West Bight. This is another area that is close to my heart because of my wife’s family who have deep roots in this area dating back to 1909. Enjoy a cocktail or shrimp platter at one of the many bars & restaurants along the boardwalk. Whether you are looking for casual or upscale dining, you will certainly find it at the Historic Seaport. At Christmas time, be sure to check out the amazing nautical themed decorations and lights that surround the boardwalk as well as the Schooner Wharf Lighted Boat Parade. There are many charter fishing boats, recreational snorkeling, parasail and sunset cruise boats docked here as well as boat slips for sale if that is your desire.

If you follow the boardwalk west all along the water, you will end up at Mallory Square. If you have never been, it’s a “must-do” for your time in Key West. Each night the sunset is celebrated with local street performers and artists selling everything from original paintings, jewelry and clothing. Once you are settled with Island Life, be sure to take your many visitors to this attraction. It’s best to arrive 90 minutes before sunset, so you can take in a few different acts and peruse the artists.

Old Town North also encompasses the historic Key West Cemetery. It is located in the northeast section of Old Town, and it is estimated that as many as 100,000 people are interred there with gravestones dating back to the mid 1800’s. Whether you love or disdain cemeteries, nothing beats taking a relaxing bike ride through the Key West cemetery where you have open sky and unobstructed views of 19 acres. These unobstructed views also make homes around the cemetery quite fetching.

Of course, I must mention the world famous Duval Street. Old Town North features the “rowdy” end of Duval Street where tourists, spring breakers, and 20-somethings go to party. During Fantasy Fest and New Year’s Eve, the 300 block is jam packed. If nightlife or day drinking is your thing, be sure to check Sloppy Joe’s and Captain Tony’s off your bucket list.

Don’t be fooled, Key West living is MUCH MORE than just this area of Duval Street! We are a community. We are culture. We are foodies. We are philanthropists.

Here are a few more reference links for you located in Old Town North:

Culture: The Studios of Key West, The Key West Theater, The Waterfront Playhouse, and The Red Barn Theatre.

Religion: Key West United Methodist Church and St. Paul’s Episcopal Church

New Listings in Old Town North

300 Southard Street Unit 103, Key West image
300 Southard Street Unit 103, Key West $950

Come and Use this precious space at a prime location! There is so much foot traffic in this area. Your business here at 300 Southard Street Unit 103 is at a Great locatio...

  • 5 Baths
  • 606701 MLS
622 Grinnell Street, Key West image
622 Grinnell Street, Key West $2,395,000

Four Licensed Rental Units in Premium Old Town Key West Location. 622 Grinnell Street and 614 Canfield Lane. 622 is a quintessential Conch-style residence with large cove...

  • 6 Beds
  • 4 Baths
  • 606666 MLS
620 Southard Street, Key West image
620 Southard Street, Key West $9,300,000

An opportunity that comes once in a lifetime... The Historic Lowe Mansion is being offered for sale. This majestic property stands alone in its beauty, historical signifi...

  • 5 Beds
  • 8 Baths
  • 606660 MLS
721 Galveston Lane, Key West image
721 Galveston Lane, Key West $1,150,000

Do not miss this renovated, spacious, and bright Key West family-style home. Very low maintenance and rare CBS home in the heart of Old Town. If you're seasonal this home...

  • 3 Beds
  • 2 Baths
  • 606655 MLS
951 Caroline Street Unit 207, Key West image
951 Caroline Street Unit 207, Key West $4,328

Hard to find office space available at Conch Harbor Retail Center. Suitable for office, at the corner of Caroline and Grinnell Streets. Men and Women's bathrooms, outdoor...

  • 2 Baths
  • 606646 MLS
718 Caroline Street Unit A, Key West image
718 Caroline Street Unit A, Key West $4,450

Excellent Opportunity to lease approximately1331sf of Commercial Lease Space on CarolineStreet next to the Historic Seaport. Perfect for professional services or retail. ...

  • 1 Baths
  • 606641 MLS
431 Front Street Unit #2, Key West image
431 Front Street Unit #2, Key West $8,150

Retail Lease Space, strip center is located on the corner of Front & Duval Streets with ample parking across the street at Mallory Square. Busiest corner in Key West, wi...

  • 2 Baths
  • 606617 MLS
612 Petronia Street Unit Rear, Key West image
612 Petronia Street Unit Rear, Key West $799,000

Discover the potential of this charming fixer-upper tucked away at 612 Petronia Street rear, nestled in the heart of Key West's historic Old Town. This cozy property offe...

  • 1 Beds
  • 1 Baths
  • 606434 MLS
600 Whitehead Street Unit C-2, Key West image
600 Whitehead Street Unit C-2, Key West $875,000

Prime location for commercial real estate in Old Town Key West. High foot traffic area directly across from the world famous Green Parrot bar and just steps from Duval St...

  • 2 Beds
  • 1 Baths
  • 606417 MLS
524 Eaton Street Unit 203, Key West image
524 Eaton Street Unit 203, Key West $950

Hard to find small office space available in Old Town! Freshly updated professional offices 160sf for $950+ per month. Join the friendly business environment at Key West ...

  • 2 Baths
  • 606411 MLS
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Key West, FL 33040
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