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Old Town South

Proximity & Location = A Great Neighborhood!

Old Town South is the area between Casa Marina and Truman Avenue. Old Town South runs from the southernmost end of Truman Avenue north to White Street then east to United Street and jogging the waterfront beginning at Simonton Street.

Just like Old Town North, the homes are rich in history and the architecture is the quintessential Conch Home style with a sprinkle of modern architecture adjacent to the Casa Marina neighborhood. Proximity and location make this section of Key West an ideal area to live. Everything that Old Town North has to offer is only a short bike ride away, as well as the many recreation opportunities available in the Casa Marina area. The always bustling El Siboney Cuban restaurant is located within this district on Catherine and Margaret Streets. For more restaurants and art galleries, saunter down to the quieter side of Duval Street south of Truman. You can sip wine and people watch at Grand Vin, savor the best homemade ice cream at Flamingo Crossing or have breakfast, lunch or dinner at Banana Cafe. For a variety of shops and restaurants, Duval Square between Simonton, Virgina & Duval Streets is a short drive or bike ride away. Be sure to visit The Key West Butterfly Conservatory for a tranquil respite or if you need to entertain your children or grandchildren!

New Listings in Old Town South

805 Virginia, Key West image
805 Virginia, Key West $1,549,000

Beautifully Restored Single Family Home in the Heart of Old Town Key West. Excellent walking location with an easy stroll to Duval St., White St., Sandy Beaches, Multiple...

  • 3 Beds
  • 2 Baths
  • 601649 MLS
1025 Grinnell Unit 101 & 102, Key West image
1025 Grinnell Unit 101 & 102, Key West $1,795,000

OPEN HOUSE this SUNDAY from 12pm -2 pm! Lovely Duplex in historic old town Key West on a large corner lot close to coffee shops, restaurants, yoga, galleries, tennis cou...

  • 3 Beds
  • 2 Baths
  • 601642 MLS
1026 Truman Unit down, Key West image
1026 Truman Unit down, Key West $2,400

Space is on US 1 (Truman Ave) coming into Old Town. Large display windows in enclosed room off entry foyer. Could be storage for merchandise below or some type of seating...

  • 1 Baths
  • 601637 MLS
1116 Watson, Key West image
1116 Watson, Key West $1,500,000

New Listing in Old Town Key West! Three unit property in the heart of Key West. This property offers a 2BR/1BA unit, Studio w bath upstairs, and 1BR/1BA cottage. Elect...

  • 3 Beds
  • 3 Baths
  • 601445 MLS
1401 Simonton Unit 6, Key West image
1401 Simonton Unit 6, Key West $1,100,000

This is a rare opportunity to have your own transient licensed condo at the beautiful Santa Maria Suites resort in Old Town Key West! Revel in the tranquil setting of th...

  • 2 Beds
  • 2 Baths
  • 601394 MLS
1007 Watson Unit R, Key West image
1007 Watson Unit R, Key West $849,000

Your Key West Tropical Island Tree House Escape awaits!! 'The Key West Tree House' is a cozy and comfortable home that will transition you from the hustle and bustle of c...

  • 1 Beds
  • 2 Baths
  • 601375 MLS
606 Truman Unit 10, Key West image
606 Truman Unit 10, Key West $1,300,000

Location! This hidden oasis, nestled in Historical Old Town Key West, is a private, gated community, walking distance to world-famous restaurants, galleries, and sunsets....

  • 2 Beds
  • 2 Baths
  • 601280 MLS
1016 Howe Unit 8-11-14, Key West image
1016 Howe Unit 8-11-14, Key West $1,750,000

Investment Opportunity: own three Transient licensed hotel rooms/condos with great rental history, new pool, in a great location of Old Town, and turnkey with renovations...

  • 3 Beds
  • 3 Baths
  • 601143 MLS
800 Catherine, Key West image
800 Catherine, Key West $1,299,000

Great corner lot in historic neighborhood just 2 blocks from Duval Street. Currently set up as 3 units including a 3BR/2BA downstairs ($3400), 1BD/1BA with full kitchen u...

  • 5 Beds
  • 4 Baths
  • 601028 MLS
1416 Catherine, Key West image
1416 Catherine, Key West $2,470,000 ▼

Nestled in a quaint Old Town neighborhood a short walk to tennis courts, galleries, coffee shops and restaurants, this quintessential Key West Conch home gives you the ke...

  • 4 Beds
  • 2 Baths
  • 601020 MLS
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Key West, FL 33040
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