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For Sale

Casa Antigua

314 Simonton St, Key West, FL 33040

Discover the allure of Key West, FL, where history and charm converge in a vibrant tropical setting. Situated in the heart of Old Town, the property offers access to a plethora of attractions such as the historic Duval Street, renowned for its eclectic mix of bars, galleries, and boutiques. Embrace the island life with proximity to the iconic Mallory Square, where daily sunset celebrations and street performers captivate visitors. Immerse in the area's rich maritime history at the Key West Historic Seaport and enjoy a stroll along the picturesque Harbor Walk. With diverse dining options, cultural experiences, and vibrant entertainment, the location promises a dynamic backdrop for any commercial venture.Step into Key West history with this remarkable property, available for the first time in generations! Located just a block from world-famous Duval Street and across from the Federal Courthouse, this property at 314 Simonton Street offers a unique blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, this three-level building is steeped in heritage. Even the legendary Ernest Hemingway chose it as his base, staying here for a month while awaiting delivery of his car in 1928. Currently set up and legally recognized as 8 units, an atrium, garage, and a pool, this property provides an unmatched opportunity for someone who loves trophy properties. Whether you envision a grand single-family estate or multi-unit living combined with commercial space on the lower level, the possibilities are endless.Don't miss the chance to own a piece of Key West's past while shaping its future with this truly one-of-a-kind property.
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Contacts

broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

Building Details

  • For Sale $4,950,000
  • Property Type Multi-Family
  • Property Size 8,472 SF
  • Units 9
  • Lot Size 0.18 Acre
  • Property Tenancy Multi-Tenant
  • Building Class C
  • Year Built 1921
  • Date Updated May 13, 2026

Getting Around

  • Walk Score ®

    Walker's Paradise (95)
  • Transit Score ®

    Some Transit (28)
  • Bike Score ®

    Biker's Paradise (92)
Powered by Walk Score ®

Location

  • City Key West, FL
  • Neighborhood Historic Seaport
  • Zip Code 33040
  • Map
  • Street

Points of Interest

Citgo

0.76 miles

Circle K

1.21 miles

Shell

1.25 miles

Owen's Oco-Pep

1.40 miles

Electrify America

2.48 miles

Mobil

2.54 miles

Old Town Garage

0.33 miles

Key West Tropical Forest & Botanical Garden

3.56 miles

Oceans Edge Resort & Marina Parking

4.75 miles

Tropical Rent-A-Car

0.82 miles

Enterprise

1.81 miles

Key West Jeep Adventures

2.78 miles

Uppy's Clean Machine

3.02 miles

Avis

3.14 miles

Dollar Rent-A-Car

3.14 miles

Fat Tuesday

0.07 miles

Fogarty's

0.08 miles

Señor Frog's

0.09 miles

Flying Monkeys

0.09 miles

Caroline's

0.09 miles

Lucy’s Retired Surfer Bar and Restaurant

0.09 miles

Wendy's

0.09 miles

Duetto Pizza

0.11 miles

The Lazy Gecko

0.12 miles

Olivia Street Grocery

0.53 miles

Fausto's Food Palace

0.85 miles

Bealls Outlet

1.76 miles

Gordon Food Service

1.78 miles

Ross

1.99 miles

Winn-Dixie

2.06 miles

Publix

2.13 miles

Atlantic Grocery

2.41 miles

TJ Maxx

2.53 miles

Key West Police Department

1.00 miles

Key West Central Fire Station

1.02 miles

Walgreens

1.98 miles

dePoo Medical Building

2.28 miles

Key West Fire Station 3

2.38 miles

Key West Police Substation

2.82 miles

Monroe County Sheriff's Office Aviation Division

3.48 miles

Monroe County Sheriff's Office Headquarters

3.54 miles

Lower Keys Medical Center

4.12 miles

314 Simonton St Listing Summary

  • What is the asking price at Casa Antigua?

    Casa Antigua is currently listed for sale at Contact for pricing.

  • What is the total size of Casa Antigua?

    Casa Antigua has a total of 8,472 square feet.

  • What is the year built for Casa Antigua?

    The year built for Casa Antigua is 1921.

Contact Listing Broker
broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

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