Casa Antigua

314 Simonton St, Key West, FL 33040

  • For Sale $5,500,000
  • 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 Sep 3, 2025
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

Location

Getting Around

  • Walk Score ®

    95/100 Walker's Paradise
  • Transit Score ®

    28/100 Some Transit
  • Bike Score ®

    92/100 Biker's Paradise
Powered by Walk Score ®
  • City Key West, FL
  • Neighborhood Historic Seaport
  • Zip Code 33040

Points of Interest

  • Chevron

    0.75 miles

  • 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

  • 201 Front Street Garage

    0.25 miles

  • Old Town Garage

    0.33 miles

  • Key West Tropical Forest & Botanical Garden

    3.56 miles

  • Oceans Edge Resort & Marina Parking

    4.75 miles

  • Ridley House - Key West Historic Inns

    0.05 miles

  • The Artist House

    0.08 miles

  • The Saint Hotel Key West, Autograph Collection

    0.13 miles

  • The Key West Harbor Inn 1

    0.15 miles

  • The Key West Harbor Inn 3

    0.15 miles

  • The Key West Harbor Inn 2

    0.15 miles

  • Marquesa Hotel

    0.16 miles

  • Crowne Plaza Key West-La Concha

    0.16 miles

  • L'Habitation

    0.16 miles

  • Seaport Inn

    0.20 miles

  • Hard Rock Cafe

    0.07 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

  • Mary Immaculate Star of the Sea School

    0.62 miles

  • Reynolds School

    0.89 miles

  • Montessori Children's School

    0.91 miles

  • Horace O'Bryant Middle School

    1.04 miles

  • Mary Sands Alternative School

    1.08 miles

  • Key West High School

    1.69 miles

  • Sigsbee Charter Elementary School

    2.37 miles

  • Poinciana Elementary School

    2.38 miles

  • SFUWO School

    2.46 miles

  • Gerald Adams Elementary School

    3.95 miles

  • Inez Martin (United Methodist Wesley House) Child Development Center

    0.80 miles

  • Lighthouse Christian Academy

    4.21 miles

Frequently Asked Questions

How much does Casa Antigua cost?

The space currently listed for sale at Casa Antigua asks for $5,500,000.

What is the total square footage of Casa Antigua?

Casa Antigua totals 8,472 square feet.

When was this property built?

Casa Antigua was built in 1921.

Looking for more in-depth information on this property?

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Contact Listing Broker
broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

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