PropertyShark
  • Property data
    • Building characteristics
    • Ownership & legal
    • Sales & financials
    • Development
    • Location & risk
  • Tools
    • Property lists
    • Comparables
    • Ownership research
    • Maps
  • CRE listings
  • Resources
    • Explore
    • Property records
    • Recently sold homes
    • Learn
    • Webinars
    • Blog
    • Knowledge library
    • Support
    • Help center
Add a Listing Advertise
  1. Commercial Properties
  2. FL
  3. Florida Keys
  4. Key West

Casa Antigua

For Sale

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.

Building Details

  • For Sale $4,950,000
  • Property Type Multi-Family
  • Property Size 8,472 SF
  • Units 9
  • Lot Size 0.18 Acre
  • Additional Rent Price on request
  • Property Tenancy Multi-Tenant
  • Building Class C
  • Year Built 1921
  • Date Updated Oct 22, 2026
Want more info on this listing?

Reach out to the broker for more info on lease terms and amenities

False

Contacts

broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

Location

  • City Key West, FL
  • Neighborhood Historic Seaport
  • Zip Code 33040
  • Map
  • Street
  • Walk score 95/100 Walker's Paradise
  • Transit score 28/100 Some Transit
  • Bike score 92/100 Biker's Paradise
Powered by Walk Score ®

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

Hydro Thunder

0.15 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

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

Faustos

0.17 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

Sunset Key Fire Station

0.70 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

Listing Summary

  • Property Financials

    314 Simonton St is currently listed for sale at $4,950,000 for a price per square foot of $584.28.

  • Property Details

    314 Simonton St totals 8,472 square feet of Multi-Family space on a lot spanning 0.18 acres. The property was initially built in 1921.

    Based on its location, amenities, and finishes, the property is listed as class C.

    Tenancy at 314 Simonton St is listed as Multi-Tenant, comprising a total of 9 units.

  • Area Characteristics

    314 Simonton St is located in the Historic Seaport neighborhood.

    In terms of ease of commuting, the area has a walk score of 95, indicating that it is perfect for walking.

Contact Team Gardner-Langley
broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Nearby Listings

818 Elizabeth St

818 Elizabeth St

818 Elizabeth St, Key West, FL
$4,549,000
Property
  • Multi-Family
  • 5,317 SF

Popular Searches

  • Miami Office Properties for Sale
  • Miami Commercial Real Estate
  • Florida Keys Commercial Real Estate
  • Doral Commercial Real Estate
  • Miami Beach Commercial Real Estate
  • Homestead Commercial Real Estate
  • Marathon Commercial Real Estate
  • Miramar Commercial Real Estate
  • Blog
  • X
  • Facebook
  • Instagram
  • LinkedIn
  • About
  • Our Services
  • Contact Us
  • Sitemaps
  • Privacy Policy
  • Your CA Privacy Rights
  • Terms Of Service
  • FAQ

Customer Service

  • (718)715-1758
  • Contact us
Copyright 2003-2026, PropertyShark.com