421 - 423 Simonton Street

For Sale

421 - 423 Simonton Street, Key West, FL 33040

This Key West property for sale is located at 421 - 423 Simonton Street. The current listed sale price for 421 - 423 Simonton Street is $6,500,000. 421 - 423 Simonton Street is situated on a lot that is 0.08 acre in size.

Contacts

broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

Property Details

  • Property Type Other
  • Property Size 3,010 SF
  • Lot Size 0.08 Acre
  • Property Tenancy Multi-Tenant
  • Year Built 2020
  • Date Updated Sep 2, 2025
Discover the vibrant and historic area surrounding the location, within walking distance to popular attractions such as the Ernest Hemingway Home and Museum, the Key West Lighthouse, and the Southernmost Point of the continental U.S. Enjoy the lively atmosphere of Duval Street lined with shops, art galleries, and restaurants offering world-class cuisine. Experience the local culture through the diverse mix of entertainment, festivals, and events that showcase the unique charm of Key West. This prime location offers a perfect blend of history, entertainment, and natural beauty, making it an exceptional investment opportunity for hospitality and limited service ventures.Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest privacy and relaxation, each home includes its own outdoor lounging space and pool—perfect for cooling off after a day in the sun or enjoying a quiet evening under the palms. Whether you're looking for a investment opportunity, a vacation retreat with rental flexibility, or a mix of both, this unique setup delivers unmatched versatility just steps from the vibrant restaurants, galleries, and nightlife of Duval Street.
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Highlights

  • 6 Total Bedrooms
  • 8 Total Bathrooms
  • Built in 2020
  • Two Transient Licensed Homes
  • X - Flood Zone

Getting around

  • 95/100

    Walk Score ®

  • 28/100

    Transit Score ®

  • 95/100

    Bike Score ®

Powered by Walk Score ®

Location

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

Points of Interest

  • Chevron

    0.64 miles

  • Citgo

    0.66 miles

  • Circle K

    1.13 miles

  • Shell

    1.17 miles

  • Owen's Oco-Pep

    1.33 miles

  • Electrify America

    2.40 miles

  • Mobil

    2.47 miles

  • Old Town Garage

    0.33 miles

  • 201 Front Street Garage

    0.34 miles

  • Key West Tropical Forest & Botanical Garden

    3.50 miles

  • Oceans Edge Resort & Marina Parking

    4.67 miles

  • Marquesa Hotel

    0.04 miles

  • The Artist House

    0.05 miles

  • Crowne Plaza Key West-La Concha

    0.13 miles

  • Gardent Cottage

    0.13 miles

  • Pegasus Hotel

    0.15 miles

  • The Saint Hotel Key West, Autograph Collection

    0.16 miles

  • Ridley House - Key West Historic Inns

    0.16 miles

  • L'Habitation

    0.17 miles

  • The Cabana Inn

    0.18 miles

  • Island City House Hotel

    0.18 miles

  • Faustos

    0.05 miles

  • Olivia Street Grocery

    0.41 miles

  • Fausto's Food Palace

    0.75 miles

  • Bealls Outlet

    1.69 miles

  • Gordon Food Service

    1.71 miles

  • Ross

    1.92 miles

  • Winn-Dixie

    1.99 miles

  • Publix

    2.07 miles

  • Atlantic Grocery

    2.33 miles

  • TJ Maxx

    2.47 miles

In-Depth Research Available for this Property

Access more in-depth information about this property — including ownership, tenant details, property characteristics and transaction history, along with local market insights and much more — on CommercialEdge.

Contact Listing Broker
broker
Team Gardner-Langley

Keys Real Estate | Knight & Gardner Realty

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