Movoto Real Estate
Sold on 07/06/2026

314 Simonton St, Key West, FL 33040

$4,500,000

Last sold 07/06/2026 after 599 Days

  • 8

    bed

  • 11

    bath

  • 8,472

    Sqft ($531/Sqft)

Multi-family not for sale

About 314 Simonton St

Property type Multi-family
Year built 1921
HOA fee $0/month
Lot size 7,750 Sqft
Property description
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.
Listed by
Listing Agent - Team Gardner/Langley
Listing Office - Berkshire Hathaway HomeServices Knight & Gardner Realty
Source: FKBOR MLS mls logo
MLS#612250 • last updated 3 months ago
Movoto checked FKBOR MLS for data 2 minutes ago
Overview
Levels/Style Other Bldg Style
MLS # 612250
Type Residential
SqFt 8472
Status Closed
SubType Multi-Units
Lot Size (Sqft) 7750
Lot Size (Acres) 0.18
Property Tax 13667.88
Year Built 1921
Interior
Total # of Bathrooms 11
# of Full Baths 7
# of Half Baths 4
Total # of Bedrooms 8
Exterior
Construction Combo Construction
Amenities / Utilities
HOA Fee Includes None
Pool In Ground, Concrete
Location
County Monroe
Subdivision Old Town - Unlisted (1.0)
APN 00004210-000000
Zoning HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
Multifamily Details
Total # of Units 8
  • Jul 2026
    mls logo MLS # 612250
  • Jul 6, 2026 Sold
    $4,500,000 (-9.1%)
  • Apr 28, 2026 Active
    —
  • Apr 28, 2026 Contingent
    —
  • Apr 25, 2026 Price Change
    $4,950,000 (-5.7%)
  • Apr 8, 2026 Price Change
    $5,250,000 (+2.9%)
  • Apr 8, 2026 Price Change
    $5,100,000 (-2.9%)
  • Jan 12, 2026 Price Change
    $5,250,000 (-4.5%)
  • Jul 28, 2025 Price Change
    $5,500,000 (-6.8%)
  • May 20, 2025 Price Change
    $5,900,000 (-7.8%)
  • Apr 1, 2025 Price Change
    $6,400,000 (-7.2%)
  • Nov 14, 2024 Listed
    $6,900,000 (+177050.2%)
  • Oct 2016
    mls logo MLS # 122571
  • Oct 11, 2016 Price Change
    $3,895 (-2.6%)
  • Oct 11, 2016 Price Change
    $4,000 (-7.0%)
  • Jun 7, 2016 Listed
    $4,300
  • Year Property taxes Tax assessment
  • 2024
    $13,814 +1.1%
    $1,258,571 +1.96%
  • 2023
    $13,668 +2.6%
    $1,234,434 +1.01%
  • 2022
    $13,318 -2.1%
    $1,222,051 +0.94%
  • 2021
    $13,605 +0.1%
    $1,210,719
  • 2020
    $13,590
    $1,210,719
  • 314 Simonton St
    $4.5M
  • —
  • 33040
    $1.1M -14% y/y
  • Key West
    $1.11M -13% y/y
No chart available
Statistics calculated by Movoto

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2/10
5/10
Key West High School
public Grades 9-12
Monroe
Source: GreatSchools.org © 2026. All rights reserved.

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