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    314 Simonton Street Key West, FL 33040

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    Claim this Listing
    For Sale
    $5,250,000

    Apartment 3 or more,Other Services,Retail,Professional Service

    Added:
    Apr 8, 2026
    Days on Market:
    14
    Last Refresh:
    Apr 21 at 12:06 am

    Property Features for 314 Simonton Street

    General Information

    Property type
    Commercial Sale
    Property subtype
    Other
    Zoning
    HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
    Bedrooms
    8
    Bathrooms
    11
    Rooms
    Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5
    Parking features
    Covered
    Interior features
    Other, Laundry Room
    Standard status
    Active
    APN
    00004210-000000

    Taxes and HOA fees

    Tax Year
    2023
    Tax Annual Amount
    13667.88

    Utilities

    Cooling system
    Ceiling Fan(s)

    Building Details

    Year built
    1921
    Floors in Building
    3
    Number of units
    8
    Architectural style
    Other

    We can help!

    Listing Contact
    Team Gardner/Langley

    Listing agent Team Gardner/Langley License #BK612006

    Listing office Berkshire Hathaway HomeServices Knight & Gardner Realty 336 Duval St., Key West, FL

    Listing date Apr 8, 2026

    MLS# 612134 Listing URL

    Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

    Overview

    Historic Key West Mixed-Use Property

    This historic three-level property, located one block from Duval Street and across from the Federal Courthouse in Key West, offers a blend of historic charm and modern potential. Originally a hotel with a Ford dealership on the ground floor, the building is steeped in heritage. The property is legally recognized as 8 units, an atrium, garage, and a pool. The property provides an unmatched opportunity for someone who loves trophy properties. The property is zoned HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med. The possibilities are endless, whether envisioning a grand single-family estate or multi-unit living combined with commercial space on the lower level.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Key West Room ... Arcade & Gaming Center Casa Antigua Tour Operator

    Suggested Use

    Law Firm Real Estate Agency Dental Office Spa & Massage Center Hair Salon Restaurant Nail Salon Building Supply Gym & Fitness Center Daycare Center

    Zoning and permitted uses should be independently verified with local authorities.

    Location Insight

    • Map
    • Local Demand
    City
    Key West
    County
    Monroe
    State
    Florida
    Longitude
    -81.803104
    Latitude
    24.558333

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    FAQs

    What type of property is this?
    Mixed-use property - Unique historic property near Duval Street with multi-use potential.
    Where is this mixed-use property located?
    The property is located at 314 Simonton Street Key West, FL.
    What is the asking price?
    The asking price for this property is $5,250,000.
    What are key features of this property?
    This property features: Prime Location: Just one block from Duval Street and across from the Federal Courthouse.; Historic Significance: Originally a hotel and Ford dealership, with a stay by Ernest Hemingway in 1928.; Multi‑Unit Potential: Legally recognized as 8 units, offering diverse usage possibilities.
    (305) 294-5155
    We can help!
    Listing Contact
    Team Gardner/Langley
    Real Estate License ID: BK612006
    Learn More
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    Realmo Value Estimations

    Realmo estimates a property’s market value using a proprietary methodology that incorporates public data and user-submitted information. This cumulative value is generated by integrating a variety of conventional and innovative methods. 

    Disclaimer

    These figures are not official appraisals and should not be used as a substitute for a valuation performed by a licensed appraiser.
    Actual market value may differ due to factors not captured in the data. Estimates are offered for informational purposes only, and users should conduct independent research before making financial or investment decisions.
    By using this feature, you acknowledge that Realmo is not responsible for actions taken based on these estimates.

    AI approach

    Realmo AI Method estimates property value using machine learning models trained on millions of comparable listings, transactions, and market signals. It analyzes property features, location intelligence data, and current market dynamics to predict the most probable market value in real time.

    Realmo CapRate Calculation

    Realmo calculates the Capitalization Rate (Cap Rate) to help estimate a property's potential return on investment. The Cap Rate is a fundamental metric in commercial real estate that measures the relationship between a property's net operating income and its market value.

    How We Calculate Cap Rate

    Cap Rate Formula:
    Cap Rate (%) = (Net Operating Income / Property Value) × 100

    Net Operating Income (NOI) Formula:
    NOI = Area × Lease Rate × (1 - Vacancy Rate) × (1 - Operating Expense Ratio)

    Components

    Net Operating Income (NOI) represents the annual income a property generates after operating expenses:

    • Area: Building square footage from property records
    • Lease Rate: Annual $/sqft based on market data for the property type and geographic location
    • Vacancy Rate: Percentage of unoccupied space based on market data for the property type and location
    • Operating Expense Ratio: Operating costs as a percentage of income, varies by property type

    Property Value is derived from:

    • Recent sale price (if available)
    • Statistical models using comparable sales
    • AI-powered valuation estimates

    Example Calculation

    For a 100,000 sqft Office Building:

    • Lease Rate: $25.00/sqft/year (market data for Office in this area)
    • Vacancy Rate: 8% (market data for Office in this area)
    • Operating Expense Ratio: 35% (typical for Office properties)
    • Property Value: $15,000,000

    Step 1: Calculate NOI

    NOI = 100,000 × $25.00 × (1 - 0.08) × (1 - 0.35)
    NOI = 100,000 × $25.00 × 0.92 × 0.65
    NOI = $1,495,000/year

    Step 2: Calculate Cap Rate

    Cap Rate = ($1,495,000 / $15,000,000) × 100
    Cap Rate = 9.97%

    Property Type Considerations

    Net Operating Income calculations vary by property type due to different operating expense ratios:

    • Office: Higher expenses (30-40%) for HVAC, utilities, maintenance
    • Retail: Moderate expenses (25-35%) for common area maintenance
    • Industrial/Warehouse: Lower expenses (15-25%) for minimal tenant services
    • Multifamily: Moderate expenses (35-45%) including property management
    • Self-Storage: Lower expenses (25-35%) due to minimal maintenance

    Market lease rates and vacancy rates are specific to each property type and geographic location, reflecting local market conditions.

    Disclaimer

    These calculations are estimates for informational purposes only and should not be used as a substitute for professional financial analysis or appraisal.

    • Cap Rate calculations depend on market data that may change over time
    • Actual operating expenses, lease rates, and vacancy rates may differ from market averages
    • Individual property conditions, lease terms, and tenant quality significantly impact actual NOI
    • Property value estimates are approximations and not official appraisals
    • Cap rates vary widely by market, property condition, and investment risk profile

    Professional Guidance Recommended: Before making any investment or financial decisions, consult with licensed appraisers, commercial real estate brokers, and financial advisors who can evaluate your specific property and circumstances.
    By using this feature, you acknowledge that Realmo is not responsible for investment decisions or actions taken based on these estimates.

    Cap approach

    Capitalization Method calculates value based on estimated net operating income (NOI) and applying a market-based capitalization rate (cap rate), we estimate what a typical investor might be willing to pay for it.

    Comparable approach

    Comparable estimate is based on recent sales of similar nearby properties, adjusted for factors like size, condition, and location.

    Relative

    Relative property class coefficient uses factors that account for typical price differences between various asset types (e.g., retail vs. industrial) to provide a more accurate market-aligned estimate.

    Geo

    Comparable Sales Method, enhanced by Geo coefficients — location-based adjustment factors that reflect differences in price levels across neighborhoods, cities, or regions ensuring a more accurate, market-sensitive valuation.

    Stat Estimate

    This method estimates value based on actual market adjusted recent (~5 years) sales of comparable properties around by location and property type.

    • Ranges - area data calculated by industry standard IQR Outlier Removal Method
    • Range-from: 75% of all similar sales ($/sqft) are above this value
    • Range-to: 75% of all similar sales ($/sqft) are below this value
    AI Estimate

    This method estimates value based on AI market estimation of comparable properties around by location and property type.

    • Ranges - area data calculated by industry standard IQR Outlier Removal Method
    • Range-from: 75% of all estimations ($/sqft) are above this value
    • Range-to: 75% of all estimations ($/sqft) are below this value
    Alternative use

    Estimate considers the property’s potential value if used for a different purpose-based on zoning, demand, and market feasibility.

    More about this property
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