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    421 - 423 Simonton Street Key West, FL 33040

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    Claim this Listing
    For Sale
    $5,850,000

    Multi-family - Key West, FL

    Type:Multi Family
    Property size:
    3,010 SF
    Lot size:
    0.08 Acres
    Price / SF:
    $1,943/SF
    Added:
    Dec 9, 2025
    Days on Market:
    133
    Last Refresh:
    Apr 21 at 12:06 pm

    Property Features for 421 - 423 Simonton Street

    General Information

    Property type
    Residential Multi Family
    Property subtype
    Multi Family
    Zoning
    HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
    Bedrooms
    6
    Bathrooms
    8
    Rooms
    Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5
    Interior features
    Built-in Cabinets, Smoke Alarms
    Exterior features
    Privacy Wall/Fence
    Fencing
    Fenced, Privacy
    Appliances
    Dryer, Microwave, Range, Refrigerator
    Standard status
    Active
    APN
    00006360-000000
    Size
    3,010 SF
    Lot size
    0.08 Acres

    Taxes and HOA fees

    Tax Year
    2024
    Tax Annual Amount
    26522.53

    Utilities

    Cooling system
    Ceiling Fan(s)

    Building Details

    Year built
    2020
    Floors in Building
    2
    Number of units
    2
    Roof type
    Metal
    Architectural style
    Other

    We can help!

    Listing Contact
    Will Langley
    Will Langley

    Listing agent Will Langley License #3242135

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

    Listing date Dec 9, 2025

    MLS# 614546 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

    Key West Multi-Family Homes

    This property features two homes, each with 3 bedrooms and 3.5 baths, and private pools. Located one block from Duval Street, these residences have a strong rental history. The homes blend island charm with modern comfort, featuring open-concept living areas, updated kitchens, and private ensuite bedrooms. Each home includes its own outdoor lounging space and pool. The property is located steps from restaurants, galleries, and nightlife. The property is zoned HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med. The lot size is 0.08 acres and the property size is 3010 square feet. This property is suitable as an investment opportunity, a vacation retreat with rental flexibility, or a mix of both.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Fixed Gears (Bike/Boat/Book/etc) Store

    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
    -81.801587
    Latitude
    24.557125

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    FAQs

    What type of property is this?
    Duplex - Two homes near Duval Street with private pools and rental history.
    Where is this duplex located?
    The property is located at 421 - 423 Simonton Street Key West, FL.
    What is the asking price?
    The asking price for this property is $5,850,000.
    What are key features of this property?
    This property features: Two separate homes on one property, each with 3 bedrooms and 3.5 baths; Each home features its own private pool; Located just one block from Duval Street
    (305) 294-5155
    We can help!
    Listing Contact
    Will Langley
    Will Langley
    Real Estate License ID: 3242135
    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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