Sign Up Successful!
You now have access to more from Realmo!
    For Sale
    • For Sale
    • For Lease
    • Recently Sold
    • Property Lookup
    • Brokers
    AI Search
    Back to Search
    The Largest CRE Database in the US with Over 1 Million Listings

    419 Simonton St Key West, FL 33040

    Sponsored
    For Sale
    $1,485,000

    Multi-family - Key West, FL

    Type:Multi Family
    Property size:
    1,123 SF
    Days on Market:
    8
    Last Refresh:
    Jan 29 at 12:06 am

    Property Features for 419 Simonton St

    General Information

    Property type
    Residential Multi Family
    Property subtype
    Multi Family
    Standard status
    Active
    Zoning
    HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med
    Rooms
    Bathroom 1, Bathroom 2, Bathroom 3, Bedroom 1, Bedroom 2
    Bedrooms
    2
    Bathrooms
    3
    APN
    00006340-000000
    Interior features
    Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Walk-in Closet(s), Smoke Alarms
    Exterior features
    Privacy Wall/Fence
    Fencing
    Fenced, Privacy
    Appliances
    Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Refrigerator, Washer
    Size
    1,123 SF

    Utilities

    Cooling system
    Ceiling Fan(s)

    Building Details

    Year built
    1889
    Floors in Building
    2
    Flooring type
    Wood
    Building materials
    Frame
    Roof type
    Metal
    Architectural style
    Other

    We can help!

    Listing Contact
    Team Kaufelt

    Truman & Co. Real Estate Services (305) 292-2244

    Listing agent Team Kaufelt (305) 292-2244 License #00000

    Listing date Jan 22, 2026

    MLS# 618250 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.

    Learn more

    Property Insight Report

    Overview

    Restored Multi-Family Property, Key West

    Located in Old Town Key West, this multi-family property at 419 Simonton Street A, originally built before 1889, has been restored for modern living. Construction was completed in January 2026. The property, once a mixed-use landmark, now features entirely new systems, surfaces, and finishes. The residence is offered fully furnished with interiors by Ben Teague Design. It includes two bedrooms and two-and-a-half baths. The upstairs primary bedroom opens to a Key West porch, and a second downstairs porch extends the living space. Architect-led design and landscaping enhance the curb appeal. The property is part of an HOA that includes one attached residential unit to the rear of the main home, and a separate detached unit at the back of the property. Situated on one of the highest elevation blocks in Old Town, it is located in the X-500 flood zone. The property size is 1123 square feet. The zoning is HNC(1-3) - Hist Nghborhd Comml 1 - 3 Coastal Med.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Multifamily properties

    Suggested Use

    Law Firm Realty agency Dental Office Spa & Massage Hair Salon Restaurant Nail Salon Building Supply Gym & Fitness 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
    -81.801594
    Latitude
    24.55727

    Nearby Similar for Sale

    • $1,499,000
      2,699 SF

      Key West Income-Producing Triplex

      Rare triplex in Key West with strong cash flow potential.
      1614 Dennis St, Key West, FL 33040
      View Details
    • New
      $2,350,000
      2,150 SF

      Key West Multifamily with Private Oasis

      Historic Key West multifamily property featuring a private outdoor oasis.
      1209 Packer St, Key West, FL 33040
      View Details
    • $499,000
      665 SF

      Turnkey Commercial Condo in Old Town

      Renovated 665 SF office condo in Key West's Old Town.
      812 Fleming St, Key West, FL 33040
      View Details
    • $19,550,000

      Key West Hotel/Motel Opportunity

      Hotel/Motel located in Old Town Key West, Florida.
      823 Fleming St, Key West, FL 33040
      View Details
    • $2,999,999

      Key West Mixed-Use Investment Property

      Fully rented mixed-use property in the heart of Old Town.
      405 Petronia St, Key West, FL 33040
      View Details
    • $2,999,999
      1,596 SF

      Key West Mixed-Use Income Property

      Fully rented mixed-use property in the heart of Old Town.
      405 Petronia St, Key West, FL 33040
      View Details
    • $2,999,000

      Prime Corner Location on Truman

      Commercial property with high visibility, development potential, and existing structure.
      1000 Truman Ave, Key West, FL 33040
      View Details
    • $11,500,000

      Boutique Guesthouse in Old Town

      Historic Key West guesthouse with 15 deluxe rooms.
      412 Frances St, Key West, FL 33040
      View Details
    • $1,400,000
      2,275 SF

      Two Homes on Contiguous Lots

      Two single-family homes on contiguous lots in the Lower Keys.
      206 4Th St, Key West, FL 33040
      View Details
    • $1,785,000
      1,932 SF

      Key West Legal Duplex

      Legal duplex in a quiet neighborhood, close to the beach.
      1505 Rose St, Key West, FL 33040
      View Details
    • $2,300,000

      Key West Townhouse Unit Complex

      Four-unit townhouse complex on a 10,000 sq ft parcel.
      Key West, FL 33040
      View Details
    • $2,950,000

      Turnkey Restaurant in Old Town

      Remodeled 150-seat restaurant with apartment in historic Key West.
      532 Margaret St, Key West, FL 33040
      View Details

    FAQs

    What type of property is this?
    Multifamily property - Restored Key West multi-family property with modern amenities and historic charm.
    Where is this multifamily property located?
    The property is located at 419 Simonton St Key West, FL.
    What is the asking price?
    The asking price for this property is $1,485,000.
    What are key features of this property?
    This property features: - Completely renovated in January 2026 with all new systems, surfaces, and finishes, blending historic charm with modern comfort.; - Offered fully furnished with bespoke interiors by Ben Teague Design, showcasing timeless materials and sophisticated style.; - Located in the desirable X-500 flood zone on one of the highest elevation blocks in Old Town Key West.
    (305) 292-2244
    Request Owner's contact information
    419 Simonton St Key West, FL 33040
    Message sent successfully
    Error
    If you are the owner or broker of this property and would like to edit or remove this listing please send a message to web site administrator.
    419 Simonton St
    Key West, FL 33040
    Message sent successfully
    Error
    Email to Your Friends
    Link copied to clipboard
    Separate multiple addresses with a comma
    Message sent successfully
    Error

    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
    419 Simonton St Key West, FL 33040
    Thanks! Your message was sent.
    Error! Your message wasn't sent.
    Please enter your name
    Please enter email
    Please enter the email in the correct format
    Please enter phone
    Please enter the number in the correct format
    Please enter message
    Thank You

    You are Unsubscribed From Notifications

    We can help!
    Listing Contact
    Team Kaufelt
    Real Estate License ID: 00000
    (305) 292-2244
    Learn more
    Google sign-in failed. Please try again or use another login method.
    Create New Password
    • At least 8 characters
    • Contains both letters and numbers
    • Contains uppercase and lowercase letters
    • At most 32 characters
    • Password required
    • Password reset link has expired. Please request a new one.