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    100 N LOUDOUN Street Winchester, VA 22601

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    For Lease
    $17 SF/Yr

    CommercialLease - WINCHESTER, VA

    Type:Retail
    Added:
    Sep 29, 2025
    Days on Market:
    216
    Last Refresh:
    May 2 at 1:06 am

    Property Features for 100 N LOUDOUN Street

    General Information

    Property type
    Other
    Property subtype
    Retail
    Parking
    500
    Parking features
    On Street, Parking Lot, Garage
    Standard status
    Active

    Utilities

    Heating system
    Central
    Cooling system
    Central Air

    Building Details

    Year built
    1900
    Building materials
    Brick

    We can help!

    Listing Contact
    Gillian Joy Greenfield
    Gillian Joy Greenfield

    Listing agent Gillian Joy Greenfield License #0225064152

    Listing office Coldwell Banker Premier 14 E Piccadilly Street, Winchester, VA

    Listing date Sep 29, 2025

    MLS# VAWI2009162

    Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

    Overview

    Downtown Winchester Restaurant Opportunity

    This commercial space presents an opportunity for experienced restaurant operators in downtown Winchester, Virginia, situated in the heart of the Old Town Walking Mall. The historical building features modern upgrades, original brick, and hardwood floors. The restaurant space includes a large bar seating area, a spacious dining area, room for live music, storage, and a kitchen that can accommodate a hood installation. Massive windows and a large outdoor dining area are suitable for seasonal use and outdoor events. The space currently offers 3500 square feet, with approximately 4000 square feet of outdoor space. The space can be expanded by an additional 2100 square feet, creating a total dining and kitchen area of up to 5600 square feet. There is also an option to add an 1800 square foot 'speakeasy' in the basement. The lease rate is $17.15 per square foot, plus $3.43 per square foot. Some tenant improvement allowance and deferred rent may be considered with acceptable lease terms.
    Property Profile Insight Report Location Intelligence

    Current Use by Public Records

    Apps Twenty Four ... (Bike/Boat/Book/etc) Store Willie Sutton’s saloon Bar & Pub ItsApriority4u LLC Physician Steinlage Insurance Agency Insurance Agency Online Marketing Winchester Advertising Agency

    Suggested Use

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

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

    Similar Places Nearby

    • Laura's Lemons — TBD, Winchester, VA 22601

    Location Insight

    • Map
    • Local Demand
    City
    Winchester
    County
    Frederick
    State
    Virginia
    Longitude
    -78.1652
    Latitude
    39.1847

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    FAQs

    What type of property is this?
    Restaurant - Restaurant space in historic downtown Winchester with outdoor dining area.
    Where is this restaurant located?
    The property is located at 100 N LOUDOUN Street Winchester, VA.
    What is the lease rate?
    The lease rate is $17 SF/Yr.
    What are key features of this property?
    This property features: Prime location in the heart of Downtown Winchester's Old Town Walking Mall.; Large outdoor dining area (approx. 4,000 SF) ideal for seasonal use and events.; Opportunity to expand the dining/kitchen area up to 5,600 SF, with an additional 1,800 SF 'speakeasy' in the basement.
    (540) 974-3927
    We can help!
    Listing Contact
    Gillian Joy Greenfield
    Gillian Joy Greenfield
    Real Estate License ID: 0225064152
    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.

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    100 N LOUDOUN Street, WINCHESTER, VA 22601

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