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    Chester, MD
    Retail

    Chester, MD Retail Space for Sale

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    Stevensville, MD Grasonville, MD Queenstown, MD Annapolis, MD Rock Hall, MD Pasadena, MD Centreville, MD Arnold, MD
    Route 50 Accessible Retail Buildings
    Updated: Nov 21, 2025
    Route 50 Accessible Retail Buildings

    100-104 Olde Point Road, Chester, MD 21619

    $1,500,000
    Direct access off of Eastbound Rt 50
    Two 4800 sf buildings
    Great location
    Many permitted office and retail uses
    Several Leases in place
    View details
    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Based on your search, we've compiled 17 Potential Opportunities for your consideration. Besides 1 Active listings in Chester, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 11 Off-Market properties to explore as potential leads, plus 1 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Boutique Downtown Storefront
    Boutique Downtown Storefront

    45 Randall Street, Annapolis, MD 21401

    $475,000
    240 sqft

    High-visibility storefront suited for retail or food concepts in a heavily visited waterfront downtown setting.

    View details
    Three-Building Retail and Service Complex
    Three-Building Retail and Service Complex

    1406 MAIN Street, Stevensville, MD 21666

    $6,000,000
    1.78 AC lot

    Three-building retail and service complex with dual frontage and nine drive-in bays for flexible commercial use.

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    Multi-Building Retail and Service Site
    Multi-Building Retail and Service Site

    1406 Main Street, Stevensville, MD 21666

    Contact for pricing
    12,034 sqft 1.78 AC lot

    Three-building retail and service complex on a corner site with dual frontage on U.S. Route 50/301 and Main Street.

    View details
    Versatile Two-Story Commercial Space
    Versatile Two-Story Commercial Space

    122 Severn Ave, Annapolis, MD 21403

    Contact for pricing

    Two-story commercial space with flexible layout, available May 2025.

    View details

    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    PUD-Zoned Commercial Land with Frontage
    PUD-Zoned Commercial Land with Frontage

    3229 State Road 207, Elkton, FL 32033

    $1,599,000
    2.07 AC lot

    2.07-acre PUD-zoned parcel on State Hwy 207 with 360 feet of frontage and an on-site renovated 2012 home.

    View details

    Off-Market Properties in Chester, MD

    Consider similar Off-Market properties in Chester, MD. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    1802 Main St
    RETAIL STORES (PERSONAL SERVICES)

    1802 Main St, Chester, MD 21619-2604

    $7,430,000
    Estimated value
    14,473 sqft 1.73 AC lot
    View details
    1713 Main St
    RETAIL STORES (PERSONAL SERVICES)

    1713 Main St, Chester, MD 21619-2641

    Value Estimation by Request
    1,920 sqft 0.49 AC lot
    View details
    115 Piney Rd
    RETAIL STORES (PERSONAL SERVICES)

    115 Piney Rd, Chester, MD 21619-2619

    $6,445,000
    Estimated value
    12,036 sqft 1.54 AC lot
    View details
    1619 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)

    1619 Postal Rd, Chester, MD 21619-2601

    Value Estimation by Request
    280 sqft 0.30 AC lot
    View details
    1607 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)

    1607 Postal Rd, Chester, MD 21619-2601

    Value Estimation by Request
    896 sqft 0.24 AC lot
    View details
    1626 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)

    1626 Postal Rd, Chester, MD 21619-2625

    Value Estimation by Request
    1,194 sqft 0.44 AC lot
    View details
    1608 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)

    1608 Postal Rd, Chester, MD 21619-2664

    Value Estimation by Request
    4,200 sqft 0.44 AC lot
    View details
    1515 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)

    1515 Postal Rd, Chester, MD 21619-2255

    Value Estimation by Request
    1,050 sqft 0.39 AC lot
    View details
    1707 Main St
    RETAIL STORES (PERSONAL SERVICES)

    1707 Main St, Chester, MD 21619-2641

    $695,000
    Estimated value
    5,157 sqft 1.92 AC lot
    View details
    1720 Main St
    RETAIL STORES (PERSONAL SERVICES)

    1720 Main St, Chester, MD 21619-2602

    $1,455,000
    Estimated value
    11,220 sqft 1.35 AC lot
    View details
    1801 Main St
    RETAIL STORES (PERSONAL SERVICES)

    1801 Main St, Chester, MD 21619-2763

    Value Estimation by Request
    2,400 sqft 0.46 AC lot
    View details

    Chester, MD Retail Space Market Trends and Statistics

    Explore 12 retail space for sale in Chester, MD on our real estate platform.

    Sale prices for retail space in Chester, MD average $1,500,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Grocery and convenience stores 2
    Shopping centers 2
    Automotive properties 1
    Gas stations 1

    Demographics Overview

    Population 5,905
    Population Growth (5Y) +0.2%
    Median Household Income $100,359
    College Educated 47.4%

    High-Yield Neighborhoods for Investment

    Identify Chester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

    Neighborhood Average Price
    21619 $1.5M

    Taxes & Financing

    Tax Rate (average for all types) 0.94%
    Property Tax per SF $25.82 per SF
    Tax Rate vs County Average 0.06 pp below county avg
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Queen Anne's County

    New Delisted

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