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    Chester, MD
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    Chester, MD Retail Space for Sale

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    Stevensville, MD Grasonville, MD Queenstown, MD
    Route 50 Accessible Retail Buildings
    $1,500,000
    Route 50 Accessible Retail Buildings

    100-104 Olde Point Road, Chester, MD 21619

    Two retail/office buildings with direct highway access for sale.
    • Direct access off of Eastbound Rt 50
    • Two 4800 sf buildings
    • Great location
    • Many permitted office and retail uses
    • Several Leases in place
    Updated: Nov 21, 2025
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    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
    $475,000
    Boutique Downtown Storefront

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

    45 Randall Street, Annapolis, MD 21401

    View details
    Versatile Two-Story Commercial Space
    Contact for pricing
    Versatile Two-Story Commercial Space

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

    122 Severn Ave, Annapolis, MD 21403

    View details
    Established Shopping Center Retail Space
    Contact for pricing
    1,300 SF
    Established Shopping Center Retail Space

    High-traffic shopping center with retail space in Easton's commercial district.

    108 Marlboro Ave, Easton, MD 21601

    View details
    High-Traffic Shopping Center For Sale
    Contact for pricing
    18,800 SF
    High-Traffic Shopping Center For Sale

    Established shopping center in Easton's commercial district with high visibility.

    108 Marlboro Ave, Easton, MD 21601

    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.

    Prime PUD-Zoned Land Opportunity
    $1,599,000
    900 SF
    Prime PUD-Zoned Land Opportunity

    2.07 acres of PUD-zoned land in a growing corridor.

    3229 State Road 207, Elkton, FL 32033

    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)
    14,473 SF Lot: 1.73 Acres
    Estimated value
    $7,430,000

    1802 Main St, Chester, MD 21619-2604

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    1713 Main St
    RETAIL STORES (PERSONAL SERVICES)
    1,920 SF Lot: 0.49 Acres
    Value Estimation by Request

    1713 Main St, Chester, MD 21619-2641

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    115 Piney Rd
    RETAIL STORES (PERSONAL SERVICES)
    12,036 SF Lot: 1.54 Acres
    Estimated value
    $6,445,000

    115 Piney Rd, Chester, MD 21619-2619

    View details
    1619 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)
    280 SF Lot: 0.30 Acres
    Value Estimation by Request

    1619 Postal Rd, Chester, MD 21619-2601

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    1607 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)
    896 SF Lot: 0.24 Acres
    Value Estimation by Request

    1607 Postal Rd, Chester, MD 21619-2601

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    1626 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)
    1,194 SF Lot: 0.44 Acres
    Value Estimation by Request

    1626 Postal Rd, Chester, MD 21619-2625

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    1608 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)
    4,200 SF Lot: 0.44 Acres
    Value Estimation by Request

    1608 Postal Rd, Chester, MD 21619-2664

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    1515 Postal Rd
    RETAIL STORES (PERSONAL SERVICES)
    1,050 SF Lot: 0.39 Acres
    Value Estimation by Request

    1515 Postal Rd, Chester, MD 21619-2255

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    1707 Main St
    RETAIL STORES (PERSONAL SERVICES)
    5,157 SF Lot: 1.92 Acres
    Estimated value
    $695,000

    1707 Main St, Chester, MD 21619-2641

    View details
    1720 Main St
    RETAIL STORES (PERSONAL SERVICES)
    11,220 SF Lot: 1.35 Acres

    1720 Main St, Chester, MD 21619-2602

    View details
    1801 Main St
    RETAIL STORES (PERSONAL SERVICES)
    2,400 SF Lot: 0.46 Acres
    Value Estimation by Request

    1801 Main St, Chester, MD 21619-2763

    View details

    Chester, MD Retail Space Investment Opportunities Market Analysis

    Explore 12 retail space for sale in Chester, MD on our real estate platform. These investment opportunities span a total of 0 square feet of properties for sale, with an estimated market value of $1,500,000.

    Sale prices for retail space in Chester, MD start at $1,500,000, averaging $1,500,000, and reaching up to $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

    Shopping centers 2

    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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