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    Chester, MD
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    Chester, MD Retail Properties & Spaces 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
    View details
    Based on your search, we've compiled 52 Potential Opportunities for your consideration. Besides 1 Active listings in Chester, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 43 Off-Market properties to explore as potential leads, plus 4 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.

    Renovated Commercial Building on Acreage
    $699,000
    1.14 Acres

    Renovated Commercial Building on Acreage

    Updated commercial building on over an acre with UC zoning.

    211 LOVE POINT RD, Stevensville, MD 21666
    View details
    Unique Church Property in Stevensville
    $975,000
    0.49 Acres

    Unique Church Property in Stevensville

    Historic church with development potential in downtown Stevensville.

    426 LOVE POINT Rd, Stevensville, MD 21666
    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
    Two-Story Office/Retail Space For Sale
    $1,699,000
    5,344 SF

    Two-Story Office/Retail Space For Sale

    Two-story office/retail space with flexible layout and parking.

    122 Severn Ave, Annapolis, MD
    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 Grasonville Development Opportunity
    $1,400,000
    4.41 Acres

    Prime Grasonville Development Opportunity

    Retail or office space development zone with waterfront potential.

    VFW AVE, Grasonville, MD 21638
    View details
    50 Acres Mixed-Use Development Land
    $1,250,000
    49.83 Acres

    50 Acres Mixed-Use Development Land

    50 acres in Rock Hall, MD, ideal for mixed-use development.

    ROCK HALL Road, Rock Hall, MD 21661
    View details
    Retail Pad Site For Sale
    Contact for pricing
    3.38 Acres

    Retail Pad Site For Sale

    3.38 acre retail pad site on high-traffic Ritchie Highway.

    977 Ritchie Highway, Arnold, MD 21012
    View details
    Commercial Land on Ocean Gateway
    $999,000
    3.25 Acres

    Commercial Land on Ocean Gateway

    3.25 acres of commercially zoned land for sale.

    9719 Ocean Gateway, Easton, MD 21601
    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.

    12 Chester Plz

    12 Chester Plz

    DRIVE-THRU RESTAURANT, FAST FOOD • 4,915 SF
    Value Estimation by Request
    12 Chester Plz, Chester, MD 21619-2418
    View details
    1802 Main St

    1802 Main St

    RETAIL STORES (PERSONAL SERVICES) • 14,473 SF
    Value Estimation
    $7,430,000
    1802 Main St, Chester, MD 21619-2604
    View details
    1925 Main St

    1925 Main St

    MINI-MALL • 6,000 SF
    Value Estimation
    $855,000
    1925 Main St, Chester, MD 21619-2607
    View details
    1713 Main St

    1713 Main St

    RETAIL STORES (PERSONAL SERVICES) • 1,920 SF
    Value Estimation by Request
    1713 Main St, Chester, MD 21619-2641
    View details
    2106 Didonato Dr

    2106 Didonato Dr

    SHOPPING CENTER, STRIP CENTER • 17,000 SF
    Value Estimation
    $1,765,000
    2106 Didonato Dr, Chester, MD 21619-2628
    View details
    1423 Main St

    1423 Main St

    FINANCIAL BUILDING • 4,242 SF
    Value Estimation by Request
    1423 Main St, Chester, MD 21619
    View details
    110 Piney Narrows Rd

    110 Piney Narrows Rd

    RESTAURANT • 5,621 SF
    Value Estimation by Request
    110 Piney Narrows Rd, Chester, MD 21619-2439
    View details
    115 Piney Rd

    115 Piney Rd

    RETAIL STORES (PERSONAL SERVICES) • 12,036 SF
    Value Estimation
    $6,445,000
    115 Piney Rd, Chester, MD 21619-2619
    View details
    1509 Postal Rd

    1509 Postal Rd

    AUTO REPAIR, GARAGE • 3,617 SF
    Value Estimation by Request
    1509 Postal Rd, Chester, MD 21619-2255
    View details
    2212 Piney Crk Rd

    2212 Piney Crk Rd

    AUTO REPAIR, GARAGE • 7,200 SF
    Value Estimation by Request
    2212 Piney Crk Rd, Chester, MD 21619-2412
    View details
    1619 Postal Rd

    1619 Postal Rd

    RETAIL STORES (PERSONAL SERVICES) • 280 SF
    Value Estimation by Request
    1619 Postal Rd, Chester, MD 21619-2601
    View details
    1607 Postal Rd

    1607 Postal Rd

    RETAIL STORES (PERSONAL SERVICES) • 896 SF
    Value Estimation by Request
    1607 Postal Rd, Chester, MD 21619-2601
    View details
    1539 Postal Rd

    1539 Postal Rd

    SHOPPING CENTER, STRIP CENTER • 36,420 SF
    Value Estimation
    $3,585,000
    1539 Postal Rd, Chester, MD 21619-2255
    View details
    1814 Crab Aly Dr

    1814 Crab Aly Dr

    AUTO REPAIR, GARAGE • 1,728 SF
    Value Estimation by Request
    1814 Crab Aly Dr, Chester, MD 21619-2757
    View details
    100 Dominion Rd

    100 Dominion Rd

    CONVENIENCE STORE • 1,431 SF
    Value Estimation by Request
    100 Dominion Rd, Chester, MD 21619-2707
    View details
    120 Chester Sta Ln

    120 Chester Sta Ln

    CONVENIENCE STORE • 3,685 SF
    Value Estimation by Request
    120 Chester Sta Ln, Chester, MD 21619-2803
    View details
    210 Country Day Rd

    210 Country Day Rd

    GYM, HEALTH SPA • 37,202 SF
    Value Estimation
    $1,080,000
    210 Country Day Rd, Chester, MD 21619-2603
    View details
    1845 Main St

    1845 Main St

    DRIVE-THRU RESTAURANT, FAST FOOD • 4,451 SF
    Value Estimation by Request
    1845 Main St, Chester, MD 21619-2605
    View details
    1626 Postal Rd

    1626 Postal Rd

    RETAIL STORES (PERSONAL SERVICES) • 1,194 SF
    Value Estimation by Request
    1626 Postal Rd, Chester, MD 21619-2625
    View details
    101 Castle Marina Rd

    101 Castle Marina Rd

    SERVICE STATION (FULL SERVICE) • 1,411 SF
    Value Estimation by Request
    101 Castle Marina Rd, Chester, MD 21619-2417
    View details
    600 Abruzzi Dr

    600 Abruzzi Dr

    SHOPPING CENTER, STRIP CENTER • 2,400 SF
    Value Estimation by Request
    600 Abruzzi Dr, Chester, MD 21619-2198
    View details
    1608 Postal Rd

    1608 Postal Rd

    RETAIL STORES (PERSONAL SERVICES) • 4,200 SF
    Value Estimation by Request
    1608 Postal Rd, Chester, MD 21619-2664
    View details
    2325 Main St

    2325 Main St

    AUTO REPAIR, GARAGE • 7,750 SF
    Value Estimation
    $590,000
    2325 Main St, Chester, MD 21619-2699
    View details

    Chester, MD Retail Properties & Spaces Investment Opportunities Market Analysis

    Explore 44 retail properties & spaces 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 stores 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

    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 Strategic Investment

    Identify Chester submarkets with the highest inventory density on the market and evaluate the median 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 sq ft
    Tax Rate vs County Average 0.06 pp below county avg
    Average Loan-to-Value 65.0%

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