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    Chestertown, MD Commercial Real Estate for Sale

    79 results
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    Meticulously Maintained Waterfront Townhome
    $559,000

    Meticulously Maintained Waterfront Townhome

    103 Landing Ln, Chestertown, MD 21620

    Elegant 2-bedroom townhome in Chester River Landing community.

    • Waterfront community with easy Chester River access, including a community dock with available slips.
    • Maintenance‑free living with condo association handling exterior maintenance, yardwork, and repairs.
    • Turn‑key, meticulously maintained 2‑bedroom townhome with potential for a 3rd bedroom conversion.
    • Modern kitchen featuring new stainless‑steel appliances, granite countertops, and a large island.
    • Oversized second‑story deck perfect for grilling and Chester River sunset views.
    Updated: Sep 10, 2025
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    High Street Chestertown Office Building
    $397,500
    2,204 SF

    High Street Chestertown Office Building

    830 High St, Chestertown, MD 21620

    Prime Chestertown Office Space, High Visibility

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    Historic Chestertown Mixed-Use Gem
    $860,000
    3,114 SF

    Historic Chestertown Mixed-Use Gem

    3,114 sq ft, Wellness Center, Cafe Included

    860 High St, Chestertown, MD 21620
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    Chestertown Office Space for Lease
    Contact for pricing
    2.32 Acres

    Chestertown Office Space for Lease

    Historic building, furnished offices, great location.

    870 High St, Chestertown, MD 21620
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    Chestertown Office Space: Prime Location
    Contact for pricing
    2.32 Acres

    Chestertown Office Space: Prime Location

    Historic Charm, Modern Amenities, 8 Offices

    870 High St, Chestertown, MD 21620
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    Chestertown Retail Space - Great Potential
    Contact for pricing
    0.92 Acres

    Chestertown Retail Space - Great Potential

    Prime Retail Location, Rent-Free Incentive!

    903 Washington Ave, Chestertown, MD 21620
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    Chestertown Ground Lease Opportunity
    Contact for pricing
    0.76 Acres

    Chestertown Ground Lease Opportunity

    Prime Chestertown location, lucrative ground lease.

    140 Scheeler Rd, Chestertown, MD 21620
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    Chestertown Mixed-Use Investment
    $1,870,000
    16,977 SF

    Chestertown Mixed-Use Investment

    Historic Mill, Endless Potential

    870 High St, Chestertown, MD 21620
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    Historic Chestertown Office Suite
    Contact for pricing
    2.32 Acres

    Historic Chestertown Office Suite

    Premium Office Space, Award-Winning Building

    870 High St, Chestertown, MD 21620
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    Chestertown Commercial Development Site
    $895,000
    0.97 Acres

    Chestertown Commercial Development Site

    Prime 1-acre lot, high traffic location.

    515 Washington Ave, Chestertown, MD 21620
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    Downtown Chestertown Development Opportunity
    $1,250,000
    1,588 SF

    Downtown Chestertown Development Opportunity

    Prime 1.56-acre lot, multiple zoning options.

    206 Cannon St, Chestertown, MD 21620
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    Prime Chestertown Office Space
    Contact for pricing
    2.32 Acres

    Prime Chestertown Office Space

    Historic Mill Building, Premium Office Suite

    870 High St, Chestertown, MD 21620
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    Historic Chestertown Multifamily Renovation Opportunity
    $395,000

    Historic Chestertown Multifamily Renovation Opportunity

    Multi-family property in Chestertown's Historic and Arts & Entertainment District.

    349 High St, Chestertown, MD 21620
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    Historic Chestertown Multi-Family Renovation Opportunity
    $395,000

    Historic Chestertown Multi-Family Renovation Opportunity

    Multi-family property in historic Chestertown, ideal for renovation.

    349 High St, Chestertown, MD 21620
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    Chestertown Specialty Property For Sale
    $315,000

    Chestertown Specialty Property For Sale

    Specialty property available for purchase in Chestertown, Maryland.

    119 Darden Rd, Chestertown, MD 21620
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    Waterfront Land For Sale
    $4,850,000

    Waterfront Land For Sale

    Waterfront land available for sale.

    23620 Lands End Rd, Chestertown, MD 21620
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    Chestertown Specialty Property For Sale
    $579,000

    Chestertown Specialty Property For Sale

    Specialty property available in Chestertown, Maryland.

    216 Blakefield Dr, Chestertown, MD 21620
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    Chestertown Specialty Property For Sale
    $410,000

    Chestertown Specialty Property For Sale

    Specialty property available for purchase in Chestertown, Maryland.

    907 N Meadowview Dr, Chestertown, MD 21620
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    Calvert Street Specialty Property
    $165,000

    Calvert Street Specialty Property

    Specialty property available for sale in Chestertown, Maryland.

    423 Calvert St, Chestertown, MD 21620
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    Specialty Property For Sale
    $750,000

    Specialty Property For Sale

    Specialty property available for purchase.

    10230 John Carvill Rd, Chestertown, MD 21620
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    SILVER HEEL Dr, Chestertown, MD
    $369,900

    SILVER HEEL Dr, Chestertown, MD

    Specialty property for sale in Chestertown, MD.

    112 Silver Heel Dr, Chestertown, MD 21620
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    Chestertown Specialty Property For Sale
    $425,000

    Chestertown Specialty Property For Sale

    Specialty property available for purchase in Chestertown, Maryland.

    304 Hadaway Dr, Chestertown, MD 21620
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    Orchard Drive Specialty Property
    $695,000

    Orchard Drive Specialty Property

    Specialty property available for sale on Orchard Drive.

    8951 Orchard Dr, Chestertown, MD 21620
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    Chestertown Multifamily Investment Opportunity
    $1,195,000

    Chestertown Multifamily Investment Opportunity

    Multifamily property for sale in Chestertown, Maryland.

    23393 Cacaway Farm Ln, Chestertown, MD 21620
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    Chestertown, MD Commercial Real Estate Investment Opportunities Market Analysis

    Explore 451 commercial real estate investment opportunities in Chestertown, MD with 79 listings featured on our commercial real estate marketplace. The current inventory includes 30,451,528 square feet of properties with an estimated value of $157,860,000.

    Estimated prices for commercial real estate in Chestertown, MD begin at $35,000, with an average of $550,034 and extend to $11,540,000.

    In Chestertown, MD, current investment values show:

    • Retail properties positioned at $813,455
    • Office Properties & Spaces measuring $345,117
    • Mixed-use properties assessed at $288,548
    • Investment properties calculated at $288,524
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    Browse Commercial real estate for Sale Near Chestertown, MD

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    Most Searched ZIP Codes in Chestertown, MD

    • 21620

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