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    Chestertown, MD
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    Chestertown, MD Commercial Real Estate for Sale

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    Worton, MD Kennedyville, MD Still Pond, MD
    11 results
    Cleared Acreage Near Commercial Corridor
    $200,000
    5.81 Acres

    Cleared Acreage Near Commercial Corridor

    ROUND TOP ROAD, Chestertown, MD 21620

    5.81 acres of suburban commercial land near Downtown Chestertown.

    • Cleared and level acreage ready for development
    • Suburban Commercial Zoning allows for a variety of uses
    • Located just off a commercial corridor
    • Minutes from Downtown Chestertown
    • Investment opportunity
    Updated: Mar 20
    View details
    Unimproved Land in Chestertown, MD
    Contact for pricing
    0.69 Acres

    Unimproved Land in Chestertown, MD

    23683 L Road, Chestertown, MD 21620

    0.69 acre of unimproved land suitable for village development.

    • 0.69+/- Acres of Unimproved Land
    • Located in Chestertown, Kent County
    • Zoning - Village (V) district: Suitable for residential and low‑intensity commercial uses
    • Online Auction: Bidding begins June 3rd and ends June 8th, 2026
    • Intended for walkable, community‑centered development
    Updated: May 18
    View details
    Vacant Land in Chestertown, MD
    Contact for pricing
    1.05 Acres

    Vacant Land in Chestertown, MD

    1.05-acre vacant land, close to local amenities.

    206 BURCHARD SAWMILL Road, Chestertown, MD 21620
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    Chestertown Church and Additional Parcels
    $795,000
    3,500 SF

    Chestertown Church and Additional Parcels

    Church and additional parcels in the heart of Chestertown.

    201 N LYNCHBURG St, Chestertown, MD 21620
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    Chestertown Land with Redevelopment Potential
    $750,000
    0.10 Acres

    Chestertown Land with Redevelopment Potential

    Land in Chestertown, MD with redevelopment potential.

    201 N LYNCHBURG Street, Chestertown, MD 21620
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    Unique Radcliffe Mill Annex/Seed House
    $860,000

    Unique Radcliffe Mill Annex/Seed House

    Restored wellness center with cafe, studio, and office spaces.

    860 HIGH STREET, Chestertown, MD 21620
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    Commercial Lot in Downtown Chestertown
    $109,999

    Commercial Lot in Downtown Chestertown

    Downtown commercial lot with development potential near established businesses.

    116 CROSS St, Chestertown, MD 21620
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    Turnkey Investment Property in Chestertown
    $2,300,000

    Turnkey Investment Property in Chestertown

    Profitable mixed-use property with apartments and storefronts in downtown Chestertown.

    200 HIGH St, Chestertown, MD 21620
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    Historic Chestertown Mixed-Use Property
    $1,300,000
    1,300 SF

    Historic Chestertown Mixed-Use Property

    Mixed-use property with commercial kitchen and residential apartment in Chestertown.

    327 CANNON St, Chestertown, MD 21620
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    Commercial Development Site on MD
    $899,000
    0.97 Acres

    Commercial Development Site on MD

    Commercial development site suitable for retail, restaurant, or service uses.

    515 WASHINGTON AVENUE, Chestertown, MD 21620
    View details
    Land in Chestertown, Maryland
    $40,000
    0.11 Acres

    Land in Chestertown, Maryland

    Commercial land available for sale in Chestertown, Maryland.

    MONTGOMERY AVENUE, Chestertown, MD 21620
    View details
    Based on your search, we've compiled 488 Potential Opportunities for your consideration. Besides 11 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 473 Off-Market properties to explore as potential leads

    Opportunities in Nearby Cities

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

    Veterinary Hospital on Route 20
    $399,900
    3,000 SF

    Veterinary Hospital on Route 20

    3,000 SF commercial building, ideal for user-owner or investor.

    6270 ROCK HALL Rd, Rock Hall, MD 21661
    View details
    Worton Land: Versatile Village Zoning
    $59,999
    1.09 Acres

    Worton Land: Versatile Village Zoning

    1+ acre lot in Worton, MD, with flexible zoning.

    LAMBS MEADOW Road, Worton, MD 21678
    View details
    Rock Hall Agricultural Property
    $3,665,000
    3,200 SF

    Rock Hall Agricultural Property

    3200 sqft farm property for sale in Rock Hall.

    22537 Shipyard Ln, Rock Hall, MD 21661
    View details
    Worton Farmland Opportunity
    $425,000
    1,328 SF

    Worton Farmland Opportunity

    Land available in Worton, Maryland.

    25051 Smithville Rd, Worton, MD 21678
    View details

    Off-Market Properties in Chestertown, MD

    Consider similar Off-Market properties in Chestertown, 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.

    176 Flatland Rd

    176 Flatland Rd

    CONVENIENCE STORE • 3,476 SF
    Value Estimation
    $800,000
    176 Flatland Rd, Chestertown, MD 21620-3363
    View details
    120 Speer Rd

    120 Speer Rd

    MEDICAL BUILDING • 4,201 SF
    Value Estimation
    $1,100,000
    120 Speer Rd, Chestertown, MD 21620-1044
    View details
    846 High St

    846 High St

    COMMERCIAL (GENERAL) • 522 SF
    Value Estimation
    $685,000
    846 High St, Chestertown, MD 21620-1135
    View details
    301 Morgnec Rd

    301 Morgnec Rd

    OFFICE BUILDING • 4,100 SF
    Value Estimation by Request
    301 Morgnec Rd, Chestertown, MD 21620-1025
    View details
    830 High St

    830 High St

    OFFICE BUILDING • 2,204 SF
    Value Estimation by Request
    830 High St, Chestertown, MD 21620-1135
    View details
    Lndg Ln, Unit 26

    Lndg Ln, Unit 26

    RESIDENTIAL PARKING GARAGE • 0.01 Acres
    Value Estimation
    $1,100,000
    Lndg Ln, Chestertown, MD 21620
    View details
    1 Little Hbr Way

    1 Little Hbr Way

    RESIDENTIAL PARKING GARAGE • 0.01 Acres
    Value Estimation by Request
    1 Little Hbr Way, Chestertown, MD 21620
    View details
    Lndg Ln, Unit 33

    Lndg Ln, Unit 33

    RESIDENTIAL PARKING GARAGE • 0.01 Acres
    Value Estimation by Request
    Lndg Ln, Chestertown, MD 21620
    View details
    903 Washington Ave

    903 Washington Ave

    RESTAURANT • 3,528 SF
    Value Estimation
    $525,000
    903 Washington Ave, Chestertown, MD 21620-3331
    View details
    9 Lndg Ln

    9 Lndg Ln

    RESIDENTIAL PARKING GARAGE • 0.01 Acres
    Value Estimation
    $795,000
    9 Lndg Ln, Chestertown, MD 21620
    View details
    110 Queen St

    110 Queen St

    OFFICE BUILDING • 778 SF
    Value Estimation by Request
    110 Queen St, Chestertown, MD 21620-1522
    View details
    502 Washington Ave

    502 Washington Ave

    VACANT COMMERCIAL LAND • 0.22 Acres
    Value Estimation by Request
    502 Washington Ave, Chestertown, MD 21620-1239
    View details
    504 Washington Ave

    504 Washington Ave

    RETAIL STORES (PERSONAL SERVICES) • 828 SF
    Value Estimation by Request
    504 Washington Ave, Chestertown, MD 21620-1239
    View details

    Chestertown, MD Commercial Real Estate Investment Opportunities Market Analysis

    Explore 484 commercial real estate for sale in Chestertown, MD, showcased through 11 active listings on our real estate platform. These investment opportunities span a total of 4,800 square feet of properties for sale, with an estimated market value of $2,095,000.

    Sale prices for business properties in Chestertown, MD start at $795,000, averaging $1,047,500, and reaching up to $1,300,000 — 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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    Property Size Breakdown

    The majority of commercial real estate listings in Chestertown fall within the 10,000 to 25,000 square foot range.

    Demographics Overview

    Population 14K
    Population Growth (5Y) +2.9%
    Median Household Income $76,094
    College Educated 32.4%

    High-Yield Neighborhoods for Strategic Investment

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

    Neighborhood Average Price
    21620 $725.4K

    Taxes & Financing

    Tax Rate (average for all types) 1.34%
    Property Tax per SF $23.81 per sq ft
    Tax Rate vs County Average 0.07 pp above county avg
    Average Loan-to-Value 65.0%

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