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    Chestertown, MD Land for Sale

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    Worton, MD Kennedyville, MD Still Pond, MD
    21 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
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    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
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    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 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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    Private Wooded Lot For Sale
    $79,000
    1.95 Acres

    Private Wooded Lot For Sale

    Secluded 2-acre lot perfect for recreation and nature.

    SANDY BOTTOM Road, Chestertown, MD 21620
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    Chesapeake Landing Land Parcel
    $39,000
    1.51 Acres

    Chesapeake Landing Land Parcel

    1.51 acre land parcel in Chesapeake Landing community.

    CLOQUET Road, Chestertown, MD 21620
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    Wooded Land Parcel in Chestertown
    $90,000
    3.92 Acres

    Wooded Land Parcel in Chestertown

    Almost 4-acre wooded parcel with paid water and sewer allocation.

    GEORGETOWN Road, Chestertown, MD 21620
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    Secluded Wooded Lot in Chestertown
    Contact for pricing
    0.52 Acres

    Secluded Wooded Lot in Chestertown

    Half acre wooded lot, potential hunting or building site.

    22681 WOOD YARD Lane, 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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    Vacant Land in Chestertown, MD
    Contact for pricing
    0.90 Acres

    Vacant Land in Chestertown, MD

    Vacant land at Johnsontown Rd and Willow Oak Lane.

    JOHNSONTOWN Road, Chestertown, MD 21620
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    87 Acres Residential Development Land
    $3,000,000
    87.34 Acres

    87 Acres Residential Development Land

    87-acre residential development land annexed to Chestertown, Maryland.

    CROMWELL CLARK Road, Chestertown, MD 21620
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    Secluded Wooded Lot For Sale
    Contact for pricing
    0.50 Acres

    Secluded Wooded Lot For Sale

    Half acre wooded lot, potential hunting property.

    22681 WOOD YARD Ln, Chestertown, MD 21620
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    Land For Sale Chestertown, MD
    $150,000
    2.00 Acres

    Land For Sale Chestertown, MD

    Two acre land parcel available in Chestertown, Maryland.

    CAULKS FIELD ROAD, Chestertown, MD 21620
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    Picturesque 2-Acre Lot
    $150,000
    2.00 Acres

    Picturesque 2-Acre Lot

    Build your dream home on this beautiful 2-acre lot!

    GEORGETOWN Road SE, Chestertown, MD 21620
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    Recreational Land in Chestertown, MD
    Contact for pricing
    0.34 Acres

    Recreational Land in Chestertown, MD

    Recreational lot available for gardening or property extension.

    KINGLET Road, Chestertown, MD 21620
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    Two Lots in Chesapeake Landing
    Contact for pricing
    0.34 Acres

    Two Lots in Chesapeake Landing

    Two combined lots to build your dream home near Chesapeake!

    CLARISSA Road, 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
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    Recreational Land in Chestertown, MD
    Contact for pricing
    0.34 Acres

    Recreational Land in Chestertown, MD

    Recreational lot, potential for future public utilities.

    BUCK NECK Road, Chestertown, MD 21620
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    Residential Land in Chestertown, MD
    Contact for pricing
    0.55 Acres

    Residential Land in Chestertown, MD

    Residential land available in Chestertown, Maryland.

    BUCK NECK LANDING Road, Chestertown, MD 21620
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    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
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    Chesapeake Landing Lot Opportunity
    Contact for pricing
    0.34 Acres

    Chesapeake Landing Lot Opportunity

    Residential lot in Chestertown with water access potential.

    SHELDRAKE Drive, Chestertown, MD 21620
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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 21 Active Listings in Chestertown, MD, we suggest to view alternatives - similar 56 Off-Market properties to explore as potential leads.

    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.

    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
    125 Scheeler Rd

    125 Scheeler Rd

    VACANT COMMERCIAL LAND • 2.79 Acres
    Value Estimation by Request
    125 Scheeler Rd, Chestertown, MD 21620
    View details
    123 Philosophers Ter

    123 Philosophers Ter

    VACANT COMMERCIAL LAND • 0.20 Acres
    Value Estimation
    $500,000
    123 Philosophers Ter, Chestertown, MD 21620-1684
    View details

    Chestertown, MD Land Investment Opportunities Market Analysis

    Explore 77 land for sale in Chestertown, MD, showcased through 21 active listings 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 $5,649,999.

    Sale prices for lots in Chestertown, MD start at $6,000, averaging $269,047, and reaching up to $3,000,000 — 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 land 9
    Residential land & home lots 7
    Recreation land 5
    Hunting land 2

    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 $271.4K

    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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