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    Chestertown, MD
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    Chestertown, MD Land for Sale

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    Cleared Acreage Near Commercial Corridor
    Updated: Mar 20
    Cleared Acreage Near Commercial Corridor

    ROUND TOP ROAD, Chestertown, MD 21620

    $200,000
    5.81 AC lot
    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
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    Chestertown Land with Redevelopment Potential
    Updated: Feb 27
    Chestertown Land with Redevelopment Potential

    201 N LYNCHBURG Street, Chestertown, MD 21620

    $750,000
    0.10 AC lot
    Potential for dense affordable housing project
    Six lots included in the property
    Four vacant lots available, presenting immediate development opportunities
    Multiple potential uses for the property
    Church currently located on two of the lots
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    Recreation Land with Community Amenities
    Recreation Land with Community Amenities

    SANDPIPER Road, Chestertown, MD 21620

    Contact for pricing
    0.52 AC lot

    Wooded recreational parcel with access to community trails, a boat ramp, and marina dining.

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    C-3 Commercial Development Site
    C-3 Commercial Development Site

    515 Washington Ave, Chestertown, MD 21620

    $795,000
    1.00 AC lot

    Approximately one-acre site on MD Route 213 with C-3 zoning and utilities available for commercial development.

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    Wooded Recreational Land
    Wooded Recreational Land

    SANDY BOTTOM Road, Chestertown, MD 21620

    $49,000
    1.95 AC lot

    Wooded acreage with a partially open entrance, seasonal well, and electric service available at the road.

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    Corner Vacant Land Parcel
    Corner Vacant Land Parcel

    620 CANNON Street, Chestertown, MD 21620

    $99,999
    0.07 AC lot

    Vacant corner parcel with available water and sewer hookups and direct Rail Trail adjacency.

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    Fairlee Open Lot Opportunity
    Fairlee Open Lot Opportunity

    MAP 36 PARCEL 80 WATERTOWER Road, Chestertown, MD 21620

    $55,000
    0.70 AC lot

    0.69-acre lot near waterfront with development potential.

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    Commercial Development Site on MD
    Commercial Development Site on MD

    515 WASHINGTON Ave, Chestertown, MD 21620

    $795,000
    0.97 AC lot

    Prime commercial land suitable for retail, restaurant, or service uses.

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    Land in Chestertown, Maryland
    Land in Chestertown, Maryland

    404 SPRING Road, Chestertown, MD 21620

    Contact for pricing
    0.99 AC lot

    0.99-acre lot in Queen Anne's County, Maryland.

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    Surveyed Hunting Land Parcel
    Surveyed Hunting Land Parcel

    8886 GEORGETOWN Road, Chestertown, MD 21620

    $69,900
    4.03 AC lot

    Surveyed acreage with water and sewer allocations already paid supports recreational land planning.

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    Perc-Approved Wooded Home Site
    Perc-Approved Wooded Home Site

    1906 Pondtown Road, Chestertown, MD 21620

    $110,000
    1.93 AC lot

    Build on a wooded, perc-approved lot in Queen Anne’s County with established site suitability.

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    Picturesque 2-Acre Lot
    Picturesque 2-Acre Lot

    GEORGETOWN Road SE, Chestertown, MD 21620

    $150,000
    2.00 AC lot

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

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    LAND - CHESTERTOWN, MD
    LAND - CHESTERTOWN, MD

    CANNON Street, Chestertown, MD 21620

    $350,000
    0.22 AC lot

    Residential land & home lots · 0.22 Acres

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    Waterfront Lot in Chester River
    Waterfront Lot in Chester River

    108 LITTLE HARBOR Way, Chestertown, MD 21620

    $635,000
    0.09 AC lot

    Buildable waterfront lot with Chester River views and community amenities.

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    LAND - CHESTERTOWN, MD
    LAND - CHESTERTOWN, MD

    CANNON Street, Chestertown, MD 21620

    $450,000
    0.29 AC lot

    Residential land & home lots · 0.29 Acres

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    Wooded Land Parcel in Chestertown
    Wooded Land Parcel in Chestertown

    GEORGETOWN Road, Chestertown, MD 21620

    $90,000
    3.92 AC lot

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

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    Two-Acre Lot Near Tolchester Beach
    Two-Acre Lot Near Tolchester Beach

    GEORGETOWN Rd SE, Chestertown, MD 21620

    $150,000
    2.00 AC lot

    Picturesque two-acre lot near Tolchester Beach, ready for your dream home.

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    Secluded Wooded Lot in Chestertown
    Secluded Wooded Lot in Chestertown

    22681 WOOD YARD Lane, Chestertown, MD 21620

    Contact for pricing
    0.52 AC lot

    Half acre wooded lot, potential hunting or building site.

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    Zoned Village Development Lot
    Zoned Village Development Lot

    MAP 36 PARCEL 80 WATERTOWER Rd, Chestertown, MD 21620

    $55,000
    0.69 AC lot

    Open village-zoned lot with deeded right-of-way access, offering flexibility for housing plans buyers should verify.

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    Land For Sale Chestertown, MD
    Land For Sale Chestertown, MD

    CAULKS FIELD ROAD, Chestertown, MD 21620

    $150,000
    2.00 AC lot

    Two acre land parcel available in Chestertown, Maryland.

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    Fairlee Vacant Lot Opportunity
    Fairlee Vacant Lot Opportunity

    36 Parcel 80 Watertower Road, Chestertown, MD 21620

    $55,000
    0.69 AC lot

    0.69-acre lot in Fairlee with development potential.

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    Two Lots in Chesapeake Landing
    Two Lots in Chesapeake Landing

    CLARISSA Road, Chestertown, MD 21620

    Contact for pricing
    0.34 AC lot

    Two combined lots to build your dream home near Chesapeake!

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    Secluded Wooded Lot For Sale
    Secluded Wooded Lot For Sale

    22681 WOOD YARD Ln, Chestertown, MD 21620

    Contact for pricing
    0.50 AC lot

    Half acre wooded lot, potential hunting property.

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    Vacant Land in Chestertown, MD
    Vacant Land in Chestertown, MD

    JOHNSONTOWN Road, Chestertown, MD 21620

    Contact for pricing
    0.90 AC lot

    Vacant land at Johnsontown Rd and Willow Oak Lane.

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    Chestertown, MD Land Market Trends and Statistics

    Explore 72 land for sale in Chestertown, MD, showcased through 43 active listings on our real estate platform. These investment opportunities span a total of 5,540,854 square feet of properties for sale, with an estimated market value of $8,706,798.

    Sale prices for lots in Chestertown, MD start at $40,000, averaging $348,271, 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 property segments ranked by active listings on the market

    Residential land & home lots 20
    Commercial land 9
    Recreation land 5
    Hunting land 3
    Waterfront Land 2

    Demographics Overview

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

    High-Yield Neighborhoods for Investment

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

    Neighborhood Average Price
    21620 $96.2K

    Taxes & Financing

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

    Listings Trend

    New vs delisted commercial listings in Kent County

    New Delisted

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