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    Chestertown, MD
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    Chestertown, MD Residential Land & Home Lots for Sale

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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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    Fairlee Open Lot Opportunity
    Updated: May 22
    Fairlee Open Lot Opportunity

    MAP 36 PARCEL 80 WATERTOWER Road, Chestertown, MD 21620

    $55,000
    0.70 AC lot
    Large .69‑acre lot with potential for future development or building a dream home.
    Zoned Village, potentially allowing for a duplex or multiple dwellings.
    Convenient access to public water and sewer (buyer to verify availability and fees).
    Peaceful, private setting nestled off the main road with deeded right‑of‑way access.
    Conveniently close to local amenities, recreation, and the Eastern Shore waterfront.
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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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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    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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    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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    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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    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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    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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    Land Near Chestertown, Maryland
    Land Near Chestertown, Maryland

    OLD MORGNEC Road, Chestertown, MD 21620

    $59,000
    1.37 AC lot

    Two lots totaling 1.37 acres near Chestertown.

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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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    Chesapeake Landing Lot Opportunity
    Chesapeake Landing Lot Opportunity

    SHELDRAKE Drive, Chestertown, MD 21620

    Contact for pricing
    0.34 AC lot

    Residential lot in Chestertown with water access potential.

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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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    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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    Vacant Residential Land Parcel
    Vacant Residential Land Parcel

    206 Burchard Sawmill Road, Chestertown, MD 21620

    Contact for pricing
    1.05 AC lot

    1.05-acre vacant land parcel offered for sale in Queen Anne’s County, sold as-is with buyer to verify zoning and utilities.

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    Residential Development Land in Chestertown
    Residential Development Land in Chestertown

    CROMWELL CLARK Rd, Chestertown, MD 21620

    $3,000,000
    87.34 AC lot

    87-acre residential development land annexed into the town of Chestertown.

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    Unimproved Land
    Unimproved Land

    620 CANNON ST, Chestertown, MD 21620

    $350,000

    Residential land & home lots

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    Two Lots in Chesapeake Landing
    Two Lots in Chesapeake Landing

    CLARISSA Rd, Chestertown, MD 21620

    Contact for pricing
    0.34 AC lot

    Two combined lots to build your dream home!

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    Cleared Residential Building Lot
    Cleared Residential Building Lot

    305 Roosevelt Drive, Chestertown, MD 21620

    $60,000

    Cleared lot in an established community with public water and sewer available.

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    Corner Lot Near Chester River
    Corner Lot Near Chester River

    EAST St, Chestertown, MD 21620

    $88,900
    0.48 AC lot

    Build your dream home minutes from Downtown Chestertown.

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    Residential Development Land Parcel
    Residential Development Land Parcel

    327 Pine Tree Rd, Chestertown, MD 21620

    Contact for pricing

    8.27± acres in Queen Anne’s County with one approved building site and two additional perc tests pending.

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    Based on your search, we've compiled Potential Opportunities for your consideration. Besides 21 Active Listings in Chestertown, MD

    Chestertown, MD Residential Land & Home Lots Market Trends and Statistics

    Explore 21 residential land & home lots for sale in Chestertown, MD, showcased through 21 active listings on our real estate platform. These investment opportunities span a total of 4,525,466 square feet of properties for sale, with an estimated market value of $6,407,900.

    Sale prices for home sites in Chestertown, MD start at $55,000, averaging $400,493, 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 $157.7K

    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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    • 21620

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