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    Chestertown, MD
    Residential Income

    Chestertown, MD Residential Income Properties for Sale

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    Worton, MD Church Hill, MD Kennedyville, MD Still Pond, MD Rock Hall, MD Millington, MD Barclay, MD Centreville, MD
    Renovated Mixed-Use Property
    Updated: Jul 18
    Renovated Mixed-Use Property

    200-204 HIGH ST, Chestertown, MD 21620

    $2,300,000
    Five apartments and three storefronts at 200‑204 High Street
    Residential mix includes two 2‑bedroom units and three 1‑bedroom units
    Comprehensive renovation completed in 2022
    New electrical service, meters, wiring, plumbing, and water and septic lines
    Property tax credit extends through 2032; buyer to verify transferability
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    Mixed-Use Income Property with Retail
    Updated: May 13
    Mixed-Use Income Property with Retail

    200204 High Street, Chestertown, MD 21620

    $2,300,000
    1860‑built downtown Chestertown building with 5 apartments and 3 storefronts
    Renovated to the studs in 2022; since renovations, no vacancies reported
    Replaced major systems in 2022: new electric service, wiring, plumbing (PEX), water and septic lines, and energy‑efficient water heaters and appliances
    New windows, insulation, and air sealing; monitored fire alarm system and rebuilt foundation
    Roof work includes new rear portions roof (front 50‑year cedar roof replaced in early 2000s)
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    Historic Chestertown Multi-Family Opportunity
    Historic Chestertown Multi-Family Opportunity

    349 & 351 HIGH STREET, Chestertown, MD 21620

    $395,000
    3,664 sqft 0.13 AC lot

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

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    Turn a Listing Into an Investment Snapshot Cap Rate, Potential NOI, Demand score for every listing. Go To Analytics Center
    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 3 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

    Opportunities in Nearby Cities

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

    Duplex with Attached Garage
    Duplex with Attached Garage

    12712 and 12714 STILL POND Road, Still Pond, MD 21667

    $549,000
    4,305 sqft 0.43 AC lot

    Two-unit property featuring a sunroom, rear-yard improvements, and additional flexible space within the attached garage.

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    Duplex with Finished Garage
    Duplex with Finished Garage

    12712 AND 12714 STILL POND RD, Still Pond, MD 21667

    $549,000
    4,305 sqft

    Two-unit property with a garage apartment-style setup, sunroom, and landscaped rear gathering area.

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    Waterfront Residential Income Property
    Waterfront Residential Income Property

    130 OYSTER COVE DRIVE Unit: 130, Grasonville, MD 21638

    $749,900

    Third-floor corner residence with elevator access, three bedrooms, a private porch, and a deeded boat slip.

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    Grasonville Multifamily Property for Sale
    Grasonville Multifamily Property for Sale

    111 BEACH HARBOR F, Grasonville, MD 21638

    $70,000

    Multifamily property in Grasonville, MD, available for purchase.

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    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    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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    Commercial Land with Highway Access
    Commercial Land with Highway Access

    ROCK HALL Road, Rock Hall, MD 21661

    $1,250,000
    49.83 AC lot

    Partially cleared development land with access to a state highway and three town roads.

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    Development Opportunity on Bengies Road
    Development Opportunity on Bengies Road

    Middle River, MD 21220

    Contact for pricing
    13.82 AC lot

    13.82 acres zoned MH IM and DR 5.5.

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    Subdividable Lots in Aberdeen, MD
    Subdividable Lots in Aberdeen, MD

    HARFORD Street, Aberdeen, MD 21001

    $95,333
    0.92 AC lot

    Four subdividable lots totaling 0.92 acres with water and sewer access.

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    Chestertown, MD Residential Income Properties Market Trends and Statistics

    Explore 3 residential income properties for sale in Chestertown, MD, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 3,664 square feet of properties for sale, with an estimated market value of $4,995,000.

    Sale prices for residential income properties in Chestertown, MD start at $395,000, averaging $1,665,000, and reaching up to $2,300,000 — 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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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Multifamily properties 3
    Apartment buildings 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 $1.4M

    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

    Property Size Breakdown

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

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