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    Chestertown, MD
    Residential Income

    Chestertown, MD Residential Income Properties for Sale

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    Worton, MD Millington, MD Kennedyville, MD Still Pond, MD Church Hill, MD Rock Hall, MD Centreville, MD Barclay, MD
    Triplex with Updated Unit Interiors
    Updated: Oct 26
    Triplex with Updated Unit Interiors

    501 HIGH STREET, Chestertown, MD 21620

    $349,900
    2,008 sqft
    Three occupied residential units
    2,008 square feet; built in 1900
    Hardwood floors in the units
    Mini‑split systems in units 1 and 2
    Unit 3 has a new bathroom
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    2-Bedroom Waterfront Condominium
    Updated: Sep 24
    2-Bedroom Waterfront Condominium

    105 N WATER STREET Unit: 3, Chestertown, MD 21620

    $459,000
    1,098 sqft
    1,098‑square‑foot residence with 2 bedrooms and 2 full baths
    Private boat slip at the end of the dock
    Patio with views of the Chester River
    Built in 1900
    Located in historic Chestertown
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    Renovated Mixed-Use Property
    Renovated Mixed-Use Property

    200-204 HIGH ST, Chestertown, MD 21620

    $2,300,000

    Downtown asset combines apartments with leased storefront space.

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    Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads
    Mixed-Use Income Property with Retail
    Mixed-Use Income Property with Retail

    200204 High Street, Chestertown, MD 21620

    $2,300,000

    Turnkey building features five apartments and three storefronts, fully renovated in 2022 and currently occupied.

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    4 active listings match your search: Residential Income for sale in Chestertown, MD. Based on your search, we've also compiled 8 Potential Opportunities for your consideration: 4 properties in nearby cities and 4 land listings with development potential.

    Opportunities in Nearby Cities

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

    Waterfront Residential Income Property
    Waterfront Residential Income Property

    116 OYSTER COVE DRIVE Unit: 1D, Grasonville, MD 21638

    $579,900
    1,651 sqft

    The single-level residence has three bedrooms, two full bathrooms, and a deck overlooking the water.

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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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    Top-Floor Penthouse Residence
    Top-Floor Penthouse Residence

    111 MARSHGRASS WAY #43, Chester, MD 21619

    $744,900

    Open-plan living areas, upgraded finishes and community recreation amenities shape this Chester River-view home.

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    Waterfront Residential Income Property
    Waterfront Residential Income Property

    111 MARSHGRASS WAY #41, Chester, MD 21619

    $998,000

    Fourth-floor penthouse condominium with bay views, extensive custom finishes, resort amenities, and dedicated garage storage.

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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.

    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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    Pasadena Land Parcel for Sale
    Pasadena Land Parcel for Sale

    MARYLAND Avenue, Pasadena, MD 21122

    $289,900
    2.57 AC lot

    2.57 acre lot in Boulevard Park neighborhood, Pasadena, MD.

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    Chestertown, MD Residential Income Properties Market Trends and Statistics

    Explore 4 residential income properties for sale in Chestertown, MD, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 3,106 square feet of properties for sale, with an estimated market value of $5,408,900.

    Sale prices for residential investment properties in Chestertown, MD start at $349,900, averaging $1,352,225, 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
    Triplexes 1

    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 $1.2M

    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%

    Property Size Breakdown

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

    How Realmo verifies these figures

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    Popular Searches in Chestertown, MD

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    Most Searched ZIP Codes in Chestertown, MD

    • 21620

    Featured Chestertown Real Estate Agencies

    Realmo connects you with licensed Chestertown CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Doug Ashley REALTORS, LLC
    227 1/2 HIGH ST Chestertown, MD 21620
    Phone: (410) 810-0010
    www.dougashleyrealtors.com
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