Chestertown, MD Commercial Real Estate for Sale

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Worton, MD Church Hill, MD Kennedyville, MD

8 properties

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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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Updated: May 18

Unimproved Village Zoning Land

23683 L Road, Chestertown, MD 21620

Contact for pricing

0.69 AC lot

0.69+/- acres of unimproved land in Chestertown, Kent County
Zoned Village (V) district, intended for small historic/traditional rural villages
Village (V) zoning allows a mix of residential uses, mostly single‑family with limited multi‑family
Village (V) zoning also allows low‑intensity commercial uses such as small shops, offices, or services
Online auction runs Saturday, July 4 through Thursday, July 9, 2026 at 2:30 PM

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Chestertown Church and Additional Parcels

201 N LYNCHBURG St, Chestertown, MD 21620

$750,000

3,500 sqft

Church and additional parcels in the heart of Chestertown.

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Historic Chestertown Mixed-Use Property

327 CANNON St, Chestertown, MD 21620

$1,300,000

1,300 sqft

Mixed-use property with commercial kitchen and residential apartment in Chestertown.

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Commercial Lot in Downtown Chestertown

116 CROSS St, Chestertown, MD 21620

$109,999

Downtown commercial lot with development potential near established businesses.

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Land in Chestertown, Maryland

404 SPRING Road, Chestertown, MD 21620

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0.99 AC lot

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

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Unimproved Land in Chestertown

23683 L Rd, Chestertown, MD 21620

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0.69 AC lot

0.69 acre of unimproved land in Kent County, Maryland.

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Land in Chestertown, Maryland

MONTGOMERY AVENUE, Chestertown, MD 21620

$40,000

0.11 AC lot

Commercial land available for sale in Chestertown, Maryland.

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Based on your search, we've compiled 76 Potential Opportunities for your consideration. Besides 8 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 64 Off-Market properties to explore as potential leads

Opportunities in Nearby Cities

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

Live-Work Duplex with Rental Potential

11955 AUGUSTINE HERMAN Highway, Kennedyville, MD 21645

$339,000

2,236 sqft · 0.18 AC lot

Move-in-ready duplex offering flexible live-work or multi-unit income, with fenced parking for up to six vehicles.

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Partially Wooded Village-Zoned Land

LAMBS MEADOW Road, Worton, MD 21678

$49,000

1.09 AC lot

Over an acre in a Village zoning district with confirmed utility hookup allocation, supporting a range of residential and limited commercial uses.

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Live-Work Duplex with Private Entrances

11955 Augustine Herman Highway, Kennedyville, MD 21645

$339,000

2,236 sqft

Flexible two-unit home offers live-work capability with potential storefront space and on-site parking for up to six vehicles.

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Worton Specialty Property for Sale

0 will be 11037 BOTTOM Rd, Worton, MD 21678

$310,000

0.43 AC lot

Specialty property available for sale in Worton, Maryland.

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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.

CONVENIENCE STORE

176 Flatland Rd, Chestertown, MD 21620-3363

$800,000

Estimated value

3,476 sqft · 0.62 AC lot

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MEDICAL BUILDING

120 Speer Rd, Chestertown, MD 21620-1044

$1,100,000

Estimated value

4,201 sqft · 1.21 AC lot

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COMMERCIAL (GENERAL)

846 High St, Chestertown, MD 21620-1135

$685,000

Estimated value

522 sqft · 0.18 AC lot

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OFFICE BUILDING

301 Morgnec Rd, Chestertown, MD 21620-1025

Value Estimation by Request

4,100 sqft · 0.70 AC lot

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OFFICE BUILDING

830 High St, Chestertown, MD 21620-1135

Value Estimation by Request

2,204 sqft · 0.51 AC lot

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RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 26

$1,100,000

Estimated value

0.01 AC lot

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RESIDENTIAL PARKING GARAGE

1 Little Hbr Way, Chestertown, MD 21620

Value Estimation by Request

0.01 AC lot

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RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 33

Value Estimation by Request

0.01 AC lot

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RESTAURANT

903 Washington Ave, Chestertown, MD 21620-3331

$525,000

Estimated value

3,528 sqft · 0.92 AC lot

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RESIDENTIAL PARKING GARAGE

9 Lndg Ln, Chestertown, MD 21620

$795,000

Estimated value

0.01 AC lot

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OFFICE BUILDING

110 Queen St, Chestertown, MD 21620-1522

Value Estimation by Request

778 sqft · 0.14 AC lot

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VACANT COMMERCIAL LAND

502 Washington Ave, Chestertown, MD 21620-1239

Value Estimation by Request

0.22 AC lot

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RETAIL STORES (PERSONAL SERVICES)

504 Washington Ave, Chestertown, MD 21620-1239

Value Estimation by Request

828 sqft · 0.85 AC lot

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AUTO REPAIR, GARAGE

824 High St, Chestertown, MD 21620-1135

Value Estimation by Request

4,135 sqft · 0.50 AC lot

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OFFICE/RESIDENTIAL (MIXED USE)

7404 Church Hl Rd, Chestertown, MD 21620-2808

Value Estimation by Request

1,224 sqft · 0.20 AC lot

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OFFICE/RESIDENTIAL (MIXED USE)

22532 Tolchester Bch Rd, Chestertown, MD 21620-4259

Value Estimation by Request

1,248 sqft · 0.59 AC lot

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Chestertown, MD Commercial Real Estate Market Trends and Statistics

Explore 72 commercial real estate for sale in Chestertown, MD, showcased through 8 active listings on our real estate platform. These investment opportunities span a total of 4,800 square feet of properties for sale, with an estimated market value of $2,095,000.

Sale prices for business properties in Chestertown, MD start at $795,000, averaging $1,047,500, and reaching up to $1,300,000 — 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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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	$589.5K

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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Chestertown, MD Commercial Real Estate for Sale

ROUND TOP ROAD, Chestertown, MD 21620

23683 L Road, Chestertown, MD 21620

201 N LYNCHBURG St, Chestertown, MD 21620

327 CANNON St, Chestertown, MD 21620

116 CROSS St, Chestertown, MD 21620

404 SPRING Road, Chestertown, MD 21620

23683 L Rd, Chestertown, MD 21620

MONTGOMERY AVENUE, Chestertown, MD 21620

Opportunities in Nearby Cities

11955 AUGUSTINE HERMAN Highway, Kennedyville, MD 21645

LAMBS MEADOW Road, Worton, MD 21678

11955 Augustine Herman Highway, Kennedyville, MD 21645

0 will be 11037 BOTTOM Rd, Worton, MD 21678

Off-Market Properties in Chestertown, MD

176 Flatland Rd, Chestertown, MD 21620-3363

120 Speer Rd, Chestertown, MD 21620-1044

846 High St, Chestertown, MD 21620-1135

301 Morgnec Rd, Chestertown, MD 21620-1025

830 High St, Chestertown, MD 21620-1135

Lndg Ln, Chestertown, MD 21620

1 Little Hbr Way, Chestertown, MD 21620

Lndg Ln, Chestertown, MD 21620

903 Washington Ave, Chestertown, MD 21620-3331

9 Lndg Ln, Chestertown, MD 21620

110 Queen St, Chestertown, MD 21620-1522

502 Washington Ave, Chestertown, MD 21620-1239

504 Washington Ave, Chestertown, MD 21620-1239

824 High St, Chestertown, MD 21620-1135

7404 Church Hl Rd, Chestertown, MD 21620-2808

22532 Tolchester Bch Rd, Chestertown, MD 21620-4259

Chestertown, MD Commercial Real Estate Market Trends and Statistics

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

Listings Trend

Property Size Breakdown

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