Chestertown, MD Commercial Real Estate for Sale

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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: Sep 26, 2025

Land in Chestertown, Maryland

404 SPRING Road, Chestertown, MD 21620

Contact for pricing

0.99 AC lot

Large 0.99‑acre lot provides ample space.
Located in Queen Anne's County.
Blank canvas for customization and development.
Potential for outdoor activities.
Opportunity for future expansion.

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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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Church Building with On-Site Parking

201 N LYNCHBURG STREET, Chestertown, MD 21620

$500,000

2,045 sqft

Church building with wheelchair accessibility and on-site parking, offered with additional parcels separately or together.

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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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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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Medical Office Park Buildings

120 Speer Rd, Chestertown, MD 21620

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9,604 sqft

Two single-story medical office buildings in a three-unit park, offering former medical layouts with exam rooms and x-ray spaces.

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Office Suite with Common Area

903 WASHINGTON AVENUE #4, Chestertown, MD 21620

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1,233 sqft

Office suite offers a large common space, three private offices, a conference room, and a kitchen and bath break area.

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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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Industrial Flex Building with Radiant Heat

25416 Commerce Ln, Chestertown, MD 21620

$1,100,000

Industrial flex building with radiant floor heating, offices and shop space, and tractor-trailer access.

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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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Rail Trail Commercial Land

620 CANNON St, Chestertown, MD 21620

$99,999

Vacant corner parcel with available water and sewer hookups near downtown Chestertown.

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Restaurant Building with Conversion Potential

903 Washington Avenue, Chestertown, MD 21620

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Restaurant building with an existing layout suited for a new branded restaurant and possible renovation for medical tenants.

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Turnkey Bed and Breakfast Inn

25227 Chestertown Road, Chestertown, MD 21620

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20.00 AC lot

Turnkey Brampton Bed and Breakfast includes parking and a restored 1860 manor with 13 ensuite lodgings.

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Based on your search, we've compiled 76 Potential Opportunities for your consideration. Besides 15 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 57 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.

Specialty Property in Church Hill

530 KENNERSLEY FARM Ln, Church Hill, MD 21623

$949,500

5.00 AC lot

Specialty property available for sale in Church Hill, Maryland.

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Zoned B-2 Development Land

Lots 18,19,20,21 Main St, Church Hill, MD 21623

Contact for pricing

2.00 AC lot

Four lots totaling about 2 acres are zoned B-2, with paved parking, curbs, and utilities already on site.

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Worton Specialty Property for Sale

0 will be 11037 BOTTOM Rd, Worton, MD 21678

$305,000

0.43 AC lot

Specialty property available for sale in Worton, Maryland.

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Kent County Land Opportunity

25034 LAMBS MEADOW Road, Worton, MD 21678

Contact for pricing

0.11 AC lot

0.11-acre lot in Kent County, 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

View details

COMMERCIAL (GENERAL)

846 High St, Chestertown, MD 21620-1135

$530,000

Estimated value

522 sqft 0.18 AC lot

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OFFICE BUILDING

301 Morgnec Rd, Chestertown, MD 21620-1025

$445,000

Estimated value

4,100 sqft 0.70 AC lot

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OFFICE BUILDING

830 High St, Chestertown, MD 21620-1135

$430,000

Estimated value

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

View details

Chestertown, MD Commercial Real Estate Market Trends and Statistics

Explore 72 commercial real estate for sale in Chestertown, MD, showcased through 15 active listings on our real estate platform. These investment opportunities span a total of 17,682 square feet of properties for sale, with an estimated market value of $7,879,999.

Sale prices for business properties in Chestertown, MD start at $40,000, averaging $787,999, 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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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	$645K

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

404 SPRING Road, Chestertown, MD 21620

MONTGOMERY AVENUE, Chestertown, MD 21620

201 N LYNCHBURG STREET, Chestertown, MD 21620

201 N LYNCHBURG St, Chestertown, MD 21620

327 CANNON St, Chestertown, MD 21620

515 Washington Ave, Chestertown, MD 21620

120 Speer Rd, Chestertown, MD 21620

903 WASHINGTON AVENUE #4, Chestertown, MD 21620

515 WASHINGTON Ave, Chestertown, MD 21620

25416 Commerce Ln, Chestertown, MD 21620

200204 High Street, Chestertown, MD 21620

620 CANNON St, Chestertown, MD 21620

903 Washington Avenue, Chestertown, MD 21620

25227 Chestertown Road, Chestertown, MD 21620

Opportunities in Nearby Cities

530 KENNERSLEY FARM Ln, Church Hill, MD 21623

Lots 18,19,20,21 Main St, Church Hill, MD 21623

0 will be 11037 BOTTOM Rd, Worton, MD 21678

25034 LAMBS MEADOW Road, 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

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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