Chestertown, MD Commercial Real Estate for Sale

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Updated: Sep 28

Mixed-Use Ranch-Style Property

896 WASHINGTON Avenue, Chestertown, MD 21620

$325,000

0.34 AC lot

Residential and commercial zoning
Fully finished basement
0.3444‑acre lot on Washington Avenue in Chestertown
Built in 1965; vinyl siding
Heat pump and central air conditioning

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Updated: Mar 20

Cleared Commercial Land

ROUND TOP ROAD, Chestertown, MD 21620

$200,000

5.81 AC lot

5.81 acres of cleared, level commercial land
Suburban Commercial zoning
Located on Round Top Road in Chestertown, MD 21620
Just off a commercial corridor
A few minutes from Downtown Chestertown

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Land, CHESTERTOWN, MD

300 and 302 S MILL Street, Chestertown, MD 21620

$1,195,000

0.46 AC lot

Residential land & home lots · 0.46 Acres

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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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Land in Chestertown, Maryland

404 SPRING Road, Chestertown, MD 21620

Contact for pricing

0.99 AC lot

0.99-acre lot in Queen Anne's 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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Historic Chestertown Mixed-Use Property

327 CANNON STREET, Chestertown, MD 21620

$1,300,000

1,300 sqft

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

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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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Mixed-Use Property with Finished Basement

896 Washington Ave, Chestertown, MD 21620

$325,000

2,000 sqft

Residential and commercial zoning supports a range of property uses.

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Office Suite with Common Area

903 WASHINGTON AVENUE #4, Chestertown, MD 21620

Contact for pricing

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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Medical Office Park Buildings

120 Speer Rd, Chestertown, MD 21620

Contact for pricing

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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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 LANE, 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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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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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 STREET, Chestertown, MD 21620

$85,000

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

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Based on your search, we've compiled 76 Potential Opportunities for your consideration. Besides 16 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 56 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.

Rock Hall Agricultural Property

22537 Shipyard Ln, Rock Hall, MD 21661

$2,950,000

113 sqft

3200 sqft farm property for sale in Rock Hall.

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Waterfront Farm with Tillable Land

22537 Shipyard Ln, Rock Hall, MD 21661

$2,950,000

113.00 AC lot

Agricultural tract with creek shoreline, a residence, shop, woodland, and private dock access.

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Industrial Workshop and Warehouse

26566 LAMBS MEADOW ROAD, Worton, MD 21678

$2,475,000

Industrial workshop and warehouse facility with multiple rolling doors, insulated walls, and a large farm equipment storage space.

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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

Estimated value:

$800,000

3,476 sqft 0.62 AC lot

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MEDICAL BUILDING

120 Speer Rd, Chestertown, MD 21620-1044

Estimated value:

$1,100,000

4,201 sqft 1.21 AC lot

View details

COMMERCIAL (GENERAL)

846 High St, Chestertown, MD 21620-1135

Estimated value:

$530,000

522 sqft 0.18 AC lot

View details

OFFICE BUILDING

301 Morgnec Rd, Chestertown, MD 21620-1025

Estimated value:

$445,000

4,100 sqft 0.70 AC lot

View details

OFFICE BUILDING

830 High St, Chestertown, MD 21620-1135

Estimated value:

$430,000

2,204 sqft 0.51 AC lot

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RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 26

Estimated value:

$1,100,000

0.01 AC lot

View details

RESIDENTIAL PARKING GARAGE

1 Little Hbr Way, Chestertown, MD 21620

Estimated value: by Request

0.01 AC lot

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RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 33

Estimated value: by Request

0.01 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 16 active listings on our real estate platform. These investment opportunities span a total of 19,682 square feet of properties for sale, with an estimated market value of $11,215,000.

Sale prices for business properties in Chestertown, MD start at $40,000, averaging $862,692, 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.

Chestertown, MD CRE market trends — vacancy, lease rates and price per SF, updated monthly

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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	$777.9K

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

896 WASHINGTON Avenue, Chestertown, MD 21620

ROUND TOP ROAD, Chestertown, MD 21620

300 and 302 S MILL Street, Chestertown, MD 21620

201 N LYNCHBURG STREET, Chestertown, MD 21620

404 SPRING Road, Chestertown, MD 21620

MONTGOMERY AVENUE, Chestertown, MD 21620

327 CANNON STREET, Chestertown, MD 21620

201 N LYNCHBURG St, Chestertown, MD 21620

896 Washington Ave, Chestertown, MD 21620

903 WASHINGTON AVENUE #4, Chestertown, MD 21620

120 Speer Rd, Chestertown, MD 21620

515 WASHINGTON Ave, Chestertown, MD 21620

25416 COMMERCE LANE, Chestertown, MD 21620

200-204 HIGH ST, Chestertown, MD 21620

200204 High Street, Chestertown, MD 21620

620 CANNON STREET, Chestertown, MD 21620

Opportunities in Nearby Cities

22537 Shipyard Ln, Rock Hall, MD 21661

22537 Shipyard Ln, Rock Hall, MD 21661

26566 LAMBS MEADOW ROAD, 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

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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