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Chestertown, MD

Mixed-Use

Chestertown, MD Mixed-use Properties for Sale

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Worton, MD Church Hill, MD Kennedyville, MD Still Pond, MD Rock Hall, MD Crumpton, MD Millington, MD Barclay, MD

Historic Chestertown Mixed-Use Property

Updated: Nov 7, 2025

Historic Chestertown Mixed-Use Property

327 Cannon Street, Chestertown, MD 21620

$1,300,000

1,300 sqft

Mixed‑use property in historic Chestertown offers both commercial and residential income potential.
First level features a fully equipped 1300 sq ft commercial kitchen and dining area, currently leased to Occasions Catering.
Spacious upstairs apartment includes two bedrooms, each with an ensuite full bathroom.
Apartment boasts an open living space with vaulted ceilings, hardwood floors, a gas fireplace, and ample natural light.
Newly constructed in 2006, providing modern amenities and reduced maintenance in a historic setting.

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

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 80 Potential Opportunities for your consideration. Besides 2 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 70 Off-Market properties to explore as potential leads, 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.

Mixed-Use Restaurant With Inn Rooms

Mixed-Use Restaurant With Inn Rooms

20658 WILKINS AVENUE, Rock Hall, MD 21661

$1,500,000

4,026 sqft

Renovated restaurant property combines dining, bar, outdoor service areas, and unused second-floor lodging space.

Mixed-Use Property with Retail

Mixed-Use Property with Retail

4300 MAIN STREET, Grasonville, MD 21638

$459,000

2,304 sqft

Two-level configuration pairs an occupied retail storefront with a vacant, recently renovated apartment and supporting service areas.

Historic Mixed-Use Building

Historic Mixed-Use Building

5742 +5746 N Main Street, Rock Hall, MD 21661

$575,000

2,880 sqft

Two connected buildings combine leased retail and residential space in Rock Hall’s Central Business District.

UC-Zoned Mixed-Use Property

UC-Zoned Mixed-Use Property

232 Evans Ave, Grasonville, MD 21638

Contact for pricing

UC-zoned property with prior retail and service use, front parking, and a mobile home included in the sale.

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.

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.

7.68 Acres on Dupont Highway

7.68 Acres on Dupont Highway

4391 DUPONT Pkwy, Townsend, DE 19734

$184,900

7.68 AC lot

7.68 acres with road frontage and commercial zoning.

Easton Land Parcel For Sale

Easton Land Parcel For Sale

402 Brookletts Avenue, Easton, MD 21601

$1,750,000

Land parcel in Easton, zoned BC with residential use.

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.

7404 Church Hl Rd

OFFICE/RESIDENTIAL (MIXED USE)

7404 Church Hl Rd, Chestertown, MD 21620-2808

$185,000

Estimated value

1,224 sqft 0.20 AC lot

22532 Tolchester Bch Rd

OFFICE/RESIDENTIAL (MIXED USE)

22532 Tolchester Bch Rd, Chestertown, MD 21620-4259

$75,000

Estimated value

1,248 sqft 0.59 AC lot

124 Hambleton Crk Ln

OFFICE/RESIDENTIAL (MIXED USE)

124 Hambleton Crk Ln, Chestertown, MD 21620-1441

$355,000

Estimated value

2,340 sqft 1.25 AC lot

2607 Mcginnes Rd

OFFICE/RESIDENTIAL (MIXED USE)

2607 Mcginnes Rd, Chestertown, MD 21620-2365

$300,000

Estimated value

1,216 sqft 0.95 AC lot

306 Cannon St

OFFICE/RESIDENTIAL (MIXED USE)

306 Cannon St, Chestertown, MD 21620-1379

$515,000

Estimated value

2,400 sqft 0.10 AC lot

7326 Church Hl Rd

OFFICE/RESIDENTIAL (MIXED USE)

7326 Church Hl Rd, Chestertown, MD 21620

$240,000

Estimated value

1,602 sqft 0.26 AC lot

324 Cannon St

OFFICE/RESIDENTIAL (MIXED USE)

324 Cannon St, Chestertown, MD 21620-1328

$280,000

Estimated value

2,048 sqft 0.11 AC lot

108 Fey Rd

OFFICE/RESIDENTIAL (MIXED USE)

108 Fey Rd, Chestertown, MD 21620-2119

$435,000

Estimated value

1,596 sqft 1.00 AC lot

329 Cannon St

OFFICE/RESIDENTIAL (MIXED USE)

329 Cannon St, Chestertown, MD 21620-1319

$475,000

Estimated value

2,566 sqft 0.06 AC lot

21085 Tolchester Bch Rd

OFFICE/RESIDENTIAL (MIXED USE)

21085 Tolchester Bch Rd, Chestertown, MD 21620-4230

$845,000

Estimated value

4,976 sqft 80.09 AC lot

111 Spg Ave

OFFICE/RESIDENTIAL (MIXED USE)

111 Spg Ave, Chestertown, MD 21620-1342

$270,000

Estimated value

2,070 sqft 0.18 AC lot

2010 Mcginnes Rd

OFFICE/RESIDENTIAL (MIXED USE)

2010 Mcginnes Rd, Chestertown, MD 21620-2352

$310,000

Estimated value

1,253 sqft 2.08 AC lot

518 Morgnec Rd

OFFICE/RESIDENTIAL (MIXED USE)

518 Morgnec Rd, Chestertown, MD 21620-3100

$700,000

Estimated value

3,484 sqft 4.04 AC lot

7312 Church Hl Rd

OFFICE/RESIDENTIAL (MIXED USE)

7312 Church Hl Rd, Chestertown, MD 21620-2806

$85,000

Estimated value

1,116 sqft 0.34 AC lot

355 High St

OFFICE/RESIDENTIAL (MIXED USE)

355 High St, Chestertown, MD 21620-1309

$205,000

Estimated value

2,731 sqft 0.08 AC lot

312 Park Row

OFFICE/RESIDENTIAL (MIXED USE)

312 Park Row, Chestertown, MD 21620-1550

$330,000

Estimated value

3,608 sqft 0.08 AC lot

113 Spg Ave

OFFICE/RESIDENTIAL (MIXED USE)

113 Spg Ave, Chestertown, MD 21620-1358

$215,000

Estimated value

2,394 sqft 0.15 AC lot

241 High St

OFFICE/RESIDENTIAL (MIXED USE)

241 High St, Chestertown, MD 21620-1559

$420,000

Estimated value

5,148 sqft 0.12 AC lot

321 High St

OFFICE/RESIDENTIAL (MIXED USE)

321 High St, Chestertown, MD 21620-1373

$385,000

Estimated value

3,556 sqft 0.09 AC lot

200 High St

OFFICE/RESIDENTIAL (MIXED USE)

200 High St, Chestertown, MD 21620-1586

$580,000

Estimated value

6,918 sqft 0.14 AC lot

910 Washington Ave

OFFICE/RESIDENTIAL (MIXED USE)

910 Washington Ave, Chestertown, MD 21620-1047

$225,000

Estimated value

1,806 sqft 0.52 AC lot

7316 Church Hl Rd

OFFICE/RESIDENTIAL (MIXED USE)

7316 Church Hl Rd, Chestertown, MD 21620-2806

$230,000

Estimated value

1,348 sqft 0.26 AC lot

Chestertown, MD Mixed-Use Properties Market Trends and Statistics

Explore 72 mixed-use properties for sale in Chestertown, MD on our real estate platform. These investment opportunities span a total of 1,300 square feet of properties for sale, with an estimated market value of $3,600,000.

Sale prices for multi use buildings in Chestertown, MD start at $1,300,000, averaging $1,800,000, 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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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	$1.8M

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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