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Chestertown, MD

Retail

Chestertown, MD Retail Properties & Spaces for Sale

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Worton, MD Church Hill, MD Still Pond, MD Rock Hall, MD Millington, MD Betterton, MD Sudlersville, MD Centreville, MD

Mixed-Use Income Property with Retail

Updated: Jul 10

Mixed-Use Income Property with Retail

200204 High Street, Chestertown, MD 21620

$2,300,000

1860‑built downtown Chestertown building with 5 apartments and 3 storefronts
Renovated to the studs in 2022; since renovations, no vacancies reported
Replaced major systems in 2022: new electric service, wiring, plumbing (PEX), water and septic lines, and energy‑efficient water heaters and appliances
New windows, insulation, and air sealing; monitored fire alarm system and rebuilt foundation
Roof work includes new rear portions roof (front 50‑year cedar roof replaced in early 2000s)

Turn Any Listing Into an Investment Snapshot Owner equity, real caprate, demand score for every listing. Go To Analytics Center

Based on your search, we've compiled 80 Potential Opportunities for your consideration. Besides 1 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 71 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.

Pulaski Highway Commercial Property

Pulaski Highway Commercial Property

9914, 9920, 9922 Pulaski Highway, Middle River, MD 21220

$2,800,000

10,000 sqft 2.00 AC lot

10,000 SF building space with renovated garage and warehouse.

Commercial Building in Rock Hall

Commercial Building in Rock Hall

21435 ROCK HALL Ave, Rock Hall, MD 21661

$300,000

0.36 AC lot

Commercial building suitable for office, retail, or studio space.

Retail Space

Retail Space

2919 Eastern Blvd, Middle River, MD 21220

Contact for pricing

2,592 sqft

Retail space offered for sale with 2,592 SF of available area.

Mixed-Use Commercial Property

Mixed-Use Commercial Property

6262 Rock Hall Road, Rock Hall, MD 21661

Contact for pricing

Commercially zoned property with multiple permitted uses and convenient highway access plus on-site parking.

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 Lot in Downtown Chestertown

Commercial Lot in Downtown Chestertown

116 CROSS St, Chestertown, MD 21620

$109,999

Downtown commercial lot with development potential near established businesses.

50 Acres Mixed-Use Development Land

50 Acres Mixed-Use Development Land

ROCK HALL Road, Rock Hall, MD 21661

$1,250,000

49.83 AC lot

50 acres in Rock Hall, MD, ideal for mixed-use development.

Waterfront Land in Rock Hall

Waterfront Land in Rock Hall

21190 GREEN Ln, Rock Hall, MD 21661

$850,000

10.40 AC lot

Two adjoining parcels with waterfront and commercial zoning.

Prime Development Land in Galena

Prime Development Land in Galena

CARROLL CLARK Road lot: 1, Galena, MD 21635

$1,250,000

86.00 AC lot

86 acre development land in Kent County's Rt. 301 Growth Corridor.

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.

176 Flatland Rd

CONVENIENCE STORE

176 Flatland Rd, Chestertown, MD 21620-3363

$800,000

Estimated value

3,476 sqft 0.62 AC lot

Lndg Ln, Unit 26

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 26

$1,100,000

Estimated value

0.01 AC lot

1 Little Hbr Way

RESIDENTIAL PARKING GARAGE

1 Little Hbr Way, Chestertown, MD 21620

Value Estimation by Request

0.01 AC lot

Lndg Ln, Unit 33

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 33

Value Estimation by Request

0.01 AC lot

903 Washington Ave

RESTAURANT

903 Washington Ave, Chestertown, MD 21620-3331

$525,000

Estimated value

3,528 sqft 0.92 AC lot

RESIDENTIAL PARKING GARAGE

9 Lndg Ln, Chestertown, MD 21620

$795,000

Estimated value

0.01 AC lot

504 Washington Ave

RETAIL STORES (PERSONAL SERVICES)

504 Washington Ave, Chestertown, MD 21620-1239

Value Estimation by Request

828 sqft 0.85 AC lot

AUTO REPAIR, GARAGE

824 High St, Chestertown, MD 21620-1135

Value Estimation by Request

4,135 sqft 0.50 AC lot

7306 Church Hl Rd

RETAIL STORES (PERSONAL SERVICES)

7306 Church Hl Rd, Chestertown, MD 21620-2806

Value Estimation by Request

2,484 sqft 0.75 AC lot

RESIDENTIAL PARKING GARAGE

209 Lndg Ln, Chestertown, MD 21620-4720

$535,000

Estimated value

0.01 AC lot

Lndg Ln, Unit 34

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 34

Value Estimation by Request

0.01 AC lot

Lndg Ln, Unit 13

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 13

$545,000

Estimated value

0.01 AC lot

200 Scheeler Rd

GYM, HEALTH SPA

200 Scheeler Rd, Chestertown, MD 21620-1034

Value Estimation by Request

57,976 sqft 4.83 AC lot

RESTAURANT

834 High St, Chestertown, MD 21620-1135

Value Estimation by Request

2,376 sqft 0.37 AC lot

RETAIL STORES (PERSONAL SERVICES)

315 High St, Chestertown, MD 21620-1326

$1,900,000

Estimated value

8,932 sqft 0.49 AC lot

RETAIL STORES (PERSONAL SERVICES)

206 Cannon St, Chestertown, MD 21620

$895,000

Estimated value

1,588 sqft 1.56 AC lot

SERVICE STATION (FULL SERVICE)

609 High St, Chestertown, MD 21620-1113

$500,000

Estimated value

2,665 sqft 0.43 AC lot

851 Washington Ave

MINI-MALL

851 Washington Ave, Chestertown, MD 21620

$11,850,000

Estimated value

53,811 sqft 11.25 AC lot

891 Washington Ave

MINI-MALL

891 Washington Ave, Chestertown, MD 21620

$11,850,000

Estimated value

43,200 sqft 5.99 AC lot

RESTAURANT

229 High St, Chestertown, MD 21620

$1,020,000

Estimated value

3,862 sqft 0.21 AC lot

211 Lndg Ln, Unit 32

RESIDENTIAL PARKING GARAGE

211 Lndg Ln, Chestertown, MD 21620-4720

Unit 32

Value Estimation by Request

0.01 AC lot

611 Washington Ave

FINANCIAL BUILDING

611 Washington Ave, Chestertown, MD 21620-1219

Value Estimation by Request

1,908 sqft 0.35 AC lot

801 Washington Ave

FINANCIAL BUILDING

801 Washington Ave, Chestertown, MD 21620-1003

Value Estimation by Request

3,168 sqft 0.78 AC lot

Chestertown, MD Retail Properties & Spaces Market Trends and Statistics

Explore 72 retail properties & spaces for sale in Chestertown, MD on our real estate platform.

Sale prices for stores in Chestertown, MD average $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

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	$2.3M

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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