Chestertown, MD Retail Properties & Spaces for Sale

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Worton, MD Church Hill, MD Kennedyville, MD

$2,300,000

Turnkey Investment Property in Chestertown

200 HIGH St, Chestertown, MD 21620

Profitable mixed-use property with apartments and storefronts in downtown Chestertown.

Turnkey, profitable investment property with no vacancies since 2022 renovation.
Solid leases in place for 5 apartments and 3 storefronts in downtown Chestertown.
Generous property tax credit through 2032 (buyer to verify transferability).
Complete renovation to the studs in 2022 with new electric, plumbing, water heaters, appliances, foundation, windows, insulation, roof (rear), water/sewer lines, and rear egress.
Two storefronts rented to a local arts non‑profit with a yoga/pilates studio moving into the third.

Updated: Apr 24

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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.

$325,000

0.19 Acres

Commercial Property in Rock Hall

Commercial property in the heart of Rock Hall, Maryland.

21279 W SHARP Street, Rock Hall, MD 21661

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Rock Hall Commercial Property Opportunity

$325,000

0.19 Acres

Rock Hall Commercial Property Opportunity

Commercial property in Rock Hall, MD, suitable for retail.

21279 W SHARP St, Rock Hall, MD 21661

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$350,000

0.91 Acres

Prime Commercial Land For Sale

0.91-acre commercial land with high visibility and traffic.

2707 PULASKI Hwy, Edgewood, MD 21040

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Retail Space in Edgewood, Maryland

Proposed retail development with frontage on Edgewood Road.

505-511 Edgewood Road, Edgewood, MD 21040

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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.

$109,999

Commercial Lot in Downtown Chestertown

Downtown commercial lot with development potential near established businesses.

116 CROSS St, Chestertown, MD 21620

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0.69 Acres

Unimproved Land in Chestertown

0.69 acre of unimproved land in Kent County, Maryland.

23683 L Rd, Chestertown, MD 21620

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$1,250,000

49.83 Acres

50 Acres Mixed-Use Development Land

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

ROCK HALL Road, Rock Hall, MD 21661

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$850,000

10.40 Acres

Waterfront Land in Rock Hall

Two adjoining parcels with waterfront and commercial zoning.

21190 GREEN Ln, Rock Hall, MD 21661

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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

3,476 SF Lot: 0.62 Acres

Estimated value

$800,000

176 Flatland Rd, Chestertown, MD 21620-3363

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Estimated value

$1,100,000

Unit 26

Lndg Ln, Chestertown, MD 21620

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Value Estimation by Request

1 Little Hbr Way, Chestertown, MD 21620

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Value Estimation by Request

Unit 33

Lndg Ln, Chestertown, MD 21620

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RESTAURANT

3,528 SF Lot: 0.92 Acres

Estimated value

$525,000

903 Washington Ave, Chestertown, MD 21620-3331

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Estimated value

$795,000

9 Lndg Ln, Chestertown, MD 21620

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RETAIL STORES (PERSONAL SERVICES)

828 SF Lot: 0.85 Acres

Value Estimation by Request

504 Washington Ave, Chestertown, MD 21620-1239

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AUTO REPAIR, GARAGE

4,135 SF Lot: 0.50 Acres

Value Estimation by Request

824 High St, Chestertown, MD 21620-1135

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RETAIL STORES (PERSONAL SERVICES)

2,484 SF Lot: 0.75 Acres

Value Estimation by Request

7306 Church Hl Rd, Chestertown, MD 21620-2806

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Estimated value

$535,000

209 Lndg Ln, Chestertown, MD 21620-4720

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Value Estimation by Request

Unit 34

Lndg Ln, Chestertown, MD 21620

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Estimated value

$545,000

Unit 13

Lndg Ln, Chestertown, MD 21620

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GYM, HEALTH SPA

57,976 SF Lot: 4.83 Acres

Value Estimation by Request

200 Scheeler Rd, Chestertown, MD 21620-1034

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RESTAURANT

2,376 SF Lot: 0.37 Acres

Value Estimation by Request

834 High St, Chestertown, MD 21620-1135

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RETAIL STORES (PERSONAL SERVICES)

8,932 SF Lot: 0.49 Acres

315 High St, Chestertown, MD 21620-1326

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RETAIL STORES (PERSONAL SERVICES)

1,588 SF Lot: 1.56 Acres

206 Cannon St, Chestertown, MD 21620

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SERVICE STATION (FULL SERVICE)

2,665 SF Lot: 0.43 Acres

Estimated value

$500,000

609 High St, Chestertown, MD 21620-1113

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MINI-MALL

53,811 SF Lot: 11.25 Acres

Estimated value

$11,850,000

851 Washington Ave, Chestertown, MD 21620

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MINI-MALL

43,200 SF Lot: 5.99 Acres

Estimated value

$11,850,000

891 Washington Ave, Chestertown, MD 21620

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RESTAURANT

3,862 SF Lot: 0.21 Acres

Estimated value

$1,020,000

229 High St, Chestertown, MD 21620

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RESIDENTIAL PARKING GARAGE

Lot: 0.01 Acres

Value Estimation by Request

Unit 32

211 Lndg Ln, Chestertown, MD 21620-4720

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FINANCIAL BUILDING

1,908 SF Lot: 0.35 Acres

611 Washington Ave, Chestertown, MD 21620-1219

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FINANCIAL BUILDING

3,168 SF Lot: 0.78 Acres

Value Estimation by Request

801 Washington Ave, Chestertown, MD 21620-1003

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Chestertown, MD Retail Properties & Spaces Investment Opportunities Market Analysis

Explore 72 retail properties & spaces for sale in Chestertown, MD on our real estate platform. These investment opportunities span a total of 0 square feet of properties for sale, with an estimated market value of $2,300,000.

Sale prices for stores in Chestertown, MD start at $2,300,000, averaging $2,300,000, 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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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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Chestertown, MD Retail Properties & Spaces for Sale

200 HIGH St, Chestertown, MD 21620

Opportunities in Nearby Cities

21279 W SHARP Street, Rock Hall, MD 21661

21279 W SHARP St, Rock Hall, MD 21661

2707 PULASKI Hwy, Edgewood, MD 21040

505-511 Edgewood Road, Edgewood, MD 21040

Potential Development Sites for Consideration

116 CROSS St, Chestertown, MD 21620

23683 L Rd, Chestertown, MD 21620

ROCK HALL Road, Rock Hall, MD 21661

21190 GREEN Ln, Rock Hall, MD 21661

Off-Market Properties in Chestertown, MD

176 Flatland Rd, Chestertown, MD 21620-3363

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

504 Washington Ave, Chestertown, MD 21620-1239

824 High St, Chestertown, MD 21620-1135

7306 Church Hl Rd, Chestertown, MD 21620-2806

209 Lndg Ln, Chestertown, MD 21620-4720

Lndg Ln, Chestertown, MD 21620

Lndg Ln, Chestertown, MD 21620

200 Scheeler Rd, Chestertown, MD 21620-1034

834 High St, Chestertown, MD 21620-1135

315 High St, Chestertown, MD 21620-1326

206 Cannon St, Chestertown, MD 21620

609 High St, Chestertown, MD 21620-1113

851 Washington Ave, Chestertown, MD 21620

891 Washington Ave, Chestertown, MD 21620

229 High St, Chestertown, MD 21620

211 Lndg Ln, Chestertown, MD 21620-4720

611 Washington Ave, Chestertown, MD 21620-1219

801 Washington Ave, Chestertown, MD 21620-1003

Chestertown, MD Retail Properties & Spaces Investment Opportunities Market Analysis

Top Commercial Asset Segments

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

Listings Trend

Property Size Breakdown

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