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Chestertown, MD

Retail

Chestertown, MD Retail Properties & Spaces for Sale

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

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

Mixed-Use Income Property with Retail

Updated: May 16

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 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.

Commercial Building in Rock Hall

Commercial Building in Rock Hall

21435 Rock Hall Ave, Rock Hall, MD 21661

$300,000

990 sqft

Commercial building suitable for office, retail, or studio 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.

Rock Hall Commercial Property Opportunity

Rock Hall Commercial Property Opportunity

21279 W SHARP St, Rock Hall, MD 21661

$325,000

0.19 AC lot

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

Mixed-Use Building with Apartment

Mixed-Use Building with Apartment

4300 MAIN Street, Grasonville, MD 21638

$459,000

0.24 AC lot

Two-level property combines an operating retail space with a renovated residential apartment and ground-level service areas.

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.

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.

Pulaski Highway Commercial Land Parcels

Pulaski Highway Commercial Land Parcels

3800 & 3804 PULASKI HWY, Abingdon, MD 21009

$500,000

Two commercial land parcels with billboard leases on Pulaski Highway.

Commercial Land on Pulaski Highway

Commercial Land on Pulaski Highway

1954 Pulaski Highway, Edgewood, MD 21040

$300,000

Commercial land for sale on Route 40 in Edgewood.

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

Estimated value:

$800,000

3,476 sqft 0.62 AC lot

Lndg Ln, Unit 26

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 26

Estimated value:

$1,100,000

0.01 AC lot

1 Little Hbr Way

RESIDENTIAL PARKING GARAGE

1 Little Hbr Way, Chestertown, MD 21620

Estimated value:

by Request

0.01 AC lot

Lndg Ln, Unit 33

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 33

Estimated value:

by Request

0.01 AC lot

903 Washington Ave

RESTAURANT

903 Washington Ave, Chestertown, MD 21620-3331

Estimated value:

$525,000

3,528 sqft 0.92 AC lot

9 Lndg Ln

RESIDENTIAL PARKING GARAGE

9 Lndg Ln, Chestertown, MD 21620

Estimated value:

$795,000

0.01 AC lot

504 Washington Ave

RETAIL STORES (PERSONAL SERVICES)

504 Washington Ave, Chestertown, MD 21620-1239

Estimated value:

$445,000

828 sqft 0.85 AC lot

824 High St

AUTO REPAIR, GARAGE

824 High St, Chestertown, MD 21620-1135

Estimated value:

$200,000

4,135 sqft 0.50 AC lot

7306 Church Hl Rd

RETAIL STORES (PERSONAL SERVICES)

7306 Church Hl Rd, Chestertown, MD 21620-2806

Estimated value:

$155,000

2,484 sqft 0.75 AC lot

209 Lndg Ln

RESIDENTIAL PARKING GARAGE

209 Lndg Ln, Chestertown, MD 21620-4720

Estimated value:

$545,000

0.01 AC lot

Lndg Ln, Unit 34

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 34

Estimated value:

$245,000

0.01 AC lot

Lndg Ln, Unit 13

RESIDENTIAL PARKING GARAGE

Lndg Ln, Chestertown, MD 21620

Unit 13

Estimated value:

$560,000

0.01 AC lot

200 Scheeler Rd

GYM, HEALTH SPA

200 Scheeler Rd, Chestertown, MD 21620-1034

Estimated value:

by Request

57,976 sqft 4.83 AC lot

834 High St

RESTAURANT

834 High St, Chestertown, MD 21620-1135

Estimated value:

$355,000

2,376 sqft 0.37 AC lot

315 High St

RETAIL STORES (PERSONAL SERVICES)

315 High St, Chestertown, MD 21620-1326

Estimated value:

$1,710,000

8,932 sqft 0.49 AC lot

206 Cannon St

RETAIL STORES (PERSONAL SERVICES)

206 Cannon St, Chestertown, MD 21620

Estimated value:

$790,000

1,588 sqft 1.56 AC lot

609 High St

SERVICE STATION (FULL SERVICE)

609 High St, Chestertown, MD 21620-1113

Estimated value:

$490,000

2,665 sqft 0.43 AC lot

851 Washington Ave

MINI-MALL

851 Washington Ave, Chestertown, MD 21620

Estimated value:

$11,540,000

53,811 sqft 11.25 AC lot

891 Washington Ave

MINI-MALL

891 Washington Ave, Chestertown, MD 21620

Estimated value:

$11,540,000

43,200 sqft 5.99 AC lot

229 High St

RESTAURANT

229 High St, Chestertown, MD 21620

Estimated value:

$790,000

3,862 sqft 0.21 AC lot

211 Lndg Ln, Unit 32

RESIDENTIAL PARKING GARAGE

211 Lndg Ln, Chestertown, MD 21620-4720

Unit 32

Estimated value:

$485,000

0.01 AC lot

611 Washington Ave

FINANCIAL BUILDING

611 Washington Ave, Chestertown, MD 21620-1219

Estimated value:

$450,000

1,908 sqft 0.35 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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