Chester, MD Retail Properties & Spaces for Sale

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Stevensville, MD Grasonville, MD Queenstown, MD

Updated: Nov 21, 2025

Route 50 Accessible Retail Buildings

100-104 Olde Point Road, Chester, MD 21619

$1,500,000

Direct access off of Eastbound Rt 50
Two 4800 sf buildings
Great location
Many permitted office and retail uses
Several Leases in place

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Based on your search, we've compiled 52 Potential Opportunities for your consideration. Besides 1 Active listings in Chester, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 43 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.

Stevensville Mixed-Use Investment Opportunity

104 E MAIN ST, Stevensville, MD 21666

$3,000,000

15,000 sqft · 1.32 AC lot

Four buildings with residential, retail, and office spaces on 1.32 acres.

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Renovated UC-Zoned Mixed-Use Building

211 LOVE POINT RD, Stevensville, MD 21666

$699,000

1.14 AC lot

Renovated Victorian structure with multiple rooms, new HVAC in 2025, and UC zoning supporting a wide range of commercial uses.

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Boutique Downtown Storefront

45 Randall Street, Annapolis, MD 21401

$475,000

240 sqft

High-visibility storefront suited for retail or food concepts in a heavily visited waterfront downtown setting.

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Versatile Two-Story Commercial Space

122 Severn Ave, Annapolis, MD 21403

Contact for pricing

Two-story commercial space with flexible layout, available May 2025.

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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.

Prime Grasonville Development Opportunity

VFW AVE, Grasonville, MD 21638

$1,400,000

4.41 AC lot

Retail or office space development zone with waterfront potential.

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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.

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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.

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Commercial Land on Ocean Gateway

9719 Ocean Gateway, Easton, MD 21601

$2,700,000

3.25 AC lot

3.25 acres of commercially zoned land for sale.

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Off-Market Properties in Chester, MD

Consider similar Off-Market properties in Chester, 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.

DRIVE-THRU RESTAURANT, FAST FOOD

12 Chester Plz, Chester, MD 21619-2418

Value Estimation by Request

4,915 sqft · 1.31 AC lot

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RETAIL STORES (PERSONAL SERVICES)

1802 Main St, Chester, MD 21619-2604

$7,430,000

Estimated value

14,473 sqft · 1.73 AC lot

View details

MINI-MALL

1925 Main St, Chester, MD 21619-2607

$855,000

Estimated value

6,000 sqft · 7.37 AC lot

View details

RETAIL STORES (PERSONAL SERVICES)

1713 Main St, Chester, MD 21619-2641

Value Estimation by Request

1,920 sqft · 0.49 AC lot

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SHOPPING CENTER, STRIP CENTER

2106 Didonato Dr, Chester, MD 21619-2628

$1,765,000

Estimated value

17,000 sqft · 5.49 AC lot

View details

FINANCIAL BUILDING

1423 Main St, Chester, MD 21619

Value Estimation by Request

4,242 sqft · 2.07 AC lot

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RESTAURANT

110 Piney Narrows Rd, Chester, MD 21619-2439

Value Estimation by Request

5,621 sqft · 0.55 AC lot

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RETAIL STORES (PERSONAL SERVICES)

115 Piney Rd, Chester, MD 21619-2619

$6,445,000

Estimated value

12,036 sqft · 1.54 AC lot

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AUTO REPAIR, GARAGE

1509 Postal Rd, Chester, MD 21619-2255

Value Estimation by Request

3,617 sqft · 0.59 AC lot

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AUTO REPAIR, GARAGE

2212 Piney Crk Rd, Chester, MD 21619-2412

Value Estimation by Request

7,200 sqft · 0.55 AC lot

View details

RETAIL STORES (PERSONAL SERVICES)

1619 Postal Rd, Chester, MD 21619-2601

Value Estimation by Request

280 sqft · 0.30 AC lot

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RETAIL STORES (PERSONAL SERVICES)

1607 Postal Rd, Chester, MD 21619-2601

Value Estimation by Request

896 sqft · 0.24 AC lot

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SHOPPING CENTER, STRIP CENTER

1539 Postal Rd, Chester, MD 21619-2255

$3,585,000

Estimated value

36,420 sqft · 2.54 AC lot

View details

AUTO REPAIR, GARAGE

1814 Crab Aly Dr, Chester, MD 21619-2757

Value Estimation by Request

1,728 sqft · 1.39 AC lot

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CONVENIENCE STORE

100 Dominion Rd, Chester, MD 21619-2707

Value Estimation by Request

1,431 sqft · 0.83 AC lot

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CONVENIENCE STORE

120 Chester Sta Ln, Chester, MD 21619-2803

Value Estimation by Request

3,685 sqft · 4.66 AC lot

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GYM, HEALTH SPA

210 Country Day Rd, Chester, MD 21619-2603

$1,080,000

Estimated value

37,202 sqft · 3.23 AC lot

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DRIVE-THRU RESTAURANT, FAST FOOD

1845 Main St, Chester, MD 21619-2605

Value Estimation by Request

4,451 sqft · 1.94 AC lot

View details

RETAIL STORES (PERSONAL SERVICES)

1626 Postal Rd, Chester, MD 21619-2625

Value Estimation by Request

1,194 sqft · 0.44 AC lot

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SERVICE STATION (FULL SERVICE)

101 Castle Marina Rd, Chester, MD 21619-2417

Value Estimation by Request

1,411 sqft · 0.87 AC lot

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SHOPPING CENTER, STRIP CENTER

600 Abruzzi Dr, Chester, MD 21619-2198

Value Estimation by Request

2,400 sqft · 0.96 AC lot

View details

RETAIL STORES (PERSONAL SERVICES)

1608 Postal Rd, Chester, MD 21619-2664

Value Estimation by Request

4,200 sqft · 0.44 AC lot

View details

AUTO REPAIR, GARAGE

2325 Main St, Chester, MD 21619-2699

$590,000

Estimated value

7,750 sqft · 1.00 AC lot

View details

Chester, MD Retail Properties & Spaces Market Trends and Statistics

Explore 44 retail properties & spaces for sale in Chester, 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 $1,500,000.

Sale prices for stores in Chester, MD start at $1,500,000, averaging $1,500,000, and reaching up to $1,500,000 — 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 5,905

Population Growth (5Y) +0.2%

Median Household Income $100,359

College Educated 47.4%

High-Yield Neighborhoods for Investment

Identify Chester submarkets with the highest inventory density on the market and evaluate the average listing prices of real estate assets

Neighborhood	Average Price
21619	$1.5M

Taxes & Financing

Tax Rate (average for all types) 0.94%

Property Tax per SF $25.82 per SF

Tax Rate vs County Average 0.06 pp below county avg

Average Loan-to-Value 65.0%

Listings Trend

New vs delisted commercial listings in Queen Anne's County

New Delisted

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Chester, MD Retail Properties & Spaces for Sale

100-104 Olde Point Road, Chester, MD 21619

Opportunities in Nearby Cities

104 E MAIN ST, Stevensville, MD 21666

211 LOVE POINT RD, Stevensville, MD 21666

45 Randall Street, Annapolis, MD 21401

122 Severn Ave, Annapolis, MD 21403

Potential Development Sites for Consideration

VFW AVE, Grasonville, MD 21638

21190 GREEN Ln, Rock Hall, MD 21661

ROCK HALL Road, Rock Hall, MD 21661

9719 Ocean Gateway, Easton, MD 21601

Off-Market Properties in Chester, MD

12 Chester Plz, Chester, MD 21619-2418

1802 Main St, Chester, MD 21619-2604

1925 Main St, Chester, MD 21619-2607

1713 Main St, Chester, MD 21619-2641

2106 Didonato Dr, Chester, MD 21619-2628

1423 Main St, Chester, MD 21619

110 Piney Narrows Rd, Chester, MD 21619-2439

115 Piney Rd, Chester, MD 21619-2619

1509 Postal Rd, Chester, MD 21619-2255

2212 Piney Crk Rd, Chester, MD 21619-2412

1619 Postal Rd, Chester, MD 21619-2601

1607 Postal Rd, Chester, MD 21619-2601

1539 Postal Rd, Chester, MD 21619-2255

1814 Crab Aly Dr, Chester, MD 21619-2757

100 Dominion Rd, Chester, MD 21619-2707

120 Chester Sta Ln, Chester, MD 21619-2803

210 Country Day Rd, Chester, MD 21619-2603

1845 Main St, Chester, MD 21619-2605

1626 Postal Rd, Chester, MD 21619-2625

101 Castle Marina Rd, Chester, MD 21619-2417

600 Abruzzi Dr, Chester, MD 21619-2198

1608 Postal Rd, Chester, MD 21619-2664

2325 Main St, Chester, MD 21619-2699

Chester, MD Retail Properties & Spaces Market Trends and Statistics

Top Commercial Asset Segments

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

Listings Trend

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