Chester, MD Retail properties & Spaces for sale

$1,500,000

Route 50 Accessible Retail Buildings

100-104 Olde Point Road, Chester, MD 21619

Two retail/office buildings with direct highway access for sale.

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

Updated: Nov 21, 2025

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Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Unique Stevensville Commercial Opportunity

$975,000

0.49 Acres

Unique Stevensville Commercial Opportunity

Prime location in downtown Stevensville with many potential business uses.

426 LOVE POINT RD, Stevensville, MD 21666

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$975,000

0.49 Acres

Unique Church Property in Stevensville

Historic church with development potential in downtown Stevensville.

426 LOVE POINT Rd, Stevensville, MD 21666

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$1,699,000

5,344 SF

Two-Story Office/Retail Space For Sale

Two-story office/retail space with flexible layout and parking.

122 Severn Ave, Annapolis, MD

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Eastport Annapolis Retail/Residential Opportunity

$2,690,000

5,447 SF

Eastport Annapolis Retail/Residential Opportunity

Two-story building with retail space and apartments, plus parking.

412 6th St, Annapolis, MD

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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.

$1,175,000

4.64 Acres

Grasonville Land for Lease

4.638 acre commercial land parcel in Grasonville, Maryland.

0 Main St, Grasonville, MD

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Renovated Victorian Commercial Building on Acre

$699,000

1.14 Acres

Renovated Victorian Commercial Building on Acre

Updated Victorian building on an acre with UC zoning.

211 LOVE POINT ROAD, Stevensville, MD 21666

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Contact for pricing

Commercial Lots Near Route 50

Commercial lots available near the Route 50 and Route 8 interchange.

Ellendale Farm Lane, Stevensville, MD 21666

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$799,000

Land in Grasonville, Maryland

Commercial land with waterfront potential in Grasonville, Maryland.

3700-3704 Main St, Grasonville, MD 21638

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Explore 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.

12 Chester Plz

DRIVE-THRU RESTAURANT, FAST FOOD • 4,915 SF

Value Estimation by Request

12 Chester Plz, Chester, MD 21619-2418

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1802 Main St

RETAIL STORES (PERSONAL SERVICES) • 14,473 SF

Value Estimation

$7,430,000

1802 Main St, Chester, MD 21619-2604

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1925 Main St

MINI-MALL • 6,000 SF

Value Estimation

$855,000

1925 Main St, Chester, MD 21619-2607

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1713 Main St

RETAIL STORES (PERSONAL SERVICES) • 1,920 SF

Value Estimation by Request

1713 Main St, Chester, MD 21619-2641

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2106 Didonato Dr

SHOPPING CENTER, STRIP CENTER • 17,000 SF

Value Estimation

$1,765,000

2106 Didonato Dr, Chester, MD 21619-2628

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1423 Main St

FINANCIAL BUILDING • 4,242 SF

Value Estimation by Request

1423 Main St, Chester, MD 21619

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110 Piney Narrows Rd

RESTAURANT • 5,621 SF

Value Estimation by Request

110 Piney Narrows Rd, Chester, MD 21619-2439

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115 Piney Rd

RETAIL STORES (PERSONAL SERVICES) • 12,036 SF

Value Estimation

$6,445,000

115 Piney Rd, Chester, MD 21619-2619

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1509 Postal Rd

AUTO REPAIR, GARAGE • 3,617 SF

Value Estimation by Request

1509 Postal Rd, Chester, MD 21619-2255

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2212 Piney Crk Rd

AUTO REPAIR, GARAGE • 7,200 SF

Value Estimation by Request

2212 Piney Crk Rd, Chester, MD 21619-2412

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1619 Postal Rd

RETAIL STORES (PERSONAL SERVICES) • 280 SF

Value Estimation by Request

1619 Postal Rd, Chester, MD 21619-2601

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1607 Postal Rd

RETAIL STORES (PERSONAL SERVICES) • 896 SF

Value Estimation by Request

1607 Postal Rd, Chester, MD 21619-2601

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1539 Postal Rd

SHOPPING CENTER, STRIP CENTER • 36,420 SF

Value Estimation

$3,585,000

1539 Postal Rd, Chester, MD 21619-2255

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1814 Crab Aly Dr

AUTO REPAIR, GARAGE • 1,728 SF

Value Estimation by Request

1814 Crab Aly Dr, Chester, MD 21619-2757

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100 Dominion Rd

CONVENIENCE STORE • 1,431 SF

Value Estimation by Request

100 Dominion Rd, Chester, MD 21619-2707

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120 Chester Sta Ln

CONVENIENCE STORE • 3,685 SF

Value Estimation by Request

120 Chester Sta Ln, Chester, MD 21619-2803

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210 Country Day Rd

GYM, HEALTH SPA • 37,202 SF

Value Estimation

$1,080,000

210 Country Day Rd, Chester, MD 21619-2603

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1845 Main St

DRIVE-THRU RESTAURANT, FAST FOOD • 4,451 SF

Value Estimation by Request

1845 Main St, Chester, MD 21619-2605

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1626 Postal Rd

RETAIL STORES (PERSONAL SERVICES) • 1,194 SF

Value Estimation by Request

1626 Postal Rd, Chester, MD 21619-2625

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101 Castle Marina Rd

SERVICE STATION (FULL SERVICE) • 1,411 SF

Value Estimation by Request

101 Castle Marina Rd, Chester, MD 21619-2417

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600 Abruzzi Dr

SHOPPING CENTER, STRIP CENTER • 2,400 SF

Value Estimation by Request

600 Abruzzi Dr, Chester, MD 21619-2198

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1608 Postal Rd

RETAIL STORES (PERSONAL SERVICES) • 4,200 SF

Value Estimation by Request

1608 Postal Rd, Chester, MD 21619-2664

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2325 Main St

AUTO REPAIR, GARAGE • 7,750 SF

Value Estimation

$590,000

2325 Main St, Chester, MD 21619-2699

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Chester, MD Retail Properties & Spaces Investment Opportunities Market Analysis

Explore 44 retail properties & spaces for sale in Chester, MD on our real estate platform. These investment opportunities span a total of 576,800 square feet of properties for sale, with an estimated market value of $17,935,000.

Sale prices for stores in Chester, MD start at $230,000, averaging $996,388, and reaching up to $7,265,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Chester, MD Retail Properties & Spaces for Sale

Route 50 Accessible Retail Buildings

Two retail/office buildings with direct highway access for sale.

Explore Opportunities in Nearby Cities

Unique Stevensville Commercial Opportunity

Unique Church Property in Stevensville

Two-Story Office/Retail Space For Sale

Eastport Annapolis Retail/Residential Opportunity

Potential Development Sites for Consideration

Grasonville Land for Lease

Renovated Victorian Commercial Building on Acre

Commercial Lots Near Route 50

Land in Grasonville, Maryland

Explore Off-Market Properties in Chester, MD

12 Chester Plz

1802 Main St

1925 Main St

1713 Main St

2106 Didonato Dr

1423 Main St

110 Piney Narrows Rd

115 Piney Rd

1509 Postal Rd

2212 Piney Crk Rd

1619 Postal Rd

1607 Postal Rd

1539 Postal Rd

1814 Crab Aly Dr

100 Dominion Rd

120 Chester Sta Ln

210 Country Day Rd

1845 Main St

1626 Postal Rd

101 Castle Marina Rd

600 Abruzzi Dr

1608 Postal Rd

2325 Main St

Chester, MD Retail Properties & Spaces Investment Opportunities Market Analysis

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