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    Chester, MD Office Properties & Spaces for Sale

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    Baltimore, MD Salisbury, MD Hagerstown, MD
    Route 50 Accessible Retail Buildings
    $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
    View details
    Two Buildings with Route 50 Access
    Contact for pricing
    9,600 SF

    Two Buildings with Route 50 Access

    104 Olde Point Road, Chester, MD

    Two 4,800 SF buildings with direct Route 50 access.

    • Direct access off of eastbound Rt 50
    • Two 4800 sq ft buildings
    • Many permitted office and retail uses
    • Several leases in place
    • First time listed for sale
    Updated: Aug 19, 2024
    View details
    Based on your search, we've compiled 37 Potential Opportunities for your consideration. Besides 2 Active listings in Chester, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 27 Off-Market properties to explore as potential leads, plus 4 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

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

    Renovated Commercial Building on Acreage
    $699,000
    1.14 Acres

    Renovated Commercial Building on Acreage

    Updated commercial building on over an acre with UC zoning.

    211 LOVE POINT RD, Stevensville, MD 21666
    View details
    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
    View details
    Versatile Two-Story Commercial Space
    Contact for pricing

    Versatile Two-Story Commercial Space

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

    122 Severn Ave, Annapolis, MD 21403
    View details
    Two-Story Office/Retail Space For Sale
    $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
    View details

    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
    $1,400,000
    4.41 Acres

    Prime Grasonville Development Opportunity

    Retail or office space development zone with waterfront potential.

    VFW AVE, Grasonville, MD 21638
    View details
    Talbot Commerce Park Land Opportunity
    $699,000

    Talbot Commerce Park Land Opportunity

    Development-ready commercial/industrial lot in Easton's premier business hub.

    8992 MISTLETOE Dr, Easton, MD 21601
    View details
    Commercial Lot in Easton, MD
    $895,000
    0.17 Acres

    Commercial Lot in Easton, MD

    Commercial lot available in Easton, Maryland.

    26 S WASHINGTON Street, Easton, MD 21601
    View details
    Commercial Lot in Downtown Chestertown
    $109,999

    Commercial Lot in Downtown Chestertown

    Downtown commercial lot with development potential near established businesses.

    116 CROSS St, Chestertown, MD 21620
    View details

    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.

    100 Olde Pt Vlg

    100 Olde Pt Vlg

    OFFICE BUILDING • 4,363 SF
    Value Estimation
    $1,300,000
    100 Olde Pt Vlg, Chester, MD 21619-2132
    View details
    1712 Main St

    1712 Main St

    OFFICE BUILDING • 7,352 SF
    Value Estimation
    $900,000
    1712 Main St, Chester, MD 21619-2950
    View details
    2009 Main St

    2009 Main St

    MEDICAL BUILDING • 1,500 SF
    Value Estimation by Request
    2009 Main St, Chester, MD 21619-2609
    View details
    107 Chester Sta Ln

    107 Chester Sta Ln

    OFFICE BUILDING • 3,532 SF
    Value Estimation
    $1,240,000
    107 Chester Sta Ln, Chester, MD 21619-2874
    View details
    1702 Main St

    1702 Main St

    OFFICE BUILDING • 2,012 SF
    Value Estimation by Request
    1702 Main St, Chester, MD 21619-2602
    View details
    400 Piney Narrows Rd

    400 Piney Narrows Rd

    OFFICE BUILDING • 1,830 SF
    Value Estimation by Request
    400 Piney Narrows Rd, Chester, MD 21619-2441
    View details
    210 Castle Marina Rd

    210 Castle Marina Rd

    OFFICE BUILDING • 1,098 SF
    Value Estimation by Request
    210 Castle Marina Rd, Chester, MD 21619-2425
    View details
    1630 Main St

    1630 Main St

    MEDICAL BUILDING • 53,028 SF
    Value Estimation
    $6,400,000
    1630 Main St, Chester, MD 21619-2791
    View details
    1819 Little Crk Rd

    1819 Little Crk Rd

    OFFICE BUILDING • 1,952 SF
    Value Estimation by Request
    1819 Little Crk Rd, Chester, MD 21619-2918
    View details
    1617 Postal Rd

    1617 Postal Rd

    MEDICAL BUILDING • 1,856 SF
    Value Estimation by Request
    1617 Postal Rd, Chester, MD 21619-2601
    View details
    1610 Postal Rd

    1610 Postal Rd

    OFFICE BUILDING • 1,053 SF
    Value Estimation by Request
    1610 Postal Rd, Chester, MD 21619-2664
    View details
    1522 Postal Rd

    1522 Postal Rd

    OFFICE BUILDING • 1,288 SF
    Value Estimation by Request
    1522 Postal Rd, Chester, MD 21619-2258
    View details
    110 Country Day Rd, Unit A

    110 Country Day Rd, Unit A

    CONDOMINIUM OFFICES • 975 SF
    Value Estimation by Request
    110 Country Day Rd, Chester, MD 21619-2631
    View details
    204 Castle Marina Rd

    204 Castle Marina Rd

    OFFICE BUILDING • 1,040 SF
    Value Estimation by Request
    204 Castle Marina Rd, Chester, MD 21619-2425
    View details
    200 Castle Marina Rd

    200 Castle Marina Rd

    OFFICE BUILDING • 1,056 SF
    Value Estimation by Request
    200 Castle Marina Rd, Chester, MD 21619-2425
    View details
    2 Chester Plz

    2 Chester Plz

    OFFICE BUILDING • 10,375 SF
    Value Estimation
    $1,375,000
    2 Chester Plz, Chester, MD 21619-2418
    View details
    425 Piney Narrows Rd

    425 Piney Narrows Rd

    OFFICE BUILDING • 5,784 SF
    Value Estimation
    $1,090,000
    425 Piney Narrows Rd, Chester, MD 21619-2401
    View details
    2201 F G H

    2201 F G H

    Office properties & Spaces • 1.20 Acres
    Value Estimation by Request
    2201 F G H, Chester, MD 21619
    View details
    2201 Main St

    2201 Main St

    Office properties & Spaces • 1.20 Acres
    Value Estimation by Request
    2201 Main St, Chester, MD 21619
    View details
    2201 Main St

    2201 Main St

    Office properties & Spaces • 1.20 Acres
    Value Estimation by Request
    2201 Main St, Chester, MD 21619
    View details
    109 Country Day Rd, Unit C

    109 Country Day Rd, Unit C

    CONDOMINIUM OFFICES • 898 SF
    Value Estimation by Request
    109 Country Day Rd, Chester, MD 21619-2967
    View details
    110 Country Day Rd

    110 Country Day Rd

    CONDOMINIUM OFFICES • 1,078 SF
    Value Estimation by Request
    110 Country Day Rd, Chester, MD 21619-2631
    View details

    Chester, MD Office Properties & Spaces Investment Opportunities Market Analysis

    Explore 29 office properties & spaces for sale in Chester, MD on our real estate platform. These investment opportunities span a total of 9,600 square feet of properties for sale, with an estimated market value of $1,500,000.

    Sale prices for office spaces in Chester, MD start at $0.00, averaging $750,000, 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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    Most Searched ZIP Codes in Chester, MD

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