Chester, MD Office Spaces for Sale

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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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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 36 Potential Opportunities for your consideration. Besides 1 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.

Opportunities in Nearby Cities

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

Two-Story Flex Space with Garage Door

122 Severn Ave, Annapolis, MD 21403

Contact for pricing

5,344 sqft

Two-story flex space with an upstairs office loft, flexible first-floor area, and WMM zoning.

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Renovated Victorian Commercial Building on Acre

211 LOVE POINT ROAD, Stevensville, MD 21666

$699,000

1.14 AC lot

Updated Victorian building on an acre with UC zoning.

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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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Well-Maintained Office Building

1007 Butterworth Court, Stevensville, MD 21666

Contact for pricing

Office building with reception, multiple offices, a large conference room, and ample parking for a flexible tenancy setup.

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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.

Talbot Commerce Park Land Opportunity

8992 MISTLETOE Dr, Easton, MD 21601

$699,000

5.90 AC lot

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

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Commercial Lot in Easton, MD

26 S WASHINGTON Street, Easton, MD 21601

$895,000

0.17 AC lot

Commercial lot available in Easton, Maryland.

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Commercial Lot in Downtown Chestertown

116 CROSS St, Chestertown, MD 21620

$109,999

Downtown commercial lot with development potential near established businesses.

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Glen Burnie C-2 Opportunity Land

7911 RITCHIE Highway, Glen Burnie, MD 21061

$899,900

1.43 AC lot

Highly visible 1.43 acre C-2 land near Marley Station Mall.

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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.

OFFICE BUILDING

100 Olde Pt Vlg, Chester, MD 21619-2132

$1,300,000

Estimated value

4,363 sqft 1.12 AC lot

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OFFICE BUILDING

1712 Main St, Chester, MD 21619-2950

$900,000

Estimated value

7,352 sqft 0.70 AC lot

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MEDICAL BUILDING

2009 Main St, Chester, MD 21619-2609

Value Estimation by Request

1,500 sqft 0.34 AC lot

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OFFICE BUILDING

107 Chester Sta Ln, Chester, MD 21619-2874

$1,240,000

Estimated value

3,532 sqft 0.77 AC lot

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OFFICE BUILDING

1702 Main St, Chester, MD 21619-2602

Value Estimation by Request

2,012 sqft 0.62 AC lot

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OFFICE BUILDING

400 Piney Narrows Rd, Chester, MD 21619-2441

Value Estimation by Request

1,830 sqft 1.46 AC lot

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OFFICE BUILDING

210 Castle Marina Rd, Chester, MD 21619-2425

Value Estimation by Request

1,098 sqft 0.45 AC lot

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MEDICAL BUILDING

1630 Main St, Chester, MD 21619-2791

$6,400,000

Estimated value

53,028 sqft 3.99 AC lot

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OFFICE BUILDING

1819 Little Crk Rd, Chester, MD 21619-2918

Value Estimation by Request

1,952 sqft 0.39 AC lot

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MEDICAL BUILDING

1617 Postal Rd, Chester, MD 21619-2601

Value Estimation by Request

1,856 sqft 0.52 AC lot

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OFFICE BUILDING

1610 Postal Rd, Chester, MD 21619-2664

Value Estimation by Request

1,053 sqft 0.58 AC lot

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OFFICE BUILDING

1522 Postal Rd, Chester, MD 21619-2258

Value Estimation by Request

1,288 sqft 0.35 AC lot

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CONDOMINIUM OFFICES

110 Country Day Rd, Chester, MD 21619-2631

Unit A

Value Estimation by Request

975 sqft 0.92 AC lot

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OFFICE BUILDING

204 Castle Marina Rd, Chester, MD 21619-2425

Value Estimation by Request

1,040 sqft 0.33 AC lot

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OFFICE BUILDING

200 Castle Marina Rd, Chester, MD 21619-2425

Value Estimation by Request

1,056 sqft 0.32 AC lot

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OFFICE BUILDING

2 Chester Plz, Chester, MD 21619-2418

$1,375,000

Estimated value

10,375 sqft 2.43 AC lot

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OFFICE BUILDING

425 Piney Narrows Rd, Chester, MD 21619-2401

$1,090,000

Estimated value

5,784 sqft 1.82 AC lot

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Office Spaces

2201 F G H, Chester, MD 21619

Value Estimation by Request

1.20 AC lot

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Office Spaces

2201 Main St, Chester, MD 21619

Value Estimation by Request

1.20 AC lot

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Office Spaces

2201 Main St, Chester, MD 21619

Value Estimation by Request

1.20 AC lot

View details

CONDOMINIUM OFFICES

109 Country Day Rd, Chester, MD 21619-2967

Unit C

Value Estimation by Request

898 sqft 0.92 AC lot

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CONDOMINIUM OFFICES

110 Country Day Rd, Chester, MD 21619-2631

Value Estimation by Request

1,078 sqft 0.92 AC lot

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CONDOMINIUM OFFICES

109 Country Day Rd, Chester, MD 21619-2684

Unit A

Value Estimation by Request

2,488 sqft 0.92 AC lot

View details

Chester, MD Office Spaces Market Trends and Statistics

Explore 28 office spaces for sale in Chester, MD on our real estate platform.

Sale prices for office spaces in Chester, MD average $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%

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Chester, MD Office Spaces for Sale

100-104 Olde Point Road, Chester, MD 21619

Opportunities in Nearby Cities

122 Severn Ave, Annapolis, MD 21403

211 LOVE POINT ROAD, Stevensville, MD 21666

122 Severn Ave, Annapolis, MD 21403

1007 Butterworth Court, Stevensville, MD 21666

Potential Development Sites for Consideration

8992 MISTLETOE Dr, Easton, MD 21601

26 S WASHINGTON Street, Easton, MD 21601

116 CROSS St, Chestertown, MD 21620

7911 RITCHIE Highway, Glen Burnie, MD 21061

Off-Market Properties in Chester, MD

100 Olde Pt Vlg, Chester, MD 21619-2132

1712 Main St, Chester, MD 21619-2950

2009 Main St, Chester, MD 21619-2609

107 Chester Sta Ln, Chester, MD 21619-2874

1702 Main St, Chester, MD 21619-2602

400 Piney Narrows Rd, Chester, MD 21619-2441

210 Castle Marina Rd, Chester, MD 21619-2425

1630 Main St, Chester, MD 21619-2791

1819 Little Crk Rd, Chester, MD 21619-2918

1617 Postal Rd, Chester, MD 21619-2601

1610 Postal Rd, Chester, MD 21619-2664

1522 Postal Rd, Chester, MD 21619-2258

110 Country Day Rd, Chester, MD 21619-2631

204 Castle Marina Rd, Chester, MD 21619-2425

200 Castle Marina Rd, Chester, MD 21619-2425

2 Chester Plz, Chester, MD 21619-2418

425 Piney Narrows Rd, Chester, MD 21619-2401

2201 F G H, Chester, MD 21619

2201 Main St, Chester, MD 21619

2201 Main St, Chester, MD 21619

109 Country Day Rd, Chester, MD 21619-2967

110 Country Day Rd, Chester, MD 21619-2631

109 Country Day Rd, Chester, MD 21619-2684

Chester, MD Office Spaces Market Trends and Statistics

Top Commercial Asset Segments

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

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