Chester, MD Office Spaces for Sale

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Stevensville, MD Grasonville, MD Queenstown, MD

$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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$1,500,000

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: Apr 21, 2023

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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.

Opportunities in Nearby Cities

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

Mixed-Use Multifamily and Office Building

$3,000,000

21,342 SF

Mixed-Use Multifamily and Office Building

Four-building investment property with residential units, retail, office space, and elevator-equipped school use.

104 E Main Street, Stevensville, MD 21666

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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

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Contact for pricing

Versatile Two-Story Commercial Space

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

122 Severn Ave, Annapolis, MD 21403

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Contact for pricing

Eastport Professional Building Office Space

Office space available in Eastport Professional Building.

918 Chesapeake Ave, Annapolis, MD 21403

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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

$1,400,000

4.41 Acres

Prime Grasonville Development Opportunity

Retail or office space development zone with waterfront potential.

VFW AVE, Grasonville, MD 21638

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$699,000

5.90 Acres

Talbot Commerce Park Land Opportunity

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

8992 MISTLETOE Dr, Easton, MD 21601

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$895,000

0.17 Acres

Commercial Lot in Easton, MD

Commercial lot available in Easton, Maryland.

26 S WASHINGTON Street, Easton, MD 21601

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$109,999

Commercial Lot in Downtown Chestertown

Downtown commercial lot with development potential near established businesses.

116 CROSS St, Chestertown, MD 21620

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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

4,363 SF Lot: 1.12 Acres

Estimated value

$1,300,000

100 Olde Pt Vlg, Chester, MD 21619-2132

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OFFICE BUILDING

7,352 SF Lot: 0.70 Acres

1712 Main St, Chester, MD 21619-2950

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MEDICAL BUILDING

1,500 SF Lot: 0.34 Acres

Value Estimation by Request

2009 Main St, Chester, MD 21619-2609

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OFFICE BUILDING

3,532 SF Lot: 0.77 Acres

Estimated value

$1,240,000

107 Chester Sta Ln, Chester, MD 21619-2874

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OFFICE BUILDING

2,012 SF Lot: 0.62 Acres

Value Estimation by Request

1702 Main St, Chester, MD 21619-2602

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OFFICE BUILDING

1,830 SF Lot: 1.46 Acres

Value Estimation by Request

400 Piney Narrows Rd, Chester, MD 21619-2441

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OFFICE BUILDING

1,098 SF Lot: 0.45 Acres

Value Estimation by Request

210 Castle Marina Rd, Chester, MD 21619-2425

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MEDICAL BUILDING

53,028 SF Lot: 3.99 Acres

Estimated value

$6,400,000

1630 Main St, Chester, MD 21619-2791

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OFFICE BUILDING

1,952 SF Lot: 0.39 Acres

Value Estimation by Request

1819 Little Crk Rd, Chester, MD 21619-2918

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MEDICAL BUILDING

1,856 SF Lot: 0.52 Acres

Value Estimation by Request

1617 Postal Rd, Chester, MD 21619-2601

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OFFICE BUILDING

1,053 SF Lot: 0.58 Acres

Value Estimation by Request

1610 Postal Rd, Chester, MD 21619-2664

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OFFICE BUILDING

1,288 SF Lot: 0.35 Acres

Value Estimation by Request

1522 Postal Rd, Chester, MD 21619-2258

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CONDOMINIUM OFFICES

975 SF Lot: 0.92 Acres

Value Estimation by Request

Unit A

110 Country Day Rd, Chester, MD 21619-2631

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OFFICE BUILDING

1,040 SF Lot: 0.33 Acres

Value Estimation by Request

204 Castle Marina Rd, Chester, MD 21619-2425

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OFFICE BUILDING

1,056 SF Lot: 0.32 Acres

Value Estimation by Request

200 Castle Marina Rd, Chester, MD 21619-2425

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OFFICE BUILDING

10,375 SF Lot: 2.43 Acres

Estimated value

$1,375,000

2 Chester Plz, Chester, MD 21619-2418

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OFFICE BUILDING

5,784 SF Lot: 1.82 Acres

Estimated value

$1,090,000

425 Piney Narrows Rd, Chester, MD 21619-2401

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Office Spaces

Lot: 1.20 Acres

Value Estimation by Request

2201 F G H, Chester, MD 21619

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Office Spaces

Lot: 1.20 Acres

2201 Main St, Chester, MD 21619

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Office Spaces

Lot: 1.20 Acres

2201 Main St, Chester, MD 21619

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CONDOMINIUM OFFICES

898 SF Lot: 0.92 Acres

Value Estimation by Request

Unit C

109 Country Day Rd, Chester, MD 21619-2967

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CONDOMINIUM OFFICES

1,078 SF Lot: 0.92 Acres

Value Estimation by Request

110 Country Day Rd, Chester, MD 21619-2631

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Chester, MD Office Spaces Investment Opportunities Market Analysis

Explore 29 office 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 $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 Office Spaces for Sale

100-104 Olde Point Road, Chester, MD 21619

104 Olde Point Road, Chester, MD

Opportunities in Nearby Cities

104 E Main Street, Stevensville, MD 21666

211 LOVE POINT RD, Stevensville, MD 21666

122 Severn Ave, Annapolis, MD 21403

918 Chesapeake Ave, Annapolis, MD 21403

Potential Development Sites for Consideration

VFW AVE, Grasonville, MD 21638

8992 MISTLETOE Dr, Easton, MD 21601

26 S WASHINGTON Street, Easton, MD 21601

116 CROSS St, Chestertown, MD 21620

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

Chester, MD Office Spaces Investment Opportunities Market Analysis

Top Commercial Asset Segments

Demographics Overview

High-Yield Neighborhoods for Investment

Taxes & Financing

Listings Trend

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