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20 Properties

20 Properties Available In Chestertown

Name: Open House - 10AM-12PM
Start: 2026-07-25T10:00:00.000Z
End: 2026-07-25T12:00:00.000Z
Location: 106 QUEEN ST S, Chestertown, MD 21620

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MD >Chestertown >

Market Insights

Open Sat 10AM-12PM

$829,000

106 QUEEN ST S, Chestertown, MD 21620

3 Beds4 Baths2,472 SqFt

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

Price Dropped by $25K

$299,900

517 ROUND TOP RD, Chestertown, MD 21620

3 Beds1 Bath1,248 SqFt

MLS# MDQA2017680

Listed by Keller Williams Flagship

Price Dropped by $7K

$239,900

104 CONLEY DR, Chestertown, MD 21620

3 Beds2 Baths1,280 SqFt

MLS# MDKE2006686

Listed by Cummings & Co. Realtors

Price Dropped by $9K

$275,000

104 ACORN DR, Chestertown, MD 21620

3 Beds3 Baths1,900 SqFt

MLS# MDKE2006668

Listed by Cross Street Realtors LLC

234 N COLLEGE AVE, Chestertown, MD 21620

Price Dropped by $10K

$90,000

234 N COLLEGE AVE, Chestertown, MD 21620

2 Beds1 Bath1,296 SqFt

MLS# MDKE2006670

Listed by Cummings & Co Realtors

Price Dropped by $5K

$74,900

110 PROSPECT ST, Chestertown, MD 21620

3 Beds2 Baths2,210 SqFt

MLS# MDKE2006626

Listed by ANR Realty, LLC

Price Dropped by $20K

$429,900

10781 FERMOY RD, Chestertown, MD 21620

4 Beds3 Baths2,160 SqFt

MLS# MDKE2006640

Listed by Real Broker, LLC - Chester

Price Dropped by $49K

$350,000

522 HIGH ST, Chestertown, MD 21620

2 Beds3 Baths1,518 SqFt

MLS# MDKE2006614

Listed by Benson & Mangold, LLC

Price Dropped by $24K

$365,000

240 MERGANSER DR, Chestertown, MD 21620

3 Beds2 Baths1,120 SqFt

MLS# MDQA2016900

Listed by Chesapeake Real Estate Associates, LLC

107 FLYING CLOUD DR, Chestertown, MD 21620

Price Dropped by $10K

$375,000

107 FLYING CLOUD DR, Chestertown, MD 21620

5 Beds4 Baths2,534 SqFt

MLS# MDKE2006510

Listed by CENTURY 21 New Millennium

Price Dropped by $5K

$519,900

101 COLEMAN DR, Chestertown, MD 21620

3 Beds3 Baths2,268 SqFt

MLS# MDQA2016624

Listed by Coldwell Banker Chesapeake Real Estate Company

Under Contract

$198,000

139 PROSPECT ST, Chestertown, MD 21620

3 Beds1 Bath1,200 SqFt

MLS# MDKE2006250

Listed by Redfin Corp

8886 GEORGETOWN RD, Chestertown, MD 21620

Price Dropped by $5K

$80,000

8886 GEORGETOWN RD, Chestertown, MD 21620

4.03 Acres

MLS# MDKE2006634

Listed by Samson Properties

Price Dropped by $20K

$59,000

SANDY BOTTOM RD, Chestertown, MD 21620

1.95 Acres

MLS# MDKE2006554

Listed by Village Real Estate Company LLC

Price Dropped by $15K

$59,999

228 MERGANSER DR, Chestertown, MD 21620

0.51 Acres

MLS# MDQA2017240

Listed by Benson & Mangold, LLC

Active

$1,920

104 MAPLE AVE #6, Chestertown, MD 21620

2 Beds2 Baths900 SqFt

MLS# MDKE2006408

Listed by Real Broker, LLC - Annapolis

Price Dropped by $119K

$1,350,000

104 MAPLE AVE, Chestertown, MD 21620

10,540 Sqft Lot

MLS# MDKE2006386

Listed by Real Broker, LLC - Annapolis

201 N LYNCHBURG ST, Chestertown, MD 21620

Price Dropped by $45K

$750,000

201 N LYNCHBURG ST, Chestertown, MD 21620

4,342 Sqft Lot

MLS# MDKE2006082

Listed by RE/MAX Associates-Hockessin

Price Dropped by $10K

$25,000

JOHNSONTOWN RD, Chestertown, MD 21620

0.9 Acres

MLS# MDKE2005550

Listed by Berkshire Hathaway HomeServices PenFed Realty

515 WASHINGTON AVE, Chestertown, MD 21620

Price Dropped by $104K

$795,000

515 WASHINGTON AVE, Chestertown, MD 21620

0.97 Acres Lot

MLS# MDKE2000776

Listed by EShore

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20 Properties Available In Chestertown

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