Name: Open House - 10AM-12PM
Start: 2025-07-11T10:00:00.000Z
End: 2025-07-11T12:00:00.000Z
Location: 105 HIGH ST, Chestertown, MD 21620

1/48

Open Sat 10AM-12PM

$1,245,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

1/28

Price Dropped by $25K

$324,900

3 Beds1 Bath1,248 SqFt

517 ROUND TOP RD, Chestertown, MD 21620

MLS# MDQA2017680

Listed by Keller Williams Flagship

1/27

Price Dropped by $7K

$239,900

3 Beds2 Baths1,280 SqFt

104 CONLEY DR, Chestertown, MD 21620

MLS# MDKE2006686

Listed by Cummings & Co. Realtors

234 N COLLEGE AVE, Chestertown, MD 21620

1/3

Price Dropped by $20K

$100,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006670

Listed by Cummings & Co Realtors

1/6

Price Dropped by $10K

$89,900

3 Beds2 Baths2,210 SqFt

110 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006626

Listed by ANR Realty, LLC

1/54

Price Dropped by $20K

$429,900

4 Beds3 Baths2,160 SqFt

10781 FERMOY RD, Chestertown, MD 21620

MLS# MDKE2006640

Listed by Real Broker, LLC - Chester

1/15

Price Dropped by $25K

$399,900

2 Beds3 Baths1,518 SqFt

522 HIGH ST, Chestertown, MD 21620

MLS# MDKE2006614

Listed by Benson & Mangold, LLC

102 FLYING CLOUD DR, Chestertown, MD 21620

1/41

Price Dropped by $10K

$329,900

3 Beds3 Baths1,896 SqFt

102 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006586

Listed by Long & Foster Real Estate, Inc.

1/55

Price Dropped by $24K

3D

$365,000

3 Beds2 Baths1,120 SqFt

240 MERGANSER DR, Chestertown, MD 21620

MLS# MDQA2016900

Listed by Chesapeake Real Estate Associates, LLC

107 FLYING CLOUD DR, Chestertown, MD 21620

1/51

Price Dropped by $10K

$375,000

5 Beds4 Baths2,534 SqFt

107 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006510

Listed by CENTURY 21 New Millennium

214 SILVER HEEL RD, Chestertown, MD 21620

1/26

Price Dropped by $10K

$340,000

4 Beds3 Baths1,972 SqFt

214 SILVER HEEL RD, Chestertown, MD 21620

MLS# MDKE2006498

Listed by Cross Street Realtors LLC

1/18

Under Contract

$159,000

2 Beds2 Baths1,082 SqFt

144 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006494

Listed by Doug Ashley Realtors, LLC

1/56

Price Dropped by $5K

$519,900

3 Beds3 Baths2,268 SqFt

101 COLEMAN DR, Chestertown, MD 21620

MLS# MDQA2016624

Listed by Coldwell Banker Chesapeake Real Estate Company

1/28

Under Contract

$198,000

3 Beds1 Bath1,200 SqFt

139 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006250

Listed by Redfin Corp

8276 BROAD NECK RD, Chestertown, MD 21620

1/82

Price Dropped by $100K

$1,395,000

4 Beds4 Baths3,383 SqFt

8276 BROAD NECK RD, Chestertown, MD 21620

MLS# MDKE2006216

Listed by Coldwell Banker Chesapeake Real Estate Company

222 MOUNT VERNON AVE, Chestertown, MD 21620

1/29

Price Dropped by $10K

$419,999

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005876

Listed by Long & Foster Real Estate, Inc.

8886 GEORGETOWN RD, Chestertown, MD 21620

1/3

Price Dropped by $5K

$80,000

4.03 Acres

8886 GEORGETOWN RD, Chestertown, MD 21620

MLS# MDKE2006634

Listed by Samson Properties

1/14

Active

$2,400

4 Beds2 Baths1,476 SqFt

1010 TWIN CT, Chestertown, MD 21620

MLS# MDKE2006610

Listed by Kevin Dey Realty

1/6

Price Dropped by $20K

$59,000

1.95 Acres

SANDY BOTTOM RD, Chestertown, MD 21620

MLS# MDKE2006554

Listed by Village Real Estate Company LLC

1/13

Price Dropped by $15K

$59,999

0.51 Acres

228 MERGANSER DR, Chestertown, MD 21620

MLS# MDQA2017240

Listed by Benson & Mangold, LLC

1/67

Price Dropped by $119K

$1,350,000

10,540 Sqft Lot

104 MAPLE AVE, Chestertown, MD 21620

MLS# MDKE2006386

Listed by Real Broker, LLC - Annapolis

201 N LYNCHBURG ST, Chestertown, MD 21620

1/13

Price Dropped by $45K

$750,000

4,342 Sqft Lot

201 N LYNCHBURG ST, Chestertown, MD 21620

MLS# MDKE2006082

Listed by RE/MAX Associates-Hockessin

1/16

Price Dropped by $10K

$25,000

0.9 Acres

JOHNSONTOWN RD, Chestertown, MD 21620

MLS# MDKE2005550

Listed by Berkshire Hathaway HomeServices PenFed Realty

515 WASHINGTON AVE, Chestertown, MD 21620

1/4

Price Dropped by $104K

$795,000

0.97 Acres Lot

515 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2000776

Listed by EShore

24 Properties Available In Chestertown

105 HIGH ST, Chestertown, MD 21620

517 ROUND TOP RD, Chestertown, MD 21620

104 CONLEY DR, Chestertown, MD 21620

234 N COLLEGE AVE, Chestertown, MD 21620

110 PROSPECT ST, Chestertown, MD 21620

10781 FERMOY RD, Chestertown, MD 21620

522 HIGH ST, Chestertown, MD 21620

102 FLYING CLOUD DR, Chestertown, MD 21620

240 MERGANSER DR, Chestertown, MD 21620

107 FLYING CLOUD DR, Chestertown, MD 21620

214 SILVER HEEL RD, Chestertown, MD 21620

144 PROSPECT ST, Chestertown, MD 21620

101 COLEMAN DR, Chestertown, MD 21620

139 PROSPECT ST, Chestertown, MD 21620

8276 BROAD NECK RD, Chestertown, MD 21620

222 MOUNT VERNON AVE, Chestertown, MD 21620

8886 GEORGETOWN RD, Chestertown, MD 21620

1010 TWIN CT, Chestertown, MD 21620

SANDY BOTTOM RD, Chestertown, MD 21620

228 MERGANSER DR, Chestertown, MD 21620

104 MAPLE AVE, Chestertown, MD 21620

201 N LYNCHBURG ST, Chestertown, MD 21620

JOHNSONTOWN RD, Chestertown, MD 21620

515 WASHINGTON AVE, Chestertown, MD 21620

explore listings in Chestertown