Name: Open House - 11AM-1PM
Start: 2026-07-25T11:00:00.000Z
End: 2026-07-25T13:00:00.000Z
Location: 8999 ORCHARD DR, Chestertown, MD 21620

105 N WATER ST #2, Chestertown, MD 21620

1/49

Under Contract

$475,000

2 Beds2 Baths1,011 SqFt

105 N WATER ST #2, Chestertown, MD 21620

MLS# MDKE2006680

Listed by Northrop Realty

1/74

Open Sat 11AM-1PM

$824,900

5 Beds4 Baths4,353 SqFt

8999 ORCHARD DR, Chestertown, MD 21620

MLS# MDKE2006786

Listed by Coldwell Banker Chesapeake Real Estate Company

1/10

Open Tue 5PM-7PM

$259,900

3 Beds2 Baths1,280 SqFt

115 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006826

Listed by Real Broker, LLC - Chester

21324 PERSIMMON DR, Chestertown, MD 21620

1/21

Open Sat 11AM-1PM

3D

$199,000

2 Beds1 Bath1,232 SqFt

21324 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2006816

Listed by Benson & Mangold, LLC

1/31

Open Sat 11AM-1PM

$898,000

3 Beds4 Baths2,172 SqFt

226 S WATER ST, Chestertown, MD 21620

MLS# MDKE2006354

Listed by Gunther-McClary Real Estate

1/92

Open 7/25 10AM-12PM

$829,000

3 Beds4 Baths2,472 SqFt

106 QUEEN ST S, Chestertown, MD 21620

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

7828 COUNTRY CLUB LN, Chestertown, MD 21620

1/68

Coming Soon

$799,000

3 Beds3 Baths2,857 SqFt

7828 COUNTRY CLUB LN, Chestertown, MD 21620

MLS# MDKE2006736

Listed by Cross Street Realtors LLC

1/41

Under Contract

$525,000

3 Beds3 Baths2,824 SqFt

PRESTON LANE, Chestertown, MD 21620

MLS# MDKE2006820

Listed by Shoreline Realty

1/5

Coming Soon

$240,000

3 Beds1 Bath1,140 SqFt

107 CONLEY DR, Chestertown, MD 21620

MLS# MDKE2006828

Listed by Benson & Mangold, LLC

1/36

Under Contract

$735,000

4 Beds3 Baths2,730 SqFt

210 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2006744

Listed by Coldwell Banker Chesapeake Real Estate Company

1/4

Coming Soon

$349,000

3 Beds2 Baths1,792 SqFt

123 HEATH RD, Chestertown, MD 21620

MLS# MDQA2017994

Listed by Chesapeake Real Estate Associates, LLC

1/22

Under Contract

$325,000

3 Beds3 Baths1,397 SqFt

109 CEDAR ST, Chestertown, MD 21620

MLS# MDKE2006792

Listed by TTR Sotheby's International Realty

1/34

New

$325,000

4 Beds2 Baths2,198 SqFt

200 MANOR AVE, Chestertown, MD 21620

MLS# MDKE2006808

Listed by TTR Sotheby's International Realty

1/10

Active

$264,900

3 Beds2 Baths3,920 Sqft Lot

121 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006678

Listed by Real Broker, LLC - Chester

10720 FORESTON RD, Chestertown, MD 21620

1/42

Active

$335,000

3 Beds2 Baths1,412 SqFt

10720 FORESTON RD, Chestertown, MD 21620

MLS# MDKE2006800

Listed by Compass

1/9

Active

$155,000

3 Beds2 Baths1,192 SqFt

409 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2006794

Listed by Chesapeake Real Estate Associates, LLC

7680 COUNTRY CLUB LN, Chestertown, MD 21620

1/43

Active

$885,000

5 Beds4 Baths2,639 SqFt

7680 COUNTRY CLUB LN, Chestertown, MD 21620

MLS# MDKE2006758

Listed by Gunther-McClary Real Estate

1/20

Active

$344,000

3 Beds2 Baths1,216 SqFt

9126 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006764

Listed by Chesapeake Real Estate Associates, LLC

896 WASHINGTON AVE, Chestertown, MD 21620

1/34

Active

$325,000

3 Beds1 Bath1,000 SqFt

896 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2006750

Listed by Coldwell Banker Chesapeake Real Estate Company

1/13

Under Contract

$615,000

4 Beds3 Baths4,536 SqFt

103 MAPLE AVE, Chestertown, MD 21620

MLS# MDKE2006676

Listed by Coldwell Banker Chesapeake Real Estate Company

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

1/88

Pending

$279,900

3 Beds2 Baths1,296 SqFt

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

MLS# MDKE2006682

Listed by Keller Williams Legacy

25750 COLLINS AVE, Chestertown, MD 21620

1/50

Active

$468,000

3 Beds2 Baths3,262 SqFt

25750 COLLINS AVE, Chestertown, MD 21620

MLS# MDKE2006546

Listed by Doug Ashley Realtors, LLC

1/46

Under Contract

$629,900

3 Beds2 Baths2,430 SqFt

201 RIVER RD, Chestertown, MD 21620

MLS# MDQA2017684

Listed by Coldwell Banker Chesapeake Real Estate Company

1/39

Active

$515,000

2 Beds3 Baths1,476 SqFt

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2006674

Listed by Coldwell Banker Chesapeake Real Estate Company

149 Properties Available In 21620

105 N WATER ST #2, Chestertown, MD 21620

8999 ORCHARD DR, Chestertown, MD 21620

115 METCALF RD, Chestertown, MD 21620

21324 PERSIMMON DR, Chestertown, MD 21620

226 S WATER ST, Chestertown, MD 21620

106 QUEEN ST S, Chestertown, MD 21620

7828 COUNTRY CLUB LN, Chestertown, MD 21620

PRESTON LANE, Chestertown, MD 21620

107 CONLEY DR, Chestertown, MD 21620

210 N QUEEN ST, Chestertown, MD 21620

123 HEATH RD, Chestertown, MD 21620

109 CEDAR ST, Chestertown, MD 21620

200 MANOR AVE, Chestertown, MD 21620

121 METCALF RD, Chestertown, MD 21620

10720 FORESTON RD, Chestertown, MD 21620

409 CALVERT ST, Chestertown, MD 21620

7680 COUNTRY CLUB LN, Chestertown, MD 21620

9126 FAIRLEE RD, Chestertown, MD 21620

896 WASHINGTON AVE, Chestertown, MD 21620

103 MAPLE AVE, Chestertown, MD 21620

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

25750 COLLINS AVE, Chestertown, MD 21620

201 RIVER RD, Chestertown, MD 21620

101 S MILL ST, Chestertown, MD 21620

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