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

1/74

Open 7/25 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

201 N LYNCHBURG ST, Chestertown, MD 21620

1/13

New

$500,000

4,342 Sqft Lot

201 N LYNCHBURG ST, Chestertown, MD 21620

MLS# MDKE2006844

Listed by RE/MAX Associates-Hockessin

201 N LYNCHBURG ST #LOTS 4, 5, 6 & 7, Chestertown, MD 21620

1/3

New

$300,000

0.1 Acres

201 N LYNCHBURG ST #LOTS 4, 5, 6 & 7, Chestertown, MD 21620

MLS# MDKE2006846

Listed by RE/MAX Associates-Hockessin

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

1/24

Open Sun 10AM-11AM

$1,500

3 Beds1 Bath1,272 SqFt

2201 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2018024

Listed by Chesapeake Real Estate Associates, LLC

21324 PERSIMMON DR, Chestertown, MD 21620

1/21

Open 7/25 11AM-1PM

3D

$199,000

2 Beds1 Bath1,232 SqFt

21324 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2006816

Listed by Benson & Mangold, LLC

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

1/58

Active

$2,300,000

6,000 Sqft Lot

200-204 HIGH ST, Chestertown, MD 21620

MLS# MDKE2006810

Listed by Taylor Properties

1/13

Active

$60,000

0.5 Acres

233 MERGANSER DR, Chestertown, MD 21620

MLS# MDQA2017912

Listed by Long & Foster Real Estate, Inc.

903 WASHINGTON AVE #4, Chestertown, MD 21620

1/9

Active

$1,350

0.8 Acres Lot

903 WASHINGTON AVE #4, Chestertown, MD 21620

MLS# MDKE2006832

Listed by TTR Sotheby's International Realty

Active

$60,000

0.61 Acres

305 ROOSEVELT DR, Chestertown, MD 21620

MLS# MDKE2006830

Listed by Taylor Properties

1/12

Active

$1,920

2 Beds2 Baths900 SqFt

104 MAPLE AVE #4, Chestertown, MD 21620

MLS# MDKE2006806

Listed by Real Broker, LLC - Annapolis

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

1/19

Active

$2,000

3 Beds1 Bath1,122 SqFt

351 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2006734

Listed by Coldwell Banker Chesapeake Real Estate Company

1/6

Active

$2,500

3 Beds2 Baths1,232 SqFt

8890 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006738

Listed by RE/MAX Executive

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

1/39

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

1/28

Price Dropped by $25K

$299,900

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

114 Properties Available In Chestertown

8999 ORCHARD DR, Chestertown, MD 21620

201 N LYNCHBURG ST, Chestertown, MD 21620

201 N LYNCHBURG ST #LOTS 4, 5, 6 & 7, Chestertown, MD 21620

115 METCALF RD, Chestertown, MD 21620

2201 PONDTOWN RD, Chestertown, MD 21620

21324 PERSIMMON DR, Chestertown, MD 21620

200 MANOR AVE, Chestertown, MD 21620

121 METCALF RD, Chestertown, MD 21620

200-204 HIGH ST, Chestertown, MD 21620

233 MERGANSER DR, Chestertown, MD 21620

903 WASHINGTON AVE #4, Chestertown, MD 21620

305 ROOSEVELT DR, Chestertown, MD 21620

104 MAPLE AVE #4, 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

351 CALVERT ST, Chestertown, MD 21620

8890 FAIRLEE RD, Chestertown, MD 21620

25750 COLLINS AVE, Chestertown, MD 21620

101 S MILL ST, Chestertown, MD 21620

517 ROUND TOP RD, Chestertown, MD 21620

104 CONLEY DR, Chestertown, MD 21620

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