Name: Open House - 11:00AM-1:00PM
Start: 2026-10-24T11:00:00
End: 2026-10-24T13:00:00
Location: 8986 ORCHARD DR, Chestertown, MD 21620

1/54

Open 10/24 11AM-1PM

3D

$679,900

3 Beds4 Baths3,228 SqFt

8986 ORCHARD DR, Chestertown, MD 21620

MLS# MDKE2007150

Listed by Benson & Mangold, LLC

24607 CHESTERTOWN RD, Chestertown, MD 21620

1/28

Open Sat 10AM-12PM

$365,000

3 Beds3 Baths2,294 SqFt

24607 CHESTERTOWN RD, Chestertown, MD 21620

MLS# MDKE2007204

Listed by Coldwell Banker Chesapeake Real Estate Company

10 CEDAR CHASE CT, Chestertown, MD 21620

1/39

Open Sat 11AM-1PM

$495,000

3 Beds3 Baths1,656 SqFt

10 CEDAR CHASE CT, Chestertown, MD 21620

MLS# MDKE2007124

Listed by Cross Street Realtors LLC

1/68

Open 10/24 1PM-3PM

$425,000

4 Beds3 Baths3,165 SqFt

106 HARLAN LOOP, Chestertown, MD 21620

MLS# MDKE2007190

Listed by Douglas Realty LLC

1/16

Open Thu 5:30PM-6:30PM

$259,900

3 Beds3 Baths1,280 SqFt

103 METCALF RD, Chestertown, MD 21620

MLS# MDKE2007148

Listed by Real Broker, LLC - Chester

7680 COUNTRY CLUB LN, Chestertown, MD 21620

1/43

Open 11/1 11AM-2PM

$825,000

5 Beds4 Baths2,639 SqFt

7680 COUNTRY CLUB LN, Chestertown, MD 21620

MLS# MDKE2006758

Listed by Gunther-McClary Real Estate

1/31

Open Sat 11AM-4PM

$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 11/1 1PM-3PM

$829,000

3 Beds4 Baths2,472 SqFt

106 QUEEN ST S, Chestertown, MD 21620

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

1/46

Open 11/1 11AM-1PM

$1,195,000

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

8901 S BAYVIEW DR, Chestertown, MD 21620

1/51

New

$525,000

3 Beds3 Baths1,833 SqFt

8901 S BAYVIEW DR, Chestertown, MD 21620

MLS# MDKE2007118

Listed by Doug Ashley Realtors, LLC

1/22

Under Contract

$238,000

3 Beds1 Bath1,008 SqFt

10484 COGAR RD, Chestertown, MD 21620

MLS# MDKE2007056

Listed by LPT Realty, LLC

21338 VIRGINIA AVE, Chestertown, MD 21620

1/47

New

$400,000

2 Beds2 Baths1,000 SqFt

21338 VIRGINIA AVE, Chestertown, MD 21620

MLS# MDKE2007194

Listed by Doug Ashley Realtors, LLC

1/28

Under Contract

$296,000

3 Beds2 Baths1,248 SqFt

203 MANOR AVE, Chestertown, MD 21620

MLS# MDKE2007180

Listed by Coldwell Banker Chesapeake Real Estate Company

1/27

Under Contract

$565,000

2 Beds2 Baths1,306 SqFt

204 S WATER ST, Chestertown, MD 21620

MLS# MDKE2007184

Listed by Coldwell Banker Chesapeake Real Estate Company

1/41

Active

$325,000

5 Beds2 Baths1,802 SqFt

234 N KENT ST, Chestertown, MD 21620

MLS# MDKE2007128

Listed by TTR Sotheby's International Realty

212 WASHINGTON AVE, Chestertown, MD 21620

1/39

Active

$675,000

5 Beds3 Baths2,838 SqFt

212 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2007016

Listed by Coldwell Banker Chesapeake Real Estate Company

LITTLE HARBOR WAY #1, Chestertown, MD 21620

1/29

Active

$1,800,000

4 Beds4 Baths3,540 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2007154

Listed by Gunther-McClary Real Estate

8820 CUMBERLAND ST, Chestertown, MD 21620

1/24

Active

3D

$312,500

3 Beds2 Baths1,080 SqFt

8820 CUMBERLAND ST, Chestertown, MD 21620

MLS# MDKE2007156

Listed by RE/MAX Advantage Realty

329 UNION CHURCH RD, Chestertown, MD 21620

1/142

Price Dropped by $19K

$549,900

4 Beds3 Baths2,464 SqFt

329 UNION CHURCH RD, Chestertown, MD 21620

MLS# MDQA2018610

Listed by Chesapeake Real Estate Associates, LLC

105 N WATER ST #3, Chestertown, MD 21620

1/51

Price Dropped by $30K

$459,000

2 Beds2 Baths1,098 SqFt

105 N WATER ST #3, Chestertown, MD 21620

MLS# MDKE2007112

Listed by Coldwell Banker Chesapeake Real Estate Company

7712 WATERVIEW LN, Chestertown, MD 21620

1/95

Pending

$659,999

3 Beds4 Baths2,716 SqFt

7712 WATERVIEW LN, Chestertown, MD 21620

MLS# MDKE2007104

Listed by Coldwell Banker Chesapeake Real Estate Company

6324 QUAKER NECK RD, Chestertown, MD 21620

1/56

Active

$2,895,000

5 Beds4 Baths5,938 SqFt

6324 QUAKER NECK RD, Chestertown, MD 21620

MLS# MDKE2007098

Listed by Cross Street Realtors LLC

223 MOUNT VERNON AVE, Chestertown, MD 21620

1/23

Pending

$200,000

4 Beds1 Bath1,816 SqFt

223 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2007080

Listed by Chesapeake Real Estate Associates, LLC

22974 BAY SHORE RD, Chestertown, MD 21620

1/22

Price Dropped by $14K

3D

$315,000

2 Beds2 Baths1,440 SqFt

22974 BAY SHORE RD, Chestertown, MD 21620

MLS# MDKE2007106

Listed by Benson & Mangold, LLC

141 Properties Available

8986 ORCHARD DR, Chestertown, MD 21620

24607 CHESTERTOWN RD, Chestertown, MD 21620

10 CEDAR CHASE CT, Chestertown, MD 21620

106 HARLAN LOOP, Chestertown, MD 21620

103 METCALF RD, Chestertown, MD 21620

7680 COUNTRY CLUB LN, Chestertown, MD 21620

226 S WATER ST, Chestertown, MD 21620

106 QUEEN ST S, Chestertown, MD 21620

105 HIGH ST, Chestertown, MD 21620

8901 S BAYVIEW DR, Chestertown, MD 21620

10484 COGAR RD, Chestertown, MD 21620

21338 VIRGINIA AVE, Chestertown, MD 21620

203 MANOR AVE, Chestertown, MD 21620

204 S WATER ST, Chestertown, MD 21620

234 N KENT ST, Chestertown, MD 21620

212 WASHINGTON AVE, Chestertown, MD 21620

LITTLE HARBOR WAY #1, Chestertown, MD 21620

8820 CUMBERLAND ST, Chestertown, MD 21620

329 UNION CHURCH RD, Chestertown, MD 21620

105 N WATER ST #3, Chestertown, MD 21620

7712 WATERVIEW LN, Chestertown, MD 21620

6324 QUAKER NECK RD, Chestertown, MD 21620

223 MOUNT VERNON AVE, Chestertown, MD 21620

22974 BAY SHORE RD, Chestertown, MD 21620

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