Name: Open House - 10AM-12PM
Start: 2025-10-03T10:00:00.000Z
End: 2025-10-03T12:00:00.000Z
Location: 105 HIGH ST, Chestertown, MD 21620

1/44

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

329 UNION CHURCH RD, Chestertown, MD 21620

1/142

Under Contract

$568,900

4 Beds3 Baths2,464 SqFt

329 UNION CHURCH RD, Chestertown, MD 21620

MLS# MDQA2018610

Listed by Chesapeake Real Estate Associates, LLC

22974 BAY SHORE RD, Chestertown, MD 21620

1/22

Active

3D

$329,900

2 Beds2 Baths1,440 SqFt

22974 BAY SHORE RD, Chestertown, MD 21620

MLS# MDKE2007106

Listed by Benson & Mangold, LLC

1/30

Price Dropped by $5K

$295,000

3 Beds1 Bath960 SqFt

104 LINCOLN DR, Chestertown, MD 21620

MLS# MDKE2007032

Listed by RE/MAX Executive

1/23

Active

$229,000

3 Beds1 Bath936 SqFt

7415 WILKINS LN, Chestertown, MD 21620

MLS# MDKE2007030

Listed by Doug Ashley Realtors, LLC

1/32

Under Contract

$304,000

3 Beds2 Baths1,232 SqFt

7464 SHORTALL ST, Chestertown, MD 21620

MLS# MDKE2006988

Listed by Chesapeake Real Estate Associates, LLC

1/52

Active

$750,000

3 Beds3 Baths2,176 SqFt

216 BIRCH RUN RD, Chestertown, MD 21620

MLS# MDKE2006896

Listed by TTR Sotheby's International Realty

1/23

Active

$299,900

3 Beds1 Bath1,056 SqFt

124 WILTON RD, Chestertown, MD 21620

MLS# MDQA2018272

Listed by Doug Ashley Realtors, LLC

7982 RADCLIFFE RD, Chestertown, MD 21620

1/37

Price Dropped by $56K

$399,000

2 Beds2 Baths1,904 SqFt

7982 RADCLIFFE RD, Chestertown, MD 21620

MLS# MDKE2006950

Listed by Doug Ashley Realtors, LLC

21324 PERSIMMON DR, Chestertown, MD 21620

1/21

Under Contract

3D

$179,900

2 Beds1 Bath1,232 SqFt

21324 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2006816

Listed by Benson & Mangold, LLC

1/34

Active

$325,000

4 Beds2 Baths2,198 SqFt

200 MANOR AVE, Chestertown, MD 21620

MLS# MDKE2006808

Listed by TTR Sotheby's International Realty

8796 MARYLAND PKWY, Chestertown, MD 21620

1/60

Price Dropped by $155K

$1,495,000

9 Beds7 Baths4,776 SqFt

8796 MARYLAND PKWY, Chestertown, MD 21620

MLS# MDKE2006596

Listed by Coldwell Banker Chesapeake Real Estate Company

1/39

Pending

$372,000

4 Beds2 Baths1,277 SqFt

213 BYFORD DR, Chestertown, MD 21620

MLS# MDKE2006026

Listed by Doug Ashley Realtors, LLC

956 WASHINGTON AVE, Chestertown, MD 21620

1/29

Active

$275,000

3 Beds1 Bath1,248 SqFt

956 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2006394

Listed by Doug Ashley Realtors, LLC

1/53

Price Dropped by $41K

$509,000

5 Beds4 Baths3,816 SqFt

103 SUTTON WAY, Chestertown, MD 21620

MLS# MDKE2006344

Listed by TTR Sotheby's International Realty

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

1/73

Price Dropped by $100K

$1,500,000

7 Beds5 Baths5,400 SqFt

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

MLS# MDKE2006158

Listed by TTR Sotheby's International Realty

117 WATER ST N #1A, Chestertown, MD 21620

1/46

Active

$685,000

3 Beds3 Baths3,000 SqFt

117 WATER ST N #1A, Chestertown, MD 21620

MLS# MDKE2006162

Listed by TTR Sotheby's International Realty

117 WATER ST N #2A, Chestertown, MD 21620

1/24

Active

$375,000

2 Beds1 Bath787 SqFt

117 WATER ST N #2A, Chestertown, MD 21620

MLS# MDKE2006166

Listed by TTR Sotheby's International Realty

117 WATER ST N #2B, Chestertown, MD 21620

1/23

Active

$350,000

1 Bed1 Bath850 SqFt

117 WATER ST N #2B, Chestertown, MD 21620

MLS# MDKE2006168

Listed by TTR Sotheby's International Realty

117 WATER ST N #1B, Chestertown, MD 21620

1/20

Active

$200,000

1 Bed1 Bath700 SqFt

117 WATER ST N #1B, Chestertown, MD 21620

MLS# MDKE2006164

Listed by TTR Sotheby's International Realty

204 DOUBLE CREEK RD, Chestertown, MD 21620

1/38

Under Contract

$545,000

3 Beds3 Baths2,927 SqFt

204 DOUBLE CREEK RD, Chestertown, MD 21620

MLS# MDQA2015996

Listed by Doug Ashley Realtors, LLC

LITTLE HARBOR WAY #1, Chestertown, MD 21620

1/25

Active

$1,459,000

3 Beds3 Baths2,231 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2005768

Listed by Gunther-McClary Real Estate

1/66

Under Contract

$489,900

4 Beds3 Baths2,524 SqFt

8620 PARK DR, Chestertown, MD 21620

MLS# MDKE2005850

Listed by Doug Ashley Realtors, LLC

25416 COMMERCE LN, Chestertown, MD 21620

1/39

Active

$1,100,000

2.03 Acres Lot

25416 COMMERCE LN, Chestertown, MD 21620

MLS# MDKE2006664

Listed by Coldwell Banker Chesapeake Real Estate Company

24 Properties Available In Chestertown

105 HIGH ST, Chestertown, MD 21620

329 UNION CHURCH RD, Chestertown, MD 21620

22974 BAY SHORE RD, Chestertown, MD 21620

104 LINCOLN DR, Chestertown, MD 21620

7415 WILKINS LN, Chestertown, MD 21620

7464 SHORTALL ST, Chestertown, MD 21620

216 BIRCH RUN RD, Chestertown, MD 21620

124 WILTON RD, Chestertown, MD 21620

7982 RADCLIFFE RD, Chestertown, MD 21620

21324 PERSIMMON DR, Chestertown, MD 21620

200 MANOR AVE, Chestertown, MD 21620

8796 MARYLAND PKWY, Chestertown, MD 21620

213 BYFORD DR, Chestertown, MD 21620

956 WASHINGTON AVE, Chestertown, MD 21620

103 SUTTON WAY, Chestertown, MD 21620

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

117 WATER ST N #1A, Chestertown, MD 21620

117 WATER ST N #2A, Chestertown, MD 21620

117 WATER ST N #2B, Chestertown, MD 21620

117 WATER ST N #1B, Chestertown, MD 21620

204 DOUBLE CREEK RD, Chestertown, MD 21620

LITTLE HARBOR WAY #1, Chestertown, MD 21620

8620 PARK DR, Chestertown, MD 21620

25416 COMMERCE LN, Chestertown, MD 21620

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