16 Properties Available

Name: Open House - 11AM-1PM
Start: 2025-05-25T11:00:00.000Z
End: 2025-05-25T13:00:00.000Z
Location: 105 HIGH ST, Chestertown, MD 21620

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The average price in the selected areas has remained stable. Learn more

1/52 52

5 Beds 5 Baths 3,243 SqFt

$1,395,500
Open Sun 11AM-1PM

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005002

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home
1/32 32

2 Beds 2 Baths 1,080 SqFt

$395,000
New

420 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005174

Listed by Doug Ashley Realtors, LLC

Single Family Home
1/63 63

4 Beds 2 Baths 3,050 SqFt

$529,000
Pending

107 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2005108

Listed by Doug Ashley Realtors, LLC

Single Family Home
1/3 3

4 Beds 2 Baths 1,656 SqFt

$375,000
Coming Soon

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005188

Listed by Cross Street Realtors LLC

Single Family Home
1/20 20

3 Beds 3 Baths 2,240 SqFt

$150,000
Pending

508 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005160

Listed by Coldwell Banker Realty

Single Family Home, Townhouse
1/9 9

1 Bed 1 Bath 882 SqFt

$220,000
Under Contract

619 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005050

Listed by Cross Street Realtors LLC

Single Family Home
1/38 38

3 Beds 3 Baths 2,296 SqFt

$598,500
Under Contract

129 N QUEEN ST N, Chestertown, MD 21620

MLS# MDKE2004970

Listed by Select Land & Homes, LLC

Single Family Home
1/22 22

2 Beds 3 Baths 1,476 SqFt

$485,000
Under Contract

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2004984

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home, Townhouse
1/22 22

3 Beds 4 Baths 3,782 Sqft Lot

$998,000
Active

226 S WATER ST, Chestertown, MD 21620

MLS# MDKE2004940

Listed by Gunther-McClary Real Estate

Townhouse
1/28 28

3 Beds 3 Baths

$725,000
Active

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

MLS# MDKE2004206

Listed by Gunther-McClary Real Estate

Single Family Home, Condo
1/33 33

7 Beds 4 Baths 3,664 SqFt

$395,000
Price Dropped by $30K

349 HIGH ST, Chestertown, MD 21620

MLS# MDKE2004076

Listed by Coldwell Banker Chesapeake Real Estate Company

Townhouse
1/28 28

2 Beds 1 Bath 787 SqFt

$399,000
Active

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

MLS# MDKE2003742

Listed by Gunther-McClary Real Estate

Condo
1/24 24

1 Bed 1 Bath 652 SqFt

$299,900
Price Dropped by $48K

117 N WATER ST N #3B, Chestertown, MD 21620

MLS# MDKE2003722

Listed by Gunther-McClary Real Estate

Condo
1/23 23

3 Beds 4 Baths 2,592 Sqft Lot

$898,000
Price Dropped by $52K

228 S WATER ST, Chestertown, MD 21620

MLS# MDKE2001612

Listed by Gunther-McClary Real Estate

Townhouse
1/11 11

4 Beds 2 Baths 1,106 SqFt

$1,850
New

511 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005190

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home
1/9 9

1.56 Acres

$1,150,000
Price Dropped by $100K

206 CANNON ST, Chestertown, MD 21620

MLS# MDKE2003620

Listed by Benson & Mangold, LLC

Vacant Land

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16 Properties

16 Properties Available

Default

List

The average price in the selected areas has remained stable. Learn more

1/52 52

5 Beds 5 Baths 3,243 SqFt

$1,395,500
Open Sun 11AM-1PM

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005002

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home
1/32 32

2 Beds 2 Baths 1,080 SqFt

$395,000
New

420 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005174

Listed by Doug Ashley Realtors, LLC

Single Family Home
1/63 63

4 Beds 2 Baths 3,050 SqFt

$529,000
Pending

107 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2005108

Listed by Doug Ashley Realtors, LLC

Single Family Home
1/3 3

4 Beds 2 Baths 1,656 SqFt

$375,000
Coming Soon

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005188

Listed by Cross Street Realtors LLC

Single Family Home
1/20 20

3 Beds 3 Baths 2,240 SqFt

$150,000
Pending

508 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005160

Listed by Coldwell Banker Realty

Single Family Home, Townhouse
1/9 9

1 Bed 1 Bath 882 SqFt

$220,000
Under Contract

619 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005050

Listed by Cross Street Realtors LLC

Single Family Home
1/38 38

3 Beds 3 Baths 2,296 SqFt

$598,500
Under Contract

129 N QUEEN ST N, Chestertown, MD 21620

MLS# MDKE2004970

Listed by Select Land & Homes, LLC

Single Family Home
1/22 22

2 Beds 3 Baths 1,476 SqFt

$485,000
Under Contract

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2004984

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home, Townhouse
1/22 22

3 Beds 4 Baths 3,782 Sqft Lot

$998,000
Active

226 S WATER ST, Chestertown, MD 21620

MLS# MDKE2004940

Listed by Gunther-McClary Real Estate

Townhouse
1/28 28

3 Beds 3 Baths

$725,000
Active

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

MLS# MDKE2004206

Listed by Gunther-McClary Real Estate

Single Family Home, Condo
1/33 33

7 Beds 4 Baths 3,664 SqFt

$395,000
Price Dropped by $30K

349 HIGH ST, Chestertown, MD 21620

MLS# MDKE2004076

Listed by Coldwell Banker Chesapeake Real Estate Company

Townhouse
1/28 28

2 Beds 1 Bath 787 SqFt

$399,000
Active

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

MLS# MDKE2003742

Listed by Gunther-McClary Real Estate

Condo
1/24 24

1 Bed 1 Bath 652 SqFt

$299,900
Price Dropped by $48K

117 N WATER ST N #3B, Chestertown, MD 21620

MLS# MDKE2003722

Listed by Gunther-McClary Real Estate

Condo
1/23 23

3 Beds 4 Baths 2,592 Sqft Lot

$898,000
Price Dropped by $52K

228 S WATER ST, Chestertown, MD 21620

MLS# MDKE2001612

Listed by Gunther-McClary Real Estate

Townhouse
1/11 11

4 Beds 2 Baths 1,106 SqFt

$1,850
New

511 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005190

Listed by Coldwell Banker Chesapeake Real Estate Company

Single Family Home
1/9 9

1.56 Acres

$1,150,000
Price Dropped by $100K

206 CANNON ST, Chestertown, MD 21620

MLS# MDKE2003620

Listed by Benson & Mangold, LLC

Vacant Land