Name: Open House - 11AM-1PM
Start: 2026-06-20T11:00:00.000Z
End: 2026-06-20T13:00:00.000Z
Location: 101 S MILL ST, Chestertown, MD 21620

1/13

Coming Soon

$615,000

4 Beds3 Baths4,536 SqFt

103 MAPLE AVE, Chestertown, MD 21620

MLS# MDKE2006676

Listed by Coldwell Banker Chesapeake Real Estate Company

202 ROYSTON SHORES RD, Chestertown, MD 21620

1/72

New

$1,200,000

4 Beds3 Baths2,292 SqFt

202 ROYSTON SHORES RD, Chestertown, MD 21620

MLS# MDQA2017462

Listed by Cross Street Realtors LLC

1/25

Under Contract

$325,000

3 Beds2 Baths1,404 SqFt

10572 WATONGA RD, Chestertown, MD 21620

MLS# MDKE2006644

Listed by Serhant

1/39

Coming Soon

$515,000

2 Beds3 Baths1,476 SqFt

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2006674

Listed by Coldwell Banker Chesapeake Real Estate Company

1/26

New

$284,900

3 Beds3 Baths1,900 SqFt

104 ACORN DR, Chestertown, MD 21620

MLS# MDKE2006668

Listed by Cross Street Realtors LLC

23264 CLARISSA RD, Chestertown, MD 21620

1/30

New

$365,000

3 Beds2 Baths1,248 SqFt

23264 CLARISSA RD, Chestertown, MD 21620

MLS# MDKE2006096

Listed by TTR Sotheby's International Realty

234 N COLLEGE AVE, Chestertown, MD 21620

1/3

New

$120,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006670

Listed by Cummings & Co Realtors

25750 COLLINS AVE, Chestertown, MD 21620

1/50

Coming Soon

$468,000

3 Beds2 Baths3,262 SqFt

25750 COLLINS AVE, Chestertown, MD 21620

MLS# MDKE2006546

Listed by Doug Ashley Realtors, LLC

1/7

New

$75,000

2.2 Acres

FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006672

Listed by RE/MAX Chesapeake

25416 COMMERCE LN, Chestertown, MD 21620

1/39

New

$1,100,000

2.03 Acres Lot

25416 COMMERCE LN, Chestertown, MD 21620

MLS# MDKE2006664

Listed by Coldwell Banker Chesapeake Real Estate Company

1/6

New

$119,900

3 Beds2 Baths2,210 SqFt

110 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006626

Listed by ANR Realty, LLC

8796 MARYLAND PKWY, Chestertown, MD 21620

1/60

New

$1,650,000

9 Beds7 Baths4,776 SqFt

8796 MARYLAND PKWY, Chestertown, MD 21620

MLS# MDKE2006596

Listed by Coldwell Banker Chesapeake Real Estate Company

1/11

Active

$265,000

3 Beds1 Bath1,967 SqFt

1904 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2017480

Listed by Keller Williams Flagship

1/4

Active

$110,000

1.93 Acres

1906 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2017476

Listed by Keller Williams Flagship

1/68

Pending

$869,900

4 Beds3 Baths2,877 SqFt

205 RIVER RD, Chestertown, MD 21620

MLS# MDQA2017560

Listed by Clark & Co Realty, LLC

222 MOUNT VERNON AVE, Chestertown, MD 21620

1/29

Active

$2,950

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2006624

Listed by Long & Foster Real Estate, Inc.

1/54

Active

$449,900

4 Beds3 Baths2,160 SqFt

10781 FERMOY RD, Chestertown, MD 21620

MLS# MDKE2006640

Listed by Real Broker, LLC - Chester

21172 WYOMING AVE, Chestertown, MD 21620

Active

$200,000

4 Beds1 Bath2,920 SqFt

21172 WYOMING AVE, Chestertown, MD 21620

MLS# MDKE2006642

Listed by Blue Star Real Estate, LLC

1/39

Active

$380,000

4 Beds2 Baths1,277 SqFt

213 BYFORD DR, Chestertown, MD 21620

MLS# MDKE2006026

Listed by Doug Ashley Realtors, LLC

8886 GEORGETOWN RD, Chestertown, MD 21620

1/3

Price Dropped by $5K

$80,000

4.03 Acres

8886 GEORGETOWN RD, Chestertown, MD 21620

MLS# MDKE2006634

Listed by Samson Properties

1/21

Under Contract

$215,000

3 Beds1 Bath1,373 SqFt

100 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006544

Listed by Real Broker, LLC - Chester

1/70

Active

$3,000,000

3 Beds4 Baths3,142 SqFt

25440 LEARMAN RD, Chestertown, MD 21620

MLS# MDKE2006468

Listed by TTR Sotheby's International Realty

22470 FAIRGALE FARM LN, Chestertown, MD 21620

1/49

Active

$1,450,000

4 Beds5 Baths4,257 SqFt

22470 FAIRGALE FARM LN, Chestertown, MD 21620

MLS# MDKE2006502

Listed by Gunther-McClary Real Estate

1/14

Active

$2,400

4 Beds2 Baths1,476 SqFt

1010 TWIN CT, Chestertown, MD 21620

MLS# MDKE2006610

Listed by Kevin Dey Realty

154 Properties Available In 21620

103 MAPLE AVE, Chestertown, MD 21620

202 ROYSTON SHORES RD, Chestertown, MD 21620

10572 WATONGA RD, Chestertown, MD 21620

101 S MILL ST, Chestertown, MD 21620

104 ACORN DR, Chestertown, MD 21620

23264 CLARISSA RD, Chestertown, MD 21620

234 N COLLEGE AVE, Chestertown, MD 21620

25750 COLLINS AVE, Chestertown, MD 21620

FAIRLEE RD, Chestertown, MD 21620

25416 COMMERCE LN, Chestertown, MD 21620

110 PROSPECT ST, Chestertown, MD 21620

8796 MARYLAND PKWY, Chestertown, MD 21620

1904 PONDTOWN RD, Chestertown, MD 21620

1906 PONDTOWN RD, Chestertown, MD 21620

205 RIVER RD, Chestertown, MD 21620

222 MOUNT VERNON AVE, Chestertown, MD 21620

10781 FERMOY RD, Chestertown, MD 21620

21172 WYOMING AVE, Chestertown, MD 21620

213 BYFORD DR, Chestertown, MD 21620

8886 GEORGETOWN RD, Chestertown, MD 21620

100 PROSPECT ST, Chestertown, MD 21620

25440 LEARMAN RD, Chestertown, MD 21620

22470 FAIRGALE FARM LN, Chestertown, MD 21620

1010 TWIN CT, Chestertown, MD 21620

explore listings in 21620