Name: Open House - 11AM-1PM
Start: 2026-04-25T11:00:00.000Z
End: 2026-04-25T13:00:00.000Z
Location: 108 OAK LEAF DR, Chestertown, MD 21620

104 FLYING CLOUD DR, Chestertown, MD 21620

1/31

Active

$399,900

5 Beds4 Baths2,535 SqFt

104 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006212

Listed by Real Broker, LLC

1/39

Open Sat 11AM-1PM

$299,500

2 Beds3 Baths1,867 SqFt

108 OAK LEAF DR, Chestertown, MD 21620

MLS# MDKE2006224

Listed by Doug Ashley Realtors, LLC

1/70

Open Sat 10AM-12PM

$519,999

2 Beds3 Baths2,100 SqFt

103 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005670

Listed by Coldwell Banker Chesapeake Real Estate Company

1/32

Active

$898,000

3 Beds4 Baths2,172 SqFt

226 S WATER ST, Chestertown, MD 21620

MLS# MDKE2006354

Listed by Gunther-McClary Real Estate

1/53

Active

$550,000

5 Beds4 Baths3,816 SqFt

103 SUTTON WAY, Chestertown, MD 21620

MLS# MDKE2006344

Listed by TTR Sotheby's International Realty

1/70

Active

$865,000

3 Beds4 Baths2,472 SqFt

106 QUEEN ST S, Chestertown, MD 21620

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

1/24

Active

$435,000

3 Beds2 Baths1,588 SqFt

201 BIRCH RUN RD, Chestertown, MD 21620

MLS# MDKE2006316

Listed by Coldwell Banker Chesapeake Real Estate Company

1/28

Active

$225,000

3 Beds1 Bath1,200 SqFt

139 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006250

Listed by Redfin Corp

1/3

Active

$389,000

3 Beds2 Baths2,055 SqFt

202 WALDO DR, Chestertown, MD 21620

MLS# MDKE2006260

Listed by Doug Ashley Realtors, LLC

109 S COLLEGE AVE, Chestertown, MD 21620

1/24

Active

$419,900

3 Beds3 Baths1,216 SqFt

109 S COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006040

Listed by Taylor Properties

1/40

Price Dropped by $10K

$299,900

3 Beds2 Baths1,152 SqFt

301 LINCOLN DR, Chestertown, MD 21620

MLS# MDKE2006170

Listed by Chesapeake Real Estate Associates, LLC

1/51

Price Dropped by $129K

$1,150,000

5 Beds3 Baths2,956 SqFt

231 RICHARD DR, Chestertown, MD 21620

MLS# MDKE2005900

Listed by TTR Sotheby's International Realty

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

1/73

Active

$1,600,000

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

118 LITTLE HARBOR WAY #202, Chestertown, MD 21620

1/56

Price Dropped by $20K

$675,000

3 Beds2 Baths1,600 SqFt

118 LITTLE HARBOR WAY #202, Chestertown, MD 21620

MLS# MDKE2005800

Listed by Benson & Mangold, LLC

1/44

Price Dropped by $5K

$339,000

4 Beds2 Baths1,325 SqFt

304 HADAWAY DR, Chestertown, MD 21620

MLS# MDKE2006116

Listed by Cummings & Co. Realtors

1/20

Price Dropped by $2K

$157,400

2 Beds1 Bath910 SqFt

132 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006110

Listed by ANR Realty, LLC

1/22

Price Dropped by $10K

$465,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

1/45

Price Dropped by $15K

$510,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

1/22

Active

$1,099,900

4 Beds4 Baths2,784 SqFt

#25 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005954

Listed by Gunther-McClary Real Estate

102 LITTLE HARBOR WAY, Chestertown, MD 21620

1/23

Active

$839,500

3 Beds3 Baths1,964 SqFt

102 LITTLE HARBOR WAY, Chestertown, MD 21620

MLS# MDKE2005950

Listed by Gunther-McClary Real Estate

54 Properties Available In Chestertown

104 FLYING CLOUD DR, Chestertown, MD 21620

108 OAK LEAF DR, Chestertown, MD 21620

103 LANDING LN, Chestertown, MD 21620

226 S WATER ST, Chestertown, MD 21620

103 SUTTON WAY, Chestertown, MD 21620

106 QUEEN ST S, Chestertown, MD 21620

201 BIRCH RUN RD, Chestertown, MD 21620

139 PROSPECT ST, Chestertown, MD 21620

202 WALDO DR, Chestertown, MD 21620

109 S COLLEGE AVE, Chestertown, MD 21620

301 LINCOLN DR, Chestertown, MD 21620

231 RICHARD DR, 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

118 LITTLE HARBOR WAY #202, Chestertown, MD 21620

304 HADAWAY DR, Chestertown, MD 21620

132 PROSPECT ST, Chestertown, MD 21620

110 TRAFFORD DR, Chestertown, MD 21620

218 CAMELOT DR, Chestertown, MD 21620

#25 LANDING LN, Chestertown, MD 21620

102 LITTLE HARBOR WAY, Chestertown, MD 21620

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