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Chestertown, MD
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119 Properties Available

119 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Newest Listings
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  • Baths (Most)
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105 PEARL CREEK LN, Chestertown, MD 21620
1/73
Open Sat 10AM-12PM

$449,000

3 Beds3 Baths1,961 SqFt

105 PEARL CREEK LN, Chestertown, MD 21620

MLS# MDQA2015962

Listed by Taylor Properties

Bright MLS (BMLS)
109 WATER ST, Chestertown, MD 21620
1/69
Under Contract

$650,000

4 Beds2 Baths2,064 SqFt

109 WATER ST, Chestertown, MD 21620

MLS# MDKE2006064

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
118 LITTLE HARBOR WAY #201, Chestertown, MD 21620
1/34
Coming Soon

$675,000

2 Beds3 Baths1,600 SqFt

118 LITTLE HARBOR WAY #201, Chestertown, MD 21620

MLS# MDKE2006084

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
112 METCALF RD, Chestertown, MD 21620
1/4
Coming Soon

$249,500

3 Beds2 Baths1,280 SqFt

112 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006090

Listed by Rosendale Realty

Bright MLS (BMLS)
23055 OLD FAIRLEE RD, Chestertown, MD 21620
Coming Soon

$330,000

3 Beds2 Baths1,628 SqFt

23055 OLD FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006062

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
129 PARMA RD, Chestertown, MD 21620
1/41
Active

$330,000

3 Beds2 Baths1,170 SqFt

129 PARMA RD, Chestertown, MD 21620

MLS# MDQA2015862

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
24339 CHESTERTOWN RD, Chestertown, MD 21620
1/36
Under Contract

$269,000

3 Beds1 Bath960 SqFt

24339 CHESTERTOWN RD, Chestertown, MD 21620

MLS# MDKE2006054

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
206 S WATER ST, Chestertown, MD 21620
1/45
Active

$585,000

4 Beds4 Baths2,008 SqFt

206 S WATER ST, Chestertown, MD 21620

MLS# MDKE2006058

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
10800 CLIFF RD, Chestertown, MD 21620
1/94
Pending

$1,495,000

5 Beds4 Baths5,241 SqFt

10800 CLIFF RD, Chestertown, MD 21620

MLS# MDKE2005898

Listed by Taylor Properties

Bright MLS (BMLS)
141 PROSPECT ST, Chestertown, MD 21620
1/16
Active

$165,000

4 Beds2 Baths1,156 SqFt

141 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006036

Listed by Taylor Properties

Bright MLS (BMLS)
201 GREENWOOD AVE, Chestertown, MD 21620
1/62
Under Contract

$495,000

4 Beds3 Baths3,984 SqFt

201 GREENWOOD AVE, Chestertown, MD 21620

MLS# MDKE2006030

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
24775 LANGFORD RD, Chestertown, MD 21620
1/36
Active

$319,900

3 Beds1 Bath1,008 SqFt

24775 LANGFORD RD, Chestertown, MD 21620

MLS# MDKE2005992

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
6746 QUAKER NECK RD, Chestertown, MD 21620
1/50
Active

$445,000

5 Beds3 Baths3,371 SqFt

6746 QUAKER NECK RD, Chestertown, MD 21620

MLS# MDKE2006014

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
104 IRIS RD, Chestertown, MD 21620
1/36
Under Contract

$379,000

3 Beds2 Baths1,700 SqFt

104 IRIS RD, Chestertown, MD 21620

MLS# MDQA2015798

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
110 TRAFFORD DR, Chestertown, MD 21620
1/26
Active

$475,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
22481 GOOSE HOLLOW DR, Chestertown, MD 21620
1/18
Price Dropped by $29K

$379,500

3 Beds2 Baths1,296 SqFt

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

MLS# MDKE2006012

Listed by Realty Mark Cityscape

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/45
Active

$525,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
303 CEDAR ST, Chestertown, MD 21620
1/26
Under Contract

$333,900

3 Beds3 Baths2,577 SqFt

303 CEDAR ST, Chestertown, MD 21620

MLS# MDKE2005970

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
21111 TEXAS AVE, Chestertown, MD 21620
1/16
Under Contract

$370,000

3 Beds2 Baths1,680 SqFt

21111 TEXAS AVE, Chestertown, MD 21620

MLS# MDKE2005932

Listed by Keller Williams Select Realtors of Easton

Bright MLS (BMLS)
109 METCALF RD, Chestertown, MD 21620
1/27
Active

$264,900

3 Beds2 Baths1,280 SqFt

109 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005968

Listed by Real Broker, LLC

Bright MLS (BMLS)
#25 LANDING LN, Chestertown, MD 21620
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

Bright MLS (BMLS)
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

Bright MLS (BMLS)
104 LANDING LN, Chestertown, MD 21620
1/24
Active

$813,900

3 Beds4 Baths2,192 SqFt

104 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005952

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#35 LANDING LN, Chestertown, MD 21620
1/26
Active

$786,900

3 Beds3 Baths1,964 SqFt

#35 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005956

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
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TaylorMade Team
Leisel L. Taylor
+1(240) 290-0830
leisel@taylormadeteam.net
1441 McCormick Dr Ste 1020, Largo, MD 20774

      Home
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      3. Reviews
      Buy
      1. All Listings
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      4. Book An Appointment
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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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Get My App

TaylorMade Team
Leisel L. Taylor
+1(240) 290-0830
leisel@taylormadeteam.net
1441 McCormick Dr Ste 1020, Largo, MD 20774

      Home
      About
      1. About Us
      2. Contact Us
      3. Reviews
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Book An Appointment
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Book An Appointment
      Hire Leisel
      Refer the TaylorMade Team
      Neighborhoods
      Blogs
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility