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Chestertown, MD
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128 Properties Available

128 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Newest Listings
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110 TRAFFORD DR, Chestertown, MD 21620
Coming Soon

$475,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/8
Coming Soon

$525,000

1 Bed2 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

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

$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
New

$264,900

3 Beds2 Baths1,280 SqFt

109 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005968

Listed by Real Broker, LLC

Bright MLS (BMLS)
676 DEEP LANDING RD, Chestertown, MD 21620
1/24
Under Contract

$315,000

3 Beds3 Baths1,468 SqFt

676 DEEP LANDING RD, Chestertown, MD 21620

MLS# MDQA2015466

Listed by Cross Street Realtors 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)
#37 LANDING LN, Chestertown, MD 21620
1/24
Active

$765,900

3 Beds3 Baths1,964 SqFt

#37 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005960

Listed by Gunther-McClary Real Estate

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

$753,500

3 Beds3 Baths1,964 SqFt

#36 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005958

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
213 CENTRAL DR, Chestertown, MD 21620
1/23
Active

$319,900

3 Beds2 Baths1,232 SqFt

213 CENTRAL DR, Chestertown, MD 21620

MLS# MDQA2015648

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
7521 PINE AVE, Chestertown, MD 21620
1/24
Price Dropped by $15K

$250,000

3 Beds1 Bath1,040 SqFt

7521 PINE AVE, Chestertown, MD 21620

MLS# MDKE2005920

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
204 ROLLING RD, Chestertown, MD 21620
1/31
Active

$370,000

3 Beds2 Baths2,296 SqFt

204 ROLLING RD, Chestertown, MD 21620

MLS# MDKE2005896

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
311 DEVON DR, Chestertown, MD 21620
1/40
Active

$598,000

5 Beds4 Baths3,504 SqFt

311 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005930

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
216 BLAKEFIELD DR, Chestertown, MD 21620
Active

$579,000

4 Beds3 Baths2,400 SqFt

216 BLAKEFIELD DR, Chestertown, MD 21620

MLS# MDQA2015520

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
121 PRIMROSE RD, Chestertown, MD 21620
1/22
Price Dropped by $24K

$375,000

3 Beds3 Baths2,034 SqFt

121 PRIMROSE RD, Chestertown, MD 21620

MLS# MDQA2015570

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
108 FLYING CLOUD DR, Chestertown, MD 21620
1/21
Price Dropped by $10K

$364,900

4 Beds3 Baths1,936 SqFt

108 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2005928

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
611 CANNON ST, Chestertown, MD 21620
1/18
Active

$299,000

2 Beds2 Baths920 SqFt

611 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005906

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
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

Bright MLS (BMLS)
104 LITTLE HARBOR WAY, Chestertown, MD 21620
1/23
Active

$849,900

3 Beds3 Baths1,980 SqFt

104 LITTLE HARBOR WAY, Chestertown, MD 21620

MLS# MDKE2005894

Listed by Gunther-McClary Real Estate

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

$799,900

3 Beds4 Baths2,092 SqFt

106 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005892

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
105 HIGH ST, Chestertown, MD 21620
1/51
Active

$1,395,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
304 HADAWAY DR, Chestertown, MD 21620
1/44
Price Dropped by $26K

$399,000

4 Beds2 Baths1,325 SqFt

304 HADAWAY DR, Chestertown, MD 21620

MLS# MDKE2005848

Listed by Cummings & Co. Realtors

Bright MLS (BMLS)
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TeamCaropreso-FNL-WHT-REDPrimary
      Home
      Buy
      1. Maryland's Ultimate Homebuyer's Guide
      2. All Listings
      3. Featured Listings
      4. Sold Listings
      5. Mortgage Calculator
      6. Affordability Calculator
      Sell
      1. Marylands Ultimate Home Sellers Guide
      2. Sell My Home
      3. Home Valuation
      4. Home Sale Calculator
      Neighborhoods
      1. Annapolis
      2. Crofton
      3. Glen Burnie
      4. Hanover
      5. Millersville
      6. Odenton
      7. Pasadena
      8. Severn
      9. Severna Park
      About
      1. About Us
      2. Contact Us
      3. Reviews
      4. Market Snapshot
      5. The Total Solution
      Careers
      Blogs
Maryland

Team Caropreso

+1(410) 384-4800 info@teamcaropreso.com

7466 New Ridge Road Suite 1, Hanover, MD, 21076

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

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.
TeamCaropreso-FNL-WHT-REDPrimary
      Home
      Buy
      1. Maryland's Ultimate Homebuyer's Guide
      2. All Listings
      3. Featured Listings
      4. Sold Listings
      5. Mortgage Calculator
      6. Affordability Calculator
      Sell
      1. Marylands Ultimate Home Sellers Guide
      2. Sell My Home
      3. Home Valuation
      4. Home Sale Calculator
      Neighborhoods
      1. Annapolis
      2. Crofton
      3. Glen Burnie
      4. Hanover
      5. Millersville
      6. Odenton
      7. Pasadena
      8. Severn
      9. Severna Park
      About
      1. About Us
      2. Contact Us
      3. Reviews
      4. Market Snapshot
      5. The Total Solution
      Careers
      Blogs
Maryland

Team Caropreso

+1(410) 384-4800 info@teamcaropreso.com

7466 New Ridge Road Suite 1, Hanover, MD, 21076

Get My App

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

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.