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Chestertown, MD
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127 Properties Available

127 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Newest Listings
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23110 OLD FAIRLEE RD, Chestertown, MD 21620
1/29
Price Dropped by $10K

$349,900

3 Beds1 Bath1,805 SqFt

23110 OLD FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2005676

Listed by Real Broker LLC

Bright MLS (BMLS)
7989 QUAKER NECK RD, Chestertown, MD 21620
1/90
Price Dropped by $250K
3D

$2,500,000

5 Beds5 Baths4,305 SqFt

7989 QUAKER NECK RD, Chestertown, MD 21620

MLS# MDKE2005590

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 LANDING LN, Chestertown, MD 21620
1/69
Price Dropped by $19K

$539,999

2 Beds3 Baths2,100 SqFt

103 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005670

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
100 METCALF RD, Chestertown, MD 21620
1/16
Price Dropped by $5K

$245,000

3 Beds2 Baths1,140 SqFt

100 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005634

Listed by Bayside Realty

Bright MLS (BMLS)
21316 PERSIMMON DR, Chestertown, MD 21620
1/21
Active

$179,000

2 Beds1 Bath1,232 SqFt

21316 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2005624

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10751 MILLBROOK DR, Chestertown, MD 21620
1/50
Under Contract

$350,000

3 Beds2 Baths1,942 SqFt

10751 MILLBROOK DR, Chestertown, MD 21620

MLS# MDKE2005652

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
23043 BAY SHORE SPUR, Chestertown, MD 21620
1/27
Price Dropped by $25K

$325,000

4 Beds3 Baths2,630 SqFt

23043 BAY SHORE SPUR, Chestertown, MD 21620

MLS# MDKE2005584

Listed by Rock Hall Properties Real Estate

Bright MLS (BMLS)
116 HARLAN LOOP, Chestertown, MD 21620
1/21
Active

$519,000

5 Beds4 Baths4,067 SqFt

116 HARLAN LOOP, Chestertown, MD 21620

MLS# MDKE2005610

Listed by Samson Properties

Bright MLS (BMLS)
200 WASHINGTON AVE, Chestertown, MD 21620
1/35
Under Contract

$695,000

4 Beds4 Baths2,917 SqFt

200 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2005538

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
5700 JOHNSONTOWN RD, Chestertown, MD 21620
1/7
Pending

$110,000

3 Beds1 Bath1,144 SqFt

5700 JOHNSONTOWN RD, Chestertown, MD 21620

MLS# MDKE2005562

Listed by Tesla Realty Group, LLC

Bright MLS (BMLS)
112 METCALF RD, Chestertown, MD 21620
1/20
Active

$249,950

3 Beds2 Baths1,280 SqFt

112 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005498

Listed by Engel & Volkers Annapolis

Bright MLS (BMLS)
251 DEVON DR, Chestertown, MD 21620
1/54
Active

$595,000

3 Beds3 Baths3,935 SqFt

251 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005536

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
234 N COLLEGE AVE, Chestertown, MD 21620
1/3
Under Contract

$164,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2005434

Listed by Cummings & Co Realtors

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

$167,000

4 Beds2 Baths1,156 SqFt

141 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2005504

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
165 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/67
Price Dropped by $20K

$409,900

4 Beds3 Baths2,258 SqFt

165 CHAR NOR MANOR BLVD, Chestertown, MD 21620

MLS# MDQA2013956

Listed by RE/MAX Executive

Bright MLS (BMLS)
26933 MALLARD RD, Chestertown, MD 21620
1/15
Pending

$625,000

3 Beds3 Baths1,600 SqFt

26933 MALLARD RD, Chestertown, MD 21620

MLS# MDKE2005422

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
134 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/42
Price Dropped by $6K

$279,000

3 Beds1 Bath1,128 SqFt

134 CHAR NOR MANOR BLVD, Chestertown, MD 21620

MLS# MDQA2013988

Listed by Meredith Fine Properties

Bright MLS (BMLS)
300 HICKORY LN, Chestertown, MD 21620
1/30
Pending

$1,198,000

5 Beds4 Baths3,640 SqFt

300 HICKORY LN, Chestertown, MD 21620

MLS# MDQA2013388

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
23069 RALEIGH RD, Chestertown, MD 21620
1/10
Under Contract

$175,000

2 Beds2 Baths1,160 SqFt

23069 RALEIGH RD, Chestertown, MD 21620

MLS# MDKE2005378

Listed by Keller Williams Select Realtors of Annapolis

Bright MLS (BMLS)
LITTLE HARBOR WAY #1, Chestertown, MD 21620
1/29
Active

$1,800,000

4 Beds4 Baths3,540 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2004992

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
109 WILTON RD, Chestertown, MD 21620
1/31
Price Dropped by $5K

$344,900

3 Beds2 Baths1,392 SqFt

109 WILTON RD, Chestertown, MD 21620

MLS# MDQA2011782

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
11040 KYLIE LN, Chestertown, MD 21620
1/71
Active

$649,000

4 Beds4 Baths3,684 SqFt

11040 KYLIE LN, Chestertown, MD 21620

MLS# MDKE2004586

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
24543 CHESTERTOWN RD, Chestertown, MD 21620
1/55
Pending

$425,000

3 Beds2 Baths3,280 SqFt

24543 CHESTERTOWN RD, Chestertown, MD 21620

MLS# MDKE2004580

Listed by RE/MAX Executive

Bright MLS (BMLS)
349 HIGH ST, Chestertown, MD 21620
1/33
Under Contract

$395,000

7 Beds4 Baths3,664 SqFt

349 HIGH ST, Chestertown, MD 21620

MLS# MDKE2004076

Listed by Coldwell Banker Chesapeake Real Estate Company

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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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.