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Chestertown, MD
Map
2,673 Sold Properties

2,673 Sold Properties

The average price in the selected areas has remained stable. Learn more
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420 CANNON ST, Chestertown, MD 21620
1/39

$350,000

$395,000

11.4%
2 Beds2 Baths1,080 SqFt

420 CANNON ST, Chestertown, MD 21620

MLS# MDKE2005174

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
211 DAVID DR, Chestertown, MD 21620
1/52

$795,000

$795,000

4 Beds4 Baths4,401 SqFt

211 DAVID DR, Chestertown, MD 21620

MLS# MDKE2005038

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
222 MOUNT VERNON AVE, Chestertown, MD 21620
1/29

$410,000

$375,000

9.3%
4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005188

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
10141 FLATLAND RD, Chestertown, MD 21620
1/5

$285,000

$292,900

2.7%
2 Beds1 Bath2,142 SqFt

10141 FLATLAND RD, Chestertown, MD 21620

MLS# MDKE2005136

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
25285 FOXCHASE DR, Chestertown, MD 21620
1/39

$550,000

$575,000

4.3%
3 Beds3 Baths2,010 SqFt

25285 FOXCHASE DR, Chestertown, MD 21620

MLS# MDKE2005078

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
7988 ALDAN DR, Chestertown, MD 21620
1/56

$759,000

$749,900

1.2%
5 Beds3 Baths3,394 SqFt

7988 ALDAN DR, Chestertown, MD 21620

MLS# MDKE2004966

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
209 N WATER ST, Chestertown, MD 21620

$1,100,000

$1,350,000

18.5%
5 Beds4 Baths2,909 SqFt

209 N WATER ST, Chestertown, MD 21620

MLS# MDKE2005212

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
898 WASHINGTON AVE, Chestertown, MD 21620
1/34

$237,000

$260,000

8.8%
2 Beds2 Baths1,384 SqFt

898 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2005250

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
201 PONDVIEW CT, Chestertown, MD 21620
1/37

$525,000

$519,900

1.0%
4 Beds3 Baths3,016 SqFt

201 PONDVIEW CT, Chestertown, MD 21620

MLS# MDKE2005246

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
22153 1ST POINT RD, Chestertown, MD 21620
1/87

$1,062,800

$1,200,000

11.4%
5 Beds6 Baths3,078 SqFt

22153 1ST POINT RD, Chestertown, MD 21620

MLS# MDKE2004460

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
200 HOFFMAN LN, Chestertown, MD 21620
1/8

$360,000

$408,000

11.8%
3 Beds1 Bath1,128 SqFt

200 HOFFMAN LN, Chestertown, MD 21620

MLS# MDQA2013020

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
26865 MALLARD RD, Chestertown, MD 21620
1/49

$840,000

$950,000

11.6%
4 Beds3 Baths3,355 SqFt

26865 MALLARD RD, Chestertown, MD 21620

MLS# MDKE2004550

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
205 RIVER RD, Chestertown, MD 21620
1/2

$119,500

$121,500

1.6%
1.01 Acres

205 RIVER RD, Chestertown, MD 21620

MLS# MDQA2013496

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
305 WASHINGTON AVE, Chestertown, MD 21620
1/28

$549,000

$549,000

5 Beds3 Baths2,476 SqFt

305 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2005236

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
9050 POINT LN, Chestertown, MD 21620
1/71

$745,000

$745,000

4 Beds3 Baths3,166 SqFt

9050 POINT LN, Chestertown, MD 21620

MLS# MDKE2005102

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
213 N QUEEN ST, Chestertown, MD 21620
1/3

$675,000

$638,750

5.7%
2 Beds3 Baths1,945 SqFt

213 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2005210

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
109 EDMORE RD, Chestertown, MD 21620
1/24

$344,900

$344,900

3 Beds2 Baths1,344 SqFt

109 EDMORE RD, Chestertown, MD 21620

MLS# MDQA2013256

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
811 S MEADOWVIEW DR, Chestertown, MD 21620
1/45

$459,000

$459,000

3 Beds2 Baths2,064 SqFt

811 S MEADOWVIEW DR, Chestertown, MD 21620

MLS# MDKE2005086

Listed by Redfin Corp

Bright MLS (BMLS)
104 DUTCHESS RD, Chestertown, MD 21620
1/23

$312,000

$312,000

3 Beds2 Baths1,188 SqFt

104 DUTCHESS RD, Chestertown, MD 21620

MLS# MDQA2013072

Listed by Taylor Properties

Bright MLS (BMLS)
107 N QUEEN ST, Chestertown, MD 21620

$539,000

$529,000

1.9%
4 Beds2 Baths3,050 SqFt

107 N QUEEN ST, Chestertown, MD 21620

MLS# MDKE2005108

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
325 DEVON DR, Chestertown, MD 21620
1/61

$525,000

$525,000

4 Beds3 Baths4,086 SqFt

325 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005100

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
306 CEDAR ST, Chestertown, MD 21620
1/42

$312,000

$319,000

2.2%
4 Beds2 Baths1,404 SqFt

306 CEDAR ST, Chestertown, MD 21620

MLS# MDKE2004954

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
216 SILVER HEEL RD, Chestertown, MD 21620
1/32

$360,000

$364,900

1.3%
3 Beds3 Baths1,724 SqFt

216 SILVER HEEL RD, Chestertown, MD 21620

MLS# MDKE2005024

Listed by CENTURY 21 New Millennium

Bright MLS (BMLS)
101 RIVERSHORE RD, Chestertown, MD 21620

$1,125,000

$995,000

13.1%
3 Beds2 Baths1,968 SqFt

101 RIVERSHORE RD, Chestertown, MD 21620

MLS# MDQA2013688

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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eXp Realty - White
eXp Realty
Chip Watson
      Home
      Buy
      1. All Listings
      2. Featured Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
      Explore Towns
      1. Atlantic City
      2. Avalon
      3. Beach Haven
      4. Cape May
      5. Cape May Court House
      6. Cape May Point
      7. North Cape May
      8. North Wildwood
      9. Ocean City
      10. Rio Grande
      11. Sea Isle City
      12. Stone Harbor
      13. Villas
      14. West Cape May
      15. West Wildwood
      16. Wildwood
      17. Wildwood Crest
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      Market Snapshot
      Resources
      1. Calendar
      2. Affordability Calculator
      3. Mortgage Calculator
      4. Blogs
      5. Partner Lender
+1(856) 625-5900
howard.watson@exprealty.com

Get My App

Do Not Sell or Share My Personal Data

Name: Debra Ball - Maine MLS Contact: 1-888-439-8743 Name: Deborah Penny contact: 1-805-284-0995 email: deborah.penny@exprealty.net Designation: Licensed Broker of EXP Realty for Metrolist   Name: Christopher Cribb contact: 1-816-982-5990 email: chris.cribb@exprealty.net Designation: Licensed Broker of EXP Realty for Heartland MLS   Name: Amy Logue contact:  1-503-814-9613 email:  amy.logue@exprealty.net Designation: Licensed Broker of EXP Realty for Willamette Valley MLS    

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.

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

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

eXp Realty - White
eXp Realty
Chip Watson
      Home
      Buy
      1. All Listings
      2. Featured Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
      Explore Towns
      1. Atlantic City
      2. Avalon
      3. Beach Haven
      4. Cape May
      5. Cape May Court House
      6. Cape May Point
      7. North Cape May
      8. North Wildwood
      9. Ocean City
      10. Rio Grande
      11. Sea Isle City
      12. Stone Harbor
      13. Villas
      14. West Cape May
      15. West Wildwood
      16. Wildwood
      17. Wildwood Crest
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. Reviews
      Market Snapshot
      Resources
      1. Calendar
      2. Affordability Calculator
      3. Mortgage Calculator
      4. Blogs
      5. Partner Lender
+1(856) 625-5900
howard.watson@exprealty.com

Get My App

Do Not Sell or Share My Personal Data

Name: Debra Ball - Maine MLS Contact: 1-888-439-8743 Name: Deborah Penny contact: 1-805-284-0995 email: deborah.penny@exprealty.net Designation: Licensed Broker of EXP Realty for Metrolist   Name: Christopher Cribb contact: 1-816-982-5990 email: chris.cribb@exprealty.net Designation: Licensed Broker of EXP Realty for Heartland MLS   Name: Amy Logue contact:  1-503-814-9613 email:  amy.logue@exprealty.net Designation: Licensed Broker of EXP Realty for Willamette Valley MLS    

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.

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

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