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Chestertown, Chestertown, MD
Listing Status: Active
Map
37 Properties Available In Chestertown

37 Properties Available In Chestertown

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  • Newest Listings
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  • Price-Low To High
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
MD >Chestertown >Chestertown >
Market Insights
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)
103 METCALF RD, Chestertown, MD 21620
1/25
Active

$259,900

3 Beds2 Baths1,280 SqFt

103 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005688

Listed by Real Broker, LLC

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

$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
New

$495,000

4 Beds3 Baths3,984 SqFt

201 GREENWOOD AVE, Chestertown, MD 21620

MLS# MDKE2006030

Listed by Doug Ashley Realtors, LLC

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

$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
1/45
Active

$525,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
#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)
204 ROLLING RD, Chestertown, MD 21620
1/31
Price Dropped by $25K

$345,000

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)
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)
222 MOUNT VERNON AVE, Chestertown, MD 21620
1/29
Active

$469,000

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2005876

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
228 S WATER ST, Chestertown, MD 21620
1/32
Active

$878,000

3 Beds4 Baths2,310 SqFt

228 S WATER ST, Chestertown, MD 21620

MLS# MDKE2005812

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
423 CALVERT ST, Chestertown, MD 21620
1/20
Price Dropped by $30K
3D

$135,000

3 Beds2 Baths1,136 SqFt

423 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2005718

Listed by Redfin Corp

Bright MLS (BMLS)
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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.
Logo REAL David J. Moore  - Rectangle
David J. Moore & Associates of REAL Broker, LLC
David J. Moore
+1(410) 777-5848
david@davidjmoore.net
2201 Main St, Suite 1D, Chester, MD 21619

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

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.
Logo REAL David J. Moore  - Rectangle
David J. Moore & Associates of REAL Broker, LLC
David J. Moore
+1(410) 777-5848
david@davidjmoore.net
2201 Main St, Suite 1D, Chester, MD 21619

Get My App

    • Home
      Luxury
      1. Kent Island Luxury Homes
      2. Easton Area Luxury
      3. Cambridge Area Luxury Homes
      About
      1. About Us
      2. Reviews
      3. Contact Us
    • SELL
      1. Sell Your Home
      2. Guaranteed 100% of Asking Price
      3. Instant Cash Offer
      4. Trade in Your Home
      5. Fix Up & Sell
      Communities
      1. New Construction Homes
      2. Annapolis Overview
      3. Arnold Overview
      4. Cambridge Overview
      5. Centreville Overview
      6. Chester Overview
      7. Chestertown Overview
      8. Denton Overview
      9. Easton Overview
      10. Glen Burnie Overview
      11. Grasonville Overview
      12. Odenton Overview
      13. Oxford Overview
      14. Pasadena Overview
      15. Queenstown Overview
      16. Rock Hall Overview
      17. Saint Michaels Overview
      18. Severn Overview
      19. Severna Park Overview
      20. Stevensville Overview
      Resources
      1. Real Estate Info
      2. 5 Star Referral Center
    • BUY
      1. VIP Home Buying
      2. Off Market Homes
      Local Home Prices Report

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

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