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Neighborhood: Chestertown, Chestertown, MD
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11 Properties Available In Chestertown

11 Properties Available In Chestertown

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MD >Chestertown >Chestertown >
Market Insights
104 CONLEY DR, Chestertown, MD 21620
1/27
Price Dropped by $7K

$239,900

3 Beds2 Baths1,280 SqFt

104 CONLEY DR, Chestertown, MD 21620

MLS# MDKE2006686

Listed by Cummings & Co. Realtors

Bright MLS (BMLS)
234 N COLLEGE AVE, Chestertown, MD 21620
1/3
Price Dropped by $10K

$90,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006670

Listed by Cummings & Co Realtors

Bright MLS (BMLS)
110 PROSPECT ST, Chestertown, MD 21620
1/6
Price Dropped by $10K

$79,900

3 Beds2 Baths2,210 SqFt

110 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006626

Listed by ANR Realty, LLC

Bright MLS (BMLS)
522 HIGH ST, Chestertown, MD 21620
1/15
Price Dropped by $25K

$399,900

2 Beds3 Baths1,518 SqFt

522 HIGH ST, Chestertown, MD 21620

MLS# MDKE2006614

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
102 FLYING CLOUD DR, Chestertown, MD 21620
1/41
Price Dropped by $10K

$329,900

3 Beds3 Baths1,896 SqFt

102 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006586

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
107 FLYING CLOUD DR, Chestertown, MD 21620
1/51
Price Dropped by $10K

$375,000

5 Beds4 Baths2,534 SqFt

107 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006510

Listed by CENTURY 21 New Millennium

Bright MLS (BMLS)
139 PROSPECT ST, Chestertown, MD 21620
1/28
Under Contract

$198,000

3 Beds1 Bath1,200 SqFt

139 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006250

Listed by Redfin Corp

Bright MLS (BMLS)
104 MAPLE AVE #6, Chestertown, MD 21620
1/27
Active

$1,920

2 Beds2 Baths900 SqFt

104 MAPLE AVE #6, Chestertown, MD 21620

MLS# MDKE2006408

Listed by Real Broker, LLC - Annapolis

Bright MLS (BMLS)
104 MAPLE AVE, Chestertown, MD 21620
1/30
Price Dropped by $119K

$1,350,000

10,540 Sqft Lot

104 MAPLE AVE, Chestertown, MD 21620

MLS# MDKE2006386

Listed by Real Broker, LLC - Annapolis

Bright MLS (BMLS)
201 N LYNCHBURG ST, Chestertown, MD 21620
1/13
Price Dropped by $45K

$750,000

4,342 Sqft Lot

201 N LYNCHBURG ST, Chestertown, MD 21620

MLS# MDKE2006082

Listed by RE/MAX Associates-Hockessin

Bright MLS (BMLS)
515 WASHINGTON AVE, Chestertown, MD 21620
1/4
Price Dropped by $104K

$795,000

0.97 Acres Lot

515 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2000776

Listed by EShore

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, Chester, MD, 21619, USA

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    • SELL
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      3. Instant Cash Offer
      4. Trade in Your Home
      5. Fix Up & Sell
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    • BUY
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      7. Chestertown Overview
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      12. Odenton Overview
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      16. Rock Hall Overview
      17. Saint Michaels Overview
      18. Severn Overview
      19. Severna Park Overview
      20. Stevensville Overview
      Resources
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      2. 5 Star Referral Center

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

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, Chester, MD, 21619, USA

Get My App

    • Home
      The Chesapeake Reserve
      Local Home Prices Report
    • SELL
      1. Sell Your Home
      2. Guaranteed 100% of Asking Price
      3. Instant Cash Offer
      4. Trade in Your Home
      5. Fix Up & Sell
      Luxury
      1. Chesapeake Reserve
      2. Kent Island Luxury Homes
      3. Easton Area Luxury
      4. Cambridge Area Luxury Homes
      About
      1. About Us
      2. Reviews
      3. Contact Us
    • BUY
      1. VIP Home Buying
      2. Off Market Homes
      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

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

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