+1(410) 777-5848 david@davidjmoore.net
David J. Moore Realtor
  • Home
  • SELL
    1. Sell Your Home
    2. Guaranteed 100% of Asking Price
    3. Instant Cash Offer
    4. Trade in Your Home
    5. Fix Up & Sell
  • BUY
    1. VIP Home Buying
    2. Off Market Homes
  • Luxury
    1. Kent Island Luxury Homes
    2. Easton Area Luxury
    3. Cambridge Area Luxury 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
  • Local Home Prices Report
  • About
    1. About Us
    2. Reviews
    3. Contact Us
  • Resources
    1. Real Estate Info
    2. 5 Star Referral Center
  • Register
  • Sign In
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
    Beds Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
    Baths Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
  • List
  • Mixed
  • Map
Chestertown, MD
Virtual Tour
Map
20 Properties Available In Chestertown

20 Properties Available In Chestertown

  • Default
  • Newest Listings
  • Price-High To Low
  • Price-Low To High
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
MD >Chestertown >
Market Insights
118 LITTLE HARBOR WAY #201, Chestertown, MD 21620
1/34
Coming Soon

$675,000

2 Beds3 Baths1,600 SqFt

118 LITTLE HARBOR WAY #201, Chestertown, MD 21620

MLS# MDKE2006084

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
24339 CHESTERTOWN RD, Chestertown, MD 21620
1/36
Under Contract

$269,000

3 Beds1 Bath960 SqFt

24339 CHESTERTOWN RD, Chestertown, MD 21620

MLS# MDKE2006054

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10800 CLIFF RD, Chestertown, MD 21620
1/94
Under Contract

$1,495,000

5 Beds4 Baths5,241 SqFt

10800 CLIFF RD, Chestertown, MD 21620

MLS# MDKE2005898

Listed by Taylor Properties

Bright MLS (BMLS)
201 GREENWOOD AVE, Chestertown, MD 21620
1/62
Under Contract

$495,000

4 Beds3 Baths3,984 SqFt

201 GREENWOOD AVE, Chestertown, MD 21620

MLS# MDKE2006030

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
104 IRIS RD, Chestertown, MD 21620
1/36
Under Contract

$379,000

3 Beds2 Baths1,700 SqFt

104 IRIS RD, Chestertown, MD 21620

MLS# MDQA2015798

Listed by Doug Ashley Realtors, LLC

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

$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)
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
1/49
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)
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)
8620 PARK DR, Chestertown, MD 21620
1/53
Active

$499,900

4 Beds3 Baths2,524 SqFt

8620 PARK DR, Chestertown, MD 21620

MLS# MDKE2005850

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
7844 CHESTER CT, Chestertown, MD 21620
1/51
Price Dropped by $25K

$745,000

4 Beds3 Baths3,248 SqFt

7844 CHESTER CT, Chestertown, MD 21620

MLS# MDKE2005796

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
423 CALVERT ST, Chestertown, MD 21620
1/20
Pending
3D

$135,000

3 Beds2 Baths1,136 SqFt

423 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2005718

Listed by Redfin Corp

Bright MLS (BMLS)
100 ADELA WAY, Chestertown, MD 21620
1/67
Price Dropped by $15K

$500,000

4 Beds4 Baths3,799 SqFt

100 ADELA WAY, Chestertown, MD 21620

MLS# MDKE2005636

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
7989 QUAKER NECK RD, Chestertown, MD 21620
1/90
Active
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)
21316 PERSIMMON DR, Chestertown, MD 21620
1/21
Pending

$169,000

2 Beds1 Bath1,232 SqFt

21316 PERSIMMON DR, Chestertown, MD 21620

MLS# MDKE2005624

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
165 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/67
Under Contract

$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)
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
Active

$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)
CLOQUET RD, Chestertown, MD 21620
1/32
Active

$39,000

1.51 Acres

CLOQUET RD, Chestertown, MD 21620

MLS# MDKE2005966

Listed by Berkshire Hathaway HomeServices Homesale Realty

Bright MLS (BMLS)
  • 1

explore listings in Chestertown

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
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
      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

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
      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