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City: Chestertown, MD
Listing Status: Active
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117 Properties Available In Chestertown

117 Properties Available In Chestertown

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MD >Chestertown >
Market Insights
7680 COUNTRY CLUB LN, Chestertown, MD 21620
1/43
New

$885,000

5 Beds4 Baths2,639 SqFt

7680 COUNTRY CLUB LN, Chestertown, MD 21620

MLS# MDKE2006758

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
9126 FAIRLEE RD, Chestertown, MD 21620
1/20
New

$344,000

3 Beds2 Baths1,216 SqFt

9126 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006764

Listed by Chesapeake Real Estate Associates, LLC

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

$325,000

3 Beds1 Bath1,000 SqFt

896 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2006750

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
351 CALVERT ST, Chestertown, MD 21620
1/19
New

$2,000

3 Beds1 Bath1,122 SqFt

351 CALVERT ST, Chestertown, MD 21620

MLS# MDKE2006734

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
105 N WATER ST #2, Chestertown, MD 21620
1/49
Active

$475,000

2 Beds2 Baths1,011 SqFt

105 N WATER ST #2, Chestertown, MD 21620

MLS# MDKE2006680

Listed by Northrop Realty

Bright MLS (BMLS)
22481 GOOSE HOLLOW DR, Chestertown, MD 21620
1/88
Active

$279,900

3 Beds2 Baths1,296 SqFt

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

MLS# MDKE2006682

Listed by Keller Williams Legacy

Bright MLS (BMLS)
8890 FAIRLEE RD, Chestertown, MD 21620
Active

$2,500

3 Beds2 Baths1,232 SqFt

8890 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006738

Listed by RE/MAX Executive

Bright MLS (BMLS)
25750 COLLINS AVE, Chestertown, MD 21620
1/50
Active

$468,000

3 Beds2 Baths3,262 SqFt

25750 COLLINS AVE, Chestertown, MD 21620

MLS# MDKE2006546

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
101 S MILL ST, Chestertown, MD 21620
1/39
Active

$515,000

2 Beds3 Baths1,476 SqFt

101 S MILL ST, Chestertown, MD 21620

MLS# MDKE2006674

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
517 ROUND TOP RD, Chestertown, MD 21620
1/28
Price Dropped by $25K

$324,900

3 Beds1 Bath1,248 SqFt

517 ROUND TOP RD, Chestertown, MD 21620

MLS# MDQA2017680

Listed by Keller Williams Flagship

Bright MLS (BMLS)
103 S LYNCHBURG ST, Chestertown, MD 21620
1/10
Active

$1,400

2 Beds2 Baths1,040 SqFt

103 S LYNCHBURG ST, Chestertown, MD 21620

MLS# MDKE2006688

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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)
104 ACORN DR, Chestertown, MD 21620
1/26
Active

$284,900

3 Beds3 Baths1,900 SqFt

104 ACORN DR, Chestertown, MD 21620

MLS# MDKE2006668

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
234 N COLLEGE AVE, Chestertown, MD 21620
1/3
Price Dropped by $20K

$100,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006670

Listed by Cummings & Co Realtors

Bright MLS (BMLS)
FAIRLEE RD, Chestertown, MD 21620
1/7
Active

$75,000

2.2 Acres

FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006672

Listed by RE/MAX Chesapeake

Bright MLS (BMLS)
25416 COMMERCE LN, Chestertown, MD 21620
1/39
Active

$1,100,000

2.03 Acres Lot

25416 COMMERCE LN, Chestertown, MD 21620

MLS# MDKE2006664

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$89,900

3 Beds2 Baths2,210 SqFt

110 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006626

Listed by ANR Realty, LLC

Bright MLS (BMLS)
8796 MARYLAND PKWY, Chestertown, MD 21620
1/60
Active

$1,650,000

9 Beds7 Baths4,776 SqFt

8796 MARYLAND PKWY, Chestertown, MD 21620

MLS# MDKE2006596

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
1904 PONDTOWN RD, Chestertown, MD 21620
1/11
Active

$265,000

3 Beds1 Bath1,967 SqFt

1904 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2017480

Listed by Keller Williams Flagship

Bright MLS (BMLS)
1906 PONDTOWN RD, Chestertown, MD 21620
1/4
Active

$110,000

1.93 Acres

1906 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2017476

Listed by Keller Williams Flagship

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

$2,950

4 Beds2 Baths1,656 SqFt

222 MOUNT VERNON AVE, Chestertown, MD 21620

MLS# MDKE2006624

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
10781 FERMOY RD, Chestertown, MD 21620
1/54
Price Dropped by $20K

$429,900

4 Beds3 Baths2,160 SqFt

10781 FERMOY RD, Chestertown, MD 21620

MLS# MDKE2006640

Listed by Real Broker, LLC - Chester

Bright MLS (BMLS)
21172 WYOMING AVE, Chestertown, MD 21620
Active

$200,000

4 Beds1 Bath2,920 SqFt

21172 WYOMING AVE, Chestertown, MD 21620

MLS# MDKE2006642

Listed by Blue Star Real Estate, LLC

Bright MLS (BMLS)
213 BYFORD DR, Chestertown, MD 21620
1/39
Active

$380,000

4 Beds2 Baths1,277 SqFt

213 BYFORD DR, Chestertown, MD 21620

MLS# MDKE2006026

Listed by Doug Ashley Realtors, LLC

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.
TRG White (transparent)sp-logo-white-1
The Robinson Group
Carlos And Janeen Robinson
+1(301) 802-0753
admin@therobinsongroupdmv.com
16701 Melford Blvd Ste 100, Bowie, MD, 20715, USA

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    • Buy
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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.
TRG White (transparent)sp-logo-white-1
The Robinson Group
Carlos And Janeen Robinson
+1(301) 802-0753
admin@therobinsongroupdmv.com
16701 Melford Blvd Ste 100, Bowie, MD, 20715, USA

Get My App

    • Home
      Featured Areas
      1. Bowie Overview
      2. Upper Marlboro Overview
      3. Crofton Overview
      4. Odenton Overview
      5. Laurel Overview
      6. Annapolis Overview
      7. Davidsonville Overview
      Market Snapshot
    • Buy
      1. All Listings
      2. Featured Listings
      Calculator
    • Sell
      1. Sell My Home
      2. Home Valuation
      3. Recent Sold
      About
      1. Blogs
      2. Our Team
      3. About Us
      4. Contact Us
      5. Reviews

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

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