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City: Chestertown, MD
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28 Properties Available In Chestertown

28 Properties Available In Chestertown

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MD >Chestertown >
Market Insights
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)
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)
23264 CLARISSA RD, Chestertown, MD 21620
1/30
Under Contract

$365,000

3 Beds2 Baths1,248 SqFt

23264 CLARISSA RD, Chestertown, MD 21620

MLS# MDKE2006096

Listed by TTR Sotheby's International Realty

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)
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)
25440 LEARMAN RD, Chestertown, MD 21620
1/70
Under Contract

$3,000,000

3 Beds4 Baths3,142 SqFt

25440 LEARMAN RD, Chestertown, MD 21620

MLS# MDKE2006468

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
956 WASHINGTON AVE, Chestertown, MD 21620
1/29
Active

$285,000

3 Beds1 Bath1,248 SqFt

956 WASHINGTON AVE, Chestertown, MD 21620

MLS# MDKE2006394

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
240 MERGANSER DR, Chestertown, MD 21620
1/55
Price Dropped by $24K
3D

$365,000

3 Beds2 Baths1,120 SqFt

240 MERGANSER DR, Chestertown, MD 21620

MLS# MDQA2016900

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
304 HADAWAY DR, Chestertown, MD 21620
1/38
Under Contract
3D

$309,900

4 Beds2 Baths1,325 SqFt

304 HADAWAY DR, Chestertown, MD 21620

MLS# MDKE2006482

Listed by Redfin Corporation

Bright MLS (BMLS)
215 FAIRVIEW DR, Chestertown, MD 21620
1/57
Under Contract

$425,000

3 Beds3 Baths1,784 SqFt

215 FAIRVIEW DR, Chestertown, MD 21620

MLS# MDQA2017090

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
9816 FAIRLEE RD, Chestertown, MD 21620
1/48
Pending

$535,000

3 Beds3 Baths1,624 SqFt

9816 FAIRLEE RD, Chestertown, MD 21620

MLS# MDKE2006488

Listed by Long & Foster Real Estate, Inc.

Bright MLS (BMLS)
103 SUTTON WAY, Chestertown, MD 21620
1/53
Active

$550,000

5 Beds4 Baths3,816 SqFt

103 SUTTON WAY, Chestertown, MD 21620

MLS# MDKE2006344

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
704 TRUSLOW RD, Chestertown, MD 21620
1/43
Under Contract

$440,000

3 Beds3 Baths2,060 SqFt

704 TRUSLOW RD, Chestertown, MD 21620

MLS# MDQA2016632

Listed by RE/MAX Executive

Bright MLS (BMLS)
117 WATER ST N #1A, Chestertown, MD 21620
1/46
Active

$685,000

3 Beds3 Baths3,000 SqFt

117 WATER ST N #1A, Chestertown, MD 21620

MLS# MDKE2006162

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
1/73
Active

$1,600,000

7 Beds5 Baths5,400 SqFt

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

MLS# MDKE2006158

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #1B, Chestertown, MD 21620
1/20
Active

$200,000

1 Bed1 Bath700 SqFt

117 WATER ST N #1B, Chestertown, MD 21620

MLS# MDKE2006164

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #2A, Chestertown, MD 21620
1/24
Active

$375,000

2 Beds1 Bath787 SqFt

117 WATER ST N #2A, Chestertown, MD 21620

MLS# MDKE2006166

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #2B, Chestertown, MD 21620
1/23
Active

$350,000

1 Bed1 Bath850 SqFt

117 WATER ST N #2B, Chestertown, MD 21620

MLS# MDKE2006168

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
204 DOUBLE CREEK RD, Chestertown, MD 21620
1/46
Price Dropped by $33K

$565,000

3 Beds3 Baths2,927 SqFt

204 DOUBLE CREEK RD, Chestertown, MD 21620

MLS# MDQA2015996

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/45
Price Dropped by $10K

$499,999

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
1/41
Under Contract

$475,000

4 Beds3 Baths3,504 SqFt

311 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005930

Listed by Doug Ashley Realtors, 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)
105 HIGH ST, Chestertown, MD 21620
1/48
Open Sat 10AM-12PM

$1,245,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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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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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