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Neighborhood: Chestertown, Chestertown, MD
Listing Status: Active
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55 Properties Available In Chestertown

55 Properties Available In Chestertown

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MD >Chestertown >Chestertown >
Market Insights
115 METCALF RD, Chestertown, MD 21620
1/10
Open Thu 6PM-7PM

$259,900

3 Beds2 Baths1,280 SqFt

115 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006826

Listed by Real Broker, LLC - Chester

Bright MLS (BMLS)
121 METCALF RD, Chestertown, MD 21620
1/10
Active

$264,900

3 Beds2 Baths3,920 Sqft Lot

121 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006678

Listed by Real Broker, LLC - Chester

Bright MLS (BMLS)
123 TRAFFORD DR, Chestertown, MD 21620
1/45
Open Sat 1PM-3PM

$375,000

4 Beds3 Baths2,504 SqFt

123 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2006970

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
115 CHESTER ARMS DR, Chestertown, MD 21620
New

$263,000

3 Beds2 Baths1,140 SqFt

115 CHESTER ARMS DR, Chestertown, MD 21620

MLS# MDKE2006958

Listed by Samson Properties

Bright MLS (BMLS)
302 S MILL ST, Chestertown, MD 21620
1/17
Active

$1,195,000

2 Beds1 Bath806 SqFt

302 S MILL ST, Chestertown, MD 21620

MLS# MDKE2006850

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
101 S COLLEGE AVE, Chestertown, MD 21620
1/35
Price Dropped by $10K

$359,000

2 Beds2 Baths1,036 SqFt

101 S COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006918

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
117 N WATER ST #3B, Chestertown, MD 21620
1/18
Active

$295,000

1 Bed1 Bath

117 N WATER ST #3B, Chestertown, MD 21620

MLS# MDKE2006968

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
216 BIRCH RUN RD, Chestertown, MD 21620
1/52
Active

$750,000

3 Beds3 Baths2,176 SqFt

216 BIRCH RUN RD, Chestertown, MD 21620

MLS# MDKE2006896

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
129 TRAFFORD DR, Chestertown, MD 21620
1/15
Active

$480,000

3 Beds3 Baths3,176 SqFt

129 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2006878

Listed by Elevated Real Estate Solutions

Bright MLS (BMLS)
200 MANOR AVE, Chestertown, MD 21620
1/34
Active

$325,000

4 Beds2 Baths2,198 SqFt

200 MANOR AVE, Chestertown, MD 21620

MLS# MDKE2006808

Listed by TTR Sotheby's International Realty

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

$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
Price Dropped by $9K

$275,000

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 $5K

$85,000

2 Beds1 Bath1,296 SqFt

234 N COLLEGE AVE, Chestertown, MD 21620

MLS# MDKE2006670

Listed by Cummings & Co Realtors

Bright MLS (BMLS)
213 BYFORD DR, Chestertown, MD 21620
1/39
Price Dropped by $8K

$372,000

4 Beds2 Baths1,277 SqFt

213 BYFORD DR, Chestertown, MD 21620

MLS# MDKE2006026

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
226 S WATER ST, Chestertown, MD 21620
1/31
Active

$898,000

3 Beds4 Baths2,172 SqFt

226 S WATER ST, Chestertown, MD 21620

MLS# MDKE2006354

Listed by Gunther-McClary Real Estate

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)
106 QUEEN ST S, Chestertown, MD 21620
1/92
Price Dropped by $36K

$829,000

3 Beds4 Baths2,472 SqFt

106 QUEEN ST S, Chestertown, MD 21620

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
1/73
Price Dropped by $100K

$1,500,000

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 #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 #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)
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)
#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)
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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.
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David J. Moore & Associates of REAL Broker, LLC
David J. Moore
License ID: 609287
+1(443) 249-9696
info@theparagonhometeam.com
2201 Main St, Chester, MD 21619, 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.
Logo_Paragon_Home team_white BG_D03
David J. Moore & Associates of REAL Broker, LLC
David J. Moore
License ID: 609287
+1(443) 249-9696
info@theparagonhometeam.com
2201 Main St, Chester, MD 21619, USA

Get My App

    • Home

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

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