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Chestertown, MD
Map
147 Properties Available

147 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
205 RIVER RD, Chestertown, MD 21620
1/28
Open Sat 12PM-2PM

$949,000

3 Beds3 Baths2,877 SqFt

205 RIVER RD, Chestertown, MD 21620

MLS# MDQA2016560

Listed by Clark & Co Realty, LLC

Bright MLS (BMLS)
103 METCALF RD, Chestertown, MD 21620
1/22
Open 4/26 11AM-1PM

$259,900

3 Beds2 Baths1,280 SqFt

103 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006446

Listed by Real Broker, LLC

Bright MLS (BMLS)
106 QUEEN ST S, Chestertown, MD 21620
1/92
Open Fri 5PM-7PM

$865,000

3 Beds4 Baths2,472 SqFt

106 QUEEN ST S, Chestertown, MD 21620

MLS# MDKE2006152

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/45
Open 4/26 12PM-2PM

$510,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
7989 QUAKER NECK RD, Chestertown, MD 21620
1/90
Open 5/9 11AM-1PM
3D

$2,400,000

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)
103 TRAFFORD DR, Chestertown, MD 21620
1/66
New

$450,000

3 Beds3 Baths1,944 SqFt

103 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2006416

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
301 HILLTOP LN, Chestertown, MD 21620
1/36
New

$225,000

3 Beds3 Baths1,197 SqFt

301 HILLTOP LN, Chestertown, MD 21620

MLS# MDKE2006398

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
126 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/36
New
3D

$349,000

3 Beds2 Baths1,304 SqFt

126 CHAR NOR MANOR BLVD, Chestertown, MD 21620

MLS# MDQA2016812

Listed by RE/MAX Executive

Bright MLS (BMLS)
24581 WILLOW OAK LN, Chestertown, MD 21620
1/29
New

$229,990

3 Beds2 Baths1,352 SqFt

24581 WILLOW OAK LN, Chestertown, MD 21620

MLS# MDKE2006342

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
115 ACORN DR, Chestertown, MD 21620
1/40
New

$296,000

2 Beds3 Baths1,864 SqFt

115 ACORN DR, Chestertown, MD 21620

MLS# MDKE2006360

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
25475 TURNBERRY CT, Chestertown, MD 21620
1/79
New

$867,000

4 Beds4 Baths4,145 SqFt

25475 TURNBERRY CT, Chestertown, MD 21620

MLS# MDKE2006350

Listed by Taylor Properties

Bright MLS (BMLS)
136 HILLTOP DR, Chestertown, MD 21620
1/27
Under Contract
3D

$366,000

3 Beds2 Baths1,432 SqFt

136 HILLTOP DR, Chestertown, MD 21620

MLS# MDQA2016782

Listed by Northrop Realty

Bright MLS (BMLS)
8706 ELM RD, Chestertown, MD 21620
1/7
Active

$320,000

3 Beds2 Baths1,232 SqFt

8706 ELM RD, Chestertown, MD 21620

MLS# MDKE2006390

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10584 KLAMATH RD, Chestertown, MD 21620
1/20
Pending

$319,900

3 Beds2 Baths0.37 Acres Lot

10584 KLAMATH RD, Chestertown, MD 21620

MLS# MDKE2006328

Listed by Real Broker, LLC

Bright MLS (BMLS)
108 OAK LEAF DR, Chestertown, MD 21620
1/39
Active

$299,500

2 Beds3 Baths1,867 SqFt

108 OAK LEAF DR, Chestertown, MD 21620

MLS# MDKE2006224

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
10594 MILLBROOK DR, Chestertown, MD 21620
1/14
Under Contract

$329,000

3 Beds2 Baths1,499 SqFt

10594 MILLBROOK DR, Chestertown, MD 21620

MLS# MDKE2006378

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
208 CENTRAL DR, Chestertown, MD 21620
1/19
Active
3D

$315,000

3 Beds1 Bath1,120 SqFt

208 CENTRAL DR, Chestertown, MD 21620

MLS# MDQA2016836

Listed by Redfin Corp

Bright MLS (BMLS)
24295 LANGFORD RD, Chestertown, MD 21620
1/3
Coming Soon

$445,000

3 Beds3 Baths1,857 SqFt

24295 LANGFORD RD, Chestertown, MD 21620

MLS# MDKE2006320

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
240 MERGANSER DR, Chestertown, MD 21620
1/8
Coming Soon

$425,000

3 Beds2 Baths1,120 SqFt

240 MERGANSER DR, Chestertown, MD 21620

MLS# MDQA2016900

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
10087 JOHN CARVILL RD, Chestertown, MD 21620
1/63
Pending

$695,000

3 Beds2 Baths1,566 SqFt

10087 JOHN CARVILL RD, Chestertown, MD 21620

MLS# MDKE2006324

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
2032 PONDTOWN RD, Chestertown, MD 21620
1/32
Under Contract

$325,000

3 Beds2 Baths1,120 SqFt

2032 PONDTOWN RD, Chestertown, MD 21620

MLS# MDQA2016688

Listed by Northrop Realty

Bright MLS (BMLS)
21217 TEXAS AVE, Chestertown, MD 21620
1/20
Active

$265,000

2 Beds1 Bath912 SqFt

21217 TEXAS AVE, Chestertown, MD 21620

MLS# MDKE2006364

Listed by RE/MAX Leading Edge

Bright MLS (BMLS)
226 S WATER ST, Chestertown, MD 21620
1/32
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)
720 DEEP LANDING RD, Chestertown, MD 21620
1/42
Under Contract

$369,999

3 Beds2 Baths1,271 SqFt

720 DEEP LANDING RD, Chestertown, MD 21620

MLS# MDQA2016758

Listed by Coldwell Banker Waterman Realty

Bright MLS (BMLS)
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Leisel L. Taylor
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1441 McCormick Dr Ste 1020, Largo, MD 20774

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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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Get My App

TaylorMade Team
Leisel L. Taylor
+1(240) 290-0830
leisel@taylormadeteam.net
1441 McCormick Dr Ste 1020, Largo, MD 20774

      Home
      About
      1. About Us
      2. Contact Us
      3. Reviews
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      4. Book An Appointment
      Sell
      1. Sell My Home
      2. Home Valuation
      3. Book An Appointment
      Hire Leisel
      Refer the TaylorMade Team
      Neighborhoods
      Blogs
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.

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

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