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Chestertown, MD
Price
    • Any
    • $ 50,000
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 800,000
Beds
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    • 2
    • 3
    • 4
    • 5
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    • 1
    • 2
    • 3
    • 4
    • 5
Baths
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    • 1
    • 1.5
    • 2
    • 3
    • 4
    • 5
    • Any
    • 1
    • 1.5
    • 2
    • 3
    • 4
    • 5
  • List
  • Mixed
  • Map
Map
155 Properties Available

155 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
202 VALLEY RD, Chestertown, MD 21620
Under Contract

$325,000

3 Beds1 Bath1,427 SqFt

202 VALLEY RD, Chestertown, MD 21620

MLS# MDKE2006538

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
100 PROSPECT ST, Chestertown, MD 21620
Coming Soon

$215,000

3 Beds1 Bath1,373 SqFt

100 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006544

Listed by Real Broker, LLC

Bright MLS (BMLS)
8629 AIRY HILL RD, Chestertown, MD 21620
1/10
Coming Soon

$425,000

3 Beds2 Baths1,440 SqFt

8629 AIRY HILL RD, Chestertown, MD 21620

MLS# MDKE2006526

Listed by Keller Williams Realty

Bright MLS (BMLS)
214 SILVER HEEL RD, Chestertown, MD 21620
1/26
New

$350,000

4 Beds3 Baths1,972 SqFt

214 SILVER HEEL RD, Chestertown, MD 21620

MLS# MDKE2006498

Listed by Cross Street Realtors LLC

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

$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)
110 S QUEEN ST, Chestertown, MD 21620
Coming Soon

$525,000

3 Beds2 Baths1,785 SqFt

110 S QUEEN ST, Chestertown, MD 21620

MLS# MDKE2006520

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
1014 TWIN CT, Chestertown, MD 21620
1/29
Coming Soon

$499,000

3 Beds2 Baths1,817 SqFt

1014 TWIN CT, Chestertown, MD 21620

MLS# MDKE2006516

Listed by Cross Street Realtors LLC

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)
144 PROSPECT ST, Chestertown, MD 21620
1/18
New

$179,000

2 Beds2 Baths1,082 SqFt

144 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006494

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
407 HIGH ST, Chestertown, MD 21620
1/58
Open 5/30 10AM-1PM

$828,000

3 Beds5 Baths3,047 SqFt

407 HIGH ST, Chestertown, MD 21620

MLS# MDKE2006496

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
107 FLYING CLOUD DR, Chestertown, MD 21620
Coming Soon

$395,000

5 Beds4 Baths2,534 SqFt

107 FLYING CLOUD DR, Chestertown, MD 21620

MLS# MDKE2006510

Listed by CENTURY 21 New Millennium

Bright MLS (BMLS)
22360 GREAT OAK LANDING RD, Chestertown, MD 21620
1/11
Coming Soon

$525,000

5 Beds4 Baths2,688 SqFt

22360 GREAT OAK LANDING RD, Chestertown, MD 21620

MLS# MDKE2006478

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
23416 CLOQUET RD, Chestertown, MD 21620
1/5
Coming Soon

$384,000

3 Beds2 Baths1,512 SqFt

23416 CLOQUET RD, Chestertown, MD 21620

MLS# MDKE2006486

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 TRAFFORD DR, Chestertown, MD 21620
1/66
Price Dropped by $30K

$419,900

3 Beds3 Baths1,944 SqFt

103 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2006416

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
126 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/36
Under Contract
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
Active

$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)
205 RIVER RD, Chestertown, MD 21620
1/72
Price Dropped by $20K

$899,500

4 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
Active

$259,900

3 Beds2 Baths1,280 SqFt

103 METCALF RD, Chestertown, MD 21620

MLS# MDKE2006446

Listed by Real Broker, LLC

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

$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
Pending

$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
Pending

$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)
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Weichert Realtors®

Jason Gareau License ID: 18126

+1(609) 929-4486 jason@thejasongareauteam.com

107 Taunton Blvd, Medford, NJ, 08055, USA

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Weichert Realtors®

Jason Gareau License ID: 18126

+1(609) 929-4486 jason@thejasongareauteam.com

107 Taunton Blvd, Medford, NJ, 08055, USA

    • Home
      About
      1. About Us
      Contact
    • Listings
      1. All Listings
      2. Featured Listings
      Neighborhoods
      1. Indian Mills
      2. Tabernacle
      3. Vincentown
      4. Mount Laurel
      5. Marlton
      6. Medford Lakes
      7. Medford
      Reviews
    • Selling
      1. Sell My Home
      2. Home Valuation
      Blogs

Get My App

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.