Pearson Smith Realty
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Chestertown, MD
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2,669 Sold Properties

2,669 Sold Properties

The average price in the selected areas has remained stable. Learn more
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23393 CACAWAY FARM LN, Chestertown, MD 21620
1/45

$1,150,000

$1,195,000

3.8%
3 Beds4 Baths4,446 SqFt

23393 CACAWAY FARM LN, Chestertown, MD 21620

MLS# MDKE2004002

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
109 2ND ST, Chestertown, MD 21620
1/9

$75,000

$15,000

400.0%
1.8 Acres

109 2ND ST, Chestertown, MD 21620

MLS# MDQA2014918

Listed by Ashland Auction Group LLC

Bright MLS (BMLS)
101 METCALF RD, Chestertown, MD 21620
1/26

$264,900

$264,900

3 Beds2 Baths1,280 SqFt

101 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005882

Listed by Real Broker, LLC

Bright MLS (BMLS)
600 ROSIN DR, Chestertown, MD 21620
1/35

$413,300

$415,000

0.4%
3 Beds2 Baths1,300 SqFt

600 ROSIN DR, Chestertown, MD 21620

MLS# MDQA2014896

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
302 ROSIN DR, Chestertown, MD 21620
1/70

$550,000

$574,000

4.2%
5 Beds4 Baths3,877 SqFt

302 ROSIN DR, Chestertown, MD 21620

MLS# MDQA2015470

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
7483 SHORTALL ST, Chestertown, MD 21620
1/26

$287,500

$290,000

0.9%
3 Beds2 Baths1,232 SqFt

7483 SHORTALL ST, Chestertown, MD 21620

MLS# MDKE2005616

Listed by RE/MAX Executive

Bright MLS (BMLS)
8951 ORCHARD DR, Chestertown, MD 21620
1/47

$700,000

$695,000

0.7%
4 Beds4 Baths3,735 SqFt

8951 ORCHARD DR, Chestertown, MD 21620

MLS# MDKE2005836

Listed by Rock Hall Properties Real Estate

Bright MLS (BMLS)
119 HIGH ST, Chestertown, MD 21620
1/60

$1,165,000

$1,250,000

6.8%
5 Beds5 Baths4,409 SqFt

119 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005728

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
212 LANDING LN, Chestertown, MD 21620
1/36

$750,000

$759,000

1.2%
3 Beds4 Baths

212 LANDING LN, Chestertown, MD 21620

MLS# MDKE2004782

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
907 N MEADOWVIEW DR, Chestertown, MD 21620
1/33

$375,000

$410,000

8.5%
3 Beds3 Baths1,842 SqFt

907 N MEADOWVIEW DR, Chestertown, MD 21620

MLS# MDKE2005540

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
23620 LANDS END RD, Chestertown, MD 21620
1/77

$4,221,800

$4,850,000

13.0%
5 Beds8 Baths9,852 SqFt

23620 LANDS END RD, Chestertown, MD 21620

MLS# MDKE2004760

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
221 OLD BRIDGE RD, Chestertown, MD 21620
1/29

$359,900

$369,900

2.7%
3 Beds2 Baths1,851 SqFt

221 OLD BRIDGE RD, Chestertown, MD 21620

MLS# MDQA2014888

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
10761 KASOTA RD, Chestertown, MD 21620
1/47

$872,500

$895,000

2.5%
3 Beds3 Baths2,582 SqFt

10761 KASOTA RD, Chestertown, MD 21620

MLS# MDKE2005698

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
126 METCALF RD, Chestertown, MD 21620
1/25

$230,000

$230,000

3 Beds2 Baths1,140 SqFt

126 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005734

Listed by Taylor Properties

Bright MLS (BMLS)
201 BOUNDARY AVE, Chestertown, MD 21620
1/46

$425,000

$449,000

5.3%
3 Beds3 Baths3,096 SqFt

201 BOUNDARY AVE, Chestertown, MD 21620

MLS# MDQA2014272

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
23628 CANVASBACK RD, Chestertown, MD 21620
1/5

$25,000

$15,000

66.7%
0.34 Acres

23628 CANVASBACK RD, Chestertown, MD 21620

MLS# MDKE2005696

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
105 PARMA RD, Chestertown, MD 21620
1/28

$322,000

$326,500

1.4%
3 Beds2 Baths1,232 SqFt

105 PARMA RD, Chestertown, MD 21620

MLS# MDQA2014652

Listed by Benson & Mangold, LLC

Bright MLS (BMLS)
10050 FORREST LN, Chestertown, MD 21620
1/49

$905,000

$899,000

0.7%
4 Beds2 Baths1,820 SqFt

10050 FORREST LN, Chestertown, MD 21620

MLS# MDKE2005792

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 ADELA WAY, Chestertown, MD 21620
1/90

$585,000

$595,000

1.7%
4 Beds4 Baths5,576 SqFt

103 ADELA WAY, Chestertown, MD 21620

MLS# MDKE2005594

Listed by Douglas Realty LLC

Bright MLS (BMLS)
124 CHAR NOR MANOR BLVD, Chestertown, MD 21620
1/31

$250,000

$245,000

2.0%
2 Beds2 Baths1,024 SqFt

124 CHAR NOR MANOR BLVD, Chestertown, MD 21620

MLS# MDQA2014812

Listed by RE/MAX Executive

Bright MLS (BMLS)
2010 MCGINNES RD, Chestertown, MD 21620
1/19

$354,900

$359,900

1.4%
3 Beds1 Bath1,253 SqFt

2010 MCGINNES RD, Chestertown, MD 21620

MLS# MDQA2014878

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
225 DUKE OF KENT ST, Chestertown, MD 21620
1/34

$395,000

$399,900

1.2%
3 Beds3 Baths1,850 SqFt

225 DUKE OF KENT ST, Chestertown, MD 21620

MLS# MDQA2014684

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
CHURCH HILL ( LOT 2) RD, Chestertown, MD 21620
1/12

$162,000

$165,000

1.8%
5.34 Acres

CHURCH HILL ( LOT 2) RD, Chestertown, MD 21620

MLS# MDQA2014030

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
8293 BRICES MILL RD, Chestertown, MD 21620
1/59

$775,000

$799,999

3.1%
4 Beds3 Baths2,836 SqFt

8293 BRICES MILL RD, Chestertown, MD 21620

MLS# MDKE2005646

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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Pearson Smith Realty

Urban Nest Realty Group

+1(703) 927-0606 urbannestrealtygroup@gmail.com

License ID: 0225206171

43777 Central Station Dr # 390, Ashburn, VA, 20147, United States

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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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Pearson Smith Realty

Urban Nest Realty Group

+1(703) 927-0606 urbannestrealtygroup@gmail.com

License ID: 0225206171

43777 Central Station Dr # 390, Ashburn, VA, 20147, United States

Get My App

      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      About
      1. About Us
      2. Contact Us
      3. Reviews
      Market Snapshot
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 2025. All Rights Reserved. Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility