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Chestertown, MD
Map
2,673 Sold Properties

2,673 Sold Properties

The average price in the selected areas has remained stable. Learn more
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15 BYFORD CT, Chestertown, MD 21620
1/27

$710,000

$759,900

6.6%
4 Beds3 Baths1.69 Acres Lot

15 BYFORD CT, Chestertown, MD 21620

MLS# 1000479085

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
321 TRUSLOW RD, Chestertown, MD 21620
1/19

$190,000

$190,995

0.5%
3 Beds2 Baths1,984 SqFt

321 TRUSLOW RD, Chestertown, MD 21620

MLS# 1001032143

Listed by Partners Realty LLC

Bright MLS (BMLS)
207 FEY RD, Chestertown, MD 21620

$194,000

$200,000

3.0%
4 Beds2 Baths1 Acres Lot

207 FEY RD, Chestertown, MD 21620

MLS# 1001032429

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
104 WATER ST N, Chestertown, MD 21620
1/14

$450,000

$475,000

5.3%
4 Beds2 Baths2,522 SqFt

104 WATER ST N, Chestertown, MD 21620

MLS# 1000479253

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
133 QUEEN ST, Chestertown, MD 21620
1/11

$265,000

$279,000

5.0%
3 Beds3 Baths1,652 SqFt

133 QUEEN ST, Chestertown, MD 21620

MLS# 1000479269

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
1017 TWIN CT, Chestertown, MD 21620
1/10

$245,000

$259,900

5.7%
4 Beds2 Baths3,804 SqFt

1017 TWIN CT, Chestertown, MD 21620

MLS# 1000479263

Listed by Wyble Enterprises

Bright MLS (BMLS)
10246 FLATLAND RD, Chestertown, MD 21620
1/10

$260,000

$269,000

3.3%
4 Beds2 Baths4.39 Acres Lot

10246 FLATLAND RD, Chestertown, MD 21620

MLS# 1000479345

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
202 DUTCHESS RD, Chestertown, MD 21620
1/3

$165,000

$155,000

6.5%
3 Beds2 Baths1,508 SqFt

202 DUTCHESS RD, Chestertown, MD 21620

MLS# 1003674099

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
507 HIGH ST, Chestertown, MD 21620
1/19

$225,000

$249,000

9.6%
3 Beds2 Baths3,036 Sqft Lot

507 HIGH ST, Chestertown, MD 21620

MLS# 1000479231

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
917 ROUND TOP RD, Chestertown, MD 21620
1/18

$153,000

$159,900

4.3%
3 Beds1 Bath0.34 Acres Lot

917 ROUND TOP RD, Chestertown, MD 21620

MLS# 1001031431

Listed by Rosendale Realty

Bright MLS (BMLS)
215 FAIRVIEW DR, Chestertown, MD 21620
1/12

$208,000

$210,000

1.0%
3 Beds3 Baths0.6 Acres Lot

215 FAIRVIEW DR, Chestertown, MD 21620

MLS# 1001031487

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
325 UNION CHURCH RD, Chestertown, MD 21620
1/6

$260,000

$269,900

3.7%
4 Beds3 Baths1.03 Acres Lot

325 UNION CHURCH RD, Chestertown, MD 21620

MLS# 1001032093

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
23355 BUCK NECK RD, Chestertown, MD 21620
1/14

$41,000

$44,900

8.7%
3 Beds2 Baths0.62 Acres Lot

23355 BUCK NECK RD, Chestertown, MD 21620

MLS# 1000479359

Listed by Real Estate Consultants

Bright MLS (BMLS)
113 1ST ST, Chestertown, MD 21620
1/27

$165,000

$205,000

19.5%
3 Beds2 Baths0.68 Acres Lot

113 1ST ST, Chestertown, MD 21620

MLS# 1001031719

Listed by CENTURY 21 New Millennium

Bright MLS (BMLS)
106 ACORN DR, Chestertown, MD 21620
1/22

$189,500

$199,000

4.8%
4 Beds3 Baths2,119 Sqft Lot

106 ACORN DR, Chestertown, MD 21620

MLS# 1000479059

Listed by Sommers Enterprises, Inc.

Bright MLS (BMLS)
23673 FOX POINT FARM LN, Chestertown, MD 21620

$2,880,000

$2,900,000

0.7%
4 Beds4 Baths181.01 Acres

23673 FOX POINT FARM LN, Chestertown, MD 21620

MLS# 1002566285

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
114 MALONE AVE, Chestertown, MD 21620
1/28

$182,000

$179,900

1.2%
3 Beds3 Baths0.36 Acres Lot

114 MALONE AVE, Chestertown, MD 21620

MLS# 1000478957

Listed by Home Selling Assistance Plus, LLC

Bright MLS (BMLS)
102 GANDER WAY, Chestertown, MD 21620
1/24

$275,000

$279,000

1.4%
5 Beds3 Baths1 Acres Lot

102 GANDER WAY, Chestertown, MD 21620

MLS# 1001031373

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
7938 RADCLIFFE RD, Chestertown, MD 21620
1/30

$273,000

$275,000

0.7%
5 Beds4 Baths2,408 SqFt

7938 RADCLIFFE RD, Chestertown, MD 21620

MLS# 1000479127

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
118 HILLTOP DR, Chestertown, MD 21620
1/22

$295,000

$295,000

3 Beds3 Baths2,188 SqFt

118 HILLTOP DR, Chestertown, MD 21620

MLS# 1001031601

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
9050 POINT LN, Chestertown, MD 21620
1/27

$470,000

$485,000

3.1%
4 Beds3 Baths0.92 Acres Lot

9050 POINT LN, Chestertown, MD 21620

MLS# 1000479197

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
8995 ORCHARD DR, Chestertown, MD 21620
1/28

$382,500

$392,000

2.4%
3 Beds4 Baths2.98 Acres Lot

8995 ORCHARD DR, Chestertown, MD 21620

MLS# 1000479199

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
9255 UPPER CREEK LN, Chestertown, MD 21620

$905,000

$989,000

8.5%
4 Beds3 Baths34 Acres

9255 UPPER CREEK LN, Chestertown, MD 21620

MLS# 1000479151

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
236 PRINCESS ANNE DR, Chestertown, MD 21620
1/30

$261,000

$264,900

1.5%
4 Beds3 Baths0.46 Acres Lot

236 PRINCESS ANNE DR, Chestertown, MD 21620

MLS# 1001031091

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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Keller Williams Gateway

Andrew Johns

+1(410) 627-7264 andrew@andrewjohnshometeam.com

8015 Corporate Drive, Ste C, Nottingham, Maryland, 21236, United States

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

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AJHT - Logo with KW - over black-01
Keller Williams Gateway

Andrew Johns

+1(410) 627-7264 andrew@andrewjohnshometeam.com

8015 Corporate Drive, Ste C, Nottingham, Maryland, 21236, United States

    • Home
      About
      1. About Us
      Schedule Now
      Blogs
    • Buy
      1. Buyers Guide
      2. Find Your Home
      3. Luxury Listings
      4. Mortgage Calculator
      Communities
      1. Baltimore City
      2. Baltimore County
      3. Harford County
      4. Cecil County
      Contact Us
    • Sell
      1. Sellers Guide
      2. Sell My Home
      3. Home Valuation
      4. Sold Listings
      Discover
      1. Market Snapshot
      Join our Team

Get My App

Powered by Lofty Inc. Copyright 2025. 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.