$364,900
108 Flying Cloud Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $363,448
Last Listing Agent Casey Scattergood Cross Street Realtors LLC
108 Flying Cloud Dr, Chestertown, MD 21620
$325,000
676 Deep Landing Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $333,366
Last Listing Agent Katie Stecklair Cross Street Realtors LLC
676 Deep Landing Rd, Chestertown, MD 21620
$410,000
222 Mount Vernon Ave, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $425,918
Last Listing Agent Casey Scattergood Cross Street Realtors LLC
222 Mount Vernon Ave, Chestertown, MD 21620
$825,000
25475 Turnberry Ct, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $845,087
Last Listing Agent Lona Todd Taylor Properties
25475 Turnberry Ct, Chestertown, MD 21620
$375,000
907 N Meadowview Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $381,052
Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company
907 N Meadowview Dr, Chestertown, MD 21620
$150,000
107 Conley Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $171,390
Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC
107 Conley Dr, Chestertown, MD 21620
$609,000
10175 John Carvill Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $645,961
Last Listing Agent Hayley Norris Select Land & Homes, LLC
10175 John Carvill Rd, Chestertown, MD 21620
$350,000
21111 Texas Ave, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $353,124
Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton
21111 Texas Ave, Chestertown, MD 21620
$1,524,900
10800 Cliff Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $1,489,844
Last Listing Agent Lona Todd Taylor Properties
10800 Cliff Rd, Chestertown, MD 21620
$1,100,000
209 N Water St, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $1,156,728
Last Listing Agent Richard Keaveney Cross Street Realtors LLC
209 N Water St, Chestertown, MD 21620
$287,500
7483 Shortall St, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $285,711
Last Listing Agent Christine Johnson RE/MAX Executive
7483 Shortall St, Chestertown, MD 21620
$25,000
23628 Canvasback Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $186,667
Last Listing Agent Christopher McClary Gunther-McClary Real Estate
23628 Canvasback Rd, Chestertown, MD 21620
$175,000
23069 Raleigh Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $187,318
Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis
23069 Raleigh Rd, Chestertown, MD 21620
$9,500
0 Millbrook Dr, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Dee Dee Miller Paul Wesley Real Estate
0 Millbrook Dr, Chestertown, MD 21620
$220,000
300 Hilltop Ln, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $227,337
Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company
300 Hilltop Ln, Chestertown, MD 21620
$680,000
8978 Orchard Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $706,233
Last Listing Agent Liddy Campbell TTR Sotheby's International Realty
8978 Orchard Dr, Chestertown, MD 21620
$795,000
211 David Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $817,732
Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company
211 David Dr, Chestertown, MD 21620
$1,165,000
119 High St, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $1,141,574
Last Listing Agent Richard Keaveney Cross Street Realtors LLC
119 High St, Chestertown, MD 21620
$317,000
213 Central Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $316,784
Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company
213 Central Dr, Chestertown, MD 21620
$790,000
209 Rivershore Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $811,156
Last Listing Agent Barbara McPhail Douglas Realty LLC
209 Rivershore Rd, Chestertown, MD 21620
$240,000
100 Metcalf Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $243,755
Last Listing Agent Dale Hunter Bayside Realty
100 Metcalf Rd, Chestertown, MD 21620
$480,000
101 Pine Tree Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $483,154
Last Listing Agent Michael Rosendale Rosendale Realty
101 Pine Tree Rd, Chestertown, MD 21620
$120,000
141 Prospect St, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $135,028
Last Listing Agent Jeff Guthrie Taylor Properties
141 Prospect St, Chestertown, MD 21620
$315,000
106 Wilton Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $324,750
Last Listing Agent Crystal Smith RE/MAX Executive
106 Wilton Rd, Chestertown, MD 21620
$280,000
100 Acorn Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $304,135
Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company
100 Acorn Dr, Chestertown, MD 21620
$155,000
8992 S Bayview Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $170,308
Last Listing Agent William Norris Select Land & Homes, LLC
8992 S Bayview Dr, Chestertown, MD 21620
$335,000
110 Flying Cloud Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $352,473
Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty
110 Flying Cloud Dr, Chestertown, MD 21620
$190,000
0 Hoffecker Rd, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC
0 Hoffecker Rd, Chestertown, MD 21620
$270,000
119 Darden Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $273,743
Last Listing Agent Solomon Zaldivar Compass
119 Darden Rd, Chestertown, MD 21620
$495,000
201 Greenwood Ave, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $490,279
Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC
201 Greenwood Ave, Chestertown, MD 21620
$205,000
310 Hilltop Ln, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $220,577
Last Listing Agent Clint Evans Cross Street Realtors LLC
310 Hilltop Ln, Chestertown, MD 21620
$525,000
22360 Great Oak Landing Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $594,505
Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC
22360 Great Oak Landing Rd, Chestertown, MD 21620
$237,000
898 Washington Ave, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $259,569
Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC
898 Washington Ave, Chestertown, MD 21620
$665,000
118 Little Harbor Way Unit 201, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $642,743
Last Listing Agent Richard Keaveney Cross Street Realtors LLC
118 Little Harbor Way Unit 201, Chestertown, MD 21620
$775,000
8293 Brices Mill Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $777,217
Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company
8293 Brices Mill Rd, Chestertown, MD 21620
$11,000
0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Dee Dee Miller Paul Wesley Real Estate
0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
$124,000
209 River Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $139,842
Last Listing Agent Hayley Norris Select Land & Homes, LLC
209 River Rd, Chestertown, MD 21620
$259,900
107 Metcalfe Rd, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent David Moore Real Broker, LLC
107 Metcalfe Rd, Chestertown, MD 21620
$359,000
8833 Georgetown Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $346,939
Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company
8833 Georgetown Rd, Chestertown, MD 21620
$700,000
26889 Morgnec Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $723,034
Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company
26889 Morgnec Rd, Chestertown, MD 21620Showing Results 1 - 40, Page 1 of 6
The median home sale price in Chestertown, MD is $364,900, down 1% year-over-year. Homes in Chestertown sell in 50 days on average, compared to the national average of 58 days.
|
Median Sale Price
$364,900
|
Median Single Family Sale Price
$396,500
|
|
Median Townhouse Sale Price
$264,900
|
Median 2 Bedroom Sale Price
$352,500
|
|
Median 1 Bedroom Sale Price
$242,500
|
Average Price Per Sq Ft
$211
|
|
Number of Homes for Sale
35
|
Last 12 months Home Sales
103
|
|
Months of Supply
4.10
|
Median List Price
$377,000
|
|
Median Change From 1st List Price
0%
|
Median Home Sale Price YoY Change
-1%
|
Copyright © 2026 CoStar Group
