Hilltop Dr, Chestertown, MD Property Records

Queen Anne's County property records for 17 addresses on Hilltop Dr, Chestertown, MD · Last verified September 2026

Hilltop Dr Highlights

Properties 17
Median Sale Price $355,000
Deeds and Mortgages on File 30
Median Price per Sqft $170
Owner Occupied 100%
Median Annual Tax Bill $3,161
Median Year Built 1997
Median Ownership Tenure 20 years

Properties on Hilltop Dr

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

104 Hilltop Dr

2.5 ba · 1,800 sqft · built 1997 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$144,000Jun 1998 $3,1002025 Amount on Record Feb 1997 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

105 Hilltop Dr

2 ba · 1,680 sqft · built 2001 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$31,000Aug 2000 $2,8962025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

108 Hilltop Dr

5 ba · 3,254 sqft · built 1999 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jul 2003 $3,8502025 Amount on Record Jul 1999 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

109 Hilltop Dr

3 ba · 2,100 sqft · built 1999 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$298,000Feb 2017 $3,6512025 Amount on Record Apr 2009 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

112 Hilltop Dr

2 ba · 1,941 sqft · built 2000 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$355,000Aug 2007 $3,0562025 Amount on Record May 2000 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

113 Hilltop Dr

2.5 ba · 2,114 sqft · built 1997 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Dec 2018 $3,5992025 Amount on Record Nov 1996 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

117 Hilltop Dr

2.5 ba · 1,976 sqft · built 1997 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,000Jan 1997 $2,8702025 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

118 Hilltop Dr

3 ba · 2,300 sqft · built 2000 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Mar 2023 $3,2882025 Amount on Record Jun 2015 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

121 Hilltop Dr

2.5 ba · 2,152 sqft · built 1996 · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$154,053Apr 1996 $3,3982025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

125 Hilltop Dr

2.5 ba · 1,706 sqft · built 1995 · 1.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$123,500Jan 1996 $2,8452025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

126 Hilltop Dr

2.5 ba · 2,733 sqft · built 2001 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Nov 2024 $4,0542025 Amount on Record May 1999 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

129 Hilltop Dr

2.5 ba · 2,726 sqft · built 1993 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 1994 $3,1612025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

130 Hilltop Dr

2.5 ba · 1,596 sqft · built 1995 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$133,520Oct 2007 $3,0892025 —Nov 2001 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

133 Hilltop Dr

2 ba · 1,553 sqft · built 1995 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$329,000Jun 2006 $2,5602025 Amount on Record May 2004 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Sep 2026

136 Hilltop Dr

2 ba · 1,432 sqft · built 1995 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$376,000May 2026 $2,3162025 Amount on Record Sep 2003 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

137 Hilltop Dr

2 ba · 2,136 sqft · built 1994 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$324,000Oct 2020 $3,2192025 Amount on Record Nov 2008 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

141 Hilltop Dr

2.5 ba · 2,422 sqft · built 1994 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$166,000May 1999 $3,4042025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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