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Chester Dr, Chester, MD Property Records

Queen Anne's County property records for 29 addresses on Chester Dr, Chester, MD · Last verified October 2026

Chester Dr Highlights

Properties 29
Median Sale Price $420,000
Deeds and Mortgages on File 35
Median Price per Sqft $289
Owner Occupied 79%
Median Annual Tax Bill $2,903
Median Year Built 1984
Median Ownership Tenure 11 years

Properties on Chester Dr

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

1800 Chester Dr

2.5 ba · 1,555 sqft · built 1957 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Sep 2018 $2,7882025 Amount on Record Jun 2004 Owner on Record Assessor + 2 DocumentsUpdated Sep 2026

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1802 Chester Dr

1.5 ba · 1,528 sqft · built 1963 · 0.395 acres

Last Sale Tax Bill Prior Sale Owner Records
$303,000Jun 2021 $2,7632025 —Feb 2021 2 Owners on Record Assessor + 6 DocumentsUpdated Sep 2026

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1803 Chester Dr

1 ba · 1,636 sqft · built 1960 · 0.335 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000May 2026 $2,6892025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

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1805 Chester Dr

2 ba · 1,464 sqft · built 1957 · 0.362 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Apr 2016 $2,5712025 —Sep 2007 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1806 Chester Dr

2 ba · 1,452 sqft · built 1962 · 0.413 acres

Last Sale Tax Bill Prior Sale Owner Records
$420,000Aug 2024 $3,0482025 Amount on Record Dec 2005 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1808 Chester Dr

1.5 ba · 1,288 sqft · built 1978 · 0.413 acres

Last Sale Tax Bill Prior Sale Owner Records
$383,000Nov 2023 $2,7292025 Amount on Record May 2012 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1812 Chester Dr

2 ba · 1,360 sqft · built 1964 · 0.426 acres

Last Sale Tax Bill Prior Sale Owner Records
$123,000Sep 1991 $2,7232025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1814 Chester Dr

2 ba · 2,000 sqft · built 1979 · 0.569 acres

Last Sale Tax Bill Prior Sale Owner Records
$62,000Jul 1984 $3,3472025 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

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1815 Chester Dr

1.5 ba · 2,340 sqft · built 1965 · 0.669 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2003 $3,0762025 Owner on Record Owner Occupied AssessorUpdated Oct 2026

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1817 Chester Dr

2 ba · 1,922 sqft · built 2009 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jun 2021 $4,0222025 Amount on Record Mar 2012 2 Owners on Record Owner Occupied Assessor + 5 DocumentsUpdated Sep 2026

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1818 Chester Dr

2 ba · 1,536 sqft · built 1975 · 0.293 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2004 $2,9032025 Amount on Record Apr 2003 Owner on Record AssessorUpdated Sep 2026

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1819 Chester Dr

2.5 ba · 2,558 sqft · built 2008 · 0.275 acres

Last Sale Tax Bill Prior Sale Owner Records
$399,900Sep 2008 $4,2512025 Amount on Record Jan 2008 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1820 Chester Dr

2 ba · 1,222 sqft · built 1988 · 0.263 acres

Last Sale Tax Bill Prior Sale Owner Records
$259,000Aug 2005 $2,5982025 Amount on Record Jul 1988 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1822 Chester Dr

1 ba · 1,092 sqft · built 1975 · 0.347 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2004 $2,4442025 Amount on Record Mar 1998 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1823 Chester Dr

1 ba · 1,080 sqft · built 1976 · 0.324 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Dec 2024 $2,4412025 —Dec 2024 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1825 Chester Dr

2 ba · 1,389 sqft · built 1995 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$639,900Sep 2022 $2,9042025 Amount on Record Sep 2021 Owner on Record Assessor + 2 DocumentsUpdated Sep 2026

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1900 Chester Dr

2 ba · 1,456 sqft · built 2004 · 0.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Jul 2016 $3,0692025 —Oct 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1903 Chester Dr

2 ba · 1,470 sqft · built 1987 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Aug 2024 $2,8982025 Amount on Record Aug 1987 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

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1905 Chester Dr

2.5 ba · 2,144 sqft · built 2001 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$340,000Jul 2015 $3,8732025 Amount on Record Apr 2001 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1906 Chester Dr

0.448 acres

Last Sale Tax Bill Prior Sale Owner Records
$402025 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1907 Chester Dr

2.5 ba · 1,922 sqft · built 2019 · 0.341 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,0622025 Owner on Record AssessorUpdated Aug 2026

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1908 Chester Dr

2 ba · 1,961 sqft · built 1973 · 0.886 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,8952025 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1910 Chester Dr

2.5 ba · 2,032 sqft · built 2001 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,000Mar 2002 $4,7792025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

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1912 Chester Dr

2.5 ba · 2,264 sqft · built 2001 · 0.347 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Aug 2013 $4,3922025 Amount on Record Jan 2013 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1914 Chester Dr

2.5 ba · 2,116 sqft · built 1984 · 0.384 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2005 $3,6682025 Amount on Record Feb 2002 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

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1916 Chester Dr

1.5 ba · 1,192 sqft · built 1984 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$114,900Sep 1998 $2,5582025 Amount on Record Mar 1989 Owner on Record Owner Occupied AssessorUpdated Sep 2026

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1918 Chester Dr

1.5 ba · 1,192 sqft · built 1984 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$301,000Dec 2019 $2,8142025 Amount on Record Dec 2009 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

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1920 Chester Dr

1.5 ba · 1,192 sqft · built 1984 · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$279,900Nov 2005 $2,6212025 Amount on Record Jun 1994 2 Owners on Record Owner Occupied AssessorUpdated Sep 2026

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1922 Chester Dr

4 ba · 2,448 sqft · built 1984 · 0.346 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Jun 2003 $4,2702025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2026

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Property Records in Nearby Streets