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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 exact recorded amounts are on file and can be viewed instantly on this page with a free 10-day 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