Chester Ave, Annapolis, MD Property Records

Anne Arundel County property records for 84 addresses on Chester Ave, Annapolis, MD · Last verified August 2026

Chester Ave Highlights

Properties 86
Median Sale Price $1,248,000
Deeds and Mortgages on File 128
Median Price per Sqft $505
Owner Occupied 77%
Median Annual Tax Bill $10,043
Median Year Built 1940
Median Ownership Tenure 11 years

Properties on Chester Ave

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

1 Chester Ave

2 ba · 1,428 sqft · built 1957 · 0.229 acres

Last Sale Tax Bill Prior Sale Owner Records
$643,000Mar 2017 $9,5022023 Amount on Record Jun 2013 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

2 Chester Ave

3 ba · 2,296 sqft · built 1939 · 0.136 acres

Last Sale Tax Bill Prior Sale Owner Records
$980,000Sep 2014 $11,8492023 Amount on Record Feb 2005 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

3 Chester Ave

3 ba · 2,815 sqft · built 1952 · 0.134 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,660,000Mar 2026 $14,2242025 Amount on Record Aug 2025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Mar 2026

4 Chester Ave

4 ba · 2,808 sqft · built 1999 · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$975,000May 2017 $13,9442024 Amount on Record Jun 2008 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

5 Chester Ave

2.5 ba · 2,978 sqft · built 1996 · 0.134 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Jun 2022 $13,9522024 Amount on Record May 2012 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

6 Chester Ave

3 ba · 3,171 sqft · built 1938 · 0.121 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Jul 2002 $10,3872024 Amount on Record Sep 1999 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

9 Chester Ave

2.5 ba · 1,622 sqft · built 1941 · 0.269 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5772024 Owner on Record Owner Occupied AssessorUpdated Aug 2026

11 Chester Ave

5.5 ba · 3,780 sqft · built 1949 · 0.268 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,599,000Jun 2021 $17,2892024 Amount on Record Jan 2014 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

105 Chester Ave

2 ba · 1,314 sqft · built 1920 · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,500Mar 2017 $8,3712023 Amount on Record Jun 1994 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2023

107 Chester Ave

2 ba · 1,472 sqft · built 1920 · 0.061 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6292024 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

108 Chester Ave

3 ba · 1,932 sqft · built 1981 · 0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Aug 2000 $8,9792023 Amount on Record May 2000 Owner on Record Owner Occupied AssessorUpdated Sep 2023

109 Chester Ave

1 ba · 1,384 sqft · built 1920 · 0.059 acres

Last Sale Tax Bill Prior Sale Owner Records
$599,000Aug 2015 $7,9792023 Amount on Record Jan 2001 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

110 Chester Ave

4 ba · 2,006 sqft · built 2017 · 0.158 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,299,000Nov 2020 $13,6162023 Amount on Record Mar 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

111 Chester Ave

2 ba · 946 sqft · built 1910 · 0.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Aug 2001 $6,9662023 3 Owners on Record Assessor + 1 DocumentUpdated Sep 2023

112 Chester Ave

4 ba · 2,660 sqft · built 1905 · 0.158 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Mar 2016 $13,8432024 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

113 Chester Ave

2 ba · 1,312 sqft · built 1910 · 0.068 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Aug 2017 $8,1502024 —Dec 2007 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

114 Chester Ave

2 ba · 1,514 sqft · built 1863 · 0.158 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2008 $9,0102024 Amount on Record Nov 2005 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

115 Chester Ave

4.5 ba · 3,597 sqft · built 1910 · 0.128 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,248,000Nov 2021 $16,4572024 Amount on Record Aug 2012 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

116 Chester Ave

2.5 ba · 2,984 sqft · built 2009 · 0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,294,365May 2018 $15,1972024 Amount on Record Apr 2006 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

119 Chester Ave

2 ba · 1,800 sqft · built 1910 · 0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$130,000Apr 1997 $7,7852024 Amount on Record Apr 1994 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

121 Chester Ave

2.5 ba · 1,888 sqft · built 1979 · 0.087 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2008 $7,4152024 Owner on Record Owner Occupied AssessorUpdated Apr 2026

123 Chester Ave

2.5 ba · 1,888 sqft · built 1979 · 0.083 acres

Last Sale Tax Bill Prior Sale Owner Records
$635,000Jun 2007 $9,1022024 —Jan 2005 Owner on Record Owner Occupied AssessorUpdated Apr 2026

125 Chester Ave

3 ba · 1,912 sqft · built 1979 · 0.087 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Mar 2021 $8,5912023 Amount on Record Mar 2013 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

127 Chester Ave

2 ba · 2,176 sqft · built 1937 · 0.056 acres

Last Sale Tax Bill Prior Sale Owner Records
$665,000Sep 2015 $9,9632024 Amount on Record Jan 2011 Owner on Record AssessorUpdated Apr 2026

129 Chester Ave

3 ba · 2,014 sqft · built 1910 · 0.051 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 1995 $7,0782023 Amount on Record Sep 1994 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

131 Chester Ave

3.5 ba · 2,072 sqft · built 1910 · 0.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Mar 2021 $9,2172024 Amount on Record Dec 2008 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

201 Chester Ave

2 ba · 1,551 sqft · built 1996 · 0.042 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 1997 $9,6862024 Amount on Record Feb 1997 Owner on Record AssessorUpdated Apr 2026

205 Chester Ave

2 ba · 1,332 sqft · built 1930 · 0.061 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,500Jun 1998 $6,5902024 Amount on Record Nov 1988 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

207 Chester Ave

3.5 ba · 1,608 sqft · built 1995 · 0.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$885,000Sep 2013 $12,1032024 Amount on Record Feb 2010 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

211 Chester Ave

3 ba · 2,267 sqft · built 1930 · 0.121 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,500Jul 1999 $8,4922023 Amount on Record Apr 1994 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

212 Chester Ave

4 ba · 3,656 sqft · built 1990 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,000,000May 2017 $16,0912023 Amount on Record Oct 1998 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Sep 2023

215 Chester Ave

3.5 ba · 3,421 sqft · built 2003 · 0.136 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,730,000Mar 2026 $14,6372024 Amount on Record Aug 2024 Owner on Record Assessor + 4 DocumentsUpdated May 2026

300 Chester Ave

1.5 ba · 2,124 sqft · built 1938 · 0.204 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2000 $8,0392024 Amount on Record Dec 1989 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

301 Chester Ave

2,530 sqft · 0.248 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 1983 $11,2692023 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

306 Chester Ave

1 ba · 840 sqft · built 1925 · 0.048 acres

Last Sale Tax Bill Prior Sale Owner Records
$665,000Jul 2024 $7,6202024 Amount on Record Dec 2016 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

308 Chester Ave

2.5 ba · 1,875 sqft · built 1920 · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$453,500Aug 2001 $7,5442024 Amount on Record Sep 2000 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

310 Chester Ave

2.5 ba · 1,586 sqft · built 1906 · 0.079 acres

Last Sale Tax Bill Prior Sale Owner Records
$931,000Sep 2021 $9,8982024 Amount on Record Sep 2015 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

311 Chester Ave

5,952 sqft · 0.424 acres

Last Sale Tax Bill Prior Sale Owner Records
$925,000Apr 1992 $27,4172025 Owner on Record AssessorUpdated Aug 2026

312 Chester Ave

2.5 ba · 1,360 sqft · built 1930 · 0.138 acres

Last Sale Tax Bill Prior Sale Owner Records
$898,000Jul 2019 $11,8432024 Amount on Record Sep 2005 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

314 Chester Ave

2 ba · 1,374 sqft · built 1920 · 0.097 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Dec 2014 $8,3262023 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

316 Chester Ave

2 ba · 1,200 sqft · built 1920 · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,000Oct 1979 $6,9502025 2 Owners on Record Owner Occupied AssessorUpdated Jun 2026

318 Chester Ave

2.5 ba · 1,954 sqft · built 1920 · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$267,000Apr 2011 $10,8432024 Amount on Record — 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

319 Chester Ave

1,431 sqft · 0.362 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,450,000Jun 2018 $20,8222023 Amount on Record Feb 2016 Owner on Record Assessor + 1 DocumentUpdated Sep 2023

320 Chester Ave

2 ba · 1,176 sqft · built 1920 · 0.081 acres

Last Sale Tax Bill Prior Sale Owner Records
$725,000Apr 2026 $9,3442024 Amount on Record Sep 2016 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

322 Chester Ave

2 ba · 1,672 sqft · built 1904 · 0.154 acres

Last Sale Tax Bill Prior Sale Owner Records
$231,923Dec 2021 $7,4112024 Amount on Record May 1998 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

400 Chester Ave

2 ba · 2,404 sqft · 0.108 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,6102024 2 Owners on Record AssessorUpdated Apr 2026

401 Chester Ave

3.5 ba · 4,267 sqft · built 2006 · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,949,000Feb 2021 $14,6412024 Amount on Record Feb 2013 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

402 Chester Ave

2 ba · 1,560 sqft · built 1920 · 0.051 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2005 $7,7572024 —Aug 2004 Owner on Record AssessorUpdated Apr 2026

403 Chester Ave

2.5 ba · 1,368 sqft · built 1992 · 0.031 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000May 2018 $10,1252024 Amount on Record Aug 2000 Owner on Record Assessor + 3 DocumentsUpdated May 2026

404 Chester Ave

3 ba · 1,440 sqft · built 2015 · 0.087 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2005 $10,1602024 —Aug 2004 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

405 Chester Ave

1.5 ba · 1,368 sqft · built 1992 · 0.027 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Mar 2018 $9,9012024 Owner on Record Assessor + 3 DocumentsUpdated May 2026

406 Chester Ave

2,290 sqft · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,6212023 Owner on Record Owner Occupied AssessorUpdated Sep 2023

407 Chester Ave

3 ba · 1,368 sqft · built 1992 · 0.027 acres

Last Sale Tax Bill Prior Sale Owner Records
$691,000Jul 2019 $9,5092023 Amount on Record Jul 2018 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

408 Chester Ave

1 ba · 503 sqft · built 1926 · 0.011 acres

Last Sale Tax Bill Prior Sale Owner Records
$269,000Feb 2007 $2,9962023 Amount on Record Feb 2006 Owner on Record Assessor + 1 DocumentUpdated Sep 2023

408 Chester Ave

3 units · Built 1920 · 543 sq ft

Last Sale Median Tax Bill Median Sale    
$172,972Oct 2018 $2,7282023 $185,0003 units    

409 Chester Ave

1 ba · 1,188 sqft · 0.265 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,3592024 Owner on Record Assessor + 1 DocumentUpdated May 2026

414 Chester Ave, #A

1 ba · 542 sqft · built 1920 · 0.012 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Jun 2006 $2,7242023 Amount on Record Sep 2003 Owner on Record Assessor + 1 DocumentUpdated Sep 2023

418 Chester Ave

2 ba · 1,280 sqft · built 1940 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$42,612May 1989 $6,1712023 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

420 Chester Ave

2 ba · 1,104 sqft · built 1940 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000Mar 2009 $10,6862025 —Jan 2009 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

422 Chester Ave

2 ba · 1,447 sqft · built 1944 · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000Jan 2017 $9,4452023 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

423 Chester Ave

5,442 sqft · built 1986 · 3.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$20,000,000May 2021 $94,1162023 Owner on Record Assessor + 1 DocumentUpdated Sep 2023

424 Chester Ave

1 ba · 1,372 sqft · built 1926 · 0.169 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2008 $7,3662024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

500 Chester Ave

2.5 ba · 3,190 sqft · built 1982 · 0.157 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,600,000Jan 2025 $15,4422024 Amount on Record Aug 2017 2 Owners on Record Assessor + 1 DocumentUpdated Apr 2026

502 Chester Ave

4 ba · 3,229 sqft · built 1982 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Nov 2012 $13,2672023 —Nov 2008 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

504 Chester Ave

3 ba · 3,277 sqft · built 1981 · 0.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Aug 1981 $11,0062023 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

506 Chester Ave

2.5 ba · 3,283 sqft · built 1982 · 0.137 acres

Last Sale Tax Bill Prior Sale Owner Records
$885,000Apr 2006 $14,7672025 Amount on Record Jun 1994 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

611 Chester Ave

1 ba · 768 sqft · built 1930 · 0.067 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Sep 2004 $7,0512023 Amount on Record Nov 2000 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

613 Chester Ave

1 ba · 924 sqft · built 1946 · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$480,000Jun 2021 $7,3612024 Amount on Record Jan 2020 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

717 Chester Ave

5.5 ba · 3,942 sqft · built 2018 · 0.225 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,750,000Feb 2023 $29,6882024 Amount on Record Jul 2020 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

719 Chester Ave

3 ba · 1,823 sqft · 0.171 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Apr 2019 $12,6562023 —Oct 2012 Owner on Record AssessorUpdated Sep 2023

721 Chester Ave

3 ba · 3,804 sqft · built 2002 · 0.191 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 1996 $19,7452023 Owner on Record Owner Occupied AssessorUpdated Sep 2023

809 Chester Ave

2.5 ba · 1,834 sqft · built 2008 · 0.317 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Aug 2011 $24,9912025 Amount on Record Jan 2006 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

811 Chester Ave

5 ba · 4,094 sqft · built 2003 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,695,000Dec 2015 $27,4182025 Amount on Record Sep 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jan 2026

814 Chester Ave

1 ba · 2,296 sqft · built 1926 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Dec 2006 $10,1612024 Amount on Record Sep 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

816 Chester Ave

3 ba · 3,059 sqft · built 2006 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,227,000May 2006 $14,0392023 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

817 Chester Ave

3.5 ba · 3,951 sqft · built 1998 · 0.154 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,170,000Mar 2015 $18,6072023 Amount on Record May 1998 2 Owners on Record Assessor + 3 DocumentsUpdated Jul 2026

818 Chester Ave

1 ba · 1,056 sqft · built 1926 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$284,900Sep 1999 $6,7252023 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

819 Chester Ave

5 ba · 3,072 sqft · built 1999 · 0.175 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,075,000Jun 2003 $16,2882023 Amount on Record Dec 1999 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

820 Chester Ave

3.5 ba · 4,805 sqft · built 2006 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Aug 2011 $18,3552024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

822 Chester Ave

1.5 ba · 1,231 sqft · built 1930 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$865,000Mar 2022 $10,0432024 Amount on Record Jul 2021 2 Owners on Record Assessor + 2 DocumentsUpdated Apr 2026

824 Chester Ave

4 ba · 3,078 sqft · built 2006 · 0.177 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,385,000Dec 2019 $15,7842023 Amount on Record Dec 2006 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2023

826 Chester Ave

2.5 ba · 1,871 sqft · built 1930 · 0.183 acres

Last Sale Tax Bill Prior Sale Owner Records
$875,000Aug 2022 $12,2802024 Amount on Record Nov 2000 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

828 Chester Ave

2.5 ba · 2,750 sqft · built 1993 · 0.164 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Jul 2021 $14,9532024 Amount on Record Jan 2000 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

830 Chester Ave

4 ba · 2,424 sqft · built 1930 · 0.184 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,005,000Jan 2019 $12,4982023 Amount on Record Aug 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2023

Property Records in Nearby Streets