S Winchester Rd, Annapolis, MD Property Records

Anne Arundel County property records for 14 addresses on S Winchester Rd, Annapolis, MD · Last verified June 2026

S Winchester Rd Highlights

Properties 14
Median Sale Price $1,030,000
Deeds and Mortgages on File 18
Median Price per Sqft $367
Owner Occupied 71%
Median Annual Tax Bill $10,967
Median Year Built 1950
Median Ownership Tenure 17 years

Properties on S Winchester Rd

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

3 S Winchester Rd

8 ba · 12,494 sqft · built 2009 · 5.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,585,000Apr 2007 $46,7752024 Amount on Record Jun 2006 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

4 S Winchester Rd

5 ba · 5,350 sqft · built 1900 · 9.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,7072023 Owner on Record Assessor + 1 DocumentUpdated Sep 2023

5 S Winchester Rd

1 ba · 816 sqft · built 1968 · 7.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,3442024 Owner on Record AssessorUpdated Apr 2026

53 S Winchester Rd

2 ba · 1,116 sqft · built 1940 · 0.95 acres

Last Sale Tax Bill Prior Sale Owner Records
$439,000Oct 2021 $4,5682023 —Aug 2020 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Sep 2023

55 S Winchester Rd

2 ba · 2,468 sqft · built 1968 · 1.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$254,000Dec 1999 $4,7232024 Amount on Record Jul 1997 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

71 S Winchester Rd

2 ba · 2,768 sqft · built 1957 · 1.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,030,000Dec 2015 $6,6882024 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

77 S Winchester Rd

3 ba · 2,714 sqft · built 1950 · 2.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,135,000Jul 2016 $11,4012024 Amount on Record Mar 1985 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

103 S Winchester Rd

4 ba · 2,760 sqft · built 1934 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$735,000Dec 2009 $6,9532023 Amount on Record Dec 2003 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

105 S Winchester Rd

3 ba · 2,400 sqft · built 1959 · 1.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$882,000Apr 2009 $16,0052023 2 Owners on Record AssessorUpdated Sep 2023

109 S Winchester Rd

3 ba · 2,788 sqft · built 1940 · 2.23 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 1998 $7,4962023 Amount on Record Oct 1997 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

115 S Winchester Rd

3 ba · 1,647 sqft · built 2000 · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8632023 Amount on Record Apr 1995 2 Owners on Record Owner Occupied AssessorUpdated Sep 2023

125 S Winchester Rd

4.5 ba · 4,260 sqft · built 1948 · 2.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,300,000Oct 2000 $24,8142025 Amount on Record Dec 1993 2 Owners on Record Owner Occupied AssessorUpdated Jun 2026

129 S Winchester Rd

2.5 ba · 2,018 sqft · built 1933 · 2.25 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2006 $10,5362024 Amount on Record Aug 1988 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

141 S Winchester Rd

2.5 ba · 2,224 sqft · built 1943 · 1.66 acres

Last Sale Tax Bill Prior Sale Owner Records
$717,000May 2015 $10,9672024 Amount on Record Mar 2005 Owner on Record Assessor + 2 DocumentsUpdated Apr 2026

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