Jackson Ave, Winchester, VA Property Records

Winchester City property records for 35 addresses on Jackson Ave, Winchester, VA · Last verified August 2026

Jackson Ave Highlights

Properties 35
Median Sale Price $209,000
Deeds and Mortgages on File 48
Median Price per Sqft $162
Owner Occupied 46%
Median Annual Tax Bill $2,226
Median Year Built 1952
Median Ownership Tenure 8 years

Properties on Jackson Ave

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

15 Jackson Ave

1 bd · 1 ba · 601 sqft · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$35,000Feb 2012 $6612026 1 Name on Record AssessorUpdated Aug 2026

17 Jackson Ave

3 bd · 1 ba · 1,858 sqft · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$53,405Feb 2013 $1,3702026 Amount on Record Jan 2013 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

18 Jackson Ave

0.098 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2018 $2192026 1 Name on Record AssessorUpdated Aug 2026

19 Jackson Ave

1 bd · 1 ba · 1,170 sqft · 0.171 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Dec 2020 $2,2492026 Amount on Record May 2019 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

20 Jackson Ave

2 bd · 1 ba · 1,226 sqft · 0.087 acres

Last Sale Tax Bill Prior Sale Owner Records
$89,900Aug 2017 $1,7972026 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

21 Jackson Ave

3 bd · 1.5 ba · 1,193 sqft · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
$193,349Feb 2025 $1,9102026 Amount on Record Jan 2021 1 Name on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

22 Jackson Ave

6 bd · 3 ba · 3,649 sqft · 0.13 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$330,000Aug 2020 $2,7362026 Amount on Record Mar 2015 1 Name on Record Assessor + 5 DocumentsUpdated Aug 2026

23 1/2 Jackson Ave

3 bd · 1 ba · 1,098 sqft · 0.128 acres

Last Sale Tax Bill Prior Sale Owner Records
$213,000Jul 2008 $1,6592026 —Dec 2005 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

23 Jackson Ave

3 bd · 1 ba · 1,152 sqft · 0.128 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,7702026 1 Name on Record AssessorUpdated Aug 2026

24 Jackson Ave

4 bd · 2 ba · 1,777 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3072026 1 Name on Record AssessorUpdated Aug 2026

25 Jackson Ave

2 bd · 1 ba · 919 sqft · 0.128 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Feb 2023 $1,4332026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

26 Jackson Ave

3 bd · 1 ba · 1,474 sqft · 0.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$79,000Sep 2015 $1,7652026 1 Name on Record AssessorUpdated Aug 2026

26 Jackson Ave, Apt A

4 bd · 3 ba · 2,088 sqft · 0.151 acres

Last Sale Tax Bill Prior Sale Owner Records
$400,000Feb 2026 $2,9262026 Amount on Record Jan 2016 1 Name on Record Assessor + 3 DocumentsUpdated Aug 2026

27 Jackson Ave

2 bd · 1 ba · 1,134 sqft · 0.153 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$181,000Nov 2025 $1,7252026 Amount on Record Oct 2025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

28 Jackson Ave

2 bd · 1 ba · 780 sqft · 0.15 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,3282026 1 Name on Record AssessorUpdated Aug 2026

30 Jackson Ave

2 bd · 1 ba · 836 sqft · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 1997 $1,4292026 2 Names on Record AssessorUpdated Aug 2026

31 Jackson Ave

4 bd · 3 ba · 2,480 sqft · 0.142 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1994 $2,6852026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

32 Jackson Ave

3 bd · 1 ba · 791 sqft · 0.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$118,000Oct 2022 $1,3082026 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

34 Jackson Ave

2 bd · 1 ba · 955 sqft · 0.105 acres

Last Sale Tax Bill Prior Sale Owner Records
$122,500Dec 2019 $1,4302026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

35 Jackson Ave

0.148 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2015 $4652026 1 Name on Record AssessorUpdated Aug 2026

36 Jackson Ave

2 bd · 1 ba · 1,069 sqft · 0.185 acres

Last Sale Tax Bill Prior Sale Owner Records
$73,720May 2017 $1,6092026 Amount on Record Nov 2016 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

37 Jackson Ave

2 bd · 1 ba · 995 sqft · 0.153 acres

Last Sale Tax Bill Prior Sale Owner Records
$209,000Nov 2022 $1,6762023 Amount on Record Jun 2007 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Nov 2023

102 Jackson Ave

4 bd · 1.5 ba · 1,857 sqft · 0.559 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$195,000Jun 2019 $3,2562026 —Jun 2019 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

103 Jackson Ave

3 bd · 1.5 ba · 1,316 sqft · 0.347 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$325,000Feb 2023 $2,4812026 Amount on Record Jul 2022 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

106 Jackson Ave

3 bd · 2 ba · 1,560 sqft · 0.526 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$191,000Jun 2016 $2,7762026 Amount on Record May 2010 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

107 Jackson Ave

3 bd · 1 ba · 1,234 sqft · 0.35 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2000 $2,4592026 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

110 Jackson Ave

2 bd · 2 ba · 1,060 sqft · 0.486 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$90,000Nov 2001 $2,4682026 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

111 Jackson Ave

3 bd · 1.5 ba · 1,407 sqft · 0.497 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$215,000May 2020 $2,6142026 Amount on Record May 2013 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

114 Jackson Ave

3 bd · 1 ba · 1,288 sqft · 0.493 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$135,000Mar 2017 $2,2632026 1 Name on Record Assessor + 4 DocumentsUpdated Aug 2026

115 Jackson Ave

2 bd · 1 ba · 1,403 sqft · 0.669 acres

Last Sale Tax Bill Prior Sale Owner Records
$180,000Jul 2018 $2,7052026 —Nov 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

118 Jackson Ave

3 bd · 1 ba · 1,032 sqft · 0.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$75,000Feb 2023 $2,2262026 —Feb 2023 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

119 Jackson Ave

3 bd · 2 ba · 1,776 sqft · 0.303 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$140,000Feb 2024 $2,9822026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

122 Jackson Ave

4 bd · 1 ba · 1,092 sqft · 0.38 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$116,000Aug 2015 $2,2322026 —Dec 2022 1 Name on Record Assessor + 3 DocumentsUpdated Aug 2026

123 Jackson Ave

3 bd · 1 ba · 1,176 sqft · 0.311 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2010 $2,4352026 —Oct 2005 1 Name on Record AssessorUpdated Aug 2026

127 Jackson Ave

3 bd · 1 ba · 1,176 sqft · 0.299 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jun 2017 $2,4312026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

Property Records in Nearby Streets