Gloucester Dr, Winchester, VA Property Records

Frederick County property records for 14 addresses on Gloucester Dr, Winchester, VA · Last verified August 2026

Gloucester Dr Highlights

Properties 14
Median Sale Price $407,500
Deeds and Mortgages on File 10
Median Price per Sqft $165
Owner Occupied 100%
Median Annual Tax Bill $2,950
Median Year Built 1986
Median Ownership Tenure 12 years

Properties on Gloucester Dr

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

100 Gloucester Dr

4 bd · 3 ba · 1,844 sqft · 2.31 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,8832026 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

101 Gloucester Dr

3 bd · 2.5 ba · 2,288 sqft · 2.68 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,8242026 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

109 Gloucester Dr

4 bd · 2.5 ba · 3,032 sqft · 2.31 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$56,000Dec 1991 $3,2882026 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

115 Gloucester Dr

3 bd · 2.5 ba · 1,986 sqft · 2.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,2862026 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

118 Gloucester Dr

4 bd · 2.5 ba · 2,688 sqft · 2.3 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$3,2292026 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

138 Gloucester Dr

3 bd · 2.5 ba · 1,963 sqft · 2.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$325,000Aug 2018 $2,4492026 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

139 Gloucester Dr

3 bd · 2.5 ba · 3,030 sqft · 2.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$309,000Jun 2001 $3,2772026 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

162 Gloucester Dr

3 bd · 2 ba · 1,860 sqft · 2.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$244,000May 2014 $2,3652026 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

163 Gloucester Dr

5 bd · 3 ba · 3,128 sqft · 2.31 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$574,900Jul 2022 $2,9502026 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

189 Gloucester Dr

4 bd · 2.5 ba · 2,124 sqft · 2.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$333,500Jun 2014 $2,5272026 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

217 Gloucester Dr

4 bd · 4.5 ba · 3,004 sqft · 2.33 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$755,000Apr 2024 $3,6322026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

260 Gloucester Dr

4 bd · 2.5 ba · 2,084 sqft · 2.68 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$407,500Apr 2020 $2,7202026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

287 Gloucester Dr

3 bd · 2 ba · 2,088 sqft · 5.08 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$3,2342026 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

288 Gloucester Dr

4 bd · 5.5 ba · 4,116 sqft · 2.98 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$641,000Jun 2009 $5,3322026 Sale Amount Aug 2004 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

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