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Winston Dr, Williamsburg, VA Property Records

James City County property records for 52 addresses on Winston Dr, Williamsburg, VA · Last verified August 2026

Winston Dr Highlights

Properties 52
Median Sale Price $319,900
Deeds and Mortgages on File 53
Median Price per Sqft $205
Owner Occupied 60%
Median Annual Tax Bill $1,850
Median Year Built 1960
Median Ownership Tenure 7 years

Properties on Winston Dr

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

104 Winston Dr

3 bd · 2 ba · 1,668 sqft · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,300Dec 2005 $2,4172025 1 Name on Record Owner Occupied AssessorUpdated Nov 2025

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105 Winston Dr

4 bd · 3 ba · 1,976 sqft · 0.344 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$241,500Apr 2014 $2,8602025 Amount on Record Aug 2004 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

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106 Winston Dr

3 bd · 2 ba · 1,144 sqft · 0.396 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$280,000Apr 2023 $2,1072025 Amount on Record Feb 2022 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

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107 Winston Dr

3 bd · 2 ba · 1,471 sqft · 0.344 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jun 2019 $2,4772025 Amount on Record May 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Nov 2025

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109 Winston Dr

3 bd · 2 ba · 1,248 sqft · 0.344 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4952019 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

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110 Winston Dr

3 bd · 2 ba · 1,080 sqft · 0.337 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3602019 Amount on Record Jun 1999 1 Name on Record AssessorUpdated Oct 2025

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111 Winston Dr

3 bd · 2 ba · 1,500 sqft · 0.423 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2021 $2,2142025 —Jan 2016 1 Name on Record Assessor + 2 DocumentsUpdated Nov 2025

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112 Winston Dr

4 bd · 3 ba · 1,712 sqft · 0.351 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2002 $2,6382025 1 Name on Record AssessorUpdated Nov 2025

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113 Winston Dr

3 bd · 2 ba · 1,685 sqft · 0.526 acres

Last Sale Tax Bill Prior Sale Owner Records
$354,000Feb 2024 $2,7422025 Amount on Record Jun 2020 2 Names on Record Owner Occupied Assessor + 7 DocumentsUpdated Apr 2026

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114 Winston Dr

3 bd · 2 ba · 1,450 sqft · 0.316 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Jun 2017 $2,3912025 1 Name on Record Assessor + 3 DocumentsUpdated Nov 2025

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115 Winston Dr

6 bd · 6 ba · 1,800 sqft · 0.308 acres

Last Sale Tax Bill Prior Sale Owner Records
$405,000Oct 2022 $3,8182025 —May 2021 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Nov 2025

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116 Winston Dr

3 bd · 2 ba · 1,300 sqft · 0.316 acres

Last Sale Tax Bill Prior Sale Owner Records
$124,500Sep 2003 $1,5642019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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117 Winston Dr

5 bd · 2 ba · 1,982 sqft · 0.308 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Jun 2024 $2,8602025 Amount on Record Dec 2003 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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118 Winston Dr

3 bd · 1 ba · 1,375 sqft · 0.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$328,500Jan 2025 $1,5192019 Amount on Record Jun 2023 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

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119 Winston Dr

3 bd · 2 ba · 1,080 sqft · 0.392 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$133,420Nov 2014 $1,9432025 1 Name on Record AssessorUpdated Nov 2025

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120 Winston Dr

3 bd · 3 ba · 2,047 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$275,000Jun 2019 $2,2752019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

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121 Winston Dr

2 ba · 1,080 sqft · 0.367 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2009 $1,3602019 2 Names on Record AssessorUpdated Oct 2025

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123 Winston Dr

3 bd · 2 ba · 1,182 sqft · 0.355 acres

Last Sale Tax Bill Prior Sale Owner Records
$232,000Jun 2024 $1,9972025 Amount on Record Sep 2010 1 Name on Record AssessorUpdated Nov 2025

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125 Winston Dr

4 bd · 2 ba · 1,716 sqft · 0.55 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$239,000May 2010 $2,6402025 Amount on Record Nov 2001 1 Name on Record Owner Occupied AssessorUpdated May 2026

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126 Winston Dr

2 ba · 1,296 sqft · 0.346 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,5682022 1 Name on Record Owner Occupied AssessorUpdated Apr 2026

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127 Winston Dr

3 bd · 2.5 ba · 1,716 sqft · 0.667 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$355,000Jul 2022 $1,8652022 Amount on Record Mar 2021 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jun 2026

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129 Winston Dr

2 ba · 1,505 sqft · 0.289 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,6852019 Amount on Record Apr 2007 2 Names on Record AssessorUpdated Oct 2025

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131 Winston Dr

4 bd · 2 ba · 1,716 sqft · 0.323 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$200,000Mar 2026 $1,8722022 1 Name on Record Assessor + 1 DocumentUpdated Apr 2026

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133 Winston Dr

3 bd · 1 ba · 1,008 sqft · 0.307 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4642019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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134 Winston Dr

3 bd · 1 ba · 1,300 sqft · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$84,900Mar 1996 $2,0702025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

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135 Winston Dr

3 bd · 1 ba · 960 sqft · 0.325 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$180,000Nov 2019 $1,8502025 1 Name on Record Assessor + 1 DocumentUpdated Nov 2025

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136 Winston Dr

4 bd · 3 ba · 1,752 sqft · 0.269 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$229,900Jun 2015 $2,4472025 Amount on Record Apr 2003 1 Name on Record Owner Occupied AssessorUpdated Nov 2025

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137 Winston Dr

3 bd · 1 ba · 1,120 sqft · 0.303 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$105,000Nov 2001 $1,4192019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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138 Winston Dr

3 bd · 2 ba · 1,632 sqft · 0.255 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Jan 2022 $2,3412025 Amount on Record Jun 2002 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

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139 Winston Dr

3 bd · 1 ba · 1,000 sqft · 0.298 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$151,000Jun 2020 $1,3402019 1 Name on Record Assessor + 1 DocumentUpdated Oct 2025

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140 Winston Dr

1 ba · 1,000 sqft · 0.301 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2007 $1,3402019 1 Name on Record AssessorUpdated Oct 2025

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141 Winston Dr

1 ba · 1,662 sqft · 0.298 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,7392019 2 Names on Record Owner Occupied AssessorUpdated Oct 2025

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143 Winston Dr

3 bd · 2 ba · 1,556 sqft · 0.351 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000May 2026 $1,7722022 Amount on Record May 2003 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

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145 Winston Dr

4 bd · 2 ba · 1,725 sqft · 0.666 acres

Last Sale Tax Bill Prior Sale Owner Records
$355,000Apr 2024 $1,7872019 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

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147 Winston Dr

4 bd · 2.5 ba · 1,716 sqft · 0.401 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$260,000Apr 2015 $2,0332022 Amount on Record Oct 2003 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

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149 Winston Dr

4 bd · 2 ba · 1,688 sqft · 0.321 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$2,6512025 1 Name on Record AssessorUpdated Nov 2025

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150 Winston Dr

1 ba · 1,000 sqft · 0.287 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2020 $1,3612019 Amount on Record Oct 2012 1 Name on Record AssessorUpdated Oct 2025

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151 Winston Dr

3 bd · 1 ba · 1,128 sqft · 0.369 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4072019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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152 Winston Dr

1 ba · 1,528 sqft · 0.317 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$100,000Dec 2002 $1,7522022 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

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153 Winston Dr

3 bd · 2 ba · 1,300 sqft · 0.394 acres

Last Sale Tax Bill Prior Sale Owner Records
$319,900Jul 2023 $1,5142019 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

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155 Winston Dr

3 bd · 2 ba · 1,536 sqft · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$78,500Aug 1988 $1,6482019 1 Name on Record AssessorUpdated Oct 2025

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157 Winston Dr

3 bd · 1 ba · 1,000 sqft · 0.292 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$74,500Jul 1995 $1,9232025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

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159 Winston Dr

1 ba · 1,000 sqft · 0.257 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2007 $1,3402019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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161 Winston Dr

4 bd · 3 ba · 2,085 sqft · 0.442 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$300,000Oct 2021 $3,0162025 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

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163 Winston Dr

1 ba · 1,240 sqft · 0.43 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,4962019 1 Name on Record AssessorUpdated Oct 2025

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164 Winston Dr

3 bd · 2 ba · 1,392 sqft · 0.457 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000May 2017 $2,2882025 1 Name on Record Assessor + 2 DocumentsUpdated Nov 2025

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165 Winston Dr

1 ba · 1,325 sqft · 0.303 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Sep 2023 $1,5262022 2 Names on Record Assessor + 2 DocumentsUpdated Apr 2026

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166 Winston Dr

2 ba · 1,050 sqft · 0.387 acres

Last Sale Tax Bill Prior Sale Owner Records
$89,900Jun 1992 $2,5432025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

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167 Winston Dr

1 ba · 1,000 sqft · 0.3 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$1,3732022 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

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169 Winston Dr

2 ba · 1,419 sqft · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$205,000Nov 2021 $1,5542019 —Jun 2020 2 Names on Record Assessor + 1 DocumentUpdated Oct 2025

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171 Winston Dr

3 bd · 2 ba · 1,300 sqft · 0.366 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$158,000Aug 2016 $1,6532019 Amount on Record Mar 2016 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

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173 Winston Dr

3 bd · 2 ba · 1,484 sqft · 0.305 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2000 $1,8372019 1 Name on Record AssessorUpdated Oct 2025

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Wildfire Risk on Winston Dr

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 20% of the US · above 29% of Virginia
Wildfire LikelihoodAbout 1 in 6,757 per year
ExposureDirect
3 of 5 cells directly exposed · 5 adjoin burnable vegetation

Property Records in Nearby Streets