Chestnut Grove Rd, Winchester, VA Property Records

Frederick County property records for 77 addresses on Chestnut Grove Rd, Winchester, VA · Last verified October 2026

Chestnut Grove Rd Highlights

Properties 77
Median Sale Price $370,000
Deeds and Mortgages on File 50
Median Price per Sqft $286
Owner Occupied 83%
Median Annual Tax Bill $1,895
Median Year Built 1985
Median Ownership Tenure 13 years

Properties on Chestnut Grove Rd

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

104 Chestnut Grove Rd

3 bd · 2 ba · 2,496 sqft · built 1971 · 1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$115,000Apr 2025 $2,0082026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

106 Chestnut Grove Rd

2 bd · 1.5 ba · 1,004 sqft · built 1951 · 1.71 acres

Last Sale Tax Bill Prior Sale Owner Records
$119,000Apr 2009 $1,4542026 —Apr 2009 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

139 Chestnut Grove Rd

2 bd · 2 ba · 1,222 sqft · built 1951 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,5062026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

146 Chestnut Grove Rd

3 bd · 1.5 ba · 1,152 sqft · built 1992 · 1.41 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2023 $1,6112026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$215,000Mar 2022 $3592026 Owner on Record AssessorUpdated Aug 2026

177 Chestnut Grove Rd

3 bd · 1.5 ba · 1,695 sqft · built 1961 · 3.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Apr 1991 $1,5432026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

178 Chestnut Grove Rd

2 bd · 1 ba · 720 sqft · built 1951 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Mar 2022 $1,0622026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

198 Chestnut Grove Rd

4 bd · 1 ba · 1,560 sqft · built 1956 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,8012026 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

201 Chestnut Grove Rd

2 bd · 1 ba · 1,548 sqft · built 1969 · 2.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4882026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

220 Chestnut Grove Rd

2 bd · 1.5 ba · 864 sqft · built 1988 · 15 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Feb 2026 $1,4532026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

222 Chestnut Grove Rd

3 bd · 1.5 ba · 1,040 sqft · built 1991 · 5.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,5472026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

236 Chestnut Grove Rd

3 bd · 2 ba · 1,500 sqft · built 2005 · 2.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$430,000Mar 2023 $1,8952026 Amount on Record Aug 2002 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

240 Chestnut Grove Rd

3 bd · 2 ba · 1,792 sqft · built 1996 · 33.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,000Apr 2002 $2,5722026 2 Owners on Record AssessorUpdated Aug 2026

242 Chestnut Grove Rd

3 bd · 1.5 ba · 1,408 sqft · built 1921 · 175 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1999 $1,9312026 Owner on Record AssessorUpdated Aug 2026

243 Chestnut Grove Rd

3 bd · 1 ba · 1,032 sqft · built 1977 · 0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Jun 2006 $1,1972026 Amount on Record Feb 2000 Owner on Record Owner Occupied AssessorUpdated Aug 2026

246 Chestnut Grove Rd

3 bd · 2 ba · 816 sqft · 3.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Dec 2018 $1,1002026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

278 Chestnut Grove Rd

3 bd · 1.5 ba · 1,824 sqft · built 1969 · 1.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Dec 2021 $1,6592026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

279 Chestnut Grove Rd

3 bd · 2.5 ba · 1,786 sqft · built 1951 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 1997 $1,4652026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

294 Chestnut Grove Rd

3 bd · 1 ba · 2,244 sqft · built 1951 · 1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2016 $1,2582026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

297 Chestnut Grove Rd

3 bd · 2 ba · 3,794 sqft · built 2013 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$133,000Aug 2007 $4,4652026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

301 Chestnut Grove Rd

3 bd · 2 ba · 3,105 sqft · built 2005 · 2.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6412026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

311 Chestnut Grove Rd

2 bd · 2 ba · 1,760 sqft · built 1956 · 0.769 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,000Nov 2018 $1,4152026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

314 Chestnut Grove Rd

2 bd · 2 ba · 1,632 sqft · built 1951 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,2822026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

321 Chestnut Grove Rd

3 bd · 2 ba · 2,080 sqft · built 1966 · 1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1998 $1,6802026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

333 Chestnut Grove Rd

2 bd · 2 ba · 1,144 sqft · built 1989 · 23.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,1582026 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

348 Chestnut Grove Rd

4 bd · 4 ba · 4,940 sqft · built 1975 · 12.8 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1999 $6,0482026 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

415 Chestnut Grove Rd

3 bd · 1.5 ba · 1,008 sqft · built 1981 · 2.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3702026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$6432026 2 Owners on Record AssessorUpdated Aug 2026

488 Chestnut Grove Rd

3 bd · 2.5 ba · 1,572 sqft · built 1978 · 10.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4902026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

492 Chestnut Grove Rd

3 bd · 2 ba · 1,548 sqft · built 2005 · 27.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$619,000May 2026 $2,1962026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

520 Chestnut Grove Rd

3 bd · 2 ba · 2,473 sqft · built 2007 · 63.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1972026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

575 Chestnut Grove Rd

1 bd · 2 ba · 1,084 sqft · built 1972 · 4.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$164,000Jul 2019 $1,3062026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

581 Chestnut Grove Rd

2 bd · 1 ba · 1,566 sqft · built 1939 · 7 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2007 $1,0912026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

633 Chestnut Grove Rd

2 bd · 1.5 ba · 2,250 sqft · built 1950 · 3.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3302026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

674 Chestnut Grove Rd

2 bd · 1 ba · 954 sqft · built 1961 · 6 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Aug 2012 $1,8602026 Amount on Record May 2001 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

687 Chestnut Grove Rd

3 bd · 2 ba · 2,841 sqft · built 2000 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6602026 2 Owners on Record AssessorUpdated Aug 2026

693 Chestnut Grove Rd

3 bd · 2 ba · 1,645 sqft · built 1962 · 2.25 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2012 $1,6902026 Owner on Record Owner Occupied AssessorUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
—Oct 2012 $4522026 Owner on Record AssessorUpdated Aug 2026

863 Chestnut Grove Rd

3 bd · 2 ba · 2,835 sqft · built 1801 · 193 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1996 $2,8932026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

998 Chestnut Grove Rd

3 bd · 3.5 ba · 2,436 sqft · built 2016 · 31.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Nov 2011 $4,0502026 —Nov 2011 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1012 Chestnut Grove Rd

3 bd · 1 ba · 1,686 sqft · built 1899 · 2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Nov 2011 $4032026 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

1015 Chestnut Grove Rd

1 bd · 1 ba · 480 sqft · built 1950 · 5.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$105,000Dec 2016 $9132026 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

1245 Chestnut Grove Rd

2 bd · 3 ba · 4,448 sqft · built 1933 · 129 acres

Last Sale Tax Bill Prior Sale Owner Records
$444,000Oct 2019 $3,4302026 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1292 Chestnut Grove Rd

2 bd · 1 ba · 720 sqft · built 1954 · 19.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,3822026 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

1307 Chestnut Grove Rd

3 bd · 1 ba · 1,456 sqft · built 1955 · 3 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,0902026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026
Last Sale Tax Bill Prior Sale Owner Records
$7572026 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

1399 Chestnut Grove Rd

3 bd · 2 ba · 1,680 sqft · built 1987 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Jan 2026 $1,6402026 Amount on Record Apr 2010 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1440 Chestnut Grove Rd

3 bd · 2 ba · 1,080 sqft · built 1990 · 5.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,900Sep 2017 $1,6892026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1455 Chestnut Grove Rd

3 bd · 2 ba · 1,705 sqft · built 1981 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$133,500Jul 1999 $2,0552026 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1460 Chestnut Grove Rd

3 bd · 3 ba · 1,456 sqft · built 1991 · 5.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Dec 2003 $2,2702026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1480 Chestnut Grove Rd

2 bd · 1 ba · 1,225 sqft · built 1988 · 6.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,5802026 —Sep 2015 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1499 Chestnut Grove Rd

3 bd · 2.5 ba · 1,346 sqft · built 1985 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$228,000Jun 2013 $1,9572026 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

1503 Chestnut Grove Rd

3 bd · 2.5 ba · 2,464 sqft · built 1996 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$34,000May 1995 $2,4112026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

1529 Chestnut Grove Rd

3 bd · 2.5 ba · 2,830 sqft · built 1987 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,700Oct 2004 $2,5362026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

1539 Chestnut Grove Rd

3 bd · 2.5 ba · 1,388 sqft · built 1995 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$279,300Oct 2021 $2,1352026 —Oct 2021 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1544 Chestnut Grove Rd

3 bd · 3.5 ba · 2,117 sqft · built 1824 · 10.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$324,000Feb 2007 $2,2222026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

1569 Chestnut Grove Rd

3 bd · 2.5 ba · 2,335 sqft · built 1991 · 10 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4262026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

1596 Chestnut Grove Rd

3 bd · 2 ba · 1,248 sqft · built 1982 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,000Jul 2016 $2,3092026 Amount on Record Dec 2001 Owner on Record Owner Occupied AssessorUpdated Aug 2026

1625 Chestnut Grove Rd

3 bd · 2 ba · 1,920 sqft · built 1989 · 4.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$97,000Sep 2018 $2,1742026 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

1632 Chestnut Grove Rd

3 bd · 2.5 ba · 2,176 sqft · built 1989 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Oct 2013 $2,2602026 Amount on Record May 2013 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

1641 Chestnut Grove Rd

3 bd · 2 ba · 2,772 sqft · built 2017 · 61.8 acres

Last Sale Tax Bill Prior Sale Owner Records
—May 2018 $3,6022026 —May 2018 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1651 Chestnut Grove Rd

3 bd · 2.5 ba · 4,334 sqft · built 1968 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000Dec 2019 $4,2942026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1655 Chestnut Grove Rd

3 bd · 1.5 ba · 1,632 sqft · built 1992 · 11.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,5072026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

1671 Chestnut Grove Rd

4 bd · 2 ba · 2,240 sqft · built 2000 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1999 $1,9772026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

1704 Chestnut Grove Rd

2 bd · 1 ba · 912 sqft · built 1981 · 4.91 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Aug 2014 $1,4232026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1750 Chestnut Grove Rd

3 bd · 2 ba · 1,304 sqft · built 1985 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$475,000May 2024 $1,8862026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

1802 Chestnut Grove Rd

3 bd · 2 ba · 2,304 sqft · built 1983 · 5.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$745,000Jan 2025 $3,4572026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

1833 Chestnut Grove Rd

3 bd · 2 ba · 1,872 sqft · built 2001 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,9872026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

1840 Chestnut Grove Rd

3 bd · 2 ba · 2,485 sqft · built 1992 · 112 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6332026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2036 Chestnut Grove Rd

3 bd · 2 ba · 1,744 sqft · built 1990 · 25 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,0872026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

2038 Chestnut Grove Rd

5 bd · 2 ba · 2,250 sqft · built 1960 · 5 acres

Last Sale Tax Bill Prior Sale Owner Records
$300,000May 2007 $2,1292026 —May 2007 Owner on Record Owner Occupied AssessorUpdated Aug 2026

2040 Chestnut Grove Rd

1 bd · 2.5 ba · 1,196 sqft · built 1994 · 57.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$239,000Jan 2007 $1,7762026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2047 Chestnut Grove Rd

3 bd · 2 ba · 2,688 sqft · built 1998 · 30.6 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 1996 $2,5292026 Owner on Record Owner Occupied AssessorUpdated Oct 2026

2135 Chestnut Grove Rd

3 bd · 2.5 ba · 2,995 sqft · built 2001 · 30.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,1992026 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

2260 Chestnut Grove Rd

3 bd · 2.5 ba · 1,792 sqft · built 1995 · 5.13 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2007 $1,9672026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

2267 Chestnut Grove Rd

3 bd · 2 ba · 1,132 sqft · built 2022 · 5.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Apr 2021 $1,8412026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

2281 Chestnut Grove Rd

3 bd · 1 ba · 1,054 sqft · built 1998 · 5.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$19,000Aug 1996 $1,6542026 Owner on Record Owner Occupied AssessorUpdated Aug 2026

Property Records in Nearby Streets