Rolling Woods Dr, Williamsburg, VA Property Records

James City County property records for 29 addresses on Rolling Woods Dr, Williamsburg, VA · Last verified July 2026

Rolling Woods Dr Highlights

Properties 29
Median Sale Price $330,000
Deeds and Mortgages on File 30
Median Price per Sqft $132
Owner Occupied 97%
Median Annual Tax Bill $2,863
Median Year Built 1991
Median Ownership Tenure 23 years

Properties on Rolling Woods Dr

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

5500 Rolling Woods Dr

3 bd · 3 ba · 2,721 sqft · built 1990 · 0.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Mar 1993 $3,3682025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

5501 Rolling Woods Dr

4 bd · 2 ba · 1,940 sqft · built 1997 · 0.562 acres

Last Sale Tax Bill Prior Sale Owner Records
$167,000Aug 2001 $2,6872025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

5503 Rolling Woods Dr

4 bd · 3 ba · 2,083 sqft · built 1998 · 0.387 acres

Last Sale Tax Bill Prior Sale Owner Records
$147,000Oct 1998 $2,8832025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

5505 Rolling Woods Dr

3 bd · 3 ba · 1,952 sqft · built 1999 · 0.357 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,6912025 Amount on Record May 1999 1 Name on Record Owner Occupied AssessorUpdated Nov 2025

5507 Rolling Woods Dr

3 bd · 2 ba · 2,122 sqft · built 2000 · 0.332 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2007 $2,7772025 1 Name on Record Owner Occupied AssessorUpdated Nov 2025

5511 Rolling Woods Dr

4 bd · 4 ba · 1,927 sqft · built 2003 · 0.405 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 2013 $3,1312025 Amount on Record Jul 2002 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

5513 Rolling Woods Dr

200 sqft · 0.08 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1980 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

5515 Rolling Woods Dr

4 bd · 4 ba · 2,540 sqft · built 2003 · 0.294 acres

Last Sale Tax Bill Prior Sale Owner Records
$449,000Oct 2025 $3,2332025 Amount on Record Mar 2024 2 Names on Record Owner Occupied Assessor + 6 DocumentsUpdated Nov 2025

5519 Rolling Woods Dr

4 bd · 2 ba · 2,646 sqft · built 1991 · 0.305 acres

Last Sale Tax Bill Prior Sale Owner Records
$129,900Nov 1991 $3,4052025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

5523 Rolling Woods Dr

3 bd · 3 ba · 2,556 sqft · built 2001 · 0.305 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Sep 2017 $2,5412019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025
Last Sale Tax Bill Prior Sale Owner Records
—Oct 1991 1 Name on Record AssessorUpdated Oct 2025

5527 Rolling Woods Dr

3 bd · 2 ba · 2,302 sqft · built 1991 · 0.308 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,8892025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

5531 Rolling Woods Dr

4 bd · 3 ba · 2,226 sqft · built 1991 · 0.342 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Mar 2016 $2,7862025 Amount on Record May 2003 1 Name on Record Owner Occupied AssessorUpdated May 2026

5535 Rolling Woods Dr

3 bd · 3 ba · 2,416 sqft · built 1989 · 0.428 acres

Last Sale Tax Bill Prior Sale Owner Records
$255,000Aug 2004 $3,1072025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

5539 Rolling Woods Dr

4 bd · 3 ba · 2,451 sqft · built 1987 · 0.428 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,1392019 —Dec 2019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

5540 Rolling Woods Dr

4 bd · 2.5 ba · 2,148 sqft · built 1988 · 0.276 acres

Last Sale Tax Bill Prior Sale Owner Records
$168,000Apr 2001 $2,8632025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

5543 Rolling Woods Dr

3 bd · 2.5 ba · 2,008 sqft · built 1987 · 0.367 acres

Last Sale Tax Bill Prior Sale Owner Records
1 Name on Record Owner Occupied AssessorUpdated May 2026

5544 Rolling Woods Dr

4 bd · 5 ba · 3,336 sqft · built 1987 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$138,000Dec 1987 $3,1532019 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

5547 Rolling Woods Dr

5 bd · 3 ba · 2,649 sqft · built 1992 · 0.398 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1998 $3,2662025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

5548 Rolling Woods Dr

5 bd · 4 ba · 2,788 sqft · built 1988 · 0.337 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2002 $3,3322025 1 Name on Record Owner Occupied AssessorUpdated Nov 2025

5555 Rolling Woods Dr

3 bd · 4 ba · 2,682 sqft · built 1988 · 0.458 acres

Last Sale Tax Bill Prior Sale Owner Records
$323,900Aug 2017 $2,4922019 Amount on Record Jul 2002 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

5559 Rolling Woods Dr

3 bd · 3 ba · 2,532 sqft · built 1987 · 0.362 acres

Last Sale Tax Bill Prior Sale Owner Records
$332,000Mar 2020 $2,4752019 —Jul 2019 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

5563 Rolling Woods Dr

4 bd · 3 ba · 2,506 sqft · built 1989 · 0.362 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Aug 2019 $2,5892019 Amount on Record Apr 2015 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

5567 Rolling Woods Dr

4 bd · 3 ba · 3,002 sqft · built 1992 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$208,000Apr 2003 $3,5022025 2 Names on Record Owner Occupied AssessorUpdated Nov 2025

5575 Rolling Woods Dr

4 bd · 3 ba · 2,920 sqft · built 1992 · 0.394 acres

Last Sale Tax Bill Prior Sale Owner Records
$390,000Apr 2021 $3,5082025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Nov 2025

5576 Rolling Woods Dr

2 bd · 2 ba · 1,498 sqft · built 1988 · 0.296 acres

Last Sale Tax Bill Prior Sale Owner Records
$272,000Aug 2020 $1,8672019 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2025

5579 Rolling Woods Dr

4 bd · 3 ba · 1,991 sqft · built 1989 · 0.453 acres

Last Sale Tax Bill Prior Sale Owner Records
$184,500Oct 2002 $1,9982019 1 Name on Record Owner Occupied AssessorUpdated Oct 2025

5580 Rolling Woods Dr

3 bd · 3 ba · 2,479 sqft · built 1989 · 0.321 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Dec 1989 $2,3292019 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2025

5584 Rolling Woods Dr

3 bd · 2.5 ba · 2,161 sqft · built 2011 · 0.387 acres

Last Sale Tax Bill Prior Sale Owner Records
$286,000Apr 2016 $2,3852019 1 Name on Record Owner Occupied Assessor + 5 DocumentsUpdated May 2026

Wildfire Risk on Rolling Woods 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 4,478 per year
ExposureDirect
2 of 3 cells directly exposed · 3 adjoin burnable vegetation

Property Records in Nearby Streets