Chestertown Dr, Pinehurst, NC Property Records

Moore County property records for 44 addresses on Chestertown Dr, Pinehurst, NC · Last verified August 2026

Chestertown Dr Highlights

Properties 44
Median Sale Price $285,000
Deeds and Mortgages on File 85
Median Price per Sqft $320
Owner Occupied 48%
Median Annual Tax Bill $6,008
Median Year Built 2007
Median Ownership Tenure 3 years

Properties on Chestertown Dr

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

10 Chestertown Dr

1.14 acres

Last Sale Tax Bill Prior Sale Owner Records
$145,000Aug 2025 $5292026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

11 Chestertown Dr

4 bd · 5.5 ba · 5,354 sqft · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Oct 2001 $8,1312026 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

12 Chestertown Dr

1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jul 2025 $5292026 Amount on Record Nov 2021 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

13 Chestertown Dr

4 bd · 6 ba · 3,533 sqft · 0.864 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Sep 2021 $9,9722026 Amount on Record Dec 2008 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

14 Chestertown Dr

1.32 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jun 2025 $3172026 Amount on Record Mar 2021 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

15 Chestertown Dr

0.871 acres

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2021 $1,2452026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

16 Chestertown Dr

0.987 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Jan 2022 $3962026 Amount on Record Mar 2006 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

17 Chestertown Dr

0.889 acres

Last Sale Tax Bill Prior Sale Owner Records
$320,000May 2024 $7,7462026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

18 Chestertown Dr

0.808 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Nov 2012 $3962026 1 Name on Record AssessorUpdated Aug 2026

19 Chestertown Dr

0.901 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,675,000May 2026 $6,8262026 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

20 Chestertown Dr

0.971 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Dec 2020 $7,6222026 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

21 Chestertown Dr

0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Jan 2023 $6,0892026 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

22 Chestertown Dr

1.17 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jul 2023 $6,2582026 Amount on Record Sep 2022 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

23 Chestertown Dr

0.839 acres

Last Sale Tax Bill Prior Sale Owner Records
$210,000Jan 2022 $1,3692026 Amount on Record Dec 2020 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

24 Chestertown Dr

5 bd · 5.5 ba · 5,169 sqft · 1.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$875,000Mar 2021 $6,2052026 Amount on Record Dec 2012 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

25 Chestertown Dr

0.935 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Sep 2021 $1,3692026 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

27 Chestertown Dr

0.989 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,000,000Oct 2024 $10,4352026 Amount on Record Feb 2022 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

28 Chestertown Dr

5 bd · 6.5 ba · 4,190 sqft · 5.34 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,1652026 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

29 Chestertown Dr

1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$380,000Mar 2025 $1,2452026 Amount on Record Feb 2025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

30 Chestertown Dr

2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,000Sep 2020 $3962026 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

31 Chestertown Dr

1.47 acres

Last Sale Tax Bill Prior Sale Owner Records
$315,000Sep 2023 $8,0952026 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

32 Chestertown Dr

4 bd · 2.5 ba · 2,280 sqft · 2.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,240,000Feb 2026 $4,9272026 Amount on Record Oct 2022 2 Names on Record Assessor + 8 DocumentsUpdated Aug 2026

33 Chestertown Dr

1.69 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Sep 2021 $10,8082026 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

36 Chestertown Dr

2.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$72,000May 2020 $7,6162026 Amount on Record Mar 2007 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

38 Chestertown Dr

1.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Apr 2021 $5,6272026 —May 1998 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

39 Chestertown Dr

0.742 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000May 2021 $8,1032026 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

40 Chestertown Dr

1.82 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Aug 2001 $5292026 1 Name on Record AssessorUpdated Aug 2026

41 Chestertown Dr

0.839 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,650,000Dec 2025 $1,0582026 Amount on Record Mar 2017 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

42 Chestertown Dr

3 bd · 4.5 ba · 2,914 sqft · 1.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$935,000Jun 2025 $4,2812026 Amount on Record Nov 2020 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

43 Chestertown Dr

0.919 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,650,000Dec 2025 $1,5562026 2 Names on Record AssessorUpdated Aug 2026

44 Chestertown Dr

0.908 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2023 $5,1312026 Amount on Record Mar 2021 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

45 Chestertown Dr

4 bd · 5 ba · 5,685 sqft · 0.917 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,650,000Dec 2025 $8,5312026 Amount on Record Feb 2003 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

47 Chestertown Dr

5 bd · 6 ba · 5,143 sqft · 1.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,5312026 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

49 Chestertown Dr

4 bd · 4.5 ba · 6,912 sqft · 1.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,450Mar 2022 $12,7882026 Amount on Record Apr 2018 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

51 Chestertown Dr

3 bd · 6 ba · 5,620 sqft · 1.78 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,350,000Nov 2025 $6,0652026 Amount on Record Nov 2024 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Aug 2026

53 Chestertown Dr

1.74 acres

Last Sale Tax Bill Prior Sale Owner Records
$195,000Dec 2024 $9332026 Amount on Record Aug 2023 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

55 Chestertown Dr

1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Mar 2023 $6,5452026 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

57 Chestertown Dr

1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000May 2025 $4,7912026 Amount on Record May 2024 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

59 Chestertown Dr

4 bd · 3.5 ba · 3,190 sqft · 0.887 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Feb 2007 $6,0082026 Amount on Record May 1999 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

61 Chestertown Dr

0.776 acres

Last Sale Tax Bill Prior Sale Owner Records
$112,000May 2021 $6,0242026 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

63 Chestertown Dr

0.782 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000May 2026 $9962026 Amount on Record Apr 2024 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

65 Chestertown Dr

0.953 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,800,000Jul 2025 $7,7312026 Amount on Record Feb 2024 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

67 Chestertown Dr

0.812 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Jun 2024 $9962026 2 Names on Record AssessorUpdated Aug 2026

69 Chestertown Dr

0.914 acres

Last Sale Tax Bill Prior Sale Owner Records
$545,000Jun 2026 $1,5562026 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

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