Hilltop Dr, Chappaqua, NY Property Records

Westchester County and New Castle Town property records for 37 addresses on Hilltop Dr, Chappaqua, NY · Last verified August 2026

Hilltop Dr Highlights

Properties 37
Median Sale Price $1,488,000
Deeds and Mortgages on File 34
Median Price per Sqft $473
Owner Occupied 86%
Median Annual Tax Bill $32,299
Median Year Built 1968
Median Ownership Tenure 11 years

Properties on Hilltop Dr

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

3 Hilltop Dr

4 bd · 4 ba · 5,180 sqft · built 2006 · 1.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,075,000Aug 2021 $21,1802025 Amount on Record Jun 2007 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

6 Hilltop Dr

5 bd · 2 ba · 3,740 sqft · built 1968 · 1.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,265,000Oct 2006 $37,0042025 Amount on Record Feb 2004 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

9 Hilltop Dr

4 bd · 3 ba · 3,884 sqft · built 1962 · 1.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,249,000Aug 2015 $24,2602025 Amount on Record Oct 2007 2 Owners on Record Owner Occupied AssessorUpdated May 2026

15 Hilltop Dr

4 bd · 3 ba · 2,606 sqft · built 1965 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$24,5382025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

20 Hilltop Dr

4 bd · 2.5 ba · 2,762 sqft · built 1966 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,190,000Aug 2024 $20,0262025 Amount on Record Mar 1997 2 Owners on Record Assessor + 1 DocumentUpdated May 2026

21 Hilltop Dr

4 bd · 2.5 ba · 3,094 sqft · built 1968 · 1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,3782025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

24 Hilltop Dr

3 bd · 3.5 ba · 3,186 sqft · built 1964 · 1.25 acres

Last Sale Tax Bill Prior Sale Owner Records
$999,000Jan 2024 $60,4212025 Amount on Record May 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

25 Hilltop Dr

5 bd · 2.5 ba · 2,849 sqft · built 1961 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$18,4252025 Owner on Record Owner Occupied AssessorUpdated May 2026

28 Hilltop Dr

4 bd · 2 ba · 4,782 sqft · built 1962 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$600,000Feb 1999 $24,6092025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

29 Hilltop Dr

4 bd · 3.5 ba · 2,722 sqft · built 1963 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Oct 2017 $18,2352025 Amount on Record Jun 2008 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

30 Hilltop Dr

4 bd · 2.5 ba · 2,408 sqft · built 1963 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,2942025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

34 Hilltop Dr

4 bd · 3 ba · 3,367 sqft · built 2006 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Jul 2009 $33,2792025 Amount on Record Aug 2005 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

35 Hilltop Dr

4 bd · 3.5 ba · 2,834 sqft · built 1959 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,341,000Apr 2022 $29,8102025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

36 Hilltop Dr

4 bd · 3 ba · 3,608 sqft · built 2007 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,810,000Oct 2007 $25,7162025 Amount on Record May 2006 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

40 Hilltop Dr

4 bd · 3 ba · 3,547 sqft · built 1964 · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,360,000Jul 2016 2 Owners on Record Owner Occupied AssessorUpdated May 2026

41 Hilltop Dr

4 bd · 3 ba · 2,824 sqft · built 1964 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$840,000Jul 2015 $40,1172025 2 Owners on Record Assessor + 2 DocumentsUpdated May 2026

45 Hilltop Dr

4 bd · 2.5 ba · 2,504 sqft · built 1962 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$830,000Jul 2016 $27,0672025 Amount on Record Jan 1997 2 Owners on Record Owner Occupied AssessorUpdated May 2026

48 Hilltop Dr

4 bd · 2 ba · 1,836 sqft · built 1969 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,200,000Jul 2024 $32,2992025 Amount on Record Mar 2007 2 Owners on Record AssessorUpdated May 2026

49 Hilltop Dr

4 bd · 2 ba · 2,627 sqft · built 1967 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,080,000Aug 2009 $34,4882025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

52 Hilltop Dr

4 bd · 3.5 ba · 2,870 sqft · built 1973 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$98,000Feb 2015 $26,7342025 Amount on Record — 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

58 Hilltop Dr

5 bd · 3 ba · 2,907 sqft · built 1968 · 1.08 acres

Last Sale Tax Bill Prior Sale Owner Records
$28,8922025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

62 Hilltop Dr

4 bd · 4 ba · 3,905 sqft · built 2007 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,000Jul 1996 $30,1272025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

66 Hilltop Dr

4 bd · 4 ba · 4,232 sqft · built 1966 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,415,000Dec 2024 $35,9152025 Amount on Record Apr 2015 2 Owners on Record AssessorUpdated May 2026

67 Hilltop Dr

4 bd · 3.5 ba · 3,030 sqft · built 1970 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,5082025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

69 Hilltop Dr

4 bd · 3 ba · 3,659 sqft · built 1968 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$36,4062025 Owner on Record Owner Occupied AssessorUpdated May 2026

70 Hilltop Dr

4 bd · 2.5 ba · 2,219 sqft · built 1966 · 1.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,500,000Oct 2022 $65,0122025 Amount on Record Jun 2019 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated May 2026

73 Hilltop Dr

4 bd · 2 ba · 2,806 sqft · built 1967 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,375,000Sep 2005 $38,0472025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

74 Hilltop Dr

4 bd · 3 ba · 2,708 sqft · built 1969 · 1.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,075,000Aug 2015 $55,1812025 Amount on Record Feb 2008 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

77 Hilltop Dr

5 bd · 3.5 ba · 3,531 sqft · built 1985 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$47,9262025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

78 Hilltop Dr

6 bd · 5 ba · 4,133 sqft · built 1985 · 1.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,608,000Jul 2015 $42,9332025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

81 Hilltop Dr

4 bd · 3 ba · 4,172 sqft · built 1985 · 1.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Oct 2000 $42,0532025 Amount on Record Apr 1994 Owner on Record Owner Occupied AssessorUpdated May 2026

82 Hilltop Dr

4 bd · 3 ba · 3,919 sqft · built 1985 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$39,8362025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

84 Hilltop Dr

4 bd · 4 ba · 4,559 sqft · built 1985 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$832,000Jan 1998 $40,9692025 2 Owners on Record Owner Occupied AssessorUpdated May 2026

85 Hilltop Dr

4 bd · 5 ba · 4,549 sqft · built 1985 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,337,500Oct 2007 $42,4002025 Amount on Record Jan 2004 2 Owners on Record Owner Occupied AssessorUpdated May 2026

89 Hilltop Dr

4 bd · 4 ba · 4,202 sqft · built 1985 · 1.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,100,000Jun 2022 $33,8062025 Amount on Record Jul 2001 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated May 2026

90 Hilltop Dr

4 bd · 3 ba · 3,678 sqft · built 1986 · 1.28 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,488,000Apr 2021 $30,9992025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated May 2026

94 Hilltop Dr

5 bd · 4 ba · 3,362 sqft · built 1985 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,475,000Dec 2017 $28,7002025 Amount on Record Sep 1997 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated May 2026

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