Wakeman Hill Rd, Sherman, CT Property Records

Dutchess County, Sherman Town and Pawling Town property records for 39 addresses on Wakeman Hill Rd, Sherman, CT · Last verified August 2026

Wakeman Hill Rd Highlights

Properties 39
Median Sale Price $655,000
Deeds and Mortgages on File 30
Median Price per Sqft $232
Owner Occupied 62%
Median Annual Tax Bill $4,913
Median Year Built 1985
Median Ownership Tenure 9 years

Properties on Wakeman Hill Rd

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

1 Wakeman Hill Rd

3 bd · 2.5 ba · 3,203 sqft · built 2006 · 2.38 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,5312024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

2 Wakeman Hill Rd

5 bd · 4.5 ba · 3,625 sqft · built 2002 · 2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$615,000Nov 2005 $6,9502024 Amount on Record Feb 2002 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

3 Wakeman Hill Rd

3 bd · 3.5 ba · 4,389 sqft · built 1984 · 4.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7012024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

4 Wakeman Hill Rd

5 bd · 4.5 ba · 3,793 sqft · built 2004 · 2.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$880,000Dec 2022 $8,1202024 Amount on Record Jun 2004 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

5 Wakeman Hill Rd

3 bd · 3 ba · 2,414 sqft · built 1987 · 2.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,2892024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

6 Wakeman Hill Rd

4 bd · 2.5 ba · 4,140 sqft · built 2003 · 1.93 acres

Last Sale Tax Bill Prior Sale Owner Records
$630,000Dec 2021 $7,5622024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

7 Wakeman Hill Rd

3 bd · 2.5 ba · 2,694 sqft · built 1983 · 3.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$342,000Dec 1999 $4,8532024 Owner on Record Owner Occupied AssessorUpdated Jul 2026

8 Wakeman Hill Rd

3 bd · 3 ba · 3,620 sqft · built 2005 · 5.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$95,000Oct 2016 $7,8222024 Amount on Record Jul 2006 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

9 Wakeman Hill Rd

3 bd · 1 ba · 1,316 sqft · built 1951 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$299,000Jun 2009 $3,1972024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

11 Wakeman Hill Rd

4 bd · 3 ba · 2,098 sqft · built 1989 · 2.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,9132024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

13 Wakeman Hill Rd

4 bd · 2.5 ba · 2,999 sqft · built 1992 · 2.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9352024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

14 Wakeman Hill Rd

3 bd · 1 ba · 1,446 sqft · built 1992 · 2.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,6312024 Owner on Record Owner Occupied AssessorUpdated Jul 2026

15 Wakeman Hill Rd

3 bd · 2 ba · 2,567 sqft · built 2006 · 2.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,7762024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

17 Wakeman Hill Rd

3 bd · 1 ba · 1,523 sqft · built 1966 · 2.43 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,0562024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

18 Wakeman Hill Rd

3 bd · 3 ba · 4,532 sqft · built 1985 · 6.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,145,000Sep 2006 $10,2322024 Amount on Record Sep 2003 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

19 Wakeman Hill Rd

3 bd · 3 ba · 2,648 sqft · built 1987 · 2.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$592,000Aug 2023 $4,1292024 Amount on Record Mar 2018 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

20 Wakeman Hill Rd

3 bd · 1 ba · 1,634 sqft · built 1974 · 6.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3332024 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

22 Wakeman Hill Rd

3 bd · 2.5 ba · 1,980 sqft · built 1971 · 1.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,1992024 Owner on Record AssessorUpdated Jul 2026

24 Wakeman Hill Rd

3 bd · 2.5 ba · 2,538 sqft · built 1986 · 2.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8732024 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

25 Wakeman Hill Rd

4 bd · 4 ba · 2,712 sqft · built 1966 · 3.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$655,000Nov 2022 $5,3782024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

26 Wakeman Hill Rd

2 bd · 1 ba · 1,138 sqft · built 1850 · 33.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,9472024 Owner on Record AssessorUpdated Jul 2026

32 Wakeman Hill Rd

3 bd · 2 ba · 1,780 sqft · built 1985 · 2.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,9572024 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

34 Wakeman Hill Rd

2 bd · 2 ba · 1,692 sqft · built 1955 · 3.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000May 2020 $4,9042024 Amount on Record Aug 1994 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

44 Wakeman Hill Rd

2 bd · 3 ba · 2,521 sqft · built 1986 · 6 acres

Last Sale Tax Bill Prior Sale Owner Records
$500,000Feb 2001 $5,9582024 Amount on Record Sep 1995 Owner on Record Owner Occupied AssessorUpdated Jul 2026

46 Wakeman Hill Rd

3 bd · 3 ba · 2,319 sqft · built 1990 · 2.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$525,000Apr 2016 $6,2682024 Amount on Record Nov 2004 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

52 Wakeman Hill Rd

4 bd · 2.5 ba · 3,076 sqft · built 1974 · 5.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,325,000Oct 2020 $10,3752024 Amount on Record Sep 2015 2 Owners on Record Assessor + 2 DocumentsUpdated Jul 2026

54 Wakeman Hill Rd

3 bd · 3 ba · 1,932 sqft · built 1972 · 1.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$230,000Aug 2017 $3,7972024 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

56 Wakeman Hill Rd

3 bd · 2 ba · 1,298 sqft · built 1964 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$344,600Oct 2019 $3,8162024 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

57 Wakeman Hill Rd

3 bd · 4.5 ba · 5,171 sqft · built 1940 · 168 acres

Last Sale Tax Bill Prior Sale Owner Records
$185,000Dec 2010 $15,4102018 Owner on Record AssessorUpdated Jul 2026

58 Wakeman Hill Rd

3 bd · 3.5 ba · 2,392 sqft · built 1960 · 1.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Oct 2018 $1,1622024 2 Owners on Record Assessor + 1 DocumentUpdated Jul 2026

62 Wakeman Hill Rd

4 bd · 3 ba · 2,228 sqft · built 2006 · 5.13 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,3862024 2 Owners on Record Assessor + 3 DocumentsUpdated Jul 2026

64 Wakeman Hill Rd

5 bd · 6 ba · 6,677 sqft · built 1969 · 1.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4542024 Owner on Record AssessorUpdated Jul 2026

66 Wakeman Hill Rd

4 bd · 2.5 ba · 2,786 sqft · built 2001 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1612024 2 Owners on Record AssessorUpdated Jul 2026

67 Wakeman Hill Rd

3.41 acres

Last Sale Tax Bill Prior Sale Owner Records
Owner on Record AssessorUpdated Jul 2026

68 Wakeman Hill Rd

3 bd · 1.5 ba · 1,560 sqft · built 1968 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,5722024 2 Owners on Record AssessorUpdated Jul 2026

70 Wakeman Hill Rd

4 bd · 2.5 ba · 3,973 sqft · built 1999 · 5.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$800,000Sep 2025 $6,8352024 Amount on Record May 2013 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

72 Wakeman Hill Rd

4 bd · 1 ba · 3,300 sqft · built 1860 · 9.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$76,500Oct 1998 $7,7502024 Amount on Record Oct 1997 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

73 Wakeman Hill Rd

4 bd · 5.5 ba · 4,658 sqft · built 1979 · 6.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$608,112Nov 2003 $7,2312024 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

76 Wakeman Hill Rd

5 bd · 3.5 ba · 2,586 sqft · built 1942 · 4.56 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,8622024 2 Owners on Record AssessorUpdated Jul 2026

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