Pennywise Ln, Old Saybrook, CT Property Records

Old Saybrook Town property records for 19 addresses on Pennywise Ln, Old Saybrook, CT · Last verified October 2026

Pennywise Ln Highlights

Properties 19
Median Sale Price $336,000
Deeds and Mortgages on File 23
Median Price per Sqft $174
Owner Occupied 89%
Median Annual Tax Bill $5,227
Median Year Built 1941
Median Ownership Tenure 16 years

Properties on Pennywise Ln

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

7 Pennywise Ln

3 bd · 2 ba · 1,179 sqft · built 1953 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$196,000Nov 2001 $4,3342025 Amount on Record Feb 2000 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

9 Pennywise Ln

3 bd · 2.5 ba · 2,000 sqft · built 1901 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4722025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

10 Pennywise Ln

4 bd · 2.5 ba · 3,493 sqft · built 1887 · 0.489 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Sep 1993 $8,3512025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

11 Pennywise Ln

3 bd · 1.5 ba · 1,176 sqft · built 1941 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$139,750Jun 2024 $3,3392025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

14 Pennywise Ln

3 bd · 3.5 ba · 1,950 sqft · built 1800 · 0.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6462025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

17 Pennywise Ln

4 bd · 3.5 ba · 1,853 sqft · built 1950 · 0.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$179,052Jun 1996 $4,8482025 —Jun 1996 Owner on Record Owner Occupied AssessorUpdated Jul 2026

21 Pennywise Ln

3 bd · 1.5 ba · 1,980 sqft · built 1951 · 0.2 acres

Last Sale Tax Bill Prior Sale Owner Records
$345,000Oct 2014 $5,0582025 Amount on Record Dec 2010 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

22 Pennywise Ln

3 bd · 2 ba · 2,036 sqft · built 1906 · 0.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$336,000May 2015 $5,8922025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

27 Pennywise Ln

3 bd · 2.5 ba · 2,079 sqft · built 1953 · 0.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$358,500Dec 2019 $5,2272025 Amount on Record Oct 2018 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

28 Pennywise Ln

3 bd · 1.5 ba · 2,424 sqft · built 1810 · 1.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,9942025 Owner on Record AssessorUpdated Oct 2026

29 Pennywise Ln

2 bd · 1 ba · 1,052 sqft · built 1950 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$225,000Feb 2010 $4,3112025 Amount on Record Nov 1998 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

33 Pennywise Ln

4 bd · 3 ba · 2,677 sqft · built 1962 · 0.439 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Jan 2003 $6,1012025 Amount on Record Sep 1995 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

36 Pennywise Ln

3 bd · 2.5 ba · 2,640 sqft · built 2021 · 0.8 acres

Last Sale Tax Bill Prior Sale Owner Records
$10,2702025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

37 Pennywise Ln

5 bd · 2.5 ba · 2,059 sqft · built 1930 · 0.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$175,000Jun 1994 $5,6312025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

40 Pennywise Ln

4 bd · 1.5 ba · 2,224 sqft · built 1936 · 0.569 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Aug 1994 $6,2852025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

43 Pennywise Ln

1 bd · 1 ba · 1,436 sqft · built 1800 · 0.23 acres

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jun 2020 $4,1992025 Amount on Record Jan 2009 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

46 Pennywise Ln

2 bd · 1.5 ba · 1,270 sqft · built 1950 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,5462025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

54 Pennywise Ln

2 bd · 3 ba · 1,736 sqft · built 1951 · 0.76 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,000Mar 1998 $5,5472025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

66 Pennywise Ln

4 bd · 3 ba · 2,425 sqft · built 1790 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,495,000Dec 2025 $9,8642025 Amount on Record Apr 2018 2 Owners on Record Assessor + 4 DocumentsUpdated Jul 2026

Property Records in Nearby Streets