Pleasant St, Chester, CT Property Records

Chester Town property records for 38 addresses on Pleasant St, Chester, CT · Last verified October 2026

Pleasant St Highlights

Properties 38
Median Sale Price $385,000
Deeds and Mortgages on File 48
Median Price per Sqft $199
Owner Occupied 87%
Median Annual Tax Bill $6,451
Median Year Built 1915
Median Ownership Tenure 19 years

Properties on Pleasant St

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

5 Pleasant St

3 bd · 1 ba · 1,476 sqft · built 1852 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,3002025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

6 Pleasant St

4 bd · 2.5 ba · 3,230 sqft · built 1850 · 0.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$475,000May 2021 $9,3472025 Owner on Record Assessor + 1 DocumentUpdated Jul 2026

10 Pleasant St

3 bd · 3.5 ba · 2,340 sqft · built 1900 · 1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$279,900Aug 2000 $7,5052025 Amount on Record Dec 1994 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

11 Pleasant St

4 bd · 2 ba · 1,862 sqft · built 1895 · 0.689 acres

Last Sale Tax Bill Prior Sale Owner Records
$16,500Jul 1968 $5,8252025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

12 Pleasant St

3 bd · 2.5 ba · 2,104 sqft · built 1890 · 0.369 acres

Last Sale Tax Bill Prior Sale Owner Records
$432,500Apr 2017 $8,3842025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

14 Pleasant St

3 bd · 1.5 ba · 1,364 sqft · built 1900 · 0.339 acres

Last Sale Tax Bill Prior Sale Owner Records
$201,000Apr 2003 $4,4772025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

15 Pleasant St

2 bd · 2 ba · 1,834 sqft · built 1855 · 0.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,3772025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

16 Pleasant St

3 bd · 2 ba · 2,038 sqft · built 1938 · 0.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Sep 2020 $6,4512025 Amount on Record May 2018 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

17 Pleasant St

3 bd · 2.5 ba · 2,216 sqft · built 1951 · 0.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,0612025 Owner on Record AssessorUpdated Jul 2026

18 Pleasant St

3 bd · 2.5 ba · 2,322 sqft · built 1875 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$318,000Apr 2014 $8,8262025 Amount on Record Oct 2010 2 Owners on Record Assessor + 3 DocumentsUpdated Jul 2026

21 Pleasant St

3 bd · 2 ba · 2,010 sqft · built 1850 · 0.589 acres

Last Sale Tax Bill Prior Sale Owner Records
$84,950May 2019 $5,7852025 Owner on Record Assessor + 2 DocumentsUpdated Jul 2026

24 Pleasant St

3 bd · 2.5 ba · 2,380 sqft · built 1850 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,2622025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

25 Pleasant St

3 bd · 1 ba · 1,002 sqft · built 1920 · 0.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$102,500Mar 1997 $3,6322025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

27 Pleasant St

3 bd · 2.5 ba · 1,726 sqft · built 1915 · 2.41 acres

Last Sale Tax Bill Prior Sale Owner Records
$250,000Sep 1999 $6,2712025 Amount on Record Oct 1992 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

29 Pleasant St

3 bd · 1 ba · 1,328 sqft · built 1920 · 0.319 acres

Last Sale Tax Bill Prior Sale Owner Records
$25,000Jun 1972 $4,6372025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

30 Pleasant St

3 bd · 2 ba · 2,249 sqft · built 1938 · 4.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$425,000Jun 2012 $8,8582025 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

31 Pleasant St

4 bd · 1.5 ba · 1,788 sqft · built 1918 · 0.26 acres

Last Sale Tax Bill Prior Sale Owner Records
$270,000Mar 2003 $5,8652025 Amount on Record Feb 2000 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

32 Pleasant St

2 bd · 2 ba · 1,645 sqft · built 1835 · 0.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,9572025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

33 Pleasant St

3 bd · 1 ba · 1,364 sqft · built 1871 · 0.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,8872025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

34 Pleasant St

4 bd · 2 ba · 1,927 sqft · built 1953 · 0.719 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,000Jun 2023 $6,4872025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

35 Pleasant St

3 bd · 2.5 ba · 2,007 sqft · built 1986 · 1.31 acres

Last Sale Tax Bill Prior Sale Owner Records
$189,000May 1994 $8,0322025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

37 Pleasant St

2 bd · 1.5 ba · 1,217 sqft · built 1890 · 0.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$305,000Oct 2004 $5,0972025 Amount on Record Oct 1995 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

38 Pleasant St

3 bd · 1.5 ba · 1,482 sqft · built 1850 · 0.519 acres

Last Sale Tax Bill Prior Sale Owner Records
$296,000Jul 2014 $5,7512025 Amount on Record Apr 2001 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Jul 2026

39 Pleasant St

3 bd · 1.5 ba · 1,224 sqft · built 1977 · 1.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,4672025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

40 Pleasant St

4 bd · 2 ba · 2,689 sqft · built 1947 · 1.11 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2015 $7,4762025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

41 Pleasant St

3 bd · 2 ba · 1,728 sqft · built 1900 · 2.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$220,000Jul 1994 $6,9472025 —Jul 1994 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

45 Pleasant St

2 bd · 2 ba · 1,753 sqft · built 1860 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,9502025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

47 Pleasant St

1 bd · 1.5 ba · 792 sqft · built 1900 · 1.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,6722025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

48 Pleasant St

4 bd · 3 ba · 3,103 sqft · built 2007 · 1.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$111,000May 2007 $10,8182025 Amount on Record Mar 2006 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

54 Pleasant St

4 bd · 3.5 ba · 2,880 sqft · built 2006 · 1.46 acres

Last Sale Tax Bill Prior Sale Owner Records
$481,136May 2007 $10,3332025 Amount on Record Dec 2006 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

55 Pleasant St

3 bd · 2.5 ba · 2,531 sqft · built 2017 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$429,900Jul 2018 $11,0232025 Amount on Record Feb 2017 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

56 Pleasant St

3 bd · 2 ba · 1,436 sqft · built 1959 · 1.3 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,4732025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

57 Pleasant St

3 bd · 1 ba · 1,298 sqft · built 1947 · 3.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4092025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

59 Pleasant St

3 bd · 2 ba · 1,568 sqft · built 2010 · 1.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,0822025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

61 Pleasant St

3 bd · 2.5 ba · 1,680 sqft · built 1989 · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,1762025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

62 Pleasant St

3 bd · 1 ba · 1,242 sqft · built 1963 · 0.7 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Sep 2024 $5,6202025 Amount on Record Dec 2021 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

64 Pleasant St

3 bd · 2 ba · 1,719 sqft · built 1888 · 0.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,6642025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

66 Pleasant St

4 bd · 3.5 ba · 2,118 sqft · built 1895 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$88,875Jul 1996 $8,2142025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

Property Records in Nearby Streets