Winthrop Rd, Chester, CT Property Records

Chester Town property records for 45 addresses on Winthrop Rd, Chester, CT · Last verified August 2026

Winthrop Rd Highlights

Properties 47
Median Sale Price $360,000
Deeds and Mortgages on File 50
Median Price per Sqft $230
Owner Occupied 77%
Median Annual Tax Bill $7,692
Median Year Built 1979
Median Ownership Tenure 16 years

Properties on Winthrop Rd

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

1 Winthrop Rd

3 bd · 2.5 ba · 2,727 sqft · built 1960 · 7.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$485,000Aug 2006 $15,5382025 Amount on Record Jul 1990 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

2 Winthrop Rd

4 bd · 3.5 ba · 3,257 sqft · built 2006 · 1.66 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000May 2017 $12,3522025 —May 2017 2 Names on Record Assessor + 4 DocumentsUpdated Jul 2026

5 Winthrop Rd

3 bd · 2.5 ba · 1,687 sqft · built 1994 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$253,000Jul 2000 $7,6922025 Amount on Record Oct 1994 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

6 Winthrop Rd

2 bd · 1 ba · 828 sqft · built 1938 · 0.85 acres

Last Sale Tax Bill Prior Sale Owner Records
$173,500Dec 2015 $3,8612025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

7 Winthrop Rd

3 bd · 2 ba · 2,218 sqft · built 1961 · 1.71 acres

Last Sale Tax Bill Prior Sale Owner Records
$238,000Aug 1999 $8,1252025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

8 Winthrop Rd

3 bd · 1.5 ba · 1,344 sqft · built 1953 · 1.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000May 2008 $5,7702025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

10 Winthrop Rd

3 bd · 2 ba · 1,344 sqft · built 1950 · 0.969 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Aug 2007 $5,3042025 Amount on Record Jun 2005 1 Name on Record AssessorUpdated Jul 2026

12 Winthrop Rd

5 bd · 4 ba · 4,117 sqft · built 1985 · 2.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$399,900Jul 2020 $13,9192025 Amount on Record Aug 1989 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

14 Winthrop Rd

3 bd · 2 ba · 1,716 sqft · built 1985 · 2.35 acres

Last Sale Tax Bill Prior Sale Owner Records
$304,000Jun 2011 $7,3742025 Amount on Record Nov 1996 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

15 Winthrop Rd

3 bd · 1.5 ba · 2,039 sqft · built 1946 · 2 acres

Last Sale Tax Bill Prior Sale Owner Records
$335,000Oct 2018 $7,8972025 Amount on Record Oct 2002 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated Jul 2026

16 Winthrop Rd

3 bd · 2 ba · 1,656 sqft · built 1986 · 2.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,1672025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

21 Winthrop Rd

2 bd · 1 ba · 1,260 sqft · built 1930 · 2.81 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Nov 2006 $4,5672025 2 Names on Record Assessor + 1 DocumentUpdated Jul 2026

25 Winthrop Rd

3 bd · 2.5 ba · 2,876 sqft · built 1987 · 6.05 acres

Last Sale Tax Bill Prior Sale Owner Records
$330,000Dec 2012 $10,2062025 Amount on Record May 1995 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

27 Winthrop Rd

4 bd · 2.5 ba · 2,609 sqft · built 1984 · 2.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Sep 2017 $9,4272025 Amount on Record Sep 1988 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

28 Winthrop Rd

3 bd · 2.5 ba · 1,721 sqft · built 1947 · 13 acres

Last Sale Tax Bill Prior Sale Owner Records
$359,900Jun 2020 $7,9242025 Amount on Record Jan 2018 2 Names on Record Owner Occupied Assessor + 5 DocumentsUpdated Jul 2026

29 Winthrop Rd

3 units · Built 1983 · 1,496 sq ft

Last Sale Median Tax Bill Median Sale    
$227,000Apr 2000 $6,4732025 —3 units    

31 Winthrop Rd

2 bd · 2 ba · 1,238 sqft · built 1983 · 2.16 acres

Last Sale Tax Bill Prior Sale Owner Records
$285,000Dec 2019 $5,7232025 Amount on Record Mar 2000 1 Name on Record Owner Occupied Assessor + 3 DocumentsUpdated Jul 2026

32 Winthrop Rd

3 bd · 1 ba · 1,654 sqft · built 1973 · 4.68 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7792025 1 Name on Record AssessorUpdated Jul 2026

35 Winthrop Rd

1 bd · 1 ba · 624 sqft · built 1958 · 8.61 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,2062025 2 Names on Record AssessorUpdated Jul 2026

39 Winthrop Rd

3 bd · 2 ba · 1,888 sqft · built 1949 · 2.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$153,000Feb 1997 $7,5082025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

40 Winthrop Rd

3 bd · 3 ba · 1,761 sqft · built 1985 · 5.63 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,4562025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

41 Winthrop Rd

3 bd · 2 ba · 1,572 sqft · built 1977 · 3.83 acres

Last Sale Tax Bill Prior Sale Owner Records
$81,500Jan 1980 $6,8362025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

42 Winthrop Rd

3 bd · 2.5 ba · 1,578 sqft · built 1976 · 25.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$530,000Jan 2020 $8,5742025 Amount on Record Mar 1995 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

45 Winthrop Rd

4 bd · 3 ba · 1,972 sqft · built 1985 · 2.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$245,000Jun 2002 $7,8102025 Amount on Record Jan 2001 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

47 Winthrop Rd

3 bd · 2 ba · 1,408 sqft · built 1986 · 0.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$360,000Sep 2024 $4,1532025 Amount on Record Jan 2023 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

48 Winthrop Rd

4 bd · 2 ba · 1,683 sqft · built 1950 · 5.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$440,000Jul 2026 $7,2092025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

49 Winthrop Rd

3 bd · 1 ba · 1,064 sqft · built 1958 · 1.06 acres

Last Sale Tax Bill Prior Sale Owner Records
$201,000Oct 2010 $5,1122025 Amount on Record Jun 1995 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

51 Winthrop Rd

52,000 sqft · built 1983 · 17.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$186,1612025 1 Name on Record AssessorUpdated Jul 2026

52 Winthrop Rd

1.88 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Mar 2000 $1,5962025 1 Name on Record AssessorUpdated Jul 2026

54 Winthrop Rd

2 bd · 1 ba · 840 sqft · built 1839 · 0.53 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2013 $3,8402025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

59 Winthrop Rd

2,898 sqft · built 1960 · 3.18 acres

Last Sale Tax Bill Prior Sale Owner Records
$159,659Jul 2018 $8,0112025 1 Name on Record Assessor + 2 DocumentsUpdated Aug 2026

61 Winthrop Rd

7,152 sqft · built 1958 · 122 acres

Last Sale Tax Bill Prior Sale Owner Records
$99,8682025 2 Names on Record AssessorUpdated Jul 2026

64 Winthrop Rd

4 bd · 1.5 ba · 1,606 sqft · built 1958 · 0.569 acres

Last Sale Tax Bill Prior Sale Owner Records
$204,000Jan 2012 $5,0952025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

66 Winthrop Rd

3 bd · 1 ba · 1,140 sqft · built 1955 · 0.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$4,4152025 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

67 Winthrop Rd

4 bd · 4 ba · 27,904 sqft · built 1997 · 4.71 acres

Last Sale Tax Bill Prior Sale Owner Records
$34,6422025 2 Names on Record AssessorUpdated Jul 2026

68 Winthrop Rd

2 bd · 1 ba · 1,164 sqft · built 1957 · 0.98 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Apr 2007 $5,4212025 Amount on Record Dec 2006 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

70 Winthrop Rd

3 bd · 2.5 ba · 1,872 sqft · built 2008 · 2.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$116,000Mar 2007 $8,9702025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

72 Winthrop Rd

2 bd · 1.5 ba · 1,818 sqft · built 1976 · 9.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Dec 2015 $7,9012025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

78 Winthrop Rd

3 bd · 2 ba · 1,419 sqft · built 1980 · 5.73 acres

Last Sale Tax Bill Prior Sale Owner Records
$14,000Sep 1977 $7,2752025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

80 Winthrop Rd

1 bd · 1 ba · 1,152 sqft · built 1979 · 4.45 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,1352025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

84 Winthrop Rd

3 bd · 2 ba · 1,496 sqft · built 1986 · 2.33 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Oct 2015 $6,0942025 Amount on Record Jun 2000 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

86 Winthrop Rd

4 bd · 2.5 ba · 2,494 sqft · built 1999 · 2.58 acres

Last Sale Tax Bill Prior Sale Owner Records
$383,000Jul 2009 $9,7742025 Amount on Record Sep 1999 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Jul 2026

87 Winthrop Rd

4 bd · 2 ba · 2,791 sqft · built 1984 · 6 acres

Last Sale Tax Bill Prior Sale Owner Records
$482,000Nov 1989 $9,7432025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

88 Winthrop Rd

2 bd · 2.5 ba · 2,240 sqft · built 1980 · 33.9 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,1982025 1 Name on Record Owner Occupied AssessorUpdated Jul 2026

96 Winthrop Rd

4 bd · 3.5 ba · 2,583 sqft · built 1790 · 5.15 acres

Last Sale Tax Bill Prior Sale Owner Records
$150,000Jul 1982 $12,1032025 2 Names on Record Owner Occupied AssessorUpdated Jul 2026

Wildfire Risk on Winthrop Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskLow
this street's cells rank above 25% of the US · above 70% of Connecticut
Wildfire LikelihoodAbout 1 in 3,953 per year
ExposureDirect
11 of 17 cells directly exposed · 17 adjoin burnable vegetation

Property Records in Nearby Streets