Sunnyside Ave, Winthrop, MA Property Records

Suffolk County and Winthrop Town City property records for 39 addresses on Sunnyside Ave, Winthrop, MA · Last verified October 2026

Sunnyside Ave Highlights

Properties 41
Median Sale Price $654,750
Deeds and Mortgages on File 53
Median Price per Sqft $319
Owner Occupied 83%
Median Annual Tax Bill $7,607
Median Year Built 1920
Median Ownership Tenure 17 years

Properties on Sunnyside Ave

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

14 Sunnyside Ave

2 bd · 2 ba · 875 sqft · built 1900 · 0.126 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Oct 1993 $7,0932026 Owner on Record Owner Occupied AssessorUpdated Oct 2026

16 Sunnyside Ave

3 bd · 2 ba · 1,489 sqft · built 1920 · 0.157 acres

Last Sale Tax Bill Prior Sale Owner Records
$370,000Jun 2004 $6,8892025 Amount on Record Aug 1990 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

17 Sunnyside Ave

4 bd · 1.5 ba · 2,485 sqft · built 1890 · 0.158 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,6972025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

24 Sunnyside Ave

3 bd · 1.5 ba · 1,550 sqft · built 1920 · 0.228 acres

Last Sale Tax Bill Prior Sale Owner Records
$470,000Mar 2018 $9,1622026 Amount on Record Mar 2017 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

28 Sunnyside Ave, #30

0.259 acres

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

29 Sunnyside Ave

5 bd · 2.5 ba · 2,038 sqft · built 1900 · 0.199 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,6822025 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

33 Sunnyside Ave

5 bd · 2.5 ba · 3,394 sqft · built 1900 · 0.121 acres

Last Sale Tax Bill Prior Sale Owner Records
$72,500Feb 1998 $10,8632026 Amount on Record Dec 1995 Owner on Record Owner Occupied AssessorUpdated Oct 2026

34 Sunnyside Ave

4 bd · 2 ba · 1,999 sqft · built 1900 · 0.259 acres

Last Sale Tax Bill Prior Sale Owner Records
$700,000Nov 2020 $9,7122026 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

36 Sunnyside Ave

3 bd · 2 ba · 1,362 sqft · built 1900 · 0.086 acres

Last Sale Tax Bill Prior Sale Owner Records
$720,000Feb 2022 $8,2672026 Amount on Record Jun 2015 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

37 Sunnyside Ave

5 bd · 2 ba · 2,111 sqft · built 1890 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,0262026 Owner on Record Owner Occupied AssessorUpdated Oct 2026

40 Sunnyside Ave

4 bd · 1 ba · 2,067 sqft · built 1900

Last Sale Tax Bill Prior Sale Owner Records
$260,000Jul 2015 $4,3712025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

41 Sunnyside Ave

5 bd · 2 ba · 2,343 sqft · built 1890 · 0.109 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000Sep 2007 $8,0332025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

42 Sunnyside Ave

3 bd · 2 ba · 2,040 sqft · built 1900

Last Sale Tax Bill Prior Sale Owner Records
$320,000Jul 2015 $4,3192025 Amount on Record Jul 2005 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

46 Sunnyside Ave

3 bd · 1 ba · 1,426 sqft · built 1920 · 0.087 acres

Last Sale Tax Bill Prior Sale Owner Records
$455,000Aug 2017 $7,6012026 —Apr 2016 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

47 Sunnyside Ave

5 bd · 3 ba · 3,434 sqft · built 1880 · 0.104 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Mar 1997 $10,0082026 Amount on Record May 1993 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

51 Sunnyside Ave

5 bd · 3 ba · 2,835 sqft · built 1900 · 0.101 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,000May 1991 $9,7912026 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

55 Sunnyside Ave

3 units · Built 1920 · 1,207 sq ft

Last Sale Median Tax Bill Median Sale    
$335,000Nov 2016 $4,4402025 $263,0003 units    

59 Sunnyside Ave

5 bd · 2 ba · 2,320 sqft · built 1900 · 0.097 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2018 $9,2052026 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

61 Sunnyside Ave

3 bd · 1 ba · 1,502 sqft · built 1925 · 0.095 acres

Last Sale Tax Bill Prior Sale Owner Records
$457,500Oct 2017 $6,5522025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

65 Sunnyside Ave

3 bd · 1 ba · 2,053 sqft · built 1890 · 0.093 acres

Last Sale Tax Bill Prior Sale Owner Records
$135,000Jul 1996 $7,1562025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

66 Sunnyside Ave

4 bd · 2 ba · 2,635 sqft · built 1920 · 0.122 acres

Last Sale Tax Bill Prior Sale Owner Records
$915,000Apr 2024 $9,9282026 Amount on Record Oct 2023 Owner on Record Assessor + 2 DocumentsUpdated Oct 2026

67 Sunnyside Ave

3 bd · 1 ba · 1,431 sqft · built 1910 · 0.077 acres

Last Sale Tax Bill Prior Sale Owner Records
$254,900Jun 2009 $6,9902026 Amount on Record Nov 2001 Owner on Record Owner Occupied AssessorUpdated Oct 2026

72 Sunnyside Ave

5 bd · 2 ba · 2,503 sqft · built 1900 · 0.149 acres

Last Sale Tax Bill Prior Sale Owner Records
$170,000Oct 1996 $10,0512026 Amount on Record Mar 1989 Owner on Record AssessorUpdated Oct 2026

76 Sunnyside Ave

5 bd · 3 ba · 2,570 sqft · built 1900 · 0.072 acres

Last Sale Tax Bill Prior Sale Owner Records
$654,750Feb 2024 $9,4472026 —Jul 2013 Owner on Record Assessor + 2 DocumentsUpdated Oct 2026

81 Sunnyside Ave

5 bd · 2 ba · 3,135 sqft · built 1900 · 0.102 acres

Last Sale Tax Bill Prior Sale Owner Records
—Aug 2009 $8,4242025 Owner on Record AssessorUpdated Apr 2026

82 Sunnyside Ave

3 bd · 2.5 ba · 1,076 sqft · built 1900 · 0.071 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,7212025 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

83 Sunnyside Ave

4 bd · 1 ba · 1,443 sqft · built 1929 · 0.097 acres

Last Sale Tax Bill Prior Sale Owner Records
$182,000Aug 1998 $6,4212025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

85 Sunnyside Ave

4 bd · 2.5 ba · 2,410 sqft · built 1920 · 0.112 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2018 $7,3782025 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Apr 2026

94 Sunnyside Ave

3 bd · 1.5 ba · 2,168 sqft · built 1950 · 0.102 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,9572025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

100 Sunnyside Ave

3 bd · 1.5 ba · 2,144 sqft · built 1931 · 0.103 acres

Last Sale Tax Bill Prior Sale Owner Records
$156,250Jul 1999 $7,8952025 Amount on Record Mar 1993 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

101 Sunnyside Ave

2 bd · 2.5 ba · 2,380 sqft · built 1937 · 0.188 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000Jun 2017 $10,2892026 Amount on Record Jun 2003 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

105 Sunnyside Ave

4 bd · 1 ba · 1,440 sqft · built 1938 · 0.082 acres

Last Sale Tax Bill Prior Sale Owner Records
$181,000Jul 1987 $7,0102025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

106 Sunnyside Ave

3 bd · 1.5 ba · 2,042 sqft · built 1948 · 0.103 acres

Last Sale Tax Bill Prior Sale Owner Records
$371,000Dec 2013 $8,2002025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

110 Sunnyside Ave

4 bd · 2.5 ba · 1,644 sqft · built 1943 · 0.103 acres

Last Sale Tax Bill Prior Sale Owner Records
$480,000Feb 2018 $8,5222026 Amount on Record Mar 2015 2 Owners on Record Owner Occupied Assessor + 2 DocumentsUpdated Oct 2026

111 Sunnyside Ave

3 bd · 1.5 ba · 1,320 sqft · built 1938 · 0.079 acres

Last Sale Tax Bill Prior Sale Owner Records
$395,000Jul 2004 $6,5532025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

115 Sunnyside Ave

4 bd · 1.5 ba · 1,560 sqft · built 1938 · 0.076 acres

Last Sale Tax Bill Prior Sale Owner Records
$165,000Jun 1993 $7,2502025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

116 Sunnyside Ave

3 bd · 1 ba · 800 sqft · built 1968 · 0.103 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000Jan 2011 $5,9442025 —Sep 2006 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

118 Sunnyside Ave

3 bd · 1.5 ba · 1,755 sqft · built 1900 · 0.183 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2009 $7,5282025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Jun 2026

119 Sunnyside Ave

3 bd · 2.5 ba · 1,776 sqft · built 1940 · 0.077 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,1022025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

Property Records in Nearby Streets