Upland Rd, Winthrop, MA Property Records

Suffolk County and Winthrop Town City property records for 35 addresses on Upland Rd, Winthrop, MA · Last verified October 2026

Upland Rd Highlights

Properties 35
Median Sale Price $750,000
Deeds and Mortgages on File 38
Median Price per Sqft $517
Owner Occupied 77%
Median Annual Tax Bill $7,878
Median Year Built 1920
Median Ownership Tenure 15 years

Properties on Upland Rd

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

18 Upland Rd

8 bd · 2 ba · 3,505 sqft · built 1925 · 0.107 acres

Last Sale Tax Bill Prior Sale Owner Records
$215,000Oct 1990 $8,3312025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

22 Upland Rd

5 bd · 3 ba · 4,062 sqft · built 1900 · 0.089 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,175,000Apr 2026 $9,5842026 —Sep 2018 2 Owners on Record Assessor + 3 DocumentsUpdated Oct 2026

24 Upland Rd

6 bd · 3 ba · 3,701 sqft · built 1900 · 0.146 acres

Last Sale Tax Bill Prior Sale Owner Records
$495,000Oct 2009 $9,8362025 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Apr 2026

28 Upland Rd, #32

4 bd · 3 ba · 2,940 sqft · built 1920 · 0.178 acres

Last Sale Tax Bill Prior Sale Owner Records
$540,000Sep 2004 $8,4502025 2 Owners on Record AssessorUpdated Apr 2026

35 Upland Rd

2 bd · 2 ba · 1,960 sqft · built 1955 · 0.239 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,0042025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

40 Upland Rd

7 bd · 6 ba · 4,234 sqft · built 1965 · 0.175 acres

Last Sale Tax Bill Prior Sale Owner Records
$465,000Nov 2016 $11,7842025 Owner on Record Assessor + 3 DocumentsUpdated Apr 2026

41 Upland Rd

5 bd · 2.5 ba · 2,741 sqft · built 1902 · 0.217 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,6412025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

46 Upland Rd

0.099 acres

Last Sale Tax Bill Prior Sale Owner Records
$6832025 Owner on Record AssessorUpdated Apr 2026

52 Upland Rd

3 bd · 1.5 ba · 1,656 sqft · built 1938 · 0.094 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2004 $6,6872025 Amount on Record May 1990 Owner on Record Owner Occupied AssessorUpdated Aug 2026

53 Upland Rd

3 bd · 2 ba · 1,516 sqft · built 1961 · 0.183 acres

Last Sale Tax Bill Prior Sale Owner Records
$785,000Oct 2024 $8,6442025 Amount on Record Jul 1992 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

57 Upland Rd

2 bd · 2 ba · 1,652 sqft · built 1945 · 0.171 acres

Last Sale Tax Bill Prior Sale Owner Records
—Feb 2014 $7,0672025 Amount on Record Nov 1988 Owner on Record Owner Occupied AssessorUpdated Apr 2026

62 Upland Rd

7 bd · 5 ba · 5,437 sqft · built 1912 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$800,000Jan 2004 $13,8672025 2 Owners on Record Owner Occupied AssessorUpdated Apr 2026

63 Upland Rd

3 bd · 1.5 ba · 1,358 sqft · built 1948 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$965,000May 2024 $9,3752025 Amount on Record Oct 2016 Owner on Record Owner Occupied Assessor + 5 DocumentsUpdated Apr 2026

69 Upland Rd

3 bd · 1.5 ba · 2,249 sqft · built 1950 · 0.133 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2011 $8,4032025 Amount on Record Nov 1994 Owner on Record Owner Occupied AssessorUpdated Apr 2026

75 Upland Rd

3 bd · 3 ba · 1,339 sqft · built 1930 · 0.194 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2005 $7,6052025 2 Owners on Record Owner Occupied AssessorUpdated Jul 2026

80 Upland Rd

3 bd · 2.5 ba · 2,102 sqft · built 1920 · 0.203 acres

Last Sale Tax Bill Prior Sale Owner Records
$560,000Jan 2020 $8,9882026 Amount on Record Jun 1988 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

81 Upland Rd, #83

5 bd · 2 ba · 2,604 sqft · built 1952 · 0.389 acres

Last Sale Tax Bill Prior Sale Owner Records
$510,000Sep 2010 $10,9722025 Amount on Record Dec 2009 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

86 Upland Rd, #92

5 bd · 3 ba · 2,876 sqft · built 1920 · 0.159 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,4262025 Owner on Record AssessorUpdated Apr 2026

87 Upland Rd

4 bd · 3 ba · 1,953 sqft · built 1920 · 0.139 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8242025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

89R Upland Rd

3 bd · 1 ba · 964 sqft · built 1930 · 0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,325,000Sep 2026 $7,6172025 Amount on Record Oct 2023 Owner on Record Assessor + 3 DocumentsUpdated Oct 2026

94 Upland Rd

3 bd · 2.5 ba · 1,494 sqft · built 1977 · 0.123 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,6492025 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

95 Upland Rd

3 bd · 1 ba · 1,290 sqft · built 1930 · 0.119 acres

Last Sale Tax Bill Prior Sale Owner Records
$7,8192025 Owner on Record Owner Occupied AssessorUpdated Jul 2026

96 Upland Rd

2 bd · 2.5 ba · 1,021 sqft · built 1916 · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$590,000Jun 2021 $6,4912026 Amount on Record Nov 2018 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

98 Upland Rd

2 bd · 1 ba · 690 sqft · built 1916 · 0.055 acres

Last Sale Tax Bill Prior Sale Owner Records
$190,000Jun 2007 $4,3132025 Amount on Record Feb 2007 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

100 Upland Rd

3 bd · 1.5 ba · 1,424 sqft · built 1920 · 0.09 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,5772025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

101 Upland Rd

6 bd · 2 ba · 2,206 sqft · built 1900 · 0.193 acres

Last Sale Tax Bill Prior Sale Owner Records
$60,000Mar 1999 $8,4672025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

103 Upland Rd

3 bd · 2 ba · 1,050 sqft · built 1900 · 0.077 acres

Last Sale Tax Bill Prior Sale Owner Records
$329,000Aug 2007 $7,0152026 Amount on Record Oct 1997 2 Owners on Record Owner Occupied AssessorUpdated Oct 2026

105 Upland Rd

5 bd · 3 ba · 2,553 sqft · built 1800 · 0.12 acres

Last Sale Tax Bill Prior Sale Owner Records
$9,5742025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

106 Upland Rd

4 bd · 4 ba · 3,014 sqft · built 1895 · 0.101 acres

Last Sale Tax Bill Prior Sale Owner Records
$800,000Sep 2021 $9,0412026 Amount on Record Jul 1999 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

113 Upland Rd

2 bd · 1 ba · 1,449 sqft · built 1957 · 0.098 acres

Last Sale Tax Bill Prior Sale Owner Records
$100,000Sep 1994 $7,8962025 Amount on Record May 1991 Owner on Record Owner Occupied AssessorUpdated Apr 2026

115 Upland Rd

2 bd · 1.5 ba · 1,260 sqft · built 2009 · 0.077 acres

Last Sale Tax Bill Prior Sale Owner Records
$375,000Aug 2004 $8,1552025 —Oct 2003 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

117 Upland Rd

2 bd · 2.5 ba · 1,601 sqft · built 1910 · 0.066 acres

Last Sale Tax Bill Prior Sale Owner Records
$380,000Aug 2013 $7,8782025 Amount on Record Oct 2002 Owner on Record AssessorUpdated Apr 2026

119 Upland Rd

2 bd · 2 ba · 1,712 sqft · built 1920 · 0.075 acres

Last Sale Tax Bill Prior Sale Owner Records
$665,000Mar 2023 $7,7802025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

121 Upland Rd

2 bd · 1.5 ba · 1,140 sqft · built 1900 · 0.025 acres

Last Sale Tax Bill Prior Sale Owner Records
$332,900Oct 2004 $5,8582025 Amount on Record Oct 1997 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Apr 2026

123 Upland Rd

2 bd · 1.5 ba · 1,047 sqft · built 1935 · 0.023 acres

Last Sale Tax Bill Prior Sale Owner Records
$720,000Jun 2022 $7,8042026 Amount on Record Apr 2021 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

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