Pearl Ave, Winthrop, MA Property Records

Suffolk County and Winthrop Town City property records for 21 addresses on Pearl Ave, Winthrop, MA · Last verified October 2026

Pearl Ave Highlights

Properties 27
Median Sale Price $536,000
Deeds and Mortgages on File 50
Median Price per Sqft $418
Owner Occupied 67%
Median Annual Tax Bill $6,251
Median Year Built 1900
Median Ownership Tenure 9 years

Properties on Pearl Ave

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

3 Pearl Ave

2 bd · 1 ba · 831 sqft · built 1900

Last Sale Tax Bill Prior Sale Owner Records
$360,000May 2021 $4,1342025 Amount on Record Jun 2016 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Sep 2026

3 Pearl Ave, Apt 2

2 bd · 1 ba · 812 sqft · built 1900

Last Sale Tax Bill Prior Sale Owner Records
$294,900May 2016 $4,0702025 Owner on Record Owner Occupied AssessorUpdated Apr 2026

5 Pearl Ave

3 units · Built 1900 · 812 sq ft

Last Sale Median Tax Bill Median Sale    
$440,000Aug 2025 $4,2492025 $415,0003 units    

11 Pearl Ave

9 bd · 3 ba · 4,032 sqft · built 1890 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,107,000May 2026 Amount on Record Jul 1998 Owner on Record Assessor + 1 DocumentUpdated Oct 2026

15 Pearl Ave

2 bd · 2 ba · 2,011 sqft · built 1925 · 0.091 acres

Last Sale Tax Bill Prior Sale Owner Records
$140,000Aug 1990 $7,7122026 Owner on Record Owner Occupied AssessorUpdated Oct 2026

16 Pearl Ave

4 bd · 2.5 ba · 2,428 sqft · built 1910 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$381,000Jun 2016 $7,9082026 Amount on Record Apr 2004 2 Owners on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

19 Pearl Ave, #21

4 bd · 2 ba · 2,284 sqft · built 1920 · 0.091 acres

Last Sale Tax Bill Prior Sale Owner Records
$655,000Mar 2018 $8,3002025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Jul 2026

20 Pearl Ave

2 bd · 2 ba · 1,195 sqft · built 1890 · 0.057 acres

Last Sale Tax Bill Prior Sale Owner Records
$156,000Sep 2008 $6,2432026 Amount on Record Jul 1994 Owner on Record Owner Occupied AssessorUpdated Oct 2026

22 Pearl Ave

4 bd · 1.5 ba · 1,395 sqft · built 1920 · 0.057 acres

Last Sale Tax Bill Prior Sale Owner Records
$235,000May 2008 $6,4142026 Amount on Record Aug 2001 Owner on Record AssessorUpdated Oct 2026

25 Pearl Ave

3 bd · 2 ba · 1,632 sqft · built 2006 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Jan 2009 $7,4832026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

28 Pearl Ave

3 units · Built 1900 · 1,280 sq ft

Last Sale Median Tax Bill Median Sale    
$536,000Jan 2026 $5,2102025 $530,0003 units    

31 Pearl Ave

4 bd · 2 ba · 2,808 sqft · built 1900 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$850,000Dec 2022 $9,2032026 Amount on Record Oct 1993 2 Owners on Record Assessor + 2 DocumentsUpdated Oct 2026

32 Pearl Ave

3 bd · 2 ba · 1,362 sqft · built 1900 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$699,000Dec 2025 $7,1912026 Amount on Record Nov 2019 2 Owners on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

35 Pearl Ave

5 bd · 3 ba · 1,924 sqft · built 1950 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$6,6382025 Owner on Record Assessor + 1 DocumentUpdated Aug 2026

36 Pearl Ave

5 bd · 2.5 ba · 2,108 sqft · built 1910 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$550,000May 2020 $7,7162026 Amount on Record Jan 2015 Owner on Record Owner Occupied Assessor + 4 DocumentsUpdated Oct 2026

39 Pearl Ave, #41

5 bd · 3 ba · 4,212 sqft · built 1900 · 0.114 acres

Last Sale Tax Bill Prior Sale Owner Records
$740,000Oct 2017 $11,1742025 Amount on Record Mar 2005 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Sep 2026

42 Pearl Ave

5 bd · 3 ba · 2,628 sqft · built 1900 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$8,3552026 Owner on Record Owner Occupied Assessor + 3 DocumentsUpdated Oct 2026

45 Pearl Ave

3 units · Built 1925 · 1,115 sq ft

Last Sale Median Tax Bill Median Sale    
$435,000May 2022 $4,4732025 $279,9003 units    

46 Pearl Ave

4 bd · 2 ba · 1,953 sqft · built 1900 · 0.11 acres

Last Sale Tax Bill Prior Sale Owner Records
$290,000Sep 2015 $8,2682026 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Oct 2026

49 Pearl Ave

5 bd · 3 ba · 3,985 sqft · built 1925 · 0.115 acres

Last Sale Tax Bill Prior Sale Owner Records
$200,000Aug 1998 $9,7282025 Owner on Record Owner Occupied Assessor + 2 DocumentsUpdated Apr 2026

50 Pearl Ave

8 bd · 6 ba · 4,379 sqft · built 1920 · 0.123 acres

Last Sale Tax Bill Prior Sale Owner Records
$450,000May 2001 $12,5062026 2 Owners on Record Assessor + 1 DocumentUpdated Oct 2026

Property Records in Nearby Streets