Suffolk County and Winthrop Town City property records for 35 addresses on Highland Ave, Winthrop, MA · Last verified October 2026
| Properties | 39 |
|---|---|
| Median Sale Price | $562,500 |
| Deeds and Mortgages on File | 45 |
| Median Price per Sqft | $316 |
| Owner Occupied | 72% |
| Median Annual Tax Bill | $7,553 |
| Median Year Built | 1910 |
| Median Ownership Tenure | 16 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 2 ba · 2,672 sqft · built 1910 · 0.163 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $250,000Jun 1998 | $8,2642025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
6 bd · 3 ba · 2,944 sqft · built 2000 · 0.154 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,9992025 | Owner on Record | Assessor + 1 DocumentUpdated Aug 2026 |
2 bd · 1 ba · 1,086 sqft · built 1921 · 0.161 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $281,000May 2010 | $5,8202025 | Amount on Record Sep 1994 | 2 Owners on Record Owner Occupied | AssessorUpdated Apr 2026 |
4 bd · 2 ba · 2,772 sqft · built 1890 · 0.197 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $355,000Sep 2008 | $8,5712025 | Owner on Record | AssessorUpdated Apr 2026 |
4 bd · 2 ba · 1,972 sqft · built 1949 · 0.172 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000Jun 1998 | $8,3322025 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
3 bd · 2.5 ba · 1,126 sqft · built 1958 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $369,900May 2004 | $6,3852025 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
9 bd · 4 ba · 3,903 sqft · built 1900 · 0.131 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,325,000Aug 2025 | $11,2942026 | —Jun 2016 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
3 bd · 1 ba · 1,728 sqft · built 1920 · 0.057 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,2382025 | 2 Owners on Record Owner Occupied | AssessorUpdated Aug 2026 |
4 bd · 2.5 ba · 1,853 sqft · built 1904 · 0.239 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $178,000Oct 1997 | $7,8702025 | Amount on Record Aug 1995 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
6 bd · 3 ba · 2,696 sqft · built 1892 · 0.115 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $560,000Jul 2004 | $9,6142025 | Amount on Record Jun 2000 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 2 ba · 1,676 sqft · built 1910 · 0.052 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $470,000Mar 2018 | $7,9602026 | —Feb 2018 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
5 bd · 2.5 ba · 2,845 sqft · built 1889 · 0.133 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $755,000Feb 2021 | $10,3712026 | —Aug 2012 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1 ba · 1,701 sqft · built 1860 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,8252025 | Owner on Record | AssessorUpdated Apr 2026 |
5 bd · 4 ba · 3,748 sqft · built 1900 · 0.132 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $410,000May 2009 | $9,2422025 | Owner on Record | AssessorUpdated Apr 2026 |
0.137 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $4,0632025 | Owner on Record | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,996 sqft · built 1994 · 0.16 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $75,000Feb 1994 | $7,9272025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
5 bd · 2 ba · 3,531 sqft · built 1880 · 0.183 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $13,9732025 | Owner on Record | Assessor + 4 DocumentsUpdated Aug 2026 |
5 bd · 1.5 ba · 2,716 sqft · built 1882 · 0.185 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Jun 2017 | $8,8792025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,323 sqft · built 1965 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,4282025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
3 bd · 2.5 ba · 1,644 sqft · built 1965 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $510,000Sep 2018 | $7,9342026 | Amount on Record May 2013 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
3 units · Built 1902 · 1,200 sq ft
| Last Sale | Median Tax Bill | Median Sale | ||
|---|---|---|---|---|
| $390,000Oct 2019 | $3,9152025 | $305,0003 units |
4 bd · 2 ba · 2,047 sqft · built 1910 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Dec 2015 | $6,8982025 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Apr 2026 |
5 bd · 2 ba · 2,136 sqft · built 1890 · 0.191 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $372,250Jun 2012 | $7,5532025 | Amount on Record Sep 2004 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 1.5 ba · 1,607 sqft · built 1910 · 0.126 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $562,500Aug 2020 | $7,9912026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
5 bd · 3 ba · 3,122 sqft · built 1910 · 0.116 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $510,000Sep 2006 | $7,9342025 | Owner on Record | Assessor + 3 DocumentsUpdated Apr 2026 |
0.103 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $243,000Oct 1997 | $1972025 | Owner on Record | Assessor + 1 DocumentUpdated Apr 2026 |
3 units · Built 1910 · 1,210 sq ft
| Last Sale | Median Tax Bill | Median Sale | ||
|---|---|---|---|---|
| $490,000May 2021 | $5,2832025 | $360,0003 units |
4 bd · 2.5 ba · 3,085 sqft · built 1925 · 0.103 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $10,0892026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
5 bd · 2 ba · 3,571 sqft · built 1900 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $8,5662025 | Owner on Record Owner Occupied | AssessorUpdated Apr 2026 |
3 bd · 1.5 ba · 1,840 sqft · built 1928 · 0.107 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $186,250Jan 1992 | $6,8572025 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
6 bd · 3 ba · 4,102 sqft · built 1906 · 0.128 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,300,000Jun 2025 | $10,6852025 | Amount on Record Sep 2009 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,585 sqft · built 1920 · 0.126 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,0112025 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Apr 2026 |
5 bd · 2 ba · 3,046 sqft · built 1954 · 0.111 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000Aug 1998 | $9,5052026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
8 bd · 4 ba · 3,516 sqft · built 1900 · 0.106 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $13,228Jan 2019 | $11,7242025 | —Feb 2013 | Owner on Record | Assessor + 2 DocumentsUpdated Jul 2026 |
9 bd · 5 ba · 3,542 sqft · built 1900 · 0.111 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $12,0042025 | Owner on Record | Assessor + 2 DocumentsUpdated Apr 2026 |