Suffolk County and Winthrop Town City property records for 28 addresses on Chester Ave, Winthrop, MA · Last verified October 2026
| Properties | 28 |
|---|---|
| Median Sale Price | $720,000 |
| Deeds and Mortgages on File | 47 |
| Median Price per Sqft | $426 |
| Owner Occupied | 93% |
| Median Annual Tax Bill | $6,876 |
| Median Year Built | 1900 |
| Median Ownership Tenure | 20 years |
Owner names and prior sale amounts shown locked below are available instantly with a free trial.
3 bd · 3 ba · 2,285 sqft · built 1940 · 0.098 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $560,000Dec 2022 | $9,4902026 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
5 bd · 2.5 ba · 1,788 sqft · built 1900 · 0.115 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $71,250Feb 2014 | $8,0102026 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
5 bd · 2 ba · 2,517 sqft · built 1900 · 0.108 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $170,000Jul 1995 | $8,7202026 | Owner on Record | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 2 ba · 1,682 sqft · built 1890 · 0.108 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $128,500Mar 1993 | $7,4702026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
2 bd · 3 ba · 2,040 sqft · built 1920 · 0.109 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $246,000Aug 1999 | $7,9832026 | Amount on Record Jun 1997 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
5 bd · 2 ba · 2,094 sqft · built 1912 · 0.108 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000Aug 2000 | $8,1542026 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
5 bd · 1.5 ba · 1,752 sqft · built 1900 · 0.109 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $518,000Sep 2006 | $8,5722026 | Amount on Record Jun 2003 | 2 Owners on Record Owner Occupied | AssessorUpdated Oct 2026 |
4 bd · 1.5 ba · 1,703 sqft · built 1900 · 0.108 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $200,000Jan 1999 | $7,0162026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 2 ba · 2,183 sqft · built 1900 · 0.109 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $233,000Jun 1999 | $7,8972026 | Amount on Record Sep 1992 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 1.5 ba · 1,874 sqft · built 1900 · 0.113 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,7032026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 1.5 ba · 1,837 sqft · built 1900 · 0.108 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $320,000Dec 2006 | $7,7202026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1.5 ba · 1,924 sqft · built 1900 · 0.104 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —May 2015 | $8,0292026 | Owner on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 1 ba · 1,627 sqft · built 1900 · 0.103 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $260,000Feb 2001 | $7,5512026 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
4 bd · 1.5 ba · 1,723 sqft · built 1910 · 0.109 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $435,000Sep 2015 | $8,0442026 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
4 bd · 1.5 ba · 1,958 sqft · built 1900 · 0.112 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $930,000Jan 2024 | $9,1072026 | Amount on Record Jul 2015 | Owner on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
3 bd · 2 ba · 1,971 sqft · built 1900 · 0.106 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,8242026 | Owner on Record | AssessorUpdated Oct 2026 |
3 bd · 1.5 ba · 1,184 sqft · built 1880 · 0.068 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $375,000May 2016 | $6,3452026 | Amount on Record May 2004 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 2 ba · 2,313 sqft · built 1900 · 0.099 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $7,7872026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 3.5 ba · 1,401 sqft · built 1900 · 0.147 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,275,000Dec 2019 | $7,7812026 | Amount on Record Oct 2005 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,599 sqft · built 1929 · 0.129 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| —Sep 2018 | $7,4582026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
4 bd · 1 ba · 1,916 sqft · built 1900 · 0.143 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $169,000Oct 1999 | $8,0072026 | 2 Owners on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1.5 ba · 1,584 sqft · built 1936 · 0.157 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $230,000May 2000 | $7,3182026 | 2 Owners on Record Owner Occupied | Assessor + 2 DocumentsUpdated Oct 2026 |
4 bd · 1 ba · 1,464 sqft · built 1900 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $182,500Jun 1987 | $7,3402026 | 2 Owners on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1 ba · 1,418 sqft · built 1936 · 0.091 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,9352026 | Owner on Record Owner Occupied | AssessorUpdated Oct 2026 |
3 bd · 1.5 ba · 1,689 sqft · built 1920 · 0.129 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $720,000Jan 2021 | $9,1432026 | Owner on Record Owner Occupied | Assessor + 1 DocumentUpdated Oct 2026 |
3 bd · 1 ba · 1,269 sqft · built 1930 · 0.091 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $6,8102026 | Owner on Record Owner Occupied | Assessor + 3 DocumentsUpdated Oct 2026 |
3 bd · 1 ba · 1,050 sqft · built 1900 · 0.114 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $640,000May 2025 | $6,6462026 | —Mar 2018 | Owner on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |
4 bd · 3.5 ba · 2,692 sqft · built 1900 · 0.1 acres
| Last Sale | Tax Bill | Prior Sale | Owner | Records |
|---|---|---|---|---|
| $1,060,000Aug 2025 | $9,0982026 | Amount on Record Nov 2012 | 2 Owners on Record Owner Occupied | Assessor + 4 DocumentsUpdated Oct 2026 |