Middlesex County and Winchester Town property records for 20 addresses on Chester St, Winchester, MA · Last verified October 2026
| Properties | 20 |
|---|---|
| Median Sale Price | $1,100,000 |
| Deeds and Mortgages on File | 37 |
| Median Price per Sqft | $464 |
| Owner Occupied | 85% |
| Median Annual Tax Bill | $12,165 |
| Median Year Built | 1925 |
| Median Ownership Tenure | 9 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1 Chester St |
3 bd · 2 ba · 2,493 sqft built 1950 · 0.166 acres | $852,000 May 2017 | $12,165 2026 | Assessor + 9 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
10, #1 Chester St |
2 bd · 1 ba · 676 sqft built 1910 | $50,000 Apr 2019 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
10, #2 Chester St |
4 bd · 1 ba · 1,274 sqft built 1910 | $159,000 Jul 2011 | $2,347 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
14 Chester St |
3 bd · 1.5 ba · 1,280 sqft built 1891 · 0.117 acres | $365,000 Jul 2002 | $10,543 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15 Chester St |
4 bd · 1.5 ba · 2,371 sqft built 1942 · 0.248 acres | $1,270,000 Jun 2021 | $14,518 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
18 Chester St |
3 bd · 3.5 ba · 3,180 sqft built 1870 · 0.23 acres | $1,240,000 Oct 2018 | $17,191 2026 | Assessor + 7 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
19 Chester St |
3 bd · 1.5 ba · 1,696 sqft built 1991 · 0.149 acres | — Mar 2014 | $11,509 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21 Chester St |
3 bd · 2.5 ba · 1,811 sqft built 1890 · 0.382 acres | $288,000 Jun 1999 | $13,217 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
22 Chester St |
3 bd · 3.5 ba · 1,152 sqft built 1910 · 0.152 acres | $769,000 Apr 2023 | $13,822 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24 Chester St |
4 bd · 2.5 ba · 2,829 sqft built 1910 · 0.268 acres | $500,000 Dec 2008 | $13,211 2026 | Assessor + 4 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
31 Chester St |
4 bd · 4.5 ba · 2,914 sqft built 1957 · 0.441 acres | $845,000 Jun 2013 | $18,804 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
32 Chester St |
4 bd · 2.5 ba · 2,462 sqft built 1929 · 0.236 acres | $485,000 Feb 2013 | $13,596 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
36 Chester St |
5 bd · 3.5 ba · 3,445 sqft built 2020 · 0.218 acres | $1,599,900 Sep 2021 | $18,779 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
41 Chester St |
3 bd · 1.5 ba · 1,200 sqft built 1925 | $420,000 May 2018 | $5,833 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
43 Chester St |
2 bd · 1 ba · 1,400 sqft built 1925 | $6,760 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
43A Chester St |
4 bd · 2 ba · 1,706 sqft built 1963 · 0.351 acres | $785,000 Jul 2017 | $11,864 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
45 Chester St |
2 bd · 1 ba · 1,228 sqft built 1891 · 0.128 acres | $320,000 Dec 2000 | $9,315 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
55 Chester St |
10 bd · 4.5 ba · 2,994 sqft built 1880 · 0.208 acres | $12,718 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
73 Chester St |
3 bd · 1.5 ba · 1,736 sqft built 1976 · 0.124 acres | — Mar 2008 | $10,555 2026 | Assessor Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
74 Chester St |
3 bd · 2.5 ba · 1,880 sqft built 1978 · 0.127 acres | $1,100,000 Jun 2022 | $11,854 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |