Middlesex County and Lexington Town property records for 34 addresses on Winchester Dr, Lexington, MA · Last verified October 2026
| Properties | 34 |
|---|---|
| Median Sale Price | $3,350,000 |
| Deeds and Mortgages on File | 57 |
| Median Price per Sqft | $716 |
| Owner Occupied | 94% |
| Median Annual Tax Bill | $15,474 |
| Median Year Built | 1956 |
| Median Ownership Tenure | 16 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
3 Winchester Dr |
4 bd · 2.5 ba · 2,894 sqft built 2000 · 0.698 acres | $759,000 Oct 2000 | $24,226 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
5 Winchester Dr |
3 bd · 2.5 ba · 1,670 sqft built 1955 · 0.728 acres | $560,000 May 2006 | $13,049 2026 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
6 Winchester Dr |
4 bd · 3.5 ba · 1,598 sqft built 1955 · 0.698 acres | $660,000 Apr 2008 | $15,474 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7 Winchester Dr |
3 bd · 3 ba · 1,646 sqft built 1955 · 0.685 acres | $742,500 Sep 2016 | $14,095 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
8 Winchester Dr |
4 bd · 3.5 ba · 4,011 sqft built 1955 · 0.685 acres | $530,000 Apr 2002 | $23,487 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9 Winchester Dr |
4 bd · 1.5 ba · 1,885 sqft built 1955 · 0.738 acres | $14,970 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
10 Winchester Dr |
4 bd · 2.5 ba · 2,804 sqft built 2000 · 0.685 acres | $940,000 Jul 2006 | $23,044 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11 Winchester Dr |
3 bd · 2.5 ba · 1,944 sqft built 1955 · 0.685 acres | $680,100 Sep 2005 | $16,175 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
12 Winchester Dr |
3 bd · 1.5 ba · 1,248 sqft built 1955 · 0.685 acres | $40,500 Jun 1968 | $12,618 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
14 Winchester Dr |
5 bd · 4.5 ba · 1,848 sqft built 1955 · 0.758 acres | $720,000 Jan 2007 | $15,584 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
15 Winchester Dr |
3 bd · 2.5 ba · 1,512 sqft built 1955 · 0.685 acres | $930,000 Aug 2018 | $13,910 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
16 Winchester Dr |
6 bd · 6.5 ba · 4,957 sqft built 2024 · 0.748 acres | $3,550,000 Jul 2026 | $39,072 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
18 Winchester Dr |
4 bd · 3.5 ba · 1,568 sqft built 1956 · 0.768 acres | $1,250,000 Aug 2021 | $16,655 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
19 Winchester Dr |
3 bd · 2 ba · 1,604 sqft built 1955 · 0.758 acres | — Dec 2008 | $14,477 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
20 Winchester Dr |
4 bd · 3 ba · 1,984 sqft built 1956 · 0.685 acres | $530,000 Sep 2010 | $16,692 2026 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
21 Winchester Dr |
3 bd · 1.5 ba · 1,526 sqft built 1955 · 0.718 acres | $569,000 Dec 2007 | $13,775 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
22 Winchester Dr |
3 bd · 1.5 ba · 1,486 sqft built 1956 · 0.685 acres | $870,000 Aug 2020 | $14,095 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23 Winchester Dr |
3 bd · 2 ba · 1,587 sqft built 1956 · 0.708 acres | $1,260,000 Jan 2024 | $14,723 2026 | Assessor + 5 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
24 Winchester Dr |
6 bd · 6.5 ba · 5,589 sqft built 2023 · 0.685 acres | $3,450,000 Mar 2025 | $39,084 2026 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25 Winchester Dr |
3 bd · 3 ba · 2,963 sqft built 1954 · 0.685 acres | $19,204 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26 Winchester Dr |
3 bd · 3.5 ba · 2,896 sqft built 1956 · 0.685 acres | $359,900 Jun 1999 | $19,536 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27 Winchester Dr |
4 bd · 4.5 ba · 3,450 sqft built 2006 · 0.685 acres | $1,350,000 Jun 2015 | $24,558 2026 | Assessor + 5 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
28 Winchester Dr |
6 bd · 6.5 ba · 6,254 sqft built 2021 · 0.685 acres | $3,375,000 May 2023 | $40,623 2026 | Assessor + 5 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
29 Winchester Dr |
4 bd · 2.5 ba · 1,814 sqft built 1954 · 0.685 acres | — Feb 2015 | $18,551 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
30 Winchester Dr |
3 bd · 2.5 ba · 1,200 sqft built 1956 · 0.698 acres | $1,456,000 Jul 2026 | $14,760 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
31 Winchester Dr |
3 bd · 1.5 ba · 1,518 sqft built 1954 · 0.688 acres | $670,000 Dec 2013 | $14,144 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
32 Winchester Dr |
3 bd · 2.5 ba · 1,572 sqft built 1957 · 0.685 acres | $50,000 Jul 1973 | $13,935 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
33 Winchester Dr |
3 bd · 1.5 ba · 1,538 sqft built 1955 · 0.688 acres | $12,815 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
35 Winchester Dr |
3 bd · 3 ba · 1,419 sqft built 1955 · 0.685 acres | $282,500 Aug 1993 | $15,129 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
37 Winchester Dr |
7 bd · 5.5 ba · 3,611 sqft built 2023 · 0.688 acres | $3,625,000 Dec 2023 | $40,512 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
38 Winchester Dr |
3 bd · 2.5 ba · 1,493 sqft built 1956 · 0.685 acres | $550,750 Jul 2010 | $14,600 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
39 Winchester Dr |
3 bd · 1.5 ba · 1,488 sqft built 1955 · 0.685 acres | $358,200 Mar 2000 | $12,765 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
40 Winchester Dr |
6 bd · 6.5 ba · 5,109 sqft built 2023 · 0.778 acres | $3,350,000 Feb 2025 | $37,385 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
44 Winchester Dr |
2 bd · 1.5 ba · 1,551 sqft built 1965 · 0.685 acres | — Jul 2013 | $13,135 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |