Suffolk County and Brookhaven Town property records for 33 addresses on Winston Dr, Shirley, NY · Last verified October 2026
| Properties | 33 |
|---|---|
| Median Sale Price | $339,000 |
| Deeds and Mortgages on File | 24 |
| Median Price per Sqft | $227 |
| Owner Occupied | 85% |
| Median Annual Tax Bill | $7,812 |
| Median Year Built | 1974 |
| Median Ownership Tenure | 14 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
7 Winston Dr |
3 bd · 1 ba · 1,574 sqft built 2005 · 0.25 acres | $9,884 2024 | Assessor Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
8 Winston Dr |
2 bd · 1 ba · 996 sqft built 1940 · 0.31 acres | $2,594 2024 | Assessor Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
11 Winston Dr |
4 bd · 2 ba · 2,080 sqft built 1969 · 0.269 acres | $278,500 May 2018 | $8,867 2024 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
22 Winston Dr |
3 bd · 1 ba · 1,130 sqft built 1961 · 0.619 acres | $230,000 Aug 2014 | $8,330 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
23 Winston Dr |
4 bd · 1 ba · 2,112 sqft built 2001 · 0.5 acres | $207,000 Oct 2001 | $8,675 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
25 Winston Dr |
3 bd · 1 ba · 1,888 sqft built 1964 · 0.5 acres | $175,000 Feb 2012 | $7,460 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
29 Winston Dr |
3 bd · 1 ba · 1,579 sqft built 1950 · 0.589 acres | $246,000 Jul 2016 | $7,678 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
30 Winston Dr |
3 bd · 1 ba · 1,284 sqft built 1956 · 0.919 acres | $192,500 Nov 2001 | $8,985 2024 | Assessor Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
33 Winston Dr |
3 bd · 1 ba · 1,419 sqft built 1960 · 0.45 acres | $285,000 Sep 2003 | $5,886 2024 | Assessor Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
34 Winston Dr |
3 bd · 1 ba · 1,058 sqft built 1965 · 1.08 acres | $100,000 Jan 1997 | $6,653 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
35 Winston Dr |
0.63 acres | $10,555 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
39 Winston Dr |
4 bd · 1 ba · 1,730 sqft built 1974 · 0.369 acres | $58,000 Aug 2022 | $9,040 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
44 Winston Dr |
4 bd · 1 ba · 1,204 sqft built 1954 · 0.75 acres | $4,511 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
45 Winston Dr |
3 bd · 2 ba · 1,232 sqft built 1950 · 0.35 acres | $439,000 Jun 2025 | $8,250 2024 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
55 Winston Dr |
5 bd · 1 ba · 2,020 sqft built 1975 · 0.5 acres | $6,807 2024 | Assessor Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
56 Winston Dr |
4 bd · 1 ba · 2,067 sqft built 2002 · 0.5 acres | $262,000 Jul 2002 | $10,939 2024 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
57 Winston Dr |
3 bd · 1 ba · 1,336 sqft built 1987 · 0.5 acres | $8,284 2024 | Assessor + 1 Document Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
58 Winston Dr |
4 bd · 3 ba · 2,458 sqft built 2001 · 0.6 acres | $251,500 Sep 2001 | $8,226 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
59 Winston Dr |
5 bd · 2 ba · 1,196 sqft built 1950 · 0.6 acres | $500,000 Jun 2024 | $7,102 2024 | Assessor + 2 Documents Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
62 Winston Dr |
3 bd · 1 ba · 1,883 sqft built 1978 · 0.43 acres | $427,500 Jun 2023 | $3,503 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
65 Winston Dr |
3 bd · 1 ba · 1,056 sqft built 1988 · 0.3 acres | $85,000 Nov 1996 | $6,692 2024 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
70 Winston Dr |
4 bd · 1 ba · 2,159 sqft built 1997 · 0.55 acres | $145,000 Dec 1997 | $8,150 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
71 Winston Dr |
4 bd · 3 ba · 3,044 sqft built 1987 · 0.6 acres | $268,000 Jun 2003 | $8,330 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
73 Winston Dr |
3 bd · 1 ba · 1,008 sqft built 1973 · 0.25 acres | $280,000 Jun 2006 | $6,040 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
74 Winston Dr |
4 bd · 2 ba · 2,135 sqft built 1998 · 0.55 acres | $390,500 Mar 2006 | $11,131 2024 | Assessor + 1 Document Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
75 Winston Dr |
3 bd · 1 ba · 1,075 sqft built 1973 · 0.25 acres | $215,000 Sep 2017 | $6,910 2024 | Assessor + 1 Document Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
79 Winston Dr |
4 bd · 2 ba · 2,091 sqft built 2000 · 0.5 acres | $191,000 Dec 2000 | $5,886 2024 | Assessor Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
80 Winston Dr |
4 bd · 2 ba · 2,452 sqft built 1987 · 0.5 acres | $11,131 2024 | Assessor Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
83 Winston Dr |
5 bd · 3 ba · 2,083 sqft built 1996 · 0.6 acres | $255,000 Feb 2017 | $9,596 2024 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
84 Winston Dr |
3 bd · 1 ba · 1,222 sqft built 1988 · 0.589 acres | $280,100 Apr 2017 | $7,812 2024 | Assessor + 2 Documents Updated Aug 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
89 Winston Dr |
3 bd · 1 ba · 1,008 sqft built 1971 · 0.319 acres | $202,000 Sep 2020 | $7,678 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
93 Winston Dr |
3 bd · 1 ba · 1,008 sqft built 1971 · 0.35 acres | $4,996 2024 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
95 Winston Dr |
2 bd · 1 ba · 768 sqft built 1955 · 0.5 acres | $339,000 Aug 2019 | $7,678 2024 | Assessor + 2 Documents Updated Aug 2026 | 2 Owners on File Owner Occupied |