Chesapeake City property records for 28 addresses on Winchester Way, Chesapeake, VA · Last verified October 2026
| Properties | 28 |
|---|---|
| Median Sale Price | $550,000 |
| Deeds and Mortgages on File | 53 |
| Median Price per Sqft | $180 |
| Owner Occupied | 93% |
| Median Annual Tax Bill | $6,333 |
| Median Year Built | 1990 |
| Median Ownership Tenure | 18 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
938 Winchester Way |
4 bd · 3 ba · 2,856 sqft built 1994 · 0.423 acres | $450,000 Apr 2020 | $6,361 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
942 Winchester Way |
4 bd · 3.5 ba · 3,071 sqft built 1994 · 0.423 acres | $210,500 Jun 1995 | $6,333 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
946 Winchester Way |
4 bd · 2.5 ba · 2,875 sqft built 1993 · 0.41 acres | $310,500 Oct 2013 | $6,047 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1000 Winchester Way |
4 bd · 2.5 ba · 2,916 sqft built 1989 · 0.35 acres | $211,000 Apr 2000 | $5,666 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1002 Winchester Way |
5 bd · 4 ba · 3,413 sqft built 1993 · 0.357 acres | $515,000 Oct 2006 | $6,471 2025 | Assessor + 5 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1004 Winchester Way |
4 bd · 2.5 ba · 3,014 sqft built 1989 · 0.442 acres | $590,000 Jan 2026 | $6,536 2025 | Assessor + 6 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1005 Winchester Way |
4 bd · 4 ba · 3,460 sqft built 1992 · 0.423 acres | $246,500 Feb 1997 | $6,751 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1008 Winchester Way |
4 bd · 2.5 ba · 2,729 sqft built 1988 · 0.45 acres | $5,957 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1009 Winchester Way |
4 bd · 3 ba · 2,836 sqft built 1988 · 0.512 acres | $496,000 Nov 2006 | $5,950 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1012 Winchester Way |
4 bd · 3.5 ba · 3,214 sqft built 1988 · 0.451 acres | $250,000 Jul 1999 | $6,454 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1013 Winchester Way |
5 bd · 3 ba · 3,048 sqft built 1988 · 0.367 acres | $6,204 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1016 Winchester Way |
4 bd · 2.5 ba · 2,475 sqft built 1989 · 0.455 acres | $169,000 May 1989 | $4,992 2024 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1017 Winchester Way |
4 bd · 2.5 ba · 2,378 sqft built 1989 · 0.362 acres | $549,900 May 2026 | $5,183 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1020 Winchester Way |
4 bd · 3 ba · 2,755 sqft built 1988 · 0.43 acres | $163,000 Feb 1989 | $5,886 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1021 Winchester Way |
5 bd · 4 ba · 3,345 sqft built 1992 · 0.35 acres | $589,900 Jun 2021 | $6,911 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1024 Winchester Way |
4 bd · 3 ba · 2,864 sqft built 1989 · 0.405 acres | $476,000 Aug 2007 | $5,989 2025 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1025 Winchester Way |
5 bd · 2.5 ba · 3,568 sqft built 1989 · 0.35 acres | — Sep 2016 | $6,573 2025 | Assessor + 9 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1028 Winchester Way |
4 bd · 2 ba · 2,409 sqft built 1990 · 0.38 acres | $435,000 Aug 2020 | $1,989 2020 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1029 Winchester Way |
5 bd · 4 ba · 3,171 sqft built 1989 · 0.35 acres | $550,000 Jun 2021 | $6,779 2025 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1033 Winchester Way |
5 bd · 4 ba · 3,151 sqft built 1990 · 0.344 acres | $465,500 May 2008 | $6,447 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1037 Winchester Way |
4 bd · 2.5 ba · 3,140 sqft built 1989 · 0.344 acres | $470,000 Sep 2019 | $6,757 2025 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1041 Winchester Way |
5 bd · 3 ba · 3,063 sqft built 1991 · 0.344 acres | $215,000 Mar 1999 | $6,042 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1042 Winchester Way |
221 sqft built 1754 · 0.046 acres | Assessor Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1045 Winchester Way |
4 bd · 2.5 ba · 2,362 sqft built 1990 · 0.344 acres | $569,000 Sep 2026 | $5,047 2025 | Assessor + 4 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1049 Winchester Way |
4 bd · 4 ba · 3,938 sqft built 1992 · 0.351 acres | $298,000 Dec 2001 | $7,002 2025 | Assessor + 3 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1104 Winchester Way |
4 bd · 3 ba · 3,095 sqft built 1991 · 0.376 acres | $180,300 Sep 1991 | $6,072 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1105 Winchester Way |
4 bd · 3.5 ba · 4,143 sqft built 1990 · 0.36 acres | $7,160 2025 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
1109 Winchester Way |
5 bd · 3 ba · 3,231 sqft built 1990 · 0.344 acres | $378,000 Feb 2013 | $6,366 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |