Wicomico County property records for 49 addresses on Crooked Oak Ln, Hebron, MD · Last verified October 2026
| Properties | 49 |
|---|---|
| Median Sale Price | $235,000 |
| Deeds and Mortgages on File | 58 |
| Median Price per Sqft | $182 |
| Owner Occupied | 84% |
| Median Annual Tax Bill | $1,896 |
| Median Year Built | 1988 |
| Median Ownership Tenure | 15 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26626 Crooked Oak Ln |
2 ba · 1,560 sqft built 1989 · 1.21 acres | $294,000 Aug 2024 | $1,896 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26654 Crooked Oak Ln |
1 ba · 912 sqft built 1995 · 1.21 acres | $132,000 Mar 2018 | $1,317 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26662 Crooked Oak Ln |
1 ba · 912 sqft built 1994 · 1.08 acres | $98,000 May 2011 | $1,194 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26672 Crooked Oak Ln |
1 ba · 952 sqft built 1977 · 2.28 acres | $70,000 Jan 2004 | $968 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26675 Crooked Oak Ln |
2.5 ba · 2,437 sqft built 2023 · 31.7 acres | $114,000 Mar 2018 | $3,674 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26690 Crooked Oak Ln |
1 ba · 1,092 sqft built 1972 · 1.93 acres | $70,000 Sep 2001 | $1,763 2025 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26745 Crooked Oak Ln |
2.5 ba · 2,496 sqft built 2018 · 5.61 acres | $389,900 Mar 2021 | $3,428 2025 | Assessor + 5 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26751 Crooked Oak Ln |
4.5 ba · 4,264 sqft built 2019 · 13.1 acres | $65,000 May 2011 | $6,416 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26757 Crooked Oak Ln |
2.5 ba · 2,535 sqft built 2013 · 6.11 acres | $380,000 Aug 2017 | $3,854 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26760 Crooked Oak Ln |
2 ba · 1,792 sqft built 1995 · 4.18 acres | $1,878 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26788 Crooked Oak Ln |
2 ba · 1,756 sqft built 1973 · 1.01 acres | $13,000 Jun 1989 | $1,605 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26804 Crooked Oak Ln |
3 ba · 1,456 sqft built 1989 · 11.6 acres | $155,000 Aug 1998 | $2,912 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26815 Crooked Oak Ln |
2 ba · 2,048 sqft built 2018 · 6.01 acres | $67,000 Jun 2016 | $3,053 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26831 Crooked Oak Ln |
3.5 ba · 4,018 sqft built 2019 · 12 acres | $65,000 Sep 2014 | $5,376 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26849 Crooked Oak Ln |
2.5 ba · 2,402 sqft built 2020 · 6.31 acres | $70,000 Nov 2012 | $4,188 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26852 Crooked Oak Ln |
5 ba · 3,698 sqft built 1900 · 1.11 acres | $2,311 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26903 Crooked Oak Ln |
3.5 ba · 5,439 sqft built 2019 · 12.2 acres | $695,000 Mar 2022 | $6,334 2025 | Assessor + 4 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
26907 Crooked Oak Ln |
2 ba · 2,293 sqft built 2017 · 6.85 acres | $69,500 May 2011 | $3,651 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27004 Crooked Oak Ln |
1.5 ba · 1,850 sqft built 1964 · 1 acre | $60 2025 | Assessor + 1 Document Updated Aug 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27005 Crooked Oak Ln |
18.3 acres | $136,500 Oct 2008 | $83 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27050 Crooked Oak Ln |
3 ba · 2,318 sqft built 1993 · 1.5 acres | $20,000 Jun 1993 | $2,574 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27069 Crooked Oak Ln |
1.5 ba · 1,248 sqft built 1975 · 0.46 acres | $174,000 Nov 2020 | $1,729 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27070 Crooked Oak Ln |
2 ba · 1,620 sqft built 1981 · 1.65 acres | $97,723 Dec 1995 | $1,831 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27083 Crooked Oak Ln |
1 ba · 1,008 sqft built 1972 · 0.467 acres | $72,000 Aug 1997 | $1,223 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27084 Crooked Oak Ln |
2.5 ba · 2,332 sqft built 1988 · 1.21 acres | $114,500 Jun 1999 | $2,382 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27091 Crooked Oak Ln |
2 ba · 1,404 sqft built 1992 · 1.21 acres | $92,000 Apr 1994 | $1,995 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27098 Crooked Oak Ln |
2.5 ba · 1,800 sqft built 1988 · 1 acre | $106,000 Sep 1996 | $2,116 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27103 Crooked Oak Ln |
1 ba · 888 sqft built 1962 · 1.81 acres | — Jul 2003 | $1,160 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27104 Crooked Oak Ln |
2.5 ba · 1,664 sqft built 1988 · 1.2 acres | $89,000 Oct 1988 | $2,242 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27121 Crooked Oak Ln |
2 ba · 1,224 sqft built 1994 · 0.866 acres | $247,000 Sep 2024 | $1,733 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27140 Crooked Oak Ln |
2.5 ba · 2,612 sqft built 1988 · 1 acre | — Jan 2011 | $2,586 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27152 Crooked Oak Ln |
2.5 ba · 1,656 sqft built 1988 · 1.01 acres | $235,000 Nov 2020 | $2,084 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27164 Crooked Oak Ln |
2 ba · 1,946 sqft built 1920 · 9.36 acres | $112,500 Feb 1987 | $1,753 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27169 Crooked Oak Ln |
2.5 ba · 2,256 sqft built 1974 · 0.492 acres | $39,000 Feb 1978 | $2,185 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27174 Crooked Oak Ln |
6.65 acres | $80,000 Mar 1985 | Assessor Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27175 Crooked Oak Ln |
2 ba · 1,779 sqft built 1977 · 0.46 acres | $135,000 Aug 2012 | $1,907 2025 | Assessor Updated Sep 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27185 Crooked Oak Ln |
1.5 ba · 1,488 sqft built 1974 · 0.461 acres | — Jan 2003 | $1,567 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27201 Crooked Oak Ln |
2 ba · 1,432 sqft built 1985 · 0.461 acres | $50,000 May 2025 | $1,704 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27213 Crooked Oak Ln |
1.5 ba · 924 sqft built 1973 · 0.461 acres | $300,000 Jul 2024 | $1,629 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27219 Crooked Oak Ln |
2 ba · 1,140 sqft built 1998 · 0.461 acres | $215,000 May 2021 | $1,598 2025 | Assessor + 3 Documents Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27237 Crooked Oak Ln |
2.5 ba · 1,580 sqft built 1979 · 0.459 acres | $75,000 Nov 2025 | $1,866 2025 | Assessor + 2 Documents Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27247 Crooked Oak Ln |
1 ba · 1,068 sqft built 1964 · 0.459 acres | $195,000 Apr 2022 | $1,352 2025 | Assessor + 1 Document Updated Aug 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27251 Crooked Oak Ln |
2 ba · 1,736 sqft built 1976 · 2.46 acres | $200,000 Jun 2022 | $1,901 2025 | Assessor Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27252 Crooked Oak Ln |
1 ba · 1,025 sqft built 1968 · 0.459 acres | $212,000 May 2022 | $1,384 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27295 Crooked Oak Ln |
2.5 ba · 2,629 sqft built 1988 · 12.2 acres | $600,000 Jun 2007 | $5,560 2025 | Assessor + 2 Documents Updated Sep 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27300 Crooked Oak Ln |
1 ba · 1,016 sqft built 1900 · 70.4 acres | — Jun 2006 | $968 2025 | Assessor + 2 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27304 Crooked Oak Ln |
1.5 ba · 2,056 sqft built 1925 · 29.5 acres | — Oct 1995 | $1,289 2025 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27382 Crooked Oak Ln |
58.8 acres | $180,000 Mar 2017 | $1,242 2025 | Assessor + 1 Document Updated Sep 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
27534 Crooked Oak Ln |
4 ba · 4,412 sqft built 1959 · 5.61 acres | $1,234,500 Sep 2025 | $8,456 2025 | Assessor + 1 Document Updated Sep 2026 | 2 Owners on File Owner Occupied |