Worcester County property records for 29 addresses on Winding Trail Dr, Ocean City, MD · Last verified October 2026
| Properties | 29 |
|---|---|
| Median Sale Price | $432,000 |
| Deeds and Mortgages on File | 37 |
| Median Price per Sqft | $154 |
| Owner Occupied | 86% |
| Median Annual Tax Bill | $4,152 |
| Median Year Built | 2004 |
| Median Ownership Tenure | 16 years |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9801 Winding Trail Dr |
2.5 ba · 1,983 sqft built 2004 · 0.252 acres | $122,000 Oct 2003 | $3,131 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9802 Winding Trail Dr |
3.5 ba · 3,070 sqft built 2004 · 0.261 acres | $410,000 Jun 2008 | $3,979 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9803 Winding Trail Dr |
2.5 ba · 3,189 sqft built 2006 · 0.968 acres | $445,000 Sep 2008 | $3,908 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9804 Winding Trail Dr |
3.5 ba · 3,348 sqft built 2003 · 0.243 acres | $425,000 Aug 2003 | $4,292 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9806 Winding Trail Dr |
2.5 ba · 3,387 sqft built 2003 · 0.243 acres | $64,900 Nov 2001 | $4,232 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9808 Winding Trail Dr |
3.5 ba · 2,435 sqft built 2004 · 0.227 acres | $375,000 Dec 2017 | $4,583 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9809 Winding Trail Dr |
2.5 ba · 2,970 sqft built 2008 · 1.53 acres | $225,000 May 2006 | $3,754 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9810 Winding Trail Dr |
0.239 acres | $145,000 Dec 2021 | $1,287 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9811 Winding Trail Dr |
3 ba · 2,502 sqft built 2006 · 0.558 acres | $325,000 May 2013 | $3,341 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9812 Winding Trail Dr |
3 ba · 3,491 sqft built 2021 · 0.237 acres | $129,500 Mar 2003 | $5,316 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9813 Winding Trail Dr |
2.5 ba · 3,336 sqft built 2003 · 0.315 acres | $392,500 Jul 2012 | $3,484 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9815 Winding Trail Dr |
3.5 ba · 3,125 sqft built 2015 · 0.253 acres | $121,000 Oct 2003 | $5,794 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9817 Winding Trail Dr |
4 ba · 3,336 sqft built 2019 · 0.275 acres | $415,000 Mar 2019 | $4,152 2026 | Assessor + 4 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9818 Winding Trail Dr |
3.5 ba · 3,315 sqft built 2004 · 0.237 acres | — Aug 2008 | $5,086 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9819 Winding Trail Dr |
3 ba · 2,780 sqft built 2003 · 0.399 acres | $299,700 Mar 2017 | $4,768 2026 | Assessor + 3 Documents Updated Oct 2026 | Owner on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9821 Winding Trail Dr |
2.5 ba · 2,878 sqft built 2003 · 0.399 acres | $49,900 Dec 2001 | $3,950 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9822 Winding Trail Dr |
2.5 ba · 2,377 sqft built 2002 · 0.256 acres | $59,900 Feb 2002 | $3,696 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9824 Winding Trail Dr |
2 ba · 2,166 sqft built 2002 · 0.263 acres | $345,000 Dec 2010 | $3,444 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9825 Winding Trail Dr |
2.5 ba · 2,343 sqft built 2017 · 0.231 acres | $75,000 Apr 2017 | $3,489 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9826 Winding Trail Dr |
3.5 ba · 3,032 sqft built 2002 · 0.249 acres | $420,000 Aug 2016 | $4,031 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9827 Winding Trail Dr |
2.5 ba · 3,020 sqft built 2009 · 0.23 acres | $650,000 Dec 2025 | $4,706 2026 | Assessor + 1 Document Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9828 Winding Trail Dr |
2.5 ba · 2,136 sqft built 2016 · 0.229 acres | $100,000 Jul 2015 | $3,701 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9829 Winding Trail Dr |
3.5 ba · 4,504 sqft built 2006 · 0.232 acres | $540,000 Jan 2022 | $5,953 2026 | Assessor + 3 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9830 Winding Trail Dr |
3 ba · 3,723 sqft built 2005 · 0.229 acres | $671,500 Nov 2005 | $4,574 2026 | Assessor Updated Oct 2026 | 2 Owners on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9831 Winding Trail Dr |
4.5 ba · 3,164 sqft built 2013 · 0.229 acres | $127,900 Mar 2004 | $5,608 2026 | Assessor Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9832 Winding Trail Dr |
2.5 ba · 2,848 sqft built 2005 · 0.229 acres | $432,000 Apr 2021 | $4,692 2026 | Assessor + 1 Document Updated Oct 2026 | 2 Owners on File |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9834 Winding Trail Dr |
2.5 ba · 3,399 sqft built 2004 · 0.271 acres | $550,000 Nov 2004 | $5,970 2026 | Assessor Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9835 Winding Trail Dr |
2 ba · 1,749 sqft built 2003 · 0.309 acres | $372,500 Mar 2020 | $3,034 2026 | Assessor + 5 Documents Updated Oct 2026 | Owner on File Owner Occupied |
| Address | Details | Last Sale | Tax Bill | Records | Owner |
|---|---|---|---|---|---|
9836 Winding Trail Dr |
2.5 ba · 2,710 sqft built 2003 · 0.247 acres | $670,000 Jul 2025 | $4,520 2026 | Assessor + 2 Documents Updated Oct 2026 | 2 Owners on File Owner Occupied |