Windy Hill Rd, Trappe, MD Property Records

Talbot County property records for 31 addresses on Windy Hill Rd, Trappe, MD · Last verified August 2026

Windy Hill Rd Highlights

Properties 31
Median Sale Price $460,000
Deeds and Mortgages on File 26
Median Price per Sqft $153
Owner Occupied 81%
Median Annual Tax Bill $951
Median Year Built 1972
Median Ownership Tenure 25 years

Properties on Windy Hill Rd

Owner names and prior sale amounts shown locked below are available instantly with a free trial.

3750 Windy Hill Rd

2 ba · 1,966 sqft · built 1997 · 582 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,250,000Jun 2026 $4,3812025 Amount on Record May 2026 1 Name on Record Owner Occupied Assessor + 7 DocumentsUpdated Aug 2026

3871 Windy Hill Rd

1 ba · 1,600 sqft · built 1960 · 6 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,6202025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

3878 Windy Hill Rd

2 ba · 1,703 sqft · built 1965 · 92.5 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,4652025 2 Names on Record AssessorUpdated Aug 2026

4102 Windy Hill Rd

2 ba · 1,848 sqft · built 1972 · 2.96 acres

Last Sale Tax Bill Prior Sale Owner Records
$325,000Jun 2018 $2,8262025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

4169 Windy Hill Rd

105 acres

Last Sale Tax Bill Prior Sale Owner Records
$790,000Feb 2022 $8682025 —Oct 2003 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4239 Windy Hill Rd

1 ba · 1,890 sqft · built 1940 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Jun 1990 $7462025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

4286 Windy Hill Rd

1 ba · 1,152 sqft · built 1900 · 116 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,570,600Oct 2013 $1,0312025 Amount on Record Jul 2003 1 Name on Record AssessorUpdated Aug 2026

4347 Windy Hill Rd

2 ba · 1,680 sqft · built 2007 · 1.53 acres

Last Sale Tax Bill Prior Sale Owner Records
$120,000Mar 2006 $1,8522025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4357 Windy Hill Rd

2 ba · 1,636 sqft · built 1989 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$5642025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4393 Windy Hill Rd

1 ba · 760 sqft · built 1935 · 1 acres

Last Sale Tax Bill Prior Sale Owner Records
$163,500May 2006 $1,1162025 Amount on Record Sep 2001 2 Names on Record AssessorUpdated Aug 2026

4411 Windy Hill Rd

1 ba · 1,024 sqft · built 1954 · 2.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$55,000Oct 1996 $6922025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4423 Windy Hill Rd

1 ba · 1,472 sqft · built 1967 · 0.981 acres

Last Sale Tax Bill Prior Sale Owner Records
$15,000Mar 1999 $3902025 Amount on Record Sep 1998 1 Name on Record AssessorUpdated Aug 2026

4451 Windy Hill Rd

1 ba · 788 sqft · built 1954 · 0.859 acres

Last Sale Tax Bill Prior Sale Owner Records
$4602025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4457 Windy Hill Rd

1 ba · 1,634 sqft · built 1900 · 0.254 acres

Last Sale Tax Bill Prior Sale Owner Records
$54,500Oct 1988 $6292025 Amount on Record Jul 1986 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4504 Windy Hill Rd

2 ba · 1,538 sqft · built 1995 · 0.874 acres

Last Sale Tax Bill Prior Sale Owner Records
$164,835Apr 2022 $1,6232025 Amount on Record Jul 2012 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4510 Windy Hill Rd

2 ba · 924 sqft · built 1996 · 0.329 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000Jan 2018 $4772025 —Oct 2014 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4520 Windy Hill Rd

3 ba · 2,664 sqft · built 1994 · 3.21 acres

Last Sale Tax Bill Prior Sale Owner Records
$109,500Dec 2016 $2,7512025 Amount on Record Nov 2007 1 Name on Record AssessorUpdated Aug 2026

4529 Windy Hill Rd

1 ba · 1,394 sqft · built 1950 · 0.676 acres

Last Sale Tax Bill Prior Sale Owner Records
$30,000May 1984 $5522025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4552 Windy Hill Rd

1 ba · 924 sqft · built 1975 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$40,000Nov 1999 $6112025 Amount on Record May 1993 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4680 Windy Hill Rd

4.5 ba · 4,900 sqft · built 2024 · 126 acres

Last Sale Tax Bill Prior Sale Owner Records
$750,000Feb 2022 $10,3422025 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

4701 Windy Hill Rd

1 ba · 960 sqft · built 1974 · 177 acres

Last Sale Tax Bill Prior Sale Owner Records
—Nov 2007 $2,6712025 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

4703 Windy Hill Rd

2 ba · 2,584 sqft · built 1991 · 3 acres

Last Sale Tax Bill Prior Sale Owner Records
$12,300Dec 1986 $2,0802025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4736 Windy Hill Rd

1.5 ba · 1,782 sqft · built 1995 · 14.6 acres

Last Sale Tax Bill Prior Sale Owner Records
$151,000Feb 2000 $1,2652025 Amount on Record Apr 1995 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

4756 Windy Hill Rd

1.5 ba · 2,226 sqft · built 1900 · 3 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000May 2026 $1,5662025 Amount on Record May 2002 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4780 Windy Hill Rd

2 ba · 1,392 sqft · built 1984 · 2.7 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jan 1984 $8252025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4814 Windy Hill Rd

1 ba · 1,040 sqft · built 1970 · 0.697 acres

Last Sale Tax Bill Prior Sale Owner Records
—Mar 2001 $9512025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4820 Windy Hill Rd

1 ba · 1,020 sqft · built 1970 · 0.65 acres

Last Sale Tax Bill Prior Sale Owner Records
$22,000Jan 1999 $3442025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4830 Windy Hill Rd

2 ba · 1,483 sqft · built 1992 · 0.75 acres

Last Sale Tax Bill Prior Sale Owner Records
$5,500Jan 1985 $8822025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4860 Windy Hill Rd

1 ba · 1,916 sqft · built 1900 · 1.4 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Jun 1988 $7022025 Amount on Record Mar 1986 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

4878 Windy Hill Rd

1 ba · 1,356 sqft · built 1900 · 0.894 acres

Last Sale Tax Bill Prior Sale Owner Records
$72,500Apr 1997 $5852025 Amount on Record Jan 1990 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

4916 Windy Hill Rd

2.5 ba · 2,228 sqft · built 2016 · 0.615 acres

Last Sale Tax Bill Prior Sale Owner Records
$460,000May 2024 $3,2262025 Amount on Record Jan 2021 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

Wildfire Risk on Windy Hill Rd

Source: USDA Forest Service Wildfire Risk to Communities · 2nd edition (2024), fuels as of 2020

Wildfire RiskModerate
this street's cells rank above 43% of the US · above 79% of Maryland
Wildfire LikelihoodAbout 1 in 1,402 per year
ExposureDirect
10 of 18 cells directly exposed · 17 adjoin burnable vegetation

Property Records in Nearby Streets