Windward Dr, Tilghman, MD Property Records

Talbot County property records for 15 addresses on Windward Dr, Tilghman, MD · Last verified August 2026

Windward Dr Highlights

Properties 15
Median Sale Price $595,000
Deeds and Mortgages on File 22
Median Price per Sqft $297
Owner Occupied 53%
Median Annual Tax Bill $4,777
Median Year Built 1982
Median Ownership Tenure 8 years

Properties on Windward Dr

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

5396 Windward Dr

4.5 ba · 3,494 sqft · 0.457 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$237,500May 2022 $8,4682025 Amount on Record Jun 2020 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

5400 Windward Dr

5 ba · 4,280 sqft · 0.462 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$250,000Jul 2024 $6,9002025 Amount on Record May 2001 1 Name on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

5401 Windward Dr

2 ba · 1,248 sqft · 0.447 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$225,000Dec 2018 $2,1832025 Amount on Record Aug 1987 2 Names on Record Assessor + 3 DocumentsUpdated Aug 2026

5410 Windward Dr

3 ba · 2,686 sqft · 0.449 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$800,000May 2021 $5,8342025 Amount on Record Dec 2000 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

5411 Windward Dr

2 ba · 1,568 sqft · 0.482 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$148,000Jul 2000 $1,9942025 Amount on Record Jun 1998 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

5420 Windward Dr

2.5 ba · 2,352 sqft · 0.462 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$725,000Feb 2021 $6,5382025 Amount on Record Nov 2011 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

5423 Windward Dr

2 ba · 1,378 sqft · 0.506 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$217,500Dec 2005 $2,0552025 Amount on Record Sep 2002 2 Names on Record AssessorUpdated Aug 2026

5427 Windward Dr

3.5 ba · 2,289 sqft · 0.523 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$438,830Aug 2023 $1,5972025 Amount on Record Feb 2023 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

5434 Windward Dr

1.5 ba · 1,416 sqft · 0.436 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$2,7562025 1 Name on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

5444 Windward Dr

2 ba · 1,456 sqft · 0.443 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Mar 1999 $4,2012025 Amount on Record Apr 1997 2 Names on Record AssessorUpdated Aug 2026

5451 Windward Dr

1 ba · 1,031 sqft · 0.437 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$239,900Aug 2005 $1,3092025 Amount on Record Jun 1996 2 Names on Record Owner Occupied Assessor + 2 DocumentsUpdated Aug 2026

5454 Windward Dr

3.5 ba · 3,140 sqft · 0.445 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$75,000Aug 1983 $5,2792025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

5466 Windward Dr

2.5 ba · 2,310 sqft · 0.519 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$177,500Dec 1994 $4,7772025 Amount on Record Jan 1983 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

5480 Windward Dr

2 ba · 1,936 sqft · 0.713 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$595,000Jun 2011 $5,2332025 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

5490 Windward Dr

2 ba · 2,046 sqft · 1.29 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$1,157,500Nov 2022 $7,1292025 Amount on Record Mar 1996 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

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