Oakland Rd, Henderson, MD Property Records

Caroline County property records for 13 addresses on Oakland Rd, Henderson, MD · Last verified August 2026

Oakland Rd Highlights

Properties 13
Median Sale Price $1,596,250
Deeds and Mortgages on File 10
Median Price per Sqft $325
Owner Occupied 62%
Median Annual Tax Bill $3,651
Median Year Built 1990
Median Ownership Tenure 21 years

Properties on Oakland Rd

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

15539 Oakland Rd

1 ba · 924 sqft · built 1953 · 1.01 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Oct 2003 $1,6572025 —Nov 1996 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

15570 Oakland Rd

2 ba · 1,536 sqft · built 1986 · 5.36 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,750,000Jan 2026 $3,5792025 Amount on Record Nov 1997 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

15663 Oakland Rd

2.5 ba · 2,048 sqft · built 2009 · 5.43 acres

Last Sale Tax Bill Prior Sale Owner Records
—Apr 2006 $3,7272025 2 Owners on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

15675 Oakland Rd

2 ba · 1,448 sqft · built 2011 · 5.43 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2005 $3,6512025 Owner on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

15725 Oakland Rd

1 ba · 1,508 sqft · built 1965 · 6.56 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2005 $1,0242025 —Jun 2002 2 Owners on Record AssessorUpdated Aug 2026

15765 Oakland Rd

1 ba · 1,508 sqft · built 1965 · 20 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2001 $3,6222025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

15833 Oakland Rd

2.5 ba · 1,680 sqft · built 1987 · 5.25 acres

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2005 $2,2122025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

15890 Oakland Rd

1.5 ba · 1,232 sqft · built 1995 · 154 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,750,000Jan 2026 $16,4872025 Amount on Record Jul 1996 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

16073 Oakland Rd

2 ba · 1,888 sqft · built 1997 · 3 acres

Last Sale Tax Bill Prior Sale Owner Records
$31,368May 1996 $2,8362025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

16090 Oakland Rd

11.5 ba · 8,456 sqft · built 1990 · 505 acres

Last Sale Tax Bill Prior Sale Owner Records
$2,750,000Jan 2026 $47,2922025 Amount on Record Jul 2002 Owner on Record Assessor + 2 DocumentsUpdated Aug 2026

16343 Oakland Rd

2.5 ba · 3,024 sqft · built 2008 · 50 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2004 $7,2832025 Owner on Record Owner Occupied AssessorUpdated Aug 2026

16360 Oakland Rd

1 ba · 1,080 sqft · built 1973 · 245 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,596,250Jul 2021 $4,1342025 Amount on Record Dec 1993 2 Owners on Record Assessor + 1 DocumentUpdated Aug 2026

16373 Oakland Rd

2.5 ba · 3,946 sqft · built 2007 · 48.1 acres

Last Sale Tax Bill Prior Sale Owner Records
$275,000May 2007 $7,1812025 2 Owners on Record Owner Occupied AssessorUpdated Aug 2026

Property Records in Nearby Streets