Waterside Dr, Leonardtown, MD Property Records

St. Mary's County property records for 34 addresses on Waterside Dr, Leonardtown, MD · Last verified August 2026

Waterside Dr Highlights

Properties 34
Median Sale Price $385,125
Deeds and Mortgages on File 23
Median Price per Sqft $245
Owner Occupied 56%
Median Annual Tax Bill $4,333
Median Year Built 1952
Median Ownership Tenure 24 years

Properties on Waterside Dr

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

20642 Waterside Dr

2.5 ba · 3,969 sqft · 5.6 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$400,000Jun 2018 $10,2142025 2 Names on Record Owner Occupied Assessor + 4 DocumentsUpdated Aug 2026

20645 Waterside Dr

2 ba · 1,852 sqft · 0.317 acres

Last Sale Tax Bill Prior Sale Owner Records
$350,000Sep 2021 $3,9292025 Amount on Record Mar 2013 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

20650 Waterside Dr

2 ba · 1,958 sqft · 0.29 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$481,000Jul 2016 $5,7272025 Amount on Record Mar 1998 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20658 Waterside Dr

2 ba · 2,346 sqft · 0.362 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$6,2052025 2 Names on Record AssessorUpdated Aug 2026

20666 Waterside Dr

1 ba · 1,992 sqft · 0.13 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$450,000Aug 2008 $4,5282025 Amount on Record Jun 2000 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

20673 Waterside Dr

1 ba · 672 sqft · 1.03 acres

Last Sale Tax Bill Prior Sale Owner Records
$1,4892025 2 Names on Record Assessor + 1 DocumentUpdated Aug 2026

20674 Waterside Dr

1 ba · 768 sqft · 0.146 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$240,000Aug 2002 $3,7722025 Amount on Record Feb 1997 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20680 Waterside Dr

1.5 ba · 904 sqft · 0.135 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$120,000Jan 2001 $3,9642025 Amount on Record Oct 1993 2 Names on Record AssessorUpdated Aug 2026

20686 Waterside Dr

1 ba · 1,065 sqft · 0.137 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$273,000Sep 2010 $4,0642025 Amount on Record Aug 1991 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

20692 Waterside Dr

1 ba · 1,174 sqft · 0.14 acres

Last Sale Tax Bill Prior Sale Owner Records
$3,6392025 1 Name on Record AssessorUpdated Aug 2026

20698 Waterside Dr

2 ba · 3,204 sqft · 0.381 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Aug 1991 $5,7462025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20704 Waterside Dr

1 ba · 780 sqft · 0.141 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Jun 2004 $3,5272025 Amount on Record Dec 1993 2 Names on Record AssessorUpdated Aug 2026

20708 Waterside Dr

1 ba · 1,836 sqft · 0.286 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$638,000Oct 2024 $6,3272025 —Mar 2005 2 Names on Record AssessorUpdated Aug 2026

20720 Waterside Dr

1 ba · 1,558 sqft · 0.528 acres

Last Sale Tax Bill Prior Sale Owner Records
$385,125Jul 2020 $4,3332025 —Jan 2007 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

20734 Waterside Dr

2 ba · 1,536 sqft · 0.16 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$115,000Aug 1994 $4,7842025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

20748 Waterside Dr

2 ba · 1,824 sqft · 0.254 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$89,000Dec 1987 $4,9592025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20749 Waterside Dr

0.196 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
—Dec 1987 $2052025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20754 Waterside Dr

2.5 ba · 2,150 sqft · 0.507 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$85,000Oct 1986 $6,3792025 1 Name on Record AssessorUpdated Aug 2026

20765 Waterside Dr

0.198 acres

Last Sale Tax Bill Prior Sale Owner Records
$85,000Oct 1986 $7972025 1 Name on Record AssessorUpdated Aug 2026

20768 Waterside Dr

1 ba · 624 sqft · 0.128 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$340,000Mar 2019 $3,5832025 Amount on Record Sep 2018 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

20771 Waterside Dr

0.207 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$340,000Mar 2019 $3902025 Amount on Record Sep 2018 2 Names on Record Assessor + 2 DocumentsUpdated Aug 2026

20778 Waterside Dr

1 ba · 1,630 sqft · 0.373 acres

Last Sale Tax Bill Prior Sale Owner Records
$75,000Oct 1987 $4,6292025 1 Name on Record Assessor + 1 DocumentUpdated Aug 2026

20786 Waterside Dr

3 ba · 2,510 sqft · 0.517 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$276,000Nov 2001 $5,4642025 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20798 Waterside Dr

1 ba · 816 sqft · 0.181 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
—Oct 2006 $3,7542025 Amount on Record Sep 2002 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

20802 Waterside Dr

1 ba · 1,168 sqft · 0.183 acres · Pool

Last Sale Tax Bill Prior Sale Owner Records
$269,000Sep 2003 $4,3932025 Amount on Record Jan 1995 1 Name on Record AssessorUpdated Aug 2026

20814 Waterside Dr

1 ba · 1,380 sqft · 0.188 acres

Last Sale Tax Bill Prior Sale Owner Records
$70,000Dec 2004 $4,0642025 —Dec 2004 2 Names on Record Owner Occupied AssessorUpdated Aug 2026

20817 Waterside Dr

0.206 acres

Last Sale Tax Bill Prior Sale Owner Records
—Dec 2004 $8012025 2 Names on Record AssessorUpdated Aug 2026

20820 Waterside Dr

2 ba · 2,000 sqft · 0.188 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$21,700May 1993 $5,0772025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

20823 Waterside Dr

0.103 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$21,700May 1993 $4722025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

20826 Waterside Dr

1 ba · 1,362 sqft · 0.186 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$132,500Sep 1996 $3,9392025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

20829 Waterside Dr

0.103 acres · Garage

Last Sale Tax Bill Prior Sale Owner Records
$132,500Sep 1996 $1552025 2 Names on Record Owner Occupied Assessor + 1 DocumentUpdated Aug 2026

20832 Waterside Dr

2.5 ba · 1,992 sqft · 0.188 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$10,400Nov 1990 $5,3282025 Amount on Record Jul 1987 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

20838 Waterside Dr

1 ba · 1,512 sqft · 0.191 acres

Last Sale Tax Bill Prior Sale Owner Records
$273,750Dec 2021 $4,3512025 2 Names on Record Owner Occupied Assessor + 3 DocumentsUpdated Aug 2026

20844 Waterside Dr

2.5 ba · 1,998 sqft · 1.36 acres · Garage · Pool

Last Sale Tax Bill Prior Sale Owner Records
$163,500Apr 1996 $6,7172025 1 Name on Record Owner Occupied AssessorUpdated Aug 2026

Property Records in Nearby Streets