View 0 Saint Andrews Church Rd Leonardtown, MD MLS# MDSM2029792
$98,900
Studio

Beds

0.0

Baths

0 Saint Andrews Church Rd

Leonardtown, MD

Bright
Courtesy of WHITETAIL PROPERTIES REAL ESTATE, LLC
View 22394 White Oak Road Leonardtown, MD MLS# MDSM2029800
$495,000
4

Beds

3.0

Baths

2,507

Sq.Ft.

22394 White Oak Road

Leonardtown, MD

Bright
Courtesy of KW METRO CENTER
View 20798 Waterside Drive Leonardtown, MD MLS# MDSM2029666
$450,000
2

Beds

1.0

Baths

1,018

Sq.Ft.

20798 Waterside Drive

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot 113 - 23696 Weeping Willow Way Leonardtown, MD MLS# MDSM2029482
  • New Construction with Virtual Tour
1 of 42
$479,900
4

Beds

3.1

Baths

Lot 113 - 23696 Weeping Willow Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 133 - 23691 Weeping Willow Way Leonardtown, MD MLS# MDSM2029484
  • New Construction with Virtual Tour
1 of 40
$489,900
4

Beds

3.1

Baths

Lot 133 - 23691 Weeping Willow Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 101 - 23713 Dragonfly Lane Leonardtown, MD MLS# MDSM2029486
  • New Construction with Virtual Tour
1 of 34
OPEN HOUSE: Thursday 4/30 11:00 AM - 4:00 PM
$449,900
4

Beds

3.1

Baths

Lot 101 - 23713 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 99 - 23725 Dragonfly Lane Leonardtown, MD MLS# MDSM2029488
  • New Construction with Virtual Tour
1 of 35
OPEN HOUSE: Thursday 4/30 11:00 AM - 4:00 PM
$449,900
4

Beds

3.1

Baths

Lot 99 - 23725 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 41516 Marwood Circle Leonardtown, MD MLS# MDSM2029470
$437,000
3

Beds

3.1

Baths

2,402

Sq.Ft.

41516 Marwood Circle

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 22175 Bayside Road Leonardtown, MD MLS# MDSM2029056
$315,000
2

Beds

2.0

Baths

1,192

Sq.Ft.

22175 Bayside Road

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 100 - 23719 Dragonfly Lane Leonardtown, MD MLS# MDSM2029208
$449,900
4

Beds

3.1

Baths

2,571

Sq.Ft.

Lot 100 - 23719 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 117 - 23720 Weeping Willow Way Leonardtown, MD MLS# MDSM2029218
  • New Construction with Virtual Tour
1 of 46
$489,900
4

Beds

3.1

Baths

3,095

Sq.Ft.

Lot 117 - 23720 Weeping Willow Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 102 - 23707 Dragonfly Lane Leonardtown, MD MLS# MDSM2029202
$479,900
4

Beds

3.1

Baths

Lot 102 - 23707 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View St. Andrews Church Road Leonardtown, MD MLS# MDSM2029070
$175,000
Studio

Beds

0.0

Baths

St. Andrews Church Road

Leonardtown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 20265 Hawks Way Leonardtown, MD MLS# MDSM2028774
$149,900
Studio

Beds

0.0

Baths

20265 Hawks Way

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View Lot 138 - 23671 Dragonfly Lane Leonardtown, MD MLS# MDSM2028534
  • New Construction with Virtual Tour
1 of 38
$487,400
4

Beds

3.1

Baths

3,095

Sq.Ft.

Lot 138 - 23671 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 137- 23667 Weeping Willow Way Leonardtown, MD MLS# MDSM2028536
  • New Construction with Virtual Tour
1 of 42
$479,900
4

Beds

3.1

Baths

2,966

Sq.Ft.

Lot 137- 23667 Weeping Willow Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 40412 B Somerville Lane Leonardtown, MD MLS# MDSM2027980
$149,900
Studio

Beds

0.0

Baths

40412 B Somerville Lane

Leonardtown, MD

Bright
Courtesy of TOPSIDE REALTY
View 43488 Medleys Neck Road Leonardtown, MD MLS# MDSM2027738
$190,000
Studio

Beds

0.0

Baths

43488 Medleys Neck Road

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 19921 Tower Hill Road Leonardtown, MD MLS# MDSM2026598
$130,000
Studio

Beds

0.0

Baths

19921 Tower Hill Road

Leonardtown, MD

Bright
Courtesy of RE/MAX REALTY GROUP
View Long Leaf Lane Leonardtown, MD MLS# MDSM2026482
$24,900
Studio

Beds

0.0

Baths

Long Leaf Lane

Leonardtown, MD

Bright
Courtesy of RESIDENTIAL PLUS REAL ESTATE SERVICES

About Leonardtown

Listings in Leonardtown, MD

92

Estimated median home price

$550,000
Leonardtown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Leonardtown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Leonardtown, MD.

Homes for Sale by Price in Leonardtown, MD

PriceCount
$0 - 100K2
$100K - 200K7
$200K - 300K2
$300K - 400K4
$400K - 500K28
$500K - 600K13
$600K - 700K16
$700K - 800K8
$800K - 900K4
$900K - 1M1
$1M - Max7

Homes for Sale by Type in Leonardtown, MD

Property TypeCount
Single Family56
Townhouse21
Condo1
Commercial1
Rental21
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 4/29/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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