View 21738 Pinehurst Court Leonardtown, MD MLS# MDSM2028668
Save 21738 Pinehurst Court Leonardtown, MD MLS# MDSM2028668
1 of 1
$495,000
4

Beds

2.1

Baths

1,952

Sq.Ft.

21738 Pinehurst Court

Leonardtown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 19137 Lake Drive Leonardtown, MD MLS# MDSM2028598
Save 19137 Lake Drive Leonardtown, MD MLS# MDSM2028598
1 of 58
$399,900
3

Beds

2.1

Baths

1,308

Sq.Ft.

19137 Lake Drive

Leonardtown, MD

Bright
Courtesy of EXP REALTY, LLC
View 22615 Washington Street Leonardtown, MD MLS# MDSM2028632
  • Recently Listed
Save 22615 Washington Street Leonardtown, MD MLS# MDSM2028632
1 of 4
$599,950
Studio

Beds

0.0

Baths

1,691

Sq.Ft.

22615 Washington Street

Leonardtown, MD

Bright
Courtesy of INFINITAS REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 41895 Tomey Court Leonardtown, MD MLS# MDSM2028424
Save 41895 Tomey Court Leonardtown, MD MLS# MDSM2028424
1 of 60
$529,900
5

Beds

3.1

Baths

3,482

Sq.Ft.

41895 Tomey Court

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 23593 Mitchell Drive Leonardtown, MD MLS# MDSM2028550
Save 23593 Mitchell Drive Leonardtown, MD MLS# MDSM2028550
1 of 71
$580,000
5

Beds

3.1

Baths

2,940

Sq.Ft.

23593 Mitchell Drive

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 21345 Fairwood Court Leonardtown, MD MLS# MDSM2028586
  • Recently Listed
Save 21345 Fairwood Court Leonardtown, MD MLS# MDSM2028586
1 of 33
$699,900
5

Beds

3.1

Baths

4,080

Sq.Ft.

21345 Fairwood Court

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 40855 Spring House Lane Leonardtown, MD MLS# MDSM2028400
  • Recently Listed with Virtual Tour
Save 40855 Spring House Lane Leonardtown, MD MLS# MDSM2028400
1 of 68
$650,000
5

Beds

3.0

Baths

3,464

Sq.Ft.

40855 Spring House Lane

Leonardtown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View Lot 108- 23666 Weeping Willow Way Leonardtown, MD MLS# MDSM2028518
  • New Construction with Virtual Tour
Save Lot 108- 23666 Weeping Willow Way Leonardtown, MD MLS# MDSM2028518
1 of 39
$479,900
4

Beds

3.1

Baths

Lot 108- 23666 Weeping Willow Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 138- 23671 Dragonfly Lane Leonardtown, MD MLS# MDSM2028534
  • New Construction with Virtual Tour
Save Lot 138- 23671 Dragonfly Lane Leonardtown, MD MLS# MDSM2028534
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
Save Lot 137- 23667 Weeping Willow Way Leonardtown, MD MLS# MDSM2028536
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 21060 Woodmere Drive Leonardtown, MD MLS# MDSM2028504
  • Recently Listed
Save 21060 Woodmere Drive Leonardtown, MD MLS# MDSM2028504
1 of 90
$565,000
5

Beds

3.1

Baths

3,075

Sq.Ft.

21060 Woodmere Drive

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 22547 Landing Way Leonardtown, MD MLS# MDSM2028512
  • Recently Listed
Save 22547 Landing Way Leonardtown, MD MLS# MDSM2028512
1 of 46
$520,000
3

Beds

3.1

Baths

2,764

Sq.Ft.

22547 Landing Way

Leonardtown, MD

Bright
Courtesy of EXP REALTY, LLC
View 43543 Bayberry Court Leonardtown, MD MLS# MDSM2028348
Save 43543 Bayberry Court Leonardtown, MD MLS# MDSM2028348
1 of 32
$440,000
3

Beds

2.0

Baths

1,732

Sq.Ft.

43543 Bayberry Court

Leonardtown, MD

Bright
Courtesy of O'BRIEN REALTY ERA POWERED
View 41635 Ferber Court Leonardtown, MD MLS# MDSM2028376
Save 41635 Ferber Court Leonardtown, MD MLS# MDSM2028376
1 of 2
$565,000
4

Beds

2.1

Baths

2,222

Sq.Ft.

41635 Ferber Court

Leonardtown, MD

Bright
Courtesy of HOME TOWNE REAL ESTATE
View 20250 Hawks Way Leonardtown, MD MLS# MDSM2028410
  • New Construction
Save 20250 Hawks Way Leonardtown, MD MLS# MDSM2028410
1 of 30
$519,900
3

Beds

2.0

Baths

1,557

Sq.Ft.

20250 Hawks Way

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 42975 Baywood Place Leonardtown, MD MLS# MDSM2028350
Save 42975 Baywood Place Leonardtown, MD MLS# MDSM2028350
1 of 65
$699,900
4

Beds

2.1

Baths

3,372

Sq.Ft.

42975 Baywood Place

Leonardtown, MD

Bright
Courtesy of EXP REALTY, LLC
View 23581 Gallent Fox Way Leonardtown, MD MLS# MDSM2028276
  • Virtual Tour
Save 23581 Gallent Fox Way Leonardtown, MD MLS# MDSM2028276
1 of 53
$645,900
4

Beds

3.1

Baths

3,736

Sq.Ft.

23581 Gallent Fox Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 41430 Challedon Way Leonardtown, MD MLS# MDSM2028266
  • Virtual Tour
Save 41430 Challedon Way Leonardtown, MD MLS# MDSM2028266
1 of 79
$639,000
5

Beds

3.1

Baths

4,500

Sq.Ft.

41430 Challedon Way

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 20753 Chestnut Ridge Drive Leonardtown, MD MLS# MDSM2028218
Save 20753 Chestnut Ridge Drive Leonardtown, MD MLS# MDSM2028218
1 of 45
$574,900
4

Beds

2.1

Baths

2,594

Sq.Ft.

20753 Chestnut Ridge Drive

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 20697 Chingville Road Leonardtown, MD MLS# MDSM2028196
Save 20697 Chingville Road Leonardtown, MD MLS# MDSM2028196
1 of 87
$475,000
3

Beds

2.0

Baths

2,458

Sq.Ft.

20697 Chingville Road

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM

About Leonardtown

Listings in Leonardtown, MD

66

Estimated median home price

$524,950
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

Price Count
$0 - 100K 4
$100K - 200K 6
$200K - 300K 2
$300K - 400K 1
$400K - 500K 17
$500K - 600K 14
$600K - 700K 12
$700K - 800K 4
$800K - 900K 1
$900K - 1M 0
$1M - Max 5

Homes for Sale by Type in Leonardtown, MD

Property Type Count
Single Family 40
Townhouse 10
Condo 0
Commercial 2
Rental 16
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/25/2025)

Find Properties in Leonardtown, MD

Leonardtown, MD Information

Find Properties by Zip

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.

© 2025 BrightMLS. All Rights Reserved.