View 21060 Woodmere Drive Leonardtown, MD MLS# MDSM2028504
  • Recently Listed
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 43543 Bayberry Court Leonardtown, MD MLS# MDSM2028348
  • Recently Listed
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 20260 Hawks Way Leonardtown, MD MLS# MDSM2028220
  • Recently Listed
1 of 29
OPEN HOUSE: Saturday 12/13 10:00 AM - 12:00 PM
$599,900
4

Beds

2.1

Baths

2,500

Sq.Ft.

20260 Hawks Way

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
The time to sell is now! THE TIME TO SELL IS NOW!
View 20250 Hawks Way Leonardtown, MD MLS# MDSM2028410
  • Recently Listed
1 of 30
OPEN HOUSE: Saturday 12/13 10:00 AM - 12:00 PM
$519,900
3

Beds

2.0

Baths

1,557

Sq.Ft.

20250 Hawks Way

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 23581 Gallent Fox Way Leonardtown, MD MLS# MDSM2028276
  • Recently Listed with Virtual Tour
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 22547 Landing Way Leonardtown, MD MLS# MDSM2028512
$520,000
3

Beds

3.1

Baths

2,764

Sq.Ft.

22547 Landing Way

Leonardtown, MD

Bright
Courtesy of EXP REALTY, LLC
View 41635 Ferber Court Leonardtown, MD MLS# MDSM2028376
$565,000
4

Beds

2.1

Baths

2,222

Sq.Ft.

41635 Ferber Court

Leonardtown, MD

Bright
Courtesy of HOME TOWNE REAL ESTATE
View 42975 Baywood Place Leonardtown, MD MLS# MDSM2028350
$699,900
4

Beds

2.1

Baths

3,372

Sq.Ft.

42975 Baywood Place

Leonardtown, MD

Bright
Courtesy of EXP REALTY, LLC
View 41430 Challedon Way Leonardtown, MD MLS# MDSM2028266
$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
$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
$475,000
3

Beds

2.0

Baths

2,458

Sq.Ft.

20697 Chingville Road

Leonardtown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View Lot 104 - 23695 Dragonfly Lane Leonardtown, MD MLS# MDSM2028144
  • New Construction with Virtual Tour
1 of 47
OPEN HOUSE: Saturday 12/13 3:00 PM - 5:00 PM
$449,900
4

Beds

3.1

Baths

Lot 104 - 23695 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View lot 106 - 23683 Dragonfly Lane Leonardtown, MD MLS# MDSM2028148
  • New Construction with Virtual Tour
1 of 40
OPEN HOUSE: Saturday 12/13 3:00 PM - 5:00 PM
$449,900
4

Beds

3.1

Baths

lot 106 - 23683 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View Lot 105 - 23689 Dragonfly Lane Leonardtown, MD MLS# MDSM2028150
  • New Construction with Virtual Tour
1 of 44
OPEN HOUSE: Saturday 12/13 3:00 PM - 5:00 PM
$449,900
4

Beds

3.1

Baths

Lot 105 - 23689 Dragonfly Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 41467 Osborne Lane Leonardtown, MD MLS# MDSM2028070
$525,000
4

Beds

3.1

Baths

2,827

Sq.Ft.

41467 Osborne Lane

Leonardtown, MD

Bright
Courtesy of TURTLE TOWN REAL ESTATE, LLC.
View 41492 Charismatic Way Leonardtown, MD MLS# MDSM2028074
$639,900
4

Beds

3.1

Baths

3,322

Sq.Ft.

41492 Charismatic 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 23264 Lindsay Drive Leonardtown, MD MLS# MDSM2027806
$599,000
3

Beds

2.0

Baths

2,824

Sq.Ft.

23264 Lindsay Drive

Leonardtown, MD

Bright
Courtesy of RE/MAX REALTY GROUP
View 43018 Bluejay Lane Leonardtown, MD MLS# MDSM2027792
$645,900
4

Beds

2.1

Baths

2,888

Sq.Ft.

43018 Bluejay Lane

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE
View 21117 Catnip Court Leonardtown, MD MLS# MDSM2027750
$610,000
5

Beds

3.1

Baths

3,526

Sq.Ft.

21117 Catnip Court

Leonardtown, MD

Bright
Courtesy of RE/MAX ONE

About Leonardtown

Listings in Leonardtown, MD

66

Estimated median home price

$534,950
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 7
$200K - 300K 3
$300K - 400K 0
$400K - 500K 14
$500K - 600K 14
$600K - 700K 11
$700K - 800K 4
$800K - 900K 2
$900K - 1M 0
$1M - Max 7

Homes for Sale by Type in Leonardtown, MD

Property Type Count
Single Family 39
Townhouse 8
Condo 0
Commercial 4
Rental 18
Lots and Land 15
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/13/2025)

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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