Leonardtown Maryland Homes for Sale

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 1

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 2

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 3

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 6

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 7

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 8

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 9

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 10

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 11

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 12

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 13

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 14

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 15

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 16

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 18

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 19

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 39

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 42

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 43

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22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 58

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 59

22157 Monterey Place Leonardtown, MD MLS# MDSM2033568 - Image 60

1 of 60

$649,900

Beds

2.1

Baths

3,314

Sq.Ft.

22157 Monterey Place

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 1

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 2

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 3

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 4

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 81

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 82

Virtual Tour

1 of 82

$850,000

Beds

3.0

Baths

2,731

Sq.Ft.

19445 Blake Farms Lane

Leonardtown, MD

Courtesy of O'BRIEN REALTY ERA POWERED

23444 Lindsay Drive Leonardtown, MD MLS# MDSM2033554 - Image 1

23444 Lindsay Drive Leonardtown, MD MLS# MDSM2033554 - Image 2

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23444 Lindsay Drive Leonardtown, MD MLS# MDSM2033554 - Image 43

1 of 43

$629,900

Beds

3.1

Baths

3,340

Sq.Ft.

23444 Lindsay Drive

Leonardtown, MD

Courtesy of RE/MAX ONE

THE TIME TO SELL IS NOW!

40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 1

40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 2

40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 3

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40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 58

40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 59

40717 Lake And Breton View Drive Leonardtown, MD MLS# MDSM2033362 - Image 60

Virtual Tour

1 of 60

$435,000

Beds

2.1

Baths

2,624

Sq.Ft.

40717 Lake And Breton View Drive

Leonardtown, MD

Courtesy of REDFIN CORP

21395 Fairwood Court Leonardtown, MD MLS# MDSM2033536 - Image 1

21395 Fairwood Court Leonardtown, MD MLS# MDSM2033536 - Image 2

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1 of 74

$680,000

Beds

3.1

Baths

4,066

Sq.Ft.

21395 Fairwood Court

Leonardtown, MD

Courtesy of EXP REALTY, LLC

44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 1

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44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 74

1 of 74

$675,000

Beds

2.1

Baths

2,953

Sq.Ft.

44450 Schumann Way

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

22601 Avenmar Drive Leonardtown, MD MLS# MDSM2033428 - Image 1

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22601 Avenmar Drive Leonardtown, MD MLS# MDSM2033428 - Image 90

22601 Avenmar Drive Leonardtown, MD MLS# MDSM2033428 - Image 91

1 of 91

$699,000

Beds

4.0

Baths

5,484

Sq.Ft.

22601 Avenmar Drive

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

40659 Klear Court Leonardtown, MD MLS# MDSM2033354 - Image 1

40659 Klear Court Leonardtown, MD MLS# MDSM2033354 - Image 2

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40659 Klear Court Leonardtown, MD MLS# MDSM2033354 - Image 54

1 of 54

$439,000

Beds

2.1

Baths

2,774

Sq.Ft.

40659 Klear Court

Leonardtown, MD

Courtesy of BALDUS REAL ESTATE, INC.

40751 Merlin Way Leonardtown, MD MLS# MDSM2033166 - Image 1

40751 Merlin Way Leonardtown, MD MLS# MDSM2033166 - Image 2

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40751 Merlin Way Leonardtown, MD MLS# MDSM2033166 - Image 43

40751 Merlin Way Leonardtown, MD MLS# MDSM2033166 - Image 44

1 of 44

$615,000

Beds

2.1

Baths

2,601

Sq.Ft.

40751 Merlin Way

Leonardtown, MD

Courtesy of METRO CITY REALTY

41524 Fairwood Court Leonardtown, MD MLS# MDSM2033246 - Image 1

41524 Fairwood Court Leonardtown, MD MLS# MDSM2033246 - Image 2

41524 Fairwood Court Leonardtown, MD MLS# MDSM2033246 - Image 3

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41524 Fairwood Court Leonardtown, MD MLS# MDSM2033246 - Image 28

1 of 28

$590,000

Beds

3.0

Baths

3,793

Sq.Ft.

41524 Fairwood Court

Leonardtown, MD

Courtesy of THE SOUTHSIDE GROUP REAL ESTATE

Lot 139 - 23665 Dragonfly Lane Leonardtown, MD MLS# MDSM2033224 - Image 1

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Lot 139 - 23665 Dragonfly Lane Leonardtown, MD MLS# MDSM2033224 - Image 41

Lot 139 - 23665 Dragonfly Lane Leonardtown, MD MLS# MDSM2033224 - Image 42

New Construction

1 of 42

$449,900

Beds

3.1

Baths

Lot 139 - 23665 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 1

Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 2

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Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 28

Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 29

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Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 40

Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 41

Lot 143 - 23641 Dragonfly Lane Leonardtown, MD MLS# MDSM2033226 - Image 42

New Construction

1 of 42

$454,900

Beds

3.1

Baths

Lot 143 - 23641 Dragonfly Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

40611 Merion Court Leonardtown, MD MLS# MDSM2033146 - Image 1

40611 Merion Court Leonardtown, MD MLS# MDSM2033146 - Image 2

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40611 Merion Court Leonardtown, MD MLS# MDSM2033146 - Image 57

40611 Merion Court Leonardtown, MD MLS# MDSM2033146 - Image 58

1 of 58

$624,990

Beds

3.1

Baths

2,562

Sq.Ft.

40611 Merion Court

Leonardtown, MD

Courtesy of INFINITAS REALTY GROUP

41888 Jenkins Court Leonardtown, MD MLS# MDSM2033062 - Image 1

41888 Jenkins Court Leonardtown, MD MLS# MDSM2033062 - Image 2

41888 Jenkins Court Leonardtown, MD MLS# MDSM2033062 - Image 3

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41888 Jenkins Court Leonardtown, MD MLS# MDSM2033062 - Image 53

1 of 53

OPEN HOUSE: Sunday 10/18 12:00 PM - 3:00 PM

$535,000

Beds

3.1

Baths

2,562

Sq.Ft.

41888 Jenkins Court

Leonardtown, MD

Courtesy of RE/MAX ONE

23750 Hollywood Road Leonardtown, MD MLS# MDSM2033116 - Image 1

23750 Hollywood Road Leonardtown, MD MLS# MDSM2033116 - Image 2

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23750 Hollywood Road Leonardtown, MD MLS# MDSM2033116 - Image 56

1 of 56

$390,000

Beds

3.0

Baths

1,080

Sq.Ft.

23750 Hollywood Road

Leonardtown, MD

Courtesy of CENTURY 21 REDWOOD REALTY

22501 Bull Road Leonardtown, MD MLS# MDSM2032990 - Image 1

22501 Bull Road Leonardtown, MD MLS# MDSM2032990 - Image 2

22501 Bull Road Leonardtown, MD MLS# MDSM2032990 - Image 3

1 of 3

$175,000

0.0

Baths

22501 Bull Road

Leonardtown, MD

Courtesy of GREENMARK REAL ESTATE

18937 Hodges Lane Leonardtown, MD MLS# MDSM2032956 - Image 1

18937 Hodges Lane Leonardtown, MD MLS# MDSM2032956 - Image 2

18937 Hodges Lane Leonardtown, MD MLS# MDSM2032956 - Image 3

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1 of 74

$675,000

Beds

2.0

Baths

1,834

Sq.Ft.

18937 Hodges Lane

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

25375 Loveville Road Leonardtown, MD MLS# MDSM2032802 - Image 1

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1 of 94

$680,000

Beds

2.0

Baths

2,388

Sq.Ft.

25375 Loveville Road

Leonardtown, MD

Courtesy of RMG REALTY

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 1

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 2

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 3

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 4

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 5

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 6

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 7

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 8

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 9

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 10

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 11

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 12

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 13

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 14

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 15

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 16

23011 Newtowne Neck Road Leonardtown, MD MLS# MDSM2032950 - Image 17

1 of 17

$350,000

Beds

2.0

Baths

1,552

Sq.Ft.

23011 Newtowne Neck Road

Leonardtown, MD

Courtesy of SAMSON PROPERTIES

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 1

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 2

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 3

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 4

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 5

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 6

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 7

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 8

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 9

21365 Bogies Lane Leonardtown, MD MLS# MDSM2032756 - Image 10

1 of 10

$299,000

0.0

Baths

21365 Bogies Lane

Leonardtown, MD

Courtesy of CENTURY 21 REDWOOD REALTY

About Leonardtown

Listings in Leonardtown, MD: 83
Estimated median home price: $549,000

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

Price	Count
$0 - 100K	0
$100K - 200K	5
$200K - 300K	6
$300K - 400K	6
$400K - 500K	22
$500K - 600K	10
$600K - 700K	20
$700K - 800K	5
$800K - 900K	1
$900K - 1M	1
$1M - Max	7

Homes for Sale by Type in Leonardtown, MD

Property Type	Count
Single Family	55
Townhouse	14
Condo	0
Commercial	0
Rental	12
Lots and Land	14
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 10/12/2026)

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Leonardtown, MD Information

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20650

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 Reciprocity^SM 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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Leonardtown Maryland Homes for Sale

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