Leonardtown Maryland Homes for Sale

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 1

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 2

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 3

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 11

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 27

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 31

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 37

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 40

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 41

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 42

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 43

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 46

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 47

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 49

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 51

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 53

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 54

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 55

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 56

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 57

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 58

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 59

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 60

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 61

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40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 63

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 64

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 65

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 66

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 67

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 68

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 69

40777 Center 40 Circle Leonardtown, MD MLS# MDSM2032004 - Image 70

1 of 70

$539,900

Beds

2.1

Baths

2,370

Sq.Ft.

40777 Center 40 Circle

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

41531 Kalitan Lane Leonardtown, MD MLS# MDSM2031978 - Image 1

41531 Kalitan Lane Leonardtown, MD MLS# MDSM2031978 - Image 2

41531 Kalitan Lane Leonardtown, MD MLS# MDSM2031978 - Image 3

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41531 Kalitan Lane Leonardtown, MD MLS# MDSM2031978 - Image 83

Recently Listed

1 of 83

$665,000

Beds

3.1

Baths

3,570

Sq.Ft.

41531 Kalitan Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

41462 Culpepper Way Leonardtown, MD MLS# MDSM2031988 - Image 1

1 of 1

$645,000

Beds

3.1

Baths

3,314

Sq.Ft.

41462 Culpepper Way

Leonardtown, MD

Courtesy of RE/MAX ONE

THE TIME TO SELL IS NOW!

23591 Margrave Drive Leonardtown, MD MLS# MDSM2031892 - Image 1

23591 Margrave Drive Leonardtown, MD MLS# MDSM2031892 - Image 2

23591 Margrave Drive Leonardtown, MD MLS# MDSM2031892 - Image 3

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23591 Margrave Drive Leonardtown, MD MLS# MDSM2031892 - Image 73

23591 Margrave Drive Leonardtown, MD MLS# MDSM2031892 - Image 74

Recently Listed with Virtual Tour

1 of 74

$670,000

Beds

3.1

Baths

4,051

Sq.Ft.

23591 Margrave Drive

Leonardtown, MD

Courtesy of RE/MAX ONE

41482 Pensive Street Leonardtown, MD MLS# MDSM2031768 - Image 1

41482 Pensive Street Leonardtown, MD MLS# MDSM2031768 - Image 2

41482 Pensive Street Leonardtown, MD MLS# MDSM2031768 - Image 3

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1 of 75

$571,200

Beds

3.1

Baths

4,300

Sq.Ft.

41482 Pensive Street

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

44018 Cotton Tail Court Leonardtown, MD MLS# MDSM2031718 - Image 1

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44018 Cotton Tail Court Leonardtown, MD MLS# MDSM2031718 - Image 52

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New Construction with Virtual Tour

1 of 54

$649,900

Beds

3.1

Baths

3,456

Sq.Ft.

44018 Cotton Tail Court

Leonardtown, MD

Courtesy of RE/MAX ONE

21822 Riviera Court Leonardtown, MD MLS# MDSM2031708 - Image 1

21822 Riviera Court Leonardtown, MD MLS# MDSM2031708 - Image 2

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21822 Riviera Court Leonardtown, MD MLS# MDSM2031708 - Image 78

21822 Riviera Court Leonardtown, MD MLS# MDSM2031708 - Image 79

Virtual Tour

1 of 79

$599,900

Beds

3.1

Baths

3,384

Sq.Ft.

21822 Riviera Court

Leonardtown, MD

Courtesy of RE/MAX ONE

25010 Meadowlark Court Leonardtown, MD MLS# MDSM2031670 - Image 1

25010 Meadowlark Court Leonardtown, MD MLS# MDSM2031670 - Image 2

25010 Meadowlark Court Leonardtown, MD MLS# MDSM2031670 - Image 3

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25010 Meadowlark Court Leonardtown, MD MLS# MDSM2031670 - Image 56

25010 Meadowlark Court Leonardtown, MD MLS# MDSM2031670 - Image 57

1 of 57

$650,000

Beds

3.0

Baths

2,961

Sq.Ft.

25010 Meadowlark Court

Leonardtown, MD

Courtesy of RE/MAX ONE

41992 Loker Court Leonardtown, MD MLS# MDSM2031206 - Image 1

41992 Loker Court Leonardtown, MD MLS# MDSM2031206 - Image 2

41992 Loker Court Leonardtown, MD MLS# MDSM2031206 - Image 3

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41992 Loker Court Leonardtown, MD MLS# MDSM2031206 - Image 63

41992 Loker Court Leonardtown, MD MLS# MDSM2031206 - Image 64

Virtual Tour

1 of 64

$524,900

Beds

3.1

Baths

3,260

Sq.Ft.

41992 Loker Court

Leonardtown, MD

Courtesy of INFINITAS REALTY GROUP

23642 Hansel Court Leonardtown, MD MLS# MDSM2031224 - Image 1

23642 Hansel Court Leonardtown, MD MLS# MDSM2031224 - Image 2

23642 Hansel Court Leonardtown, MD MLS# MDSM2031224 - Image 3

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23642 Hansel Court Leonardtown, MD MLS# MDSM2031224 - Image 74

1 of 74

$649,900

Beds

3.1

Baths

3,726

Sq.Ft.

23642 Hansel Court

Leonardtown, MD

Courtesy of RE/MAX ONE

21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122 - Image 1

21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122 - Image 2

21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122 - Image 3

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21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122 - Image 51

21737 Pinehurst Court Leonardtown, MD MLS# MDSM2031122 - Image 52

1 of 52

$540,000

Beds

2.0

Baths

3,014

Sq.Ft.

21737 Pinehurst Court

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 1

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 2

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 3

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40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 18

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 19

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 20

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 21

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 22

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 23

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 24

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 25

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 26

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 27

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 28

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 29

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 30

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 31

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 32

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 33

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 34

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 35

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 36

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 37

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 38

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 39

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 40

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 41

40461 Old Breton Beach Road Leonardtown, MD MLS# MDSM2030470 - Image 42

1 of 42

$650,000

Beds

2.1

Baths

2,040

Sq.Ft.

40461 Old Breton Beach Road

Leonardtown, MD

Courtesy of THE SOUTHSIDE GROUP REAL ESTATE

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 1

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 2

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 3

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 4

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 5

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 6

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 7

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 8

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 9

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 10

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 11

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 12

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 13

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 14

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 15

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 16

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 17

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 18

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 19

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 20

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 21

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 22

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 23

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 24

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 25

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 26

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 27

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 28

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 29

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 30

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 31

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 32

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 33

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 34

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 35

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 36

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 37

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 38

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 39

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 40

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 41

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 42

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 43

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 44

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 45

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 46

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 47

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 48

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 49

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 50

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 51

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 52

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 53

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 54

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 55

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 56

41377 Doctors Crossing Road Leonardtown, MD MLS# MDSM2029722 - Image 57

Virtual Tour

1 of 57

$610,000

Beds

4.0

Baths

3,724

Sq.Ft.

41377 Doctors Crossing Road

Leonardtown, MD

Courtesy of KELLER WILLIAMS REALTY/LEE BEAVER & ASSOC.

22615 Washington Street Leonardtown, MD MLS# MDSM2028632 - Image 1

22615 Washington Street Leonardtown, MD MLS# MDSM2028632 - Image 2

22615 Washington Street Leonardtown, MD MLS# MDSM2028632 - Image 3

22615 Washington Street Leonardtown, MD MLS# MDSM2028632 - Image 4

1 of 4

$599,950

Studio

Beds

0.0

Baths

1,691

Sq.Ft.

22615 Washington Street

Leonardtown, MD

Courtesy of INFINITAS REALTY GROUP

About Leonardtown

Listings in Leonardtown, MD: 71
Estimated median home price: $479,900

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	2
$100K - 200K	5
$200K - 300K	3
$300K - 400K	6
$400K - 500K	25
$500K - 600K	7
$600K - 700K	9
$700K - 800K	6
$800K - 900K	1
$900K - 1M	0
$1M - Max	7

Homes for Sale by Type in Leonardtown, MD

Property Type	Count
Single Family	34
Townhouse	23
Condo	0
Commercial	0
Rental	20
Lots and Land	14
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 7/1/2026)

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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.

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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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