Leonardtown Maryland Homes for Sale

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 1

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 2

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 3

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 9

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 13

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 16

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 18

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 39

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 41

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 42

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 43

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 44

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 45

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 47

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 89

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20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 108

20945 Greenwell Way Leonardtown, MD MLS# MDSM2033970 - Image 109

Virtual Tour

1 of 109

$929,900

Beds

3.1

Baths

4,248

Sq.Ft.

20945 Greenwell Way

Leonardtown, MD

Courtesy of O'BRIEN REALTY ERA POWERED

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

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

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 47

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 49

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 50

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 51

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 53

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 65

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 68

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 71

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 73

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 76

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19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 79

19445 Blake Farms Lane Leonardtown, MD MLS# MDSM2033518 - Image 80

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

40624 Breton Oaks Lane Leonardtown, MD MLS# MDSM2030230 - Image 1

40624 Breton Oaks Lane Leonardtown, MD MLS# MDSM2030230 - Image 2

40624 Breton Oaks Lane Leonardtown, MD MLS# MDSM2030230 - Image 3

New Construction

1 of 3

$804,983

Beds

3.1

Baths

2,745

Sq.Ft.

40624 Breton Oaks Lane

Leonardtown, MD

Courtesy of EXP REALTY, LLC

THE TIME TO SELL IS NOW!

39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258 - Image 1

39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258 - Image 2

39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258 - Image 3

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39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258 - Image 11

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39645 Sweetpea Lane Leonardtown, MD MLS# MDSM2031258 - Image 13

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1 of 67

$799,900

0.0

Baths

39645 Sweetpea Lane

Leonardtown, MD

Courtesy of CENTURY 21 NEW MILLENNIUM

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 1

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 2

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 3

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 4

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 5

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 6

44798 Medleys Neck Road Leonardtown, MD MLS# MDSM2001338 - Image 7

1 of 7

$772,000

Beds

4.1

Baths

3,000

Sq.Ft.

44798 Medleys Neck Road

Leonardtown, MD

Courtesy of RE/MAX REALTY GROUP

40533 Breton Knolls Court Leonardtown, MD MLS# MDSM2033960 - Image 1

New Construction

1 of 1

$739,900

Beds

2.1

Baths

3,460

Sq.Ft.

40533 Breton Knolls Court

Leonardtown, MD

Courtesy of RE/MAX ONE

22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2031732 - Image 1

22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2031732 - Image 2

22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2031732 - Image 3

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22393 Saint Clements Avenue Leonardtown, MD MLS# MDSM2031732 - Image 56

1 of 56

$723,987

Beds

2.2

Baths

2,097

Sq.Ft.

22393 Saint Clements Avenue

Leonardtown, MD

Courtesy of ALLFIRST REALTY, INC.

22405 Hood Lane Leonardtown, MD MLS# MDSM2034290 - Image 1

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Virtual Tour

1 of 60

$699,000

Beds

2.0

Baths

2,400

Sq.Ft.

22405 Hood Lane

Leonardtown, MD

Courtesy of INFINITAS REALTY GROUP

23603 Margrave Drive Leonardtown, MD MLS# MDSM2034184 - Image 1

23603 Margrave Drive Leonardtown, MD MLS# MDSM2034184 - Image 2

23603 Margrave Drive Leonardtown, MD MLS# MDSM2034184 - Image 3

1 of 3

$685,000

Beds

3.1

Baths

4,271

Sq.Ft.

23603 Margrave Drive

Leonardtown, MD

Courtesy of EXP REALTY, LLC

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

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25375 Loveville Road Leonardtown, MD MLS# MDSM2032802 - Image 94

1 of 94

$680,000

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Baths

2,388

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25375 Loveville Road

Leonardtown, MD

Courtesy of RMG REALTY

25033 Meadowlark Court Leonardtown, MD MLS# MDSM2034570 - Image 1

25033 Meadowlark Court Leonardtown, MD MLS# MDSM2034570 - Image 2

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25033 Meadowlark Court Leonardtown, MD MLS# MDSM2034570 - Image 72

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25033 Meadowlark Court

Leonardtown, MD

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

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

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1 of 74

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Baths

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18937 Hodges Lane

Leonardtown, MD

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

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44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 67

44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 68

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44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 72

44450 Schumann Way Leonardtown, MD MLS# MDSM2033456 - Image 73

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

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

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

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21395 Fairwood Court Leonardtown, MD MLS# MDSM2033536 - Image 74

1 of 74

$665,000

Beds

3.1

Baths

4,066

Sq.Ft.

21395 Fairwood Court

Leonardtown, MD

Courtesy of EXP REALTY, LLC

41427 Osborne Lane Leonardtown, MD MLS# MDSM2034242 - Image 1

41427 Osborne Lane Leonardtown, MD MLS# MDSM2034242 - Image 2

41427 Osborne Lane Leonardtown, MD MLS# MDSM2034242 - Image 3

41427 Osborne Lane Leonardtown, MD MLS# MDSM2034242 - Image 4

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41427 Osborne Lane Leonardtown, MD MLS# MDSM2034242 - Image 81

1 of 81

$650,000

Beds

3.1

Baths

3,264

Sq.Ft.

41427 Osborne Lane

Leonardtown, MD

Courtesy of RE/MAX ONE

Lot 7 - 42084 Wildflower Drive Leonardtown, MD MLS# MDSM2031392 - Image 1

Lot 7 - 42084 Wildflower Drive Leonardtown, MD MLS# MDSM2031392 - Image 2

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Lot 7 - 42084 Wildflower Drive Leonardtown, MD MLS# MDSM2031392 - Image 32

Lot 7 - 42084 Wildflower Drive Leonardtown, MD MLS# MDSM2031392 - Image 33

New Construction

1 of 33

$629,900

Beds

2.1

Baths

3,072

Sq.Ft.

Lot 7 - 42084 Wildflower Drive

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

40611 Merion Court Leonardtown, MD MLS# MDSM2033146 - Image 3

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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

Lot 5 - 42096 Wildflower Drive Leonardtown, MD MLS# MDSM2032286 - Image 1

Lot 5 - 42096 Wildflower Drive Leonardtown, MD MLS# MDSM2032286 - Image 2

Lot 5 - 42096 Wildflower Drive Leonardtown, MD MLS# MDSM2032286 - Image 3

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Lot 5 - 42096 Wildflower Drive Leonardtown, MD MLS# MDSM2032286 - Image 44

Lot 5 - 42096 Wildflower Drive Leonardtown, MD MLS# MDSM2032286 - Image 45

New Construction

1 of 45

$619,900

Beds

2.1

Baths

2,976

Sq.Ft.

Lot 5 - 42096 Wildflower Drive

Leonardtown, MD

Courtesy of RE/MAX ONE

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 1

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 2

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 3

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23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 38

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 39

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 40

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 41

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 42

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 43

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 44

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 45

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 46

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 47

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 48

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 49

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 50

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 51

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 52

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 53

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 54

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 55

23620 Gunnell Drive Leonardtown, MD MLS# MDSM2032660 - Image 56

Virtual Tour

1 of 56

$615,000

Beds

4.0

Baths

4,346

Sq.Ft.

23620 Gunnell Drive

Leonardtown, MD

Courtesy of COLDWELL BANKER PREMIER

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 1

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 2

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 3

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 4

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 5

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 6

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 7

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 8

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 9

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 10

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 11

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 12

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 13

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 14

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 15

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 16

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 17

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 18

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 19

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 20

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 21

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 22

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 23

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 24

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 25

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 26

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 27

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 28

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 29

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 30

Lot 3 - 42108 Wildflower Drive Leonardtown, MD MLS# MDSM2032268 - Image 31

New Construction

1 of 31

$614,900

Beds

2.1

Baths

3,072

Sq.Ft.

Lot 3 - 42108 Wildflower Drive

Leonardtown, MD

Courtesy of RE/MAX ONE

About Leonardtown

Listings in Leonardtown, MD: 87
Estimated median home price: $505,000

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	1
$100K - 200K	5
$200K - 300K	7
$300K - 400K	4
$400K - 500K	26
$500K - 600K	16
$600K - 700K	14
$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	59
Townhouse	14
Condo	1
Commercial	0
Rental	13
Lots and Land	13
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 11/14/2026)

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20650

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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

About Leonardtown

Listings in Leonardtown, MD

Estimated median home price

Homes for Sale by Price in Leonardtown, MD

Homes for Sale by Type in Leonardtown, MD

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Leonardtown, MD Information

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