Recently sold homes in Leonardtown, MD

60 homes sold in Leonardtown, MD in the last year. Each links to its full sale record — price, photos, and details.

$483,400Sold Jun 2026

Lot 137- 23667 WEEPING WILLOW WAY,LEONARDTOWN,MD,20650,SAINT MARYS

Leonardtown, MD 20650

4 bd · 4 ba · 2,966 sqft

$753,000Sold Jun 2026

21390 LITTLE SAINT ANNES LANE

Leonardtown, MD 20650

4 bd · 4 ba · 3,500 sqft

$540,000Sold Jun 2026

40855 SPRING HOUSE LANE

Leonardtown, MD 20650

5 bd · 3 ba · 3,464 sqft

$530,000Sold Jun 2026

23207 MOAKLEY STREET

Leonardtown, MD 20650

3 bd · 3 ba · 1,926 sqft

$565,000Sold Jun 2026

21767 Potomac View Dr, Leonardtown, MD 20650-2131, United States

Leonardtown, MD 20650

4 bd · 4 ba · 4,384 sqft

$646,000Sold Jun 2026

23621 MARGRAVE DRIVE

Leonardtown, MD 20650

4 bd · 4 ba · 3,664 sqft

$565,000Sold May 2026

20260 HAWKS WAY

Leonardtown, MD 20650

4 bd · 3 ba · 2,500 sqft

$449,900Sold May 2026

Lot 100 - 23719 DRAGONFLY LN,LEONARDTOWN,MD,20650,SAINT MARYS

Leonardtown, MD 20650

4 bd · 4 ba · 2,571 sqft

$479,900Sold May 2026

Lot 102- 23707 DRAGONFLY LN,LEONARDTOWN,MD,20650,SAINT MARYS

Leonardtown, MD 20650

4 bd · 4 ba · 0 sqft

$650,000Sold May 2026

23563 BELMAR DRIVE

Leonardtown, MD 20650

4 bd · 4 ba · 3,299 sqft

$646,000Sold May 2026

23073 TOWN RUN DRIVE

Leonardtown, MD 20650

3 bd · 2 ba · 2,854 sqft

$865,000Sold May 2026

40171 LITTLE WOODS LANE

Leonardtown, MD 20650

4 bd · 2 ba · 2,586 sqft

$635,000Sold May 2026

23590 MARGRAVE DRIVE

Leonardtown, MD 20650

4 bd · 4 ba · 3,736 sqft

$315,000Sold May 2026

22175 BAYSIDE RD,LEONARDTOWN,MD,20650,SAINT MARYS

Leonardtown, MD 20650

2 bd · 2 ba · 1,192 sqft

$961,000Sold May 2026

40003 TIPPIT ROAD

Leonardtown, MD 20650

3 bd · 3 ba · 2,490 sqft

$750,000Sold May 2026

20752 PENANSEY LANE

Leonardtown, MD 20650

5 bd · 4 ba · 2,936 sqft

$449,900Sold May 2026

Lot 110 - 23678 WEEPING WILLOW WAY

Leonardtown, MD 20650

4 bd · 4 ba · 2,571 sqft

$449,900Sold May 2026

Lot 134 - 23685 WEEPING WILLOW WAY

Leonardtown, MD 20650

4 bd · 4 ba · 2,554 sqft

$1,100,000Sold May 2026

20045 TOWER HILL ROAD

Leonardtown, MD 20650

5 bd · 7 ba · 7,376 sqft

$690,000Sold Mar 2026

41438 Silver Charm

Leonardtown, MD 20650

5 bd · 4 ba · 4,180 sqft

$700,000Sold Mar 2026

39825 Sweetpea

Leonardtown, MD 20650

4 bd · 4 ba · 2,442 sqft

$439,900Sold Mar 2026

Lot 105 - 23689 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$475,000Sold Mar 2026

40910 Starling

Leonardtown, MD 20650

3 bd · 3 ba · 3,012 sqft

$580,000Sold Mar 2026

23593 Mitchell

Leonardtown, MD 20650

5 bd · 4 ba · 2,940 sqft

$535,000Sold Mar 2026

41635 Ferber

Leonardtown, MD 20650

4 bd · 3 ba · 2,222 sqft

$664,900Sold Mar 2026

41515 Risen Star

Leonardtown, MD 20650

5 bd · 4 ba · 4,136 sqft

$285,500Sold Mar 2026

22745 Duke

Leonardtown, MD 20650

2 bd · 1 ba · 868 sqft

$439,900Sold Mar 2026

Lot 104 - 23695 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$560,000Sold Mar 2026

20753 Chestnut Ridge

Leonardtown, MD 20650

4 bd · 3 ba · 2,594 sqft

$575,000Sold Mar 2026

21060 Woodmere

Leonardtown, MD 20650

5 bd · 4 ba · 3,075 sqft

$475,203Sold Mar 2026

20697 Chingville

Leonardtown, MD 20650

3 bd · 2 ba · 2,458 sqft

$487,000Sold Feb 2026

21738 Pinehurst

Leonardtown, MD 20650

4 bd · 3 ba · 1,952 sqft

$519,900Sold Feb 2026

20250 Hawks

Leonardtown, MD 20650

3 bd · 2 ba · 1,557 sqft

$458,550Sold Feb 2026

lot 106 - 23683 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$690,000Sold Feb 2026

42975 Baywood

Leonardtown, MD 20650

4 bd · 3 ba · 3,372 sqft

$645,900Sold Feb 2026

23581 Gallent Fox

Leonardtown, MD 20650

4 bd · 4 ba · 3,736 sqft

$405,000Sold Feb 2026

19137 Lake Drive

Leonardtown, MD 20650

3 bd · 3 ba · 1,308 sqft

$1,052,000Sold Feb 2026

22164 Miller

Leonardtown, MD 20650

4 bd · 3 ba · 2,700 sqft

$715,000Sold Feb 2026

41832 Foxwell Point

Leonardtown, MD 20650

3 bd · 4 ba · 3,683 sqft

$340,000Sold Feb 2026

22820 Duke

Leonardtown, MD 20650

3 bd · 2 ba · 1,422 sqft

$459,900Sold Feb 2026

Lot 107-23677 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$520,000Sold Feb 2026

42043 Starlight

Leonardtown, MD 20650

4 bd · 4 ba · 2,472 sqft

$465,000Sold Feb 2026

21925 Budds Creek

Leonardtown, MD 20650

0 bd · 0 ba · 2,527 sqft

$550,000Sold Feb 2026

22338 White Oak

Leonardtown, MD 20650

4 bd · 3 ba · 2,328 sqft

$639,000Sold Feb 2026

41430 Challedon

Leonardtown, MD 20650

5 bd · 4 ba · 4,500 sqft

$520,000Sold Jan 2026

21920 Newtowne Neck

Leonardtown, MD 20650

4 bd · 3 ba · 2,291 sqft

$439,900Sold Jan 2026

Lot 95 - 23718 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$529,900Sold Jan 2026

41895 Tomey

Leonardtown, MD 20650

5 bd · 4 ba · 3,482 sqft

$425,000Sold Jan 2026

25365 Point Lookout

Leonardtown, MD 20650

3 bd · 3 ba · 2,952 sqft

$469,900Sold Jan 2026

Lot 103 - 23701 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$465,000Sold Jan 2026

43543 Bayberry

Leonardtown, MD 20650

3 bd · 2 ba · 1,732 sqft

$50,000Sold Jan 2026

44646 Medleys Neck

Leonardtown, MD 20650

3 bd · 1 ba · 924 sqft

$637,000Sold Jan 2026

41492 Charismatic

Leonardtown, MD 20650

4 bd · 4 ba · 3,322 sqft

$580,000Sold Jan 2026

21039 Woodmere

Leonardtown, MD 20650

5 bd · 3 ba · 4,112 sqft

$510,000Sold Dec 2025

41535 Singletree

Leonardtown, MD 20650

4 bd · 3 ba · 2,262 sqft

$510,000Sold Dec 2025

41467 Osborne

Leonardtown, MD 20650

4 bd · 4 ba · 2,827 sqft

$447,400Sold Dec 2025

Lot 88 - 23676 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba · 2,604 sqft

$635,000Sold Dec 2025

45474 Medleys Neck

Leonardtown, MD 20650

3 bd · 3 ba · 2,653 sqft

$447,400Sold Dec 2025

Lot 96-23724 Dragonfly

Leonardtown, MD 20650

4 bd · 4 ba

$614,900Sold Dec 2025

22626 Chickadee

Leonardtown, MD 20650

4 bd · 4 ba · 3,048 sqft

Listing information is provided through IDX courtesy Keller Williams Capital Properties.

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