Recently Sold Homes in Leonardtown, MD

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SOLD NOV 14, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
This home features 4 spacious Bedrooms, an open Kitchen & great room w/ built-in TV Niche over the gas Fireplace. There is a full basement w/ rough-in. A Walk-in jetted tub and electric stair chair have been added. The property has a large, level fenced back yard with raised garden beds and is at the end of a cul-de-sac! The back deck provides space for cooking out and private entertaining. Located within walking distance to Leonardtown’s shops, restaurants, waterfront, and hospital, and is in the Leonardtown school district.

$475,000 Last sold price

4 beds2.5 baths2,230 sq ft

41650 Matthew Ct, Leonardtown, MD 20650

(301) 862-0008

SOLD SEP 26, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
Welcome home to this beautifully maintained one-level brick front residence, offering a thoughtfully designed split-bedroom floorplan ideal for both comfort and privacy. With 3 bedrooms and 2 full baths, this home features a welcoming foyer entry that leads to a spacious formal dining area, perfect for gatherings and special occasions. The family room boasts vaulted ceilings and a cozy gas fireplace, providing a warm and inviting space to relax with family and friends. The kitchen is a perfect space for culinary creativity, featuring a large walk-in pantry, 42" cabinets, and a cozy breakfast area with a sliding door that opens directly onto the screened porch — a perfect spot to

$545,000 Last sold price

3 beds2 baths2,102 sq ft

23220 Brandon Ct, Leonardtown, MD 20650

(301) 862-2169

SOLD NOV 18, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
Welcome to your ideal home in the sought-after Hanover at Breton Bay! This beautiful, spacious home shines with thoughtful design, featuring hardwood floors that flow through a bright, open-concept layout and a striking two-story foyer. The well-appointed kitchen is a cook’s dream, with ample cabinetry, generous countertops, a spacious center island, and a cozy breakfast nook, effortlessly connecting to a warm family room with a gas fireplace and large windows that invite natural light. The elegant dining room, accented with crown molding, sets the stage for memorable gatherings. On the main level there is also flex room with an attached full bath serves as a perfect guest bedroom or

$629,000 Last sold price

4 beds3 baths3,404 sq ft

22305 Hanover Dr, Leonardtown, MD 20650

(301) 862-2169

SOLD SEP 19, 2025

$633,000 Last sold price

4 beds3.5 baths3,745 sq ft

22272 Orchard Ct, Leonardtown, MD 20650

(443) 771-8009

SOLD SEP 19, 20253D WALKTHROUGH

$520,000 Last sold price

4 beds2.5 baths2,649 sq ft

21158 Marigold St, Leonardtown, MD 20650

(855) 450-0442

Property at 21137 Marigold St, Leonardtown, MD 20650, 4 beds, 2.5 baths

$555,000 Last sold price

4 beds2.5 baths2,382 sq ft

21137 Marigold St, Leonardtown, MD 20650

(301) 452-5691

Property at 41900 Nazareth Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$460,000 Last sold price

4 beds2.5 baths2,528 sq ft

41900 Nazareth Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 41130 Cryer Ct, Leonardtown, MD 20650, 3 beds, 2 baths

$485,000 Last sold price

3 beds2 baths1,488 sq ft

41130 Cryer Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 20591 Chestnut Ridge Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$599,900 Last sold price

5 beds3.5 baths3,061 sq ft

20591 Chestnut Ridge Dr, Leonardtown, MD 20650

(888) 860-7369

Property at 43107 Gum Spring Dr, Leonardtown, MD 20650, 3 beds, 2.5 baths

$625,000 Last sold price

3 beds2.5 baths2,742 sq ft

43107 Gum Spring Dr, Leonardtown, MD 20650

(888) 860-7369

Property at 40801 Kiskadee Ln, Leonardtown, MD 20650, 5 beds, 3 baths

$740,000 Last sold price

5 beds3 baths6,064 sq ft

40801 Kiskadee Ln, Leonardtown, MD 20650

(410) 535-6291

Property at 43571 Bayberry Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$600,000 Last sold price

4 beds2.5 baths2,946 sq ft

43571 Bayberry Ct, Leonardtown, MD 20650

(888) 860-7369

Property at 21056 Woodmere Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$500,000 Last sold price

4 beds2.5 baths2,205 sq ft

21056 Woodmere Dr, Leonardtown, MD 20650

(301) 645-1700

Property at 23650 Rocky Ridge Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$599,000 Last sold price

4 beds3.5 baths3,914 sq ft

23650 Rocky Ridge Ct, Leonardtown, MD 20650

(410) 413-3575

Property at 21745 Pinehurst Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$610,000 Last sold price

4 beds2.5 baths2,860 sq ft

21745 Pinehurst Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 21055 Breton Beach Ct, Leonardtown, MD 20650, 3 beds, 2.5 baths

$1,215,200 Last sold price

3 beds2.5 baths3,052 sq ft

21055 Breton Beach Ct, Leonardtown, MD 20650

(833) 335-7433

Property at 23849 Point Lookout Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$355,000 Last sold price

3 beds2 baths1,092 sq ft

23849 Point Lookout Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 22798 Lawrence Ave, Leonardtown, MD 20650, 3 beds, 1.5 baths

$350,000 Last sold price

3 beds1.5 baths1,160 sq ft

22798 Lawrence Ave, Leonardtown, MD 20650

(410) 326-3133

Property at 21515 Our Drive Way, Leonardtown, MD 20650, 4 beds, 2 baths

$492,000 Last sold price

4 beds2 baths1,848 sq ft

21515 Our Drive Way, Leonardtown, MD 20650

(301) 862-2169

Property at 21784 Potomac View Dr, Leonardtown, MD 20650, 3 beds, 1 bath

$287,000 Last sold price

3 beds1 bath1,056 sq ft

21784 Potomac View Dr, Leonardtown, MD 20650

(410) 286-9632

Property at 23730 Hicks Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$402,000 Last sold price

3 beds2 baths1,992 sq ft

23730 Hicks Dr, Leonardtown, MD 20650

(833) 335-7433

Property at 23745 Bayside Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$415,000 Last sold price

3 beds2 baths1,344 sq ft

23745 Bayside Rd, Leonardtown, MD 20650

(301) 702-4200

Property at 22186 Monterey Pl, Leonardtown, MD 20650, 4 beds, 2 baths

$510,000 Last sold price

4 beds2 baths2,935 sq ft

22186 Monterey Pl, Leonardtown, MD 20650

(703) 535-3610 Redfin Corp

Property at 20620 Laurel Ct, Leonardtown, MD 20650, 5 beds, 3 baths

$710,000 Last sold price

5 beds3 baths3,500 sq ft

20620 Laurel Ct, Leonardtown, MD 20650

(443) 295-6123

Property at 44504 Watson Ln, Leonardtown, MD 20650, 3 beds, 2 baths

$465,000 Last sold price

3 beds2 baths2,304 sq ft

44504 Watson Ln, Leonardtown, MD 20650

(301) 863-2400

Property at 22530 Bull Rd, Leonardtown, MD 20650, 3 beds, 3 baths

$575,000 Last sold price

3 beds3 baths1,976 sq ft

22530 Bull Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 23280 Hollywood Rd, Leonardtown, MD 20650, 3 beds, 1 bath

$330,000 Last sold price

3 beds1 bath1,402 sq ft

23280 Hollywood Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 20814 Deer Wood Park Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$560,000 Last sold price

4 beds2.5 baths3,412 sq ft

20814 Deer Wood Park Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 20919 Ridge Path Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$549,000 Last sold price

4 beds3.5 baths3,465 sq ft

20919 Ridge Path Way, Leonardtown, MD 20650

(240) 925-2224

Property at 20413 Scarlet Tanager Way, Leonardtown, MD 20650, 4 beds, 3 baths

$575,000 Last sold price

4 beds3 baths3,094 sq ft

20413 Scarlet Tanager Way, Leonardtown, MD 20650

(301) 862-2169

Property at 43658 Redmond Rd, Leonardtown, MD 20650, 4 beds, 1.5 baths

$281,650 Last sold price

4 beds1.5 baths2,078 sq ft

43658 Redmond Rd, Leonardtown, MD 20650

(301) 609-9000

Property at 21983 Point Lookout Rd, Leonardtown, MD 20650, 2 beds, 1 bath

$163,500 Last sold price

2 beds1 bath1,144 sq ft

21983 Point Lookout Rd, Leonardtown, MD 20650

(410) 488-3124

Property at 21385 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 4 baths

$709,000 Last sold price

4 beds4 baths3,970 sq ft

21385 Fairwood Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 40552 Breton Knolls Ct, Leonardtown, MD 20650, 4 beds, 4.5 baths

$971,725 Last sold price

4 beds4.5 baths4,000 sq ft

40552 Breton Knolls Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 23534 Belmar Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$639,000 Last sold price

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 41430 Whimsical Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$645,000 Last sold price

5 beds3.5 baths3,907 sq ft

41430 Whimsical Ct, Leonardtown, MD 20650

(443) 256-3773

Property at 41480 Whimsical Ct, Leonardtown, MD 20650, 5 beds, 4 baths

$680,000 Last sold price

5 beds4 baths3,825 sq ft

41480 Whimsical Ct, Leonardtown, MD 20650

(703) 229-8935

Property at 23155 Greenstone, Leonardtown, MD 20650, 6 beds, 3.5 baths

$1,300,000 Last sold price

6 beds3.5 baths5,888 sq ft

23155 Greenstone, Leonardtown, MD 20650

(301) 884-9493

Property at 23647 Hansel Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$660,000 Last sold price

5 beds3.5 baths3,194 sq ft

23647 Hansel Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 23242 Clarks Rest Rd, Leonardtown, MD 20650, 5 beds, 3.5 baths

$589,000 Last sold price

5 beds3.5 baths3,296 sq ft

23242 Clarks Rest Rd, Leonardtown, MD 20650

(240) 925-2224

Property at 23246 Lindsay Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$625,000 Last sold price

5 beds3.5 baths3,876 sq ft

23246 Lindsay Dr, Leonardtown, MD 20650

(301) 862-2169

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Recently Sold Homes in Leonardtown

There are currently 63 recently sold homes for sale in Leonardtown at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Leonardtown stay on the market for 53 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 11 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 13 townhouses, and 0 multi-family units for sale in Leonardtown last month. Find your dream home in Leonardtown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Leonardtown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Leonardtown. Our Leonardtown real estate stats and trends will give you more information about home buying and selling trends in Leonardtown. If you're looking to sell your home in the Leonardtown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Leonardtown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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