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 DEC 5, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your hobbies are. There is even yoga on the wharf, You can walk to weekend concerts on the square. Leonardtown is a wonderful place to live. How about an elevator? This home has one. Send your groceries up in the elevator. Send you laundry down in the elevator, 5 decks/porches to enjoy outdoor living. Walk to the community park. Everything is right where you need it in this lovely home. A must see.

$518,500 Last sold price

3 beds3.5 baths2,764 sq ft

22539 Landing Way, Leonardtown, MD 20650

(888) 860-7369

SOLD DEC 5, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
This Colonial in the sought-after Estates at Singletree offers 5 bedrooms, 3.5 baths, and three finished levels in one of Leonardtown’s most convenient locations are just behind St. Mary’s Hospital. The fully finished basement is a highlight, featuring a home theater room, a rec room, a large bedroom with a walk-in closet, and a full bath. Upstairs, you will find four additional bedrooms, including a spacious primary suite with a soaking tub, a separate shower, and double sinks. New carpet has been installed throughout this level. The main floor includes a formal living and dining room with built-ins, an office, and a large family room with a stone front fireplace and hardwood f

$565,000 Last sold price

5 beds3.5 baths3,575 sq ft

23261 Jenifer Ct, Leonardtown, MD 20650

(301) 855-8600

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 DEC 1, 2025

ABOUT THIS HOME
Recently Sold Home in Leonardtown, MD:
Welcome to Hanover Farms at Breton Bay, one of Leonardtown’s most desirable private water-access communities. This neighborhood offers a true sense of community with its waterfront amenities, perfect for relaxing or spending time outdoors. Enjoy crabbing, fishing, or kayaking from the private neighborhood pier and beach, or gather with friends at the community pavilion, fire pit, or playground. Set in this peaceful and sought-after neighborhood, this spacious home offers a comfortable and functional layout with plenty of room for everyone. The main level includes a private office, formal dining room, and an open-concept kitchen that flows easily into the family room—great for ev

$640,000 Last sold price

5 beds4.5 baths4,206 sq ft

22216 Hanover Dr, Leonardtown, MD 20650

(443) 771-8009

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 41535 Singletree Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$510,000 Last sold price

4 beds2.5 baths2,262 sq ft

41535 Singletree Dr, Leonardtown, MD 20650

(301) 684-4895

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 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 22626 Chickadee Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$614,900 Last sold price

4 beds3.5 baths3,048 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

(240) 925-2224

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 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 22592 Quiet Ln, Leonardtown, MD 20650, 2 beds, 2 baths

$430,000 Last sold price

2 beds2 baths1,908 sq ft

22592 Quiet Ln, Leonardtown, MD 20650

(571) 814-3002

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 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 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 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 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 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 41402 Silver Charm Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$625,000 Last sold price

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 298-2892

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 40534 Miss Ettas Way, Leonardtown, MD 20650, 3 beds, 2.5 baths

$480,000 Last sold price

3 beds2.5 baths1,770 sq ft

40534 Miss Ettas Way, Leonardtown, MD 20650

(410) 535-6291

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

Property at 41474 Charismatic Way, Leonardtown, MD 20650, 5 beds, 3.5 baths

$639,000 Last sold price

5 beds3.5 baths3,647 sq ft

41474 Charismatic Way, Leonardtown, MD 20650

(443) 771-8009

Property at 41435 Osborne Ln, Leonardtown, MD 20650, 6 beds, 4.5 baths

$665,000 Last sold price

6 beds4.5 baths4,145 sq ft

41435 Osborne Ln, Leonardtown, MD 20650

(301) 702-4200

Property at 41467 Osborne Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$510,000 Last sold price

4 beds3.5 baths2,827 sq ft

41467 Osborne Ln, Leonardtown, MD 20650

(301) 892-1131

Property at 23392 Marview Ct, Leonardtown, MD 20650, 3 beds, 3.5 baths

$434,900 Last sold price

3 beds3.5 baths2,306 sq ft

23392 Marview Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 23348 Lindsay Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$570,000 Last sold price

5 beds4 baths3,540 sq ft

23348 Lindsay Dr, Leonardtown, MD 20650

(301) 439-9500

Property at 23098 Town Run Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$681,000 Last sold price

5 beds3.5 baths3,642 sq ft

23098 Town Run Dr, Leonardtown, MD 20650

(301) 702-4200

Property at 23092 Town Run Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$619,000 Last sold price

5 beds3.5 baths3,806 sq ft

23092 Town Run Dr, Leonardtown, MD 20650

(301) 862-2169

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Recently Sold Homes in Leonardtown

There are currently 72 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 56 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 7 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 7 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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