20650, MD homes for sale & real estate

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NEW 9 HRS AGO

41554 Briarwood Cir, Leonardtown, MD 20650
41554 Briarwood Cir, Leonardtown, MD 20650
41554 Briarwood Cir, Leonardtown, MD 20650

$445,000

3 beds3.5 baths2,379 sq ft

41554 Briarwood Cir, Leonardtown, MD 20650

2,280 sq ft lot • $69 HOA • 2 garage spots

(301) 884-9493

COMING SOON

41130 Cryer Ct, Leonardtown, MD 20650
41130 Cryer Ct, Leonardtown, MD 20650
41130 Cryer Ct, Leonardtown, MD 20650
ABOUT THIS HOME
20650, MD Homes for Sale
A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square foot basement, this 3 bedroom 2 bathroom home shows potential for amazing views and waterfront living. The well has a recent water quality certification. The owner will make repairs to the septic system including replacing the tank with a BAT septic system and replacing the distribution box due to its age. The Grant application has been submitted. The exceptional

$550,000

3 beds2 baths1,488 sq ft

41130 Cryer Ct, Leonardtown, MD 20650

1.05 acre lot • Garage • Car-dependent

(301) 862-2169

41997 Loker Ct, Leonardtown, MD 20650
41997 Loker Ct, Leonardtown, MD 20650
41997 Loker Ct, Leonardtown, MD 20650
ABOUT THIS HOME
20650, MD Homes for Sale
Boast in the benefit of this cul-de-sac home on the outskirts of town that backs to a farm but with the closeness and convenience of being so close to area schools, restaurants, stores, and hospital. This home is ready for you to make it your own. The backyard privacy with deck and patio are great for enjoying the nature sounds. Large shed to keep the tools needed to keep the beautiful lawn and shrubs in their pristine state or use as a workshop. Get your tour scheduled soon so you don't miss out.

$479,900

4 beds2.5 baths2,330 sq ft

41997 Loker Ct, Leonardtown, MD 20650

0.25 acre lot • $17 HOA • Car-dependent

(301) 884-9493

40461 Old Breton Beach Rd, Leonardtown, MD 20650
40461 Old Breton Beach Rd, Leonardtown, MD 20650
40461 Old Breton Beach Rd, Leonardtown, MD 20650
ABOUT THIS HOME
20650, MD Homes for Sale
Welcome to 40461 Old Breton Beach Road—a breathtaking waterfront retreat on the shores of the Potomac River in Leonardtown, Maryland. Nestled in one of Southern Maryland’s most scenic and peaceful communities, this coastal-style home offers the perfect blend of charm, functionality, and panoramic water views that will leave you speechless. Perfect for a primary or rental. From the moment you arrive, you'll be captivated by the stunning setting and relaxed elegance. Step inside to discover an open floor plan featuring wood floors, and an abundance of natural light that pours through large windows and the glass-enclosed porch—perfect for soaking in the serene river views all

$700,000

3 beds2.5 baths2,040 sq ft

40461 Old Breton Beach Rd, Leonardtown, MD 20650

0.34 acre lot • 3 garage spots • Car-dependent

(410) 535-6291

OPEN JUN 21, 1PM TO 2PM3D WALKTHROUGH

23745 Hicks Dr, Leonardtown, MD 20650
23745 Hicks Dr, Leonardtown, MD 20650
23745 Hicks Dr, Leonardtown, MD 20650
ABOUT THIS HOME
20650, MD Homes for Sale
Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA. Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed lighting, and an upgraded kitchen with granite countertops, stainless steel appliances, and stylish two tone cabinetry. Just off the kitchen, a back deck overlooks the large, fully fenced yard—perfect for relaxing, entertaining, or letting pets roam freely. The main level offers three bedroom

$398,000

3 beds2 baths984 sq ft

23745 Hicks Dr, Leonardtown, MD 20650

0.6 acre lot • 4 garage spots • Car-dependent

(443) 221-4120

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

$1,300,000

6 beds3.5 baths5,888 sq ft

23155 Greenstone, Leonardtown, MD 20650

(301) 884-9493

Property at 41699 Courthouse Dr, Leonardtown, MD 20650, 5 beds, 3 baths

$525,000

5 beds3 baths2,420 sq ft

41699 Courthouse Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 23674 Jm Gough Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$550,000

4 beds2.5 baths2,697 sq ft

23674 Jm Gough Ct, Leonardtown, MD 20650

(443) 771-8009

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

$615,000

5 beds3.5 baths3,061 sq ft

20591 Chestnut Ridge Dr, Leonardtown, MD 20650

(888) 860-7369

Property at 41535 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 4 baths

$750,000

4 beds4 baths4,829 sq ft

41535 Fairwood Ct, Leonardtown, MD 20650

(888) 860-7369

Property at 41430 Challedon Way, Leonardtown, MD 20650, 5 beds, 3.5 baths

$650,000

5 beds3.5 baths4,500 sq ft

41430 Challedon Way, Leonardtown, MD 20650

(443) 771-8009

Property at 21143 Catnip Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$635,000

4 beds2.5 baths2,642 sq ft

21143 Catnip Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 41412 Doctors Crossing Rd, Leonardtown, MD 20650, 4 beds, 3.5 baths

$540,000

4 beds3.5 baths2,686 sq ft

41412 Doctors Crossing Rd, Leonardtown, MD 20650

(301) 702-4200

Property at 41115 Paw Paw Hollow Ln, Leonardtown, MD 20650, 4 beds, 5.5 baths

$775,000

4 beds5.5 baths6,116 sq ft

41115 Paw Paw Hollow Ln, Leonardtown, MD 20650

(301) 862-2169

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

$785,000

5 beds3 baths6,064 sq ft

40801 Kiskadee Ln, Leonardtown, MD 20650

(410) 535-6291

Property at 23075 Hollywood Rd, Leonardtown, MD 20650, 5 beds, 2.5 baths

$574,000

5 beds2.5 baths3,238 sq ft

23075 Hollywood Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 44646 Medleys Neck Rd, Leonardtown, MD 20650, 3 beds, 1 bath

$125,000

3 beds1 bath924 sq ft

44646 Medleys Neck Rd, Leonardtown, MD 20650

(301) 862-4000

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

$610,000

4 beds2.5 baths3,412 sq ft

20814 Deer Wood Park Dr, Leonardtown, MD 20650

(301) 862-2169

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

$599,000

5 beds3.5 baths2,296 sq ft

23242 Clarks Rest Rd, Leonardtown, MD 20650

(240) 925-2224

Property at 41505 Knight Rd, Leonardtown, MD 20650, 5 beds, 7 baths

$5,950,000

5 beds7 baths12,113 sq ft

41505 Knight Rd, Leonardtown, MD 20650

(443) 292-6767

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

$649,900

4 beds3.5 baths2,948 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

(301) 684-4895

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

$649,999

5 beds3.5 baths3,907 sq ft

41430 Whimsical Ct, Leonardtown, MD 20650

(443) 256-3773

Property at 23275 Jenifer Ct, Leonardtown, MD 20650, 5 beds, 4.5 baths

$634,900

5 beds4.5 baths6,311 sq ft

23275 Jenifer Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 24554 Pin Cushion Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$355,000

3 beds2 baths1,856 sq ft

24554 Pin Cushion Rd, Leonardtown, MD 20650

(301) 472-4422

Property at 18937 Hodges Ln, Leonardtown, MD 20650, 3 beds, 2 baths

$699,900

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

(301) 609-9000

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

$655,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 862-2169

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

$419,500

3 beds2 baths1,992 sq ft

23730 Hicks Dr, Leonardtown, MD 20650

(833) 335-7433

Property at 23266 Clarks Rest Rd, Leonardtown, MD 20650, 4 beds, 3.5 baths

$665,000

4 beds3.5 baths3,858 sq ft

23266 Clarks Rest Rd, Leonardtown, MD 20650

(301) 862-2169

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

$659,000

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

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

$599,900

5 beds4 baths3,540 sq ft

23348 Lindsay Dr, Leonardtown, MD 20650

(301) 439-9500

Property at 22362 Armstrong Dr, Leonardtown, MD 20650, 3 beds, 3 baths

$439,900

3 beds3 baths2,028 sq ft

22362 Armstrong Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 20798 Waterside Dr, Leonardtown, MD 20650, 2 beds, 1 bath

$450,000

2 beds1 bath1,018 sq ft

20798 Waterside Dr, Leonardtown, MD 20650

(301) 472-4422

Property at Undisclosed address, Leonardtown, MD 20650, 4 beds, 2 baths

$1,750,000

4 beds2 baths2,130 sq ft

Undisclosed address, Leonardtown, MD 20650

(301) 686-0545

Property at 19700 Mulberry Fields Rd, Leonardtown, MD 20650, 6 beds, 4.5 baths

$20,000,000

6 beds4.5 baths13,458 sq ft

19700 Mulberry Fields Rd, Leonardtown, MD 20650

(202) 483-6300

Property at 20959 Redgate Ln, Leonardtown, MD 20650, 3 beds, 1 bath

$315,000

3 beds1 bath1,026 sq ft

20959 Redgate Ln, Leonardtown, MD 20650

(443) 660-9229

Property at 25365 Point Lookout Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$497,500

3 beds2 baths2,952 sq ft

25365 Point Lookout Rd, Leonardtown, MD 20650

(301) 862-2169

Property at 41810 Chelsey Faye Ln, Leonardtown, MD 20650, 4 beds, 3 baths

$675,000

4 beds3 baths2,650 sq ft

41810 Chelsey Faye Ln, Leonardtown, MD 20650

(301) 684-4895

Property at Wathen Rd, Leonardtown, MD 20650, 5 beds, 4 baths

$831,025

5 beds4 baths4,700 sq ft

Wathen Rd, Leonardtown, MD 20650

(240) 224-8005

Property at 40533 Breton Knolls Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$859,900

4 beds2.5 baths— sq ft

40533 Breton Knolls Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 40552 Breton Knolls Ct, Leonardtown, MD 20650, 5 beds, 2.5 baths

$884,900

5 beds2.5 baths3,127 sq ft

40552 Breton Knolls Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 42520 Riverwinds Dr, Leonardtown, MD 20650, 4 beds, 2 baths

$1,999,999

4 beds2 baths2,744 sq ft

42520 Riverwinds Dr, Leonardtown, MD 20650

(301) 862-2169

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Zip Codes

20650, MD real estate trends

All Home Types trends in 20650, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$607,500

+4.8% YoY | May 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2025

Growth

% YoY

20650, MD

$607,500

+4.8%

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