Leonardtown, MD homes for sale & real estate

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OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Desirable Breton Bay Brick Colonial with a NEW ROOF! Enter the soaring two-story foyer of this 4-bedroom, 2.5 bath home, and take note of the refinished hardwood floors, wide staircase with wrought iron railings, and Palladian window that allows for lots of natural light. Head past the shiplap wall treatment into the eat-in kitchen that features tall white cabinets, newer appliances, beautiful Quartz counters, tile backsplash, updated flooring, and pantry closet. For elegant gatherings, a formal living room w/ crown molding, and dining room w/ bump out, make the perfect setting. The family room with a floor-to-ceiling stone hearth, and French doors out the paver patio are great for more inf

$605,000

4 beds2.5 baths2,860 sq ft

21745 Pinehurst Ct, Leonardtown, MD 20650

0.58 acre lot • 2 garage spots • Built 1991

(301) 862-2169

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
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.

$575,000

4 beds2.5 baths2,230 sq ft

41650 Matthew Ct, Leonardtown, MD 20650

0.3 acre lot • 2 garage spots • Built 2006

(301) 862-0008

COMING SOON

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Excellent one level living in Leonardtown just past the high school, NO HOA, and sits on 1.5 acres of land. Front door was replaced in 2018; the rest of the doors and windows were replaced in 2025. Neer shingles replaced in 2015, the hall bathroom updated in 2024. Kitchen features a center island, which leads to a large outdoor deck for grilling and entertaining. Washer and dryer is being " sold as is ". LVT throughout the home, kitchen does have sheet vinyl, ceramic tile in both bathrooms. A large shed on the corner of the back yard for storing those extra yard tools. Great opportunity to live in Leonardtown.

$335,000

3 beds2 baths1,092 sq ft

23849 Point Lookout Rd, Leonardtown, MD 20650

1.52 acre lot • Car-dependent

(301) 862-2169

OPEN SAT, 11:30AM TO 1:30PM

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 baths with laminate hardwood floors throughout the first level. The kitchen features quartz countertops and opens to a living room with a cozy gas fireplace, as well as a formal dining room and sitting area, perfect for gatherings and everyday living. Upstairs, you’ll find four spacious bedrooms, while outside, a level lot and deck provide space for cooking out and private entertaining. Located within walking distance to Leonardtown’s shops, restaurants, waterfront, and hospital, and served by sought-after Leonardtown schools. This property also has a 2.25% assumable VA mortgage, offering qual

$530,000

4 beds2.5 baths2,262 sq ft

41535 Singletree Dr, Leonardtown, MD 20650

0.26 acre lot • 2 garage spots • Built 2002

(301) 684-4895

COMING SOON

$559,900

4 beds3.5 baths2,472 sq ft

42043 Starlight Dr, Leonardtown, MD 20650

1.02 acre lot • $35 HOA • 2 garage spots

(443) 771-8009

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

$675,000

6 beds4.5 baths4,145 sq ft

41435 Osborne Ln, Leonardtown, MD 20650

(301) 702-4200

Property at 21039 Woodmere Dr, Leonardtown, MD 20650, 5 beds, 2.5 baths

$595,000

5 beds2.5 baths4,112 sq ft

21039 Woodmere Dr, Leonardtown, MD 20650

(301) 884-9493

Property at 22323 Saint Clements Ave, Leonardtown, MD 20650, 2 beds, 2 baths

$249,000

2 beds2 baths1,200 sq ft

22323 Saint Clements Ave, Leonardtown, MD 20650

(240) 925-2224

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

$569,000

4 beds2.5 baths3,412 sq ft

20814 Deer Wood Park Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 41536 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths3,308 sq ft

41536 Fairwood Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 40461 Old Breton Beach Rd, Leonardtown, MD 20650, 2 beds, 2.5 baths

$689,900

2 beds2.5 baths2,040 sq ft

40461 Old Breton Beach Rd, Leonardtown, MD 20650

(855) 450-0442

Property at 21117 Catnip Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$649,900

5 beds3.5 baths3,526 sq ft

21117 Catnip Ct, Leonardtown, MD 20650

(443) 968-9595

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

$70,000

2 beds1 bath1,144 sq ft

21983 Point Lookout Rd, Leonardtown, MD 20650

(410) 488-3124

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

$550,000

3 beds2 baths1,488 sq ft

41130 Cryer Ct, Leonardtown, MD 20650

(301) 862-2169

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

$239,000

3 beds1 bath1,026 sq ft

20959 Redgate Ln, Leonardtown, MD 20650

(443) 660-9229

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

$599,900

5 beds3.5 baths3,061 sq ft

20591 Chestnut Ridge Dr, Leonardtown, MD 20650

(888) 860-7369

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

$635,000

4 beds3.5 baths3,048 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

(240) 925-2224

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

$649,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 862-2169

Property at 23676 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths2,604 sq ft

23676 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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

$470,000

4 beds2.5 baths2,528 sq ft

41900 Nazareth Ct, Leonardtown, MD 20650

(443) 771-8009

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

$549,000

4 beds3.5 baths3,465 sq ft

20919 Ridge Path Way, Leonardtown, MD 20650

(240) 925-2224

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

$599,000

5 beds3.5 baths3,296 sq ft

23242 Clarks Rest Rd, Leonardtown, MD 20650

(240) 925-2224

Property at 39825 Sweetpea Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$790,000

4 beds3.5 baths2,442 sq ft

39825 Sweetpea Ln, Leonardtown, MD 20650

(443) 771-8009

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

$470,000

3 beds2.5 baths1,770 sq ft

40534 Miss Ettas Way, Leonardtown, MD 20650

(410) 535-6291

Property at 23264 Lindsay Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$610,000

3 beds2 baths2,824 sq ft

23264 Lindsay Dr, Leonardtown, MD 20650

(301) 884-9493

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

$549,900

4 beds2.5 baths2,205 sq ft

21056 Woodmere Dr, Leonardtown, MD 20650

(301) 645-1700

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

$659,000

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

(301) 609-9000

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

$429,900

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

(410) 535-6291

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

$720,000

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

Property at 19921 Tower Hill Rd, Leonardtown, MD 20650

$130,000

— beds— baths— sq ft

19921 Tower Hill Rd, Leonardtown, MD 20650

(301) 884-9493

Property at Kiskadee Ln, Leonardtown, MD 20650

$200,000

— beds— baths— sq ft

Kiskadee Ln, Leonardtown, MD 20650

(410) 535-6291

Property at 39645 Sweetpea Ln, Leonardtown, MD 20650

$799,900

— beds— baths— sq ft

39645 Sweetpea Ln, Leonardtown, MD 20650

(301) 609-9000

Property at 41815 Chelsey Faye, Leonardtown, MD 20650

$95,000

— beds— baths— sq ft

41815 Chelsey Faye, Leonardtown, MD 20650

(301) 684-4895

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Zip Codes

Leonardtown, MD real estate trends

All Home Types trends in Leonardtown, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$630,000

+46.5% YoY | Aug 2025

1 year
3 year
5 year

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

Location

Data

Aug 2025

Growth

% YoY

Leonardtown, MD

$630,000

+46.5%

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