Leonardtown, MD homes for sale & real estate

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FLOOR PLAN

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Beautiful colonial in Breton Bay with no HOA, over 3,700 finished square feet across three levels, four bedrooms upstairs, and a private, tree-lined backyard on approximately 0.6 acres. A spacious front porch welcomes you inside to hardwood floors, 9-foot ceilings, crown molding, and custom main-level blinds. The kitchen features maple cabinets and a large pantry and opens to the family room with a gas fireplace. Enjoy the covered, screened back porch with a ceiling fan and a separate deck with a hot tub. The front and back porches feature Trex decking and vinyl railings. Upstairs, the primary suite includes crown molding, a spacious walk-in closet, and an updated bathroom with a remodeled

$590,000

4 beds4 baths3,750 sq ft

22220 Bull Rd, Leonardtown, MD 20650

Hot tub • Gas fireplace • Separate deck

(301) 855-8600

NEW 25 MINS AGO

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
RARE LEONARDTOWN INVESTMENT OPPORTUNITY ON 1.54 ACRES Bring your vision and unlock the incredible potential of this rare 1.54-acre property in one of Southern Maryland's most sought-after locations. The existing home sustained fire damage and is being sold as-is, presenting a unique opportunity for investors, builders, contractors, or buyers looking for the perfect place to renovate or build their dream home. Large parcels this close to the heart of Leonardtown are becoming increasingly difficult to find. With over an acre and a half of land, mature trees, and plenty of space for privacy, the possibilities are endless. Whether you choose to restore the existing home or start fresh, this

$79,900

— beds2 baths1,542 sq ft

21944 Point Lookout Rd, Leonardtown, MD 20650

1.54 acre lot • Built 1930

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Room to spread out comes naturally in this spacious split-foyer home, set on a level one-acre lot with no HOA. The generous setting offers flexibility for outdoor entertaining, gardening, play, or simply enjoying a little extra breathing room without a rulebook hovering nearby. Inside, the main floor delivers 4 bedrooms and 3 full bathrooms, a large family room just off the kitchen and a separate living room. With a full bathroom in the basement, the lower level adds valuable versatility for recreation, hobbies, visitors, or a comfortable retreat away from the main living areas. A oversized attached 2-car garage provides sheltered parking and plenty of room for tools, sporting gear, and the

$444,500

4 beds4 baths2,666 sq ft

20270 Beauvue Ct, Leonardtown, MD 20650

Large family room • Broad level grounds • Outdoor entertaining

(301) 645-1700

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
* * * * * * * * * * VA Assumption Available at 3.35% * * * * * * Welcome to 41427 Osborne Lane, where a charming covered front porch, striking red front door, and beautiful architectural details create an inviting first impression! Located in Clark’s Rest, this Chaptico model offers 4 bedrooms, 3.5 baths, and 3,379 square feet of living space across three finished levels. With fresh paint, new carpet, and new upgraded stainless steel appliances, this home is ready for its next chapter. Inside, nine-foot ceilings and hardwood flooring in the foyer, kitchen, and formal dining room bring warmth and elegance to the main level. The formal dining room provides a lovely settin

$650,000

4 beds3.5 baths3,264 sq ft

41427 Osborne Ln, Leonardtown, MD 20650

Covered front porch • Nine foot ceilings • Red front door

(443) 771-8009

ABOUT THIS HOME
Leonardtown, MD Homes for Sale
Over 1/2 Acre | No HOA | One-Level Living: Set on a level 0.60-acre lot, this home offers approximately 1,200 square feet of living space. New flooring and fresh paint throughout provide a clean, refreshed interior, while the covered front porch adds a welcoming touch. Conveniently located near historic downtown Leonardtown, Leonardtown Wharf, and just a short commute to Naval Air Station Patuxent River.

$299,500

3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

Covered front porch • One-level living • Level lot

(301) 862-2169

Property at 23636 Hansel Ct, Leonardtown, MD 20650, 5 beds, 2.5 baths

$599,000

5 beds2.5 baths4,836 sq ft

23636 Hansel Ct, Leonardtown, MD 20650

(301) 970-2447

Property at 20945 Greenwell Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$929,900

4 beds3.5 baths4,248 sq ft

20945 Greenwell Way, Leonardtown, MD 20650

(301) 863-2400

Property at 41495 Garrett Ct, Leonardtown, MD 20650, 3 beds, 2 baths

$474,900

3 beds2 baths1,710 sq ft

41495 Garrett Ct, Leonardtown, MD 20650

(301) 884-9493

Property at 20410 Chingville Rd, Leonardtown, MD 20650, 4 beds, 3 baths

$450,000

4 beds3 baths2,604 sq ft

20410 Chingville Rd, Leonardtown, MD 20650

(301) 298-2892

Property at 23354 Lindsay Dr, Leonardtown, MD 20650, 4 beds, 3.5 baths

$599,900

4 beds3.5 baths2,736 sq ft

23354 Lindsay Dr, Leonardtown, MD 20650

Property at 23405 Marview Ct, Leonardtown, MD 20650, 3 beds, 3.5 baths

$450,000

3 beds3.5 baths2,306 sq ft

23405 Marview Ct, Leonardtown, MD 20650

(410) 394-0990

Property at 41888 Jenkins Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$535,000

4 beds3.5 baths2,562 sq ft

41888 Jenkins Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 23444 Lindsay Dr, Leonardtown, MD 20650, 4 beds, 3.5 baths

$609,900

4 beds3.5 baths3,340 sq ft

23444 Lindsay Dr, Leonardtown, MD 20650

(443) 771-8009

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

$675,000

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

(301) 609-9000

Property at 23011 Newtowne Neck Rd, Leonardtown, MD 20650, 5 beds, 2 baths

$350,000

5 beds2 baths1,552 sq ft

23011 Newtowne Neck Rd, Leonardtown, MD 20650

(703) 378-8810

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

$739,900

4 beds2.5 baths3,460 sq ft

40533 Breton Knolls Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 22601 Avenmar Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$699,000

5 beds4 baths5,484 sq ft

22601 Avenmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 40115 Combs Creek Way, Leonardtown, MD 20650, 5 beds, 3.5 baths

$1,590,000

5 beds3.5 baths2,993 sq ft

40115 Combs Creek Way, Leonardtown, MD 20650

(301) 862-2169

Property at 22393 Saint Clements Ave, Leonardtown, MD 20650, 4 beds, 3 baths

$723,997

4 beds3 baths2,097 sq ft

22393 Saint Clements Ave, Leonardtown, MD 20650

(443) 320-1344

Property at 40751 Merlin Way, Leonardtown, MD 20650, 5 beds, 2.5 baths

$615,000

5 beds2.5 baths2,601 sq ft

40751 Merlin Way, Leonardtown, MD 20650

(240) 993-9888

Property at The Clarke Plan, Leonardtown, MD 20650, 4 beds, 2.5 baths

$629,900

4 beds2.5 baths3,072 sq ft

The Clarke Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at 40611 Merion Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$624,990

4 beds3.5 baths2,562 sq ft

40611 Merion Ct, Leonardtown, MD 20650

(240) 925-2224

Property at 41620 Church St, Leonardtown, MD 20650, 3 beds, 2 baths

$389,000

3 beds2 baths1,728 sq ft

41620 Church St, Leonardtown, MD 20650

(301) 840-8061

Property at 23620 Gunnell Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$615,000

5 beds4 baths4,346 sq ft

23620 Gunnell Dr, Leonardtown, MD 20650

(301) 645-1700

Property at 43954 Main Way Rd, Leonardtown, MD 20650, 3 beds, 3 baths

$449,900

3 beds3 baths1,691 sq ft

43954 Main Way Rd, Leonardtown, MD 20650

(410) 729-7700

Property at The Bell Plan, Leonardtown, MD 20650, 4 beds, 2.5 baths

$619,900

4 beds2.5 baths2,878 sq ft

The Bell Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at The Mattingly Plan, Leonardtown, MD 20650, 4 beds, 2.5 baths

$609,900

4 beds2.5 baths2,701 sq ft

The Mattingly Plan, Leonardtown, MD 20650

Listing provided by Zillow

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

$15,000,000

6 beds4.5 baths5,500 sq ft

19700 Mulberry Fields Rd, Leonardtown, MD 20650

(202) 483-6300

Property at The Fenwick Plan, Leonardtown, MD 20650, 3 beds, 2.5 baths

$614,900

3 beds2.5 baths2,595 sq ft

The Fenwick Plan, Leonardtown, MD 20650

Listing provided by Zillow

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 Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths— sq ft

Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,604 sq ft

Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 5 - 42096 Wildflower Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$619,900

4 beds2.5 baths2,976 sq ft

Lot 5 - 42096 Wildflower Dr, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,554 sq ft

Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 7 - 42084 Wildflower Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$629,900

4 beds2.5 baths3,072 sq ft

Lot 7 - 42084 Wildflower Dr, Leonardtown, MD 20650

(443) 771-8009

Property at Cumberland D1 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$495,900

4 beds3.5 baths3,095 sq ft

Cumberland D1 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at Lot 3 - 42108 Wildflower Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$614,900

4 beds2.5 baths3,072 sq ft

Lot 3 - 42108 Wildflower Dr, Leonardtown, MD 20650

(443) 771-8009

Property at Oakley D1 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$485,900

4 beds3.5 baths2,966 sq ft

Oakley D1 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at Lot 4 - 42102 Wildflower Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$609,900

4 beds2.5 baths2,701 sq ft

Lot 4 - 42102 Wildflower Dr, Leonardtown, MD 20650

(443) 771-8009

Property at Madison D2 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,604 sq ft

Madison D2 Plan, Leonardtown, MD 20650

Listing provided by Zillow

Property at Madison D3 Plan, Leonardtown, MD 20650, 4 beds, 3.5 baths

$454,900

4 beds3.5 baths2,554 sq ft

Madison D3 Plan, Leonardtown, MD 20650

Listing provided by Zillow

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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)

$467,277

-19.3% YoY | Sep 2026

1 year
3 year
5 year

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

Location

Data

Sep 2026

Growth

% YoY

Leonardtown, MD

$467,277

-19.3%

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* Data from the last year

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