5 Bedroom Homes in Leonardtown, MD

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3 beds New construction With a pool

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12 Listings

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5 Bedroom Homes in Leonardtown, MD

12 Listings

74Active

12 listings

5 Bedroom Homes in Leonardtown, MD

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12 Listings

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5 Bedroom Homes in Leonardtown, MD

12 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

74Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

$695,000

5 bd · 3 ba · 2,953 sqft

44450 Schumann Way, Leonardtown, MD

Jesieryl U Hartzer · CENTURY 21 New Millennium

91Active

$780,000

5 bd · 4 ba · 5,484 sqft

22601 Avenmar Dr, Leonardtown, MD

Jennifer L Goddard · CENTURY 21 New Millennium

Price Reduced65Active

$699,900

5 bd · 4 ba · 4,744 sqft

23760 Coventry Dr, Leonardtown, MD

Tracey L Summers · CENTURY 21 New Millennium

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

59Active

$749,900

5 bd · 4 ba · 4,873 sqft

41402 Omaha Ct, Leonardtown, MD

Jonathan David Powell · Real Broker, LLC

Price Reduced44Active

$635,000

5 bd · 3 ba · 2,601 sqft

40751 Merlin Way, Leonardtown, MD

Tracy A Trammel · Metro City Realty

56Active

$390,000

5 bd · 3 ba · 1,080 sqft

23750 Hollywood Rd, Leonardtown, MD

Kelly D Padgett · Century 21 Redwood Realty

44Active

$695,000

5 bd · 4 ba · 4,084 sqft

23214 Dairy Barn Dr, Leonardtown, MD

Wanda White · CENTURY 21 New Millennium

16Active

$350,000

5 bd · 2 ba · 1,552 sqft

23011 Newtowne Neck Rd, Leonardtown, MD

Kelly A Jackson · Samson Properties

56Active

$615,000

5 bd · 4 ba · 4,346 sqft

23620 Gunnell Dr, Leonardtown, MD

William T Mattingly · Coldwell Banker Premier

Price Reduced74Active

$649,000

5 bd · 4 ba · 4,051 sqft

23591 Margrave Dr, Leonardtown, MD

Heather Leigh Foster · RE/MAX One

Price Reduced90Active

$715,000

5 bd · 4 ba · 4,834 sqft

23628 Belmar Dr, Leonardtown, MD

Heather Leigh Foster · RE/MAX One

Price Reduced89Active

$1,590,000

5 bd · 4 ba · 2,993 sqft

40115 Combs Creek Way, Leonardtown, MD

Diana Washabaugh · CENTURY 21 New Millennium

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-03 22:14:33 UTC

Leonardtown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 11 sales · as of Aug 28, 2026

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $612,400
Homes for sale: 40
Median days on market: 11 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -10.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 2,221 sq. ft.

Leonardtown, MD community profile

Population: 4,615
Median income: $125,466
Housing units: 1,635
People per sq. mi.: 43.8
Area: 105.3 sq. mi.

Source: HJN community data

Explore Leonardtown homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Listing data & MLS disclosures

Bright MLS: The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-03 22:14:33 UTC

Leonardtown housing market

August 2026 · This period is still settling

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 11 sales · as of Aug 28, 2026

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Median list price: $612,400
Homes for sale: 40
Median days on market: 11 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -10.8%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 2,221 sq. ft.

Leonardtown, MD community profile

Population: 4,615
Median income: $125,466
Housing units: 1,635
People per sq. mi.: 43.8
Area: 105.3 sq. mi.

Source: HJN community data

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Leonardtown housing market

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Leonardtown, MD community profile

Explore Leonardtown homes

Your local brokerage

Listing data & MLS disclosures

Leonardtown housing market

Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Leonardtown, MD community profile