4 Bedroom Homes in Leonardtown, MD

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3 beds New construction With a pool

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20 Listings

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4 Bedroom Homes in Leonardtown, MD

20 Listings

Price Reduced74

20 listings

4 Bedroom Homes in Leonardtown, MD

Show Map

20 Listings

Map

4 Bedroom Homes in Leonardtown, MD

20 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced74

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Active

$680,000

4 bd · 4 ba · 4,066 sqft

21395 Fairwood Ct, Leonardtown, MD

Lauren Coble Garner · EXP Realty, LLC

Price Reduced43Active

$629,900

4 bd · 4 ba · 3,340 sqft

23444 Lindsay Dr, Leonardtown, MD

Natalya P. Ford · RE/MAX One

Price Reduced47Active

$439,000

4 bd · 3 ba · 2,774 sqft

40659 Klear Ct, Leonardtown, MD

Christopher W Blondin · Baldus Real Estate, Inc.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Price Reduced53Active

$609,900

4 bd · 4 ba · 2,736 sqft

23354 Lindsay Dr, Leonardtown, MD

Dorothy M Bistransin · Redfin Corp

28Active

$600,000

4 bd · 3 ba · 3,793 sqft

41524 Fairwood Ct, Leonardtown, MD

William Rabbitt · The Southside Group Real Estate

42Active

$449,900

4 bd · 4 ba · 0 sqft

Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

58Active

$624,990

4 bd · 4 ba · 2,562 sqft

40611 Merion Ct, Leonardtown, MD

Kalee Michelle Kelly · Infinitas Realty Group

26Active

$450,000

4 bd · 3 ba · 2,604 sqft

20410 Chingville Rd, Leonardtown, MD

William Rabbitt · The Southside Group Real Estate

41Active

$550,000

4 bd · 4 ba · 2,562 sqft

41888 Jenkins Ct, Leonardtown, MD

Wayne A Floyd · RE/MAX One

94Active

$680,000

4 bd · 2 ba · 2,388 sqft

25375 Loveville Rd, Leonardtown, MD

Kandy M. Moore · RMG Realty

45Active

$575,000

4 bd · 3 ba · 2,730 sqft

22010 Society Hill Rd, Leonardtown, MD

Fran Slade · Compass

45Active

$619,900

4 bd · 3 ba · 2,976 sqft

Lot 5 - 42096 Wildflower Dr, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

31Active

$614,900

4 bd · 3 ba · 3,072 sqft

Lot 3 - 42108 Wildflower Dr, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

72Active

$609,900

4 bd · 3 ba · 2,701 sqft

Lot 4 - 42102 Wildflower Dr, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

Price Reduced75Active

$624,900

4 bd · 4 ba · 3,314 sqft

41462 Culpepper Way, Leonardtown, MD

Heather Leigh Foster · RE/MAX One

Price Reduced56Active

$738,997

4 bd · 4 ba · 2,097 sqft

22393 Saint Clements Ave, Leonardtown, MD

Alyson Anderson I · Allfirst Realty, Inc.

33Active

$629,900

4 bd · 3 ba · 3,072 sqft

Lot 7 - 42084 Wildflower Dr, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

9Active

$454,900

4 bd · 4 ba · 2,554 sqft

Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

42Active

$449,900

4 bd · 4 ba · 2,604 sqft

Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

30Active

$1,750,000

4 bd · 2 ba · 2,130 sqft

Bayside Rd, Leonardtown, MD

Larry J Haley · Haley Family Realty

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: 2026-09-27 21:59:43 UTC

Leonardtown housing market

August 2026 · This period is still settling

Selling at 100.8% of asking price

Buyers here are paying above asking. MLS · 12 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $459,200$449,900–$573,636 typical range
Price per sq. ft.: $183
Sales: 20
Paid in cash: 15.0%

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

Median list price: $612,400
Homes for sale: 40
Median days on market: 7 days

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

Year-over-year: -9.5%

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: 2026-09-27 21:59:43 UTC

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

Leonardtown housing market

August 2026 · This period is still settling

Selling at 100.8% of asking price

Buyers here are paying above asking. MLS · 12 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $459,200$449,900–$573,636 typical range
Price per sq. ft.: $183
Sales: 20
Paid in cash: 15.0%

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

Median list price: $612,400
Homes for sale: 40
Median days on market: 7 days

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

Year-over-year: -9.5%

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Leonardtown housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of 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, MD community profile

Leonardtown housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of 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