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38 listings

Homes for Sale in Leonardtown, MD

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24 of 38 Listings

Map

24 of 38 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

85Active

$620,000

5 bd · 3 ba · 4,836 sqft

23636 Hansel Ct, Leonardtown, MD

John Kreamer · Taylor Properties

1Active

$739,900

4 bd · 3 ba · 3,460 sqft

40533 Breton Knolls Ct, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

102Active

$650,000

4 bd · 4 ba · 3,344 sqft

23513 Sly Fox Way, Leonardtown, MD

Heather Leigh Foster · RE/MAX One

63Active

$474,900

3 bd · 2 ba · 1,710 sqft

41495 Garrett Ct, Leonardtown, MD

Beverly Moody · RE/MAX Realty Group

109Active

$929,900

4 bd · 4 ba · 4,248 sqft

20945 Greenwell Way, Leonardtown, MD

Dawn Dawn Wood · O'Brien Realty ERA Powered

14Active

$319,000

3 bd · 1 ba · 2,068 sqft

43146 N Megan Ln, Leonardtown, MD

Lewie A Aldridge III · Berkshire Hathaway HomeServices PenFed Realty

Price Reduced72Active

$680,000

4 bd · 4 ba · 4,066 sqft

21395 Fairwood Ct, Leonardtown, MD

Lauren Coble Garner · EXP Realty, LLC

Price Reduced74Active

$675,000

5 bd · 3 ba · 2,953 sqft

44450 Schumann Way, Leonardtown, MD

Jesieryl U Hartzer · CENTURY 21 New Millennium

Price Reduced43Active

$629,900

4 bd · 4 ba · 3,340 sqft

23444 Lindsay Dr, Leonardtown, MD

Natalya P. Ford · RE/MAX One

Price Reduced91Active

$699,000

5 bd · 4 ba · 5,484 sqft

22601 Avenmar Dr, Leonardtown, MD

Jennifer L Goddard · CENTURY 21 New Millennium

Price Reduced47Active

$439,000

4 bd · 3 ba · 2,774 sqft

40659 Klear Ct, Leonardtown, MD

Christopher W Blondin · Baldus Real Estate, Inc.

Price Reduced53Active

$599,900

4 bd · 4 ba · 2,736 sqft

23354 Lindsay Dr, Leonardtown, MD

Dorothy M Bistransin · Redfin Corp

Price Reduced28Active

$590,000

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

Price Reduced43Active

$615,000

5 bd · 3 ba · 2,601 sqft

40751 Merlin Way, Leonardtown, MD

Tracy A Trammel · Metro City Realty

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

Price Reduced41Active

$535,000

4 bd · 4 ba · 2,562 sqft

41888 Jenkins Ct, Leonardtown, MD

Wayne A Floyd · RE/MAX One

17Active

$350,000

5 bd · 2 ba · 1,552 sqft

23011 Newtowne Neck Rd, Leonardtown, MD

Kelly A Jackson · Samson Properties

74Active

$699,900

3 bd · 2 ba · 1,834 sqft

18937 Hodges Ln, Leonardtown, MD

Ingrid H Butler · CENTURY 21 New Millennium

94Active

$680,000

4 bd · 2 ba · 2,388 sqft

25375 Loveville Rd, Leonardtown, MD

Kandy M. Moore · RMG Realty

Price Reduced45Active

$560,000

4 bd · 3 ba · 2,730 sqft

22010 Society Hill Rd, Leonardtown, MD

Fran Slade · Compass

56Active

$615,000

5 bd · 4 ba · 4,346 sqft

23620 Gunnell Dr, Leonardtown, MD

William T Mattingly · Coldwell Banker Premier

45Active

$619,900

4 bd · 3 ba · 2,976 sqft

Lot 5 - 42096 Wildflower Dr, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

1 2

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: 2026-10-03 17:25:14 UTC

Leonardtown housing market

September 2026 · This period is still settling

Homes that sold · County records, as of Sep 14, 2026

Median sale price: $650,000$464,900–$751,500 typical range
Sales: 11
Paid in cash: 9.1%

Homes on the market · MLS, as of Sep 27, 2026

Median list price: $614,900
Homes for sale: 33

Price trend · Assessor repeat sales, as of Sep 30, 2026

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

Nearby areas

ZIP codes

20646 (106)
20695 (103)
20657 (92)
20602 (72)
20603 (59)
20653 (47)
20659 (40)
20619 (38)

Cities

Waldorf (166)
La Plata (106)
White Plains (103)
Lusby (92)
Lexington Park (47)

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas

Nearby areas

ZIP codes

20646 (106)
20695 (103)
20657 (92)
20602 (72)
20603 (59)
20653 (47)
20659 (40)
20619 (38)

Cities

Waldorf (166)
La Plata (106)
White Plains (103)
Lusby (92)
Lexington Park (47)

Mechanicsville (40)

California (38)

Prince Frederick (37)

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: 2026-10-03 17:25:14 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

September 2026 · This period is still settling

Homes that sold · County records, as of Sep 14, 2026

Median sale price: $650,000$464,900–$751,500 typical range
Sales: 11
Paid in cash: 9.1%

Homes on the market · MLS, as of Sep 27, 2026

Median list price: $614,900
Homes for sale: 33

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year

19.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 3, 2026

Median home size: 2,221 sq. ft.

Leonardtown, MD Homes for Sale | Realty.com