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48 Properties Available In Leonardtown
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$699,900
Single Family Home
21620 COVES END CT, Leonardtown, MD 20650
Presented is your chance to own property in the highly desirable Breton Bay Golf Community of Leonardtown. Here you'll e...
MLS# MDSM2022942
Listed by Exit Landmark Realty


$455,000
Single Family Home
40905 KNIGHT RD, Leonardtown, MD 20650
Welcome to 40905 Knight Road in beautiful Leonardtown, Maryland! This inviting home offers a perfect mix of comfort and ...
MLS# MDSM2023050
Listed by EXP Realty, LLC


$499,900
Single Family Home
40827 LAKE AND BRETON VIEW DR, Leonardtown, MD 20650
Have you been searching for a home with the PERFECT Water Views!! Without; the Water view price??<br>This home may be wh...
MLS# MDSM2023068
Listed by CENTURY 21 New Millennium


$485,000
Single Family Home
41925 NAZARETH CT, Leonardtown, MD 20650
This beautiful Colonial home is nestled in the highly sought-after Academy Hills subdivision of Historic Leonardtown. Si...
MLS# MDSM2022948
Listed by RE/MAX One


$1,050,000
Single Family Home
22855 WHITE SWAN WAY, Leonardtown, MD 20650
Move right in.....this home is a showstopper....better than new! Tucked away on 3.59 acres, everything has been upgraded...
MLS# MDSM2022826
Listed by KW Metro Center


$689,900
Single Family Home
41536 FAIRWOOD CT, Leonardtown, MD 20650
Why wait for a new home to be built? This home is less than 2 years young in the sought after, planned Clarks Rest comm...
MLS# MDSM2022852
Listed by CENTURY 21 New Millennium


$670,000
Single Family Home
23348 LINDSAY DR, Leonardtown, MD 20650
Pictures coming Friday! Welcome to 23348 Lindsay Dr, a stunning 5-bedroom, 4-full-bath home nestled in the beautiful Cla...
MLS# MDSM2022602
Listed by Fairfax Realty Premier


$469,900
Single Family Home
22362 ARMSTRONG DR, Leonardtown, MD 20650
Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MD<br><br>Nestled in the desirable Society Hill neigh...
MLS# MDSM2023036
Listed by CENTURY 21 New Millennium


$445,000
Single Family Home
39880 LADY BALTIMORE AVE, Leonardtown, MD 20650
Introducing this beautiful 3 Bedroom 2 Full Bath Rambler in Leonardtown. Some updates in this beautiful home include new...
MLS# MDSM2022524
Listed by Infinitas Realty Group


$435,000
Townhouse
41434 MARGROVE CIR, Leonardtown, MD 20650
Stunning 3-Bedroom, 3.5-Bath Townhome in Clarks Rest, Leonardtown, MD<br><br>Welcome to this beautiful and spacious 3-be...
MLS# MDSM2023020
Listed by RE/MAX One


$450,000
Single Family Home
20798 WATERSIDE DR, Leonardtown, MD 20650
Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with brea...
MLS# MDSM2022922
Listed by RE/MAX Closers


$815,000
Single Family Home
41115 PAW PAW HOLLOW LN, Leonardtown, MD 20650
Stunning Brick Front Colonial in Paw Paw Hollow - 1.8 Acres of Private Luxury<br>Welcome to this well maintained and bea...
MLS# MDSM2022526
Listed by CENTURY 21 New Millennium


$729,999
Single Family Home
20503 DEER WOOD PARK DR, Leonardtown, MD 20650
Discover this expansive, custom-designed brick Colonial situated on 2 pristine acres in the highly sought-after Chestnut...
MLS# MDSM2022782
Listed by CENTURY 21 New Millennium


$20,000,000
Single Family Home
19700 MULBERRY FIELDS RD, Leonardtown, MD 20650
Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potom...
MLS# MDSM2022614
Listed by Long & Foster Real Estate, Inc.


$440,000
Single Family Home
20959 REDGATE LN, Leonardtown, MD 20650
A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland offers promising opportunities f...
MLS# MDSM2022416
Listed by Keller Williams Legacy


$739,900
Single Family Home
23773 MEREDITH CT, Leonardtown, MD 20650
Spacious home in desirable Hollywood location. (Abell's Ridge) The main level greets you with hardwood flooring in the ...
MLS# MDSM2022554
Listed by Coldwell Banker Jay Lilly Real Estate


$535,000
Single Family Home
25365 POINT LOOKOUT RD, Leonardtown, MD 20650
Unique property : Residential AND Commercial !!! Both are presently rented. The two story home has 3 bedrooms, one bath,...
MLS# MDSM2022468
Listed by CENTURY 21 New Millennium


$650,000
Single Family Home
22626 CHICKADEE LN, Leonardtown, MD 20650
PRICE REDUCED!! Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you're greeted by ...
MLS# MDSM2022382
Listed by JPAR Real Estate Professionals


$613,000
Single Family Home
40751 MERLIN WAY, Leonardtown, MD 20650
***PRICE REDUCTION!!!'' Sellers are offering a $3,000 credit to the buyer and a $600 home warranty.<br><br>Stunning 5-Be...
MLS# MDSM2022082
Listed by Metro City Realty


$650,000
Single Family Home
41810 CHELSEY FAYE LN, Leonardtown, MD 20650
Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional quality by Graham & Co Custom ...
MLS# MDSM2021276
Listed by JPAR Real Estate Professionals


$565,500
Single Family Home
40222 BRETON BEACH RD, Leonardtown, MD 20650
This dreamy waterfront getaway is the perfect spot for you to fully unwind and relax. Located directly along Breton Bay,...
MLS# MDSM2020654
Listed by Baldus Real Estate, Inc.


$530,000
Single Family Home
41815 CHELSEY FAYE, Leonardtown, MD 20650
Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one story design that is loaded w...
MLS# MDSM2016780
Listed by JPAR Real Estate Professionals


$831,025
Single Family Home
WATHEN RD, Leonardtown, MD 20650
NEW CONSTRUCTION TO BE BUILT. This stunning 7.5-acre lot is co-marketed with Caruso Homes, featuring the impressive DEER...
MLS# MDSM2016354
Listed by Amber & Company Real Estate


$859,900
Single Family Home
40533 BRETON KNOLLS CT, Leonardtown, MD 20650
TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 square feet of luxur...
MLS# MDSM2015098
Listed by RE/MAX Realty Group
