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56 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)

$843,000
Single Family Home
40738 BOBWHITE LN, Leonardtown, MD 20650
Welcome to this extraordinary 5,242 sq. ft. estate, perfectly nestled on 3.52 acres of beautifully landscaped grounds in...
MLS# MDSM2023806
Listed by CENTURY 21 New Millennium


$560,000
Single Family Home
23635 ABRAHAM DR, Leonardtown, MD 20650
Welcome Home to Comfort, Charm, and Space<br>This stunning Colonial is nestled in a peaceful, sought-after community — t...
MLS# MDSM2023696
Listed by Berkshire Hathaway HomeServices PenFed Realty


$750,000
Single Family Home
40461 OLD BRETON BEACH RD, Leonardtown, MD 20650
Welcome to 40461 Old Breton Beach Road—a breathtaking waterfront retreat on the shores of the Potomac River in Leonardto...
MLS# MDSM2023928
Listed by RE/MAX One


$649,900
Single Family Home
22626 CHICKADEE LN, Leonardtown, MD 20650
Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you're greeted by a stunningly ado...
MLS# MDSM2024686
Listed by JPAR Real Estate Professionals


$275,000
Single Family Home
44662 BLAKE CREEK RD, Leonardtown, MD 20650
This cozy cottage is located in a beautiful, peaceful setting with over an acre of mature fruit trees and flowers. This...
MLS# MDSM2024654
Listed by RE/MAX One


$599,900
Single Family Home
42261 BIRD HAVEN DR, Leonardtown, MD 20650
Welcome to this charming 4-bedroom, 3.5-bathroom home nestled in the sought-after Kingston Estates of Leonardtown. Lovin...
MLS# MDSM2023896
Listed by RE/MAX One


$574,000
Single Family Home
42439 DEAN FOREST CT, Leonardtown, MD 20650
Welcome home to this beautiful 5 Bedroom 3.5 Bath Colonial in Leonardtown!! You will not want to miss this one! This h...
MLS# MDSM2023976
Listed by EXP Realty, LLC


$629,900
Single Family Home
41430 CHALLEDON WAY, Leonardtown, MD 20650
Colonial Home in Leonard's Grant – Prime Corner Lot Across from Amenities!<br><br>Welcome to this spacious and well-app...
MLS# MDSM2023910
Listed by CENTURY 21 New Millennium


$649,999
Single Family Home
41430 WHIMSICAL CT, Leonardtown, MD 20650
This home is a MUST SEE!!!!<br><br>Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement <br><b...
MLS# MDSM2023560
Listed by Realty Navigator


$599,900
Single Family Home
23578 PINE BLUFF WAY, Leonardtown, MD 20650
LOCATION...LOCATION...LOCATION! THIS LOVELY HAYDEN MODEL IS NESTLED RIGHT AT THE HEAD OF THE VILLAGE GREEN IN DESIRABLE...
MLS# MDSM2023102
Listed by CENTURY 21 New Millennium


$649,900
Single Family Home
23275 JENIFER CT, Leonardtown, MD 20650
Welcome to this three-level home located in the Single Tree community, just a short walk from vibrant downtown. Boasti...
MLS# MDSM2023552
Listed by CENTURY 21 New Millennium


$699,900
Single Family Home
18937 HODGES LN, Leonardtown, MD 20650
Are you dreaming of living on the water? This is your perfect opportunity! Well maintained rambler featuring waterfront...
MLS# MDSM2023654
Listed by CENTURY 21 New Millennium


$699,900
Single Family Home
41402 SILVER CHARM CT, Leonardtown, MD 20650
Welcome to your new home -- this stunning Colonial with 5 bedrooms, 3 full bathrooms and 1 half bathroom, 3300+ square f...
MLS# MDSM2023568
Listed by CENTURY 21 New Millennium


$425,750
Single Family Home
23730 HICKS DR, Leonardtown, MD 20650
Welcome to 23730 Hicks Drive – a charming, move-in ready rambler with room to grow! This beautifully updated 3-bedroom, ...
MLS# MDSM2023542
Listed by EXP Realty, LLC


$665,000
Single Family Home
23687 COVENTRY DR, Leonardtown, MD 20650
Significant Price Adjustment – Now Priced Below Market Value!<br>Seize the opportunity to make this stunning, move-in-re...
MLS# MDSM2023524
Listed by Redfin Corp


$665,000
Single Family Home
23266 CLARKS REST RD, Leonardtown, MD 20650
This gorgeous Pinehurst model in Clark's Rest community is not going to last long! This home has 4BR/3.5BA located on la...
MLS# MDSM2022494
Listed by CENTURY 21 New Millennium


$435,000
Townhouse
23445 GROVEWOOD CT, Leonardtown, MD 20650
Welcome to 23445 Grovewood Court, an exquisitely maintained residence in the esteemed Clark's Rest community, where soph...
MLS# MDSM2023446
Listed by CENTURY 21 New Millennium


$649,000
Single Family Home
21897 FAIRWAY DR, Leonardtown, MD 20650
Custom-Built Beauty Overlooking Breton Bay Golf Course! ⛳<br><br>Welcome to 21897 Fairway Drive, Leonardtown, MD—a stunn...
MLS# MDSM2022878
Listed by Infinitas Realty Group


$669,900
Single Family Home
23534 BELMAR DR, Leonardtown, MD 20650
PRICE REDUCTION! Discover unparalleled luxury at 23534 Belmar Drive, an extraordinary residence nestled in the prestigio...
MLS# MDSM2022692
Listed by CENTURY 21 New Millennium


$449,900
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


$460,000
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


$695,000
Single Family Home
23055 TOWN RUN DR, Leonardtown, MD 20650
Stunning Clarke Model by Quality Built Homes<br><br>Located in the desirable Meadows at Town Run, this 4-bedroom, 3.5-ba...
MLS# MDSM2022446
Listed by RE/MAX One


$649,900
Single Family Home
41536 FAIRWOOD CT, Leonardtown, MD 20650
PRICE IMPROVEMENT! This home is less than 2 years young in the sought after, planned Clarks Rest community! Four (4) Be...
MLS# MDSM2022852
Listed by CENTURY 21 New Millennium


$635,000
Single Family Home
23348 LINDSAY DR, Leonardtown, MD 20650
Seller is offering $10,000 in closing help! It can also be used to buy down the interest rate. <br><br>Welcome to 23348 ...
MLS# MDSM2022602
Listed by Fairfax Realty Premier
