Your Complete Real Estate Guide

Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 09/18/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Leonardtown homes for sale or other Leonardtown real estate, please contact us and one of our knowledgeable Leonardtown REALTORS® would be pleased to assist you.


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$1,250,000
40111 ARMY WAY, Leonardtown MD 20650
6
BEDS
7
BATHS
8,837
SQFT
$141
$/SQFT
2.07
ACRES
2004
BUILT
"Love At First Sight! One of a Kind Beautiful Southern Maryland Coastal Retreat. Gracious & Sophisticated. Elegant Details throughout this well appointed home. The Custom 2-story Barrel Ceilings are truly Gorgeous. Stained Glass.. Gourmet Chef's kitchen, Island and walk-in pantry. Formal Dining Room with Built-Ins and a Tucked away Cozy Reading & TV Room. Enjoy the separate Library with Built-Ins. A Large Walk-In Laundry Room. Main Floor Master Suite Wing has his and her bathrooms and walk-in closets. Relax in the Great Room with built-ins, fireplace and Lovely windows to optimize all the water-views. Front and Back Deep Seating Covered porches to enjoy Alfresco Dining, Entertaining and Peaceful Tranquility. Take the Elevator or stairs up to the 2nd floor for the 2 additional master sized Suites and Baths. Lovely bonus Rooms for additional guests or a tucked away retreat. Basement has multiple rooms too and storage; a walk-in safe, a severe weather safe room, an exercise or Hobby space, a bathroom and recreation space. 4+ Car Garages are attached to the home via covered Breezeway. The entire space above the Garages is available for storage or expansion with upper access from the house via a gallery w/skylights. Heated Floors. Just too much to list here; so many well thought out details in this home. Pier is Large and has a 20,000 lb lift to meet all your boating needs. Protected water on Scenic Combs Creek (6-8' deep at Boat End) and a quick 5 minutes to Breton Bay and the Potomac. This home blends one of a kind customized luxury with Southern Living Charm. Located 5 minutes from the heart of Leonardtown you'll have all the Privacy you could desire in your Waterfront Home yet still be close to area shopping and events. So much to love and see in this stunning custom home. Almost 6000sf finished above grade alone! You will have room for everything and then some. The perfect Retreat. 30 Minutes to NAS Patuxent River and an hour to DC and VA."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,499,750 TO $1,250,000 
$949,900
42741 WAVERLY WAY, Leonardtown MD 20650
4
BEDS
3
BATHS
2,777
SQFT
$342
$/SQFT
4.07
ACRES
1956
BUILT
"Live away from the crowd on secluded 4.07 acres with over 800 feet of sandy beach on the Potomac River and situated on the beautiful Belvedere Creek on the other side of the property. Any nature lover will be overwhelmed. Tour the large lovely brick rambler with 4 bedrooms and 3 baths. When you are at this property, you are truly in The Land of Pleasant Living "
* PRICE LOWERED - $995,000 TO $949,900 
$894,950
41191 BRETON BEACH RD, Leonardtown MD 20650
4
BEDS
4
BATHS
3,941
SQFT
$227
$/SQFT
62.87
ACRES
2008
BUILT
"Amazing opportunity to own 63+ acres on the Breton Bay Peninsula within walking distance to the Potomac River and several boat ramps nearby. Nearly level land offers a mix of pasture and woods. Recently built (2007) cottage style home w/ 1st floor owner's suite, open living areas, first floor office, two story stacked stone fireplace, hardwood floors, oversized windows, 2 covered porches & an over sized 2 car garage. The property also includes a large 2 story center aisle barn w/ a 2 bedroom apartment plus office. A great place for family, friends or a business. The property offers several outbuildings, miles of board fencing, lighted riding ring & trails. Close to PAX river, St. Marys College, the historic downtown and the MedStar St. Marys Hospital. Need help with the down payment? Ask about MARBIDCO"
* LISTED OVER 120 DAYS 
$749,000
41955 SWANS CT, Leonardtown MD 20650
6
BEDS
7
BATHS
7,160
SQFT
$105
$/SQFT
1.66
ACRES
1990
BUILT
"Welcome home to this remarkable property featuring a breathtaking Virginia Plantation style home and an enchanting waterfront lot. Host friends and family, retire behind the library's pocket doors, enjoy a peaceful kayak tour, and observe stunning wildlife year round. Exceptional detail was built into this home, inside and out. Custom solid Colonial Williamsburg style doors, cherry and marble flooring, and magnificent crown molding are just a few of the features adorning the interior. The exterior features the durability of solid-stained, beaded Western Red Cedar siding and Richmond Precast concrete roofing, with steel roofing above the sunroom. Natural lighting and stunning outdoor views abound throughout the home. The updated kitchen provides ample storage space, stainless steel appliances (including double ovens), and gas cooking. The grand formal dining room, with water view, is suitable for your largest gathering or a peaceful cup of coffee. Views extend with wall to wall windows in the 330 square foot sunroom. The spacious lower level master is its own sanctuary complete with a water view, en suite bath with separate soaking tub and marble vanity, and dressing area with a very generously sized walk in closet. Step outside to magical surroundings with plentiful yard space and your private dock, (which includes electric), on Flood Creek. A breathtaking experience awaits you on the water - the 10 minute paddle to the Potomac is brimming with nature's beauty. Watch Great Blue Herons, Pileated Woodpeckers, and enjoy a front row seat to a gathering of migrating swans during some winter months. The upper level of the home includes four more spacious bedrooms, three full baths, and an office. The basement, with access to the rear patio, is filled with natural light and offers an additional bedroom and full bath (currently used for hygienic sauna, which can convey). This home is equipped with a central vacuum, four Carrier heat pumps (one with propane backup), an auto"
* PRICE LOWERED - $795,000 TO $749,000 
$708,000
40125 ARMY WAY, Leonardtown MD 20650
5
BEDS
4
BATHS
3,395
SQFT
$209
$/SQFT
1.29
ACRES
2004
BUILT
"This beautiful custom-built waterfront home has to be seen to appreciate all it offers. Equipped with large private pier, offering a mean low tide depth of five feet, an 8000 lb boat lift and 2000 lb jet ski lift. Enjoy stunning views of Coombs Creek while sitting on the large sun deck and boardwalk leading to the pier. The large and level yard and back porch overlook the water and is far above floodplain. Expansive water views from the beautiful kitchen, living room and first floor master bedroom. Gourmet eat-in kitchen has stainless steel appliances and updated countertops and additional island sink. Large formal dining room is great for hosting large gatherings. There is a bonus room that can be used as an office or den. The spacious two-story living room has efficient pellet stove and is open to the kitchen, great for entertaining. The first floor master overlooks the water and leads out to the patio so that you can enjoy the sunrise and sunset over the water. Master has two large closets and separate shower and clawfoot soaking tub. The upstairs is accessible either from the grand foyer or the mudroom staircase to three large bedrooms and two full baths. Continue to the bonus room above the garage that can be used as another bedroom or family room. This home has countless upgrades, including an additional full bathroom on the first floor, built-in safe, laundry chute, central vacuum, oversized closets, and fantastic, large front and back porches. There is plenty of garage space in the attached two-car garage and the detached, oversized one-car garage. Additionally, the detached garage has an adjoining large wood/workshop and upstairs storage space. Park your motorhome or store your boat in the oversized covered parking area. This property is 1.29 acres and is nicely landscaped. This sanctuary is very private, all while so close to Leonardtown, schools, and shopping. Make an appointment today to walk the property and tour the home. It is a "
* LISTED OVER 120 DAYS  * PRICE LOWERED - $739,900 TO $708,000 
$599,900
21082 PARKER LN, Leonardtown MD 20650
1
BEDS
2
BATHS
672
SQFT
$893
$/SQFT
0.46
ACRES
1930
BUILT
"Gorgeous Waterfront Lot. Let Rainbow Homes build your home on this lot. Renderings for home to-be-built. Will include new well, 3BR and 2.5 BA, two-story great room, kitchen with granite counters and 42 birch cabinets and energy star appliances, luxury master bath, study upstairs and more. Contact agent for specific details. Permit in hand for new sea wall and pier (not included in this price.) Can purchase land only for $184,900 under MLS# MDSM163970."
* PRICE INCREASED - $184,900 TO $599,900 
$599,900
42403 RIVERWINDS DR, Leonardtown MD 20650
3
BEDS
3
BATHS
2,079
SQFT
$289
$/SQFT
0.63
ACRES
1953
BUILT
"Waterfront on the Potomac River! Main house is 2 BR 2 BA and faces the water frontage on the Potomac River with 50' Pier and Heavy Duty Rip-Rap in place. Recently updated Large Kitchen w/ granite counters and tons of cabinet space - home sits on a full unfinished basement and has an enclosed side porch entry as well as a full deck on the waterfront side of the home. Second Unit is a 1 BR 1BA with very nice full (granite and upgraded cabinets) kitchen, Living Room and Eating Area. This unit would make an amazing short or long term rental income opportunity. The whole property has been meticulously landscaped and cared for - shed with additional storage section built to accommodate extra storage needs. Updated HVAC and Septic BAT system."
* PRICE LOWERED - $659,900 TO $599,900 
$549,900
40624 BRETON OAKS LN, Leonardtown MD 20650
4
BEDS
4
BATHS
2,760
SQFT
$199
$/SQFT
1.49
ACRES
2019
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $565,900 TO $549,900 
$544,900
20480 CHESTNUT RIDGE DR, Leonardtown MD 20650
5
BEDS
5
BATHS
4,973
SQFT
$110
$/SQFT
3.36
ACRES
1996
BUILT
"Nearly 5,000 finished sq. ft. of magnificent living! Custom-built Brick and Cedar Colonial on over 3 acres at end of cul de sac in desirable Chestnut Ridge. 5 Bedrooms. 4.5 Baths, Full Basement PLUS 2+ Car Garage with storage galore. Main level Owners Suite with Jacuzzi Tub & large shower. Hot Tub Room leads to Deck over looking wooded privacy. Gourmet Kitchen. Gas FPs. Hardwood and Ceramic Floors. Walk-out Basement with full Bath.Upper lvl 2nd Master & Library. NEW HVAC on upper level.. Floor plans, location drawing and details available."
$499,990
41505 REINS CT, Leonardtown MD 20650
4
BEDS
4
BATHS
4,508
SQFT
$111
$/SQFT
0.64
ACRES
1999
BUILT
"Pre-Appraised/offered below appraised price - Appraised in April 2019 - Beautiful home resting on .64 acs. with 4 bedrms, 3.5 baths, Formal Living and Dining Rms,Library with built ins, FamRm with Fireplace, Sun Rm, Lg. eat in Kitchen with lots of cabinets and storage, Exercise Rm.,Office. Laundry Rm., Sewing Rm., Gift Wrap Rm.,Furnace storage Rm., Lg. unfinished storage area in Lower level. Other features: Underground Sprinkler System, Elevator, Generator, Patio, Shed, Double Jazz. Tub and Lg. Walk in Closet in Master. Please make appointment to see this home. Thanks"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $525,000 TO $499,990 
$499,900
40435 WATHEN ROAD, Leonardtown MD 20650
5
BEDS
4
BATHS
4,000
SQFT
$125
$/SQFT
0.62
ACRES
2019
BUILT
"New construction in Leonardtown ready by Sept/ Oct. Custom home has Open floor plan w/ master suite on main level and another bedroom & bath on main. Upstairs has 3 additional bedrooms & a bonus room. Many upgrades include granite, wood on main level, upgraded trim package, stainless appliances, upgraded fixtures, upgraded cabinets. Beautiful center island. Two laundry areas. Over-sized garage. Porch overlooking private back yard. Custom Interior colors & upgrades throughout."
$489,000
23213 CLARKS REST RD, Leonardtown MD 20650
5
BEDS
4
BATHS
4,158
SQFT
$118
$/SQFT
0.30
ACRES
2015
BUILT
"Gorgeous Pinehurst model on private premium lot in Clarks Rest. Gourmet kitchen with granite countertops, gas cooktop, wall oven, large breakfast bar, large pantry & hardwood floors. Large upgraded morning room leads to deck with views of the woods and the pond. Family room has gas fireplace with stone surround. Upstairs boasts a large Master bed room with vaulted ceilings, 2 walk in closets and Master bath has deluxe oversized shower. Laundry room is also on the upstairs level for the extra convenience. Basement is fully finished with rec room, bedroom 5, full bath and still plenty of storage space. Sprinkler system in yard as well. Walk out basement slider leads to concrete patio. Wonderful neighborhood with community pool, playgrounds, tennis courts, basketball court and walking trails. Close to the heart of Leonardtown and walking distance to restaurants and shops."
* PRICE LOWERED - $498,900 TO $489,000 
$482,832
23056 TOWN RUN DR, Leonardtown MD 20650
4
BEDS
3
BATHS
3,072
SQFT
$157
$/SQFT
0.27
ACRES
2019
BUILT
"UNDER CONSTRUCTION! Quality Built Homes' Clarke featured in Meadows at Town Run! This home is a stunner!! Huge 2 car garage, a Grand kitchen, hardwood throughout, the famous Deluxe master bathroom shower, tray ceiling and SO MUCH MORE! September 2019 delivery!"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $428,900 TO $482,832 
$478,500
40140 WATHEN RD, Leonardtown MD 20650
4
BEDS
3
BATHS
3,527
SQFT
$136
$/SQFT
3.00
ACRES
2000
BUILT
"Huge Price Reduction! Great Value! This Property Has It All!! Huge Garage/Shop/Man Cave. Storage Galore!! Multiple Outbuildings. Private but yet close to everything. A MUST SEE to Appreciate. Located in Leonardtown area. New Carpet in all bedrooms! Immaculate 4 Bed/3 Bath Raised Rambler nestled on a 3 acre parcel of a 250 acre farm. Property is situated in a quiet and private farm setting. House has upgraded custom kitchen with huge granite center island and granite counter-tops, family room and master bathroom, all recently upgraded. Tons of storage area inside and out. Metal Roof approx 2 years old. Huge!! Heated,electric, water and bathroom 60' x 56' shop with 14 ft. doors, perfect for RV, Boat and multiple vehicles. Multiple out-buildings and livestock building with water and electric. Located minutes from shopping,entertainment, golf course and country club, marinas, boating, kayaking, parks and recreation. Lots of space. Atlantic Broadband service available for high speed internet and cable TV. Minutes from PAX River NAS and NAVSEA Dahlgren VA. Don't let this one get away!"
* PRICE LOWERED - $489,900 TO $478,500 
$475,900
41333 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
4
BATHS
3,730
SQFT
$128
$/SQFT
0.15
ACRES
2020
BUILT
"WICOMICO Inventory Home: Targeting an End of Year (2019) Delivery, Hardwood Foyer/Dining Room/Kitchen/Breakfast Nook, SS Appliances w/Double Wall Ovens, Upgraded Cabinetry, Granite at Kitchen, Butlers Pantry, Mud Room, Walk-In Pantry, Sep. DR, Office, Front Porch, Tray Ceiling at Owner's, Garage Door Opener, Recessed Lighting, Oversized Garage, 2nd Floor Laundry. Community Amenities: Pool, Clubhouse, Tennis/Pickle Ball Court, Basketball Court, Playground, Walking Trails."
* PRICE INCREASED - $474,347 TO $475,900 
$468,000
40502 PORT PL, Leonardtown MD 20650
3
BEDS
3
BATHS
1,952
SQFT
$240
$/SQFT
0.76
ACRES
1980
BUILT
"This Breton Bay Estates Waterfront home on Cherry Cove Creek with private pier and two electric boat lifts is aggressively priced and ready for you. Fully fenced rear private yard on cul-de-sac location with peaceful water views. Large rear deck connects to open concept on upper level. Beautiful natural light throughout with large skylight feature on upper level; granite counters and soft-close cabinets adorn the kitchen. Home has a detached two-car garage and a large unfinished space above the garage with so much potential. Breton Bay offers a community beach, golf, tennis, pool and country club with great restaurant. Agents, make sure you stop by the community beach to view the many optional amenities."
$465,100
25057 MEADOWLARK CT, Leonardtown MD 20650
3
BEDS
2
BATHS
2,339
SQFT
$199
$/SQFT
0.21
ACRES
2019
BUILT
"** TO BE BUILT ASHLAND MODEL ** Open floor plan that offers a split bedroom plan, an open family room to kitchen, a breakfast nook that feels like a sunroom and a pantry like no other!! There is a huge unfinished basement waiting for your personal touches! Contact us today to get your customized color scheme!"
$429,900
23616 GUNNELL DR, Leonardtown MD 20650
4
BEDS
4
BATHS
3,008
SQFT
$143
$/SQFT
0.35
ACRES
2005
BUILT
"Like new construction but without the wait!!! This stunning colonial spares no detail. Entry way includes beautiful hardwood floors and large columns. Perfect for entertaining, the main level has a very spacious open floor plan throughout. Enjoy dinners in the formal dinning area, then cozy up by the fireplace in the formal living room. Kitchen includes beautiful wooden cabinets with tons of storage and an additional pantry. Large master bedroom with his and her walk-in closets, soaking tub, and separate vanities. Pergo/vinyl flooring in the additional bedrooms. Every bedroom comes with its own custom trim work. Partially finished basement is the ideal man cave, equipped with a wet bar, theatre seating, and surround sound. Basement also has a full bath and a huge storage area that could also be turned into additional rooms. Large size deck with covered pergola. Two car garage has one bay with a 2-foot extension for extra space. Brand new roof put on in August 2018 with 30 year architectural shingles. Stainless steel appliances in kitchen replaced less than 2 years ago. Close to the city of Leonardtown with lots of great restaurants and shopping. All schools located within a 5 mile radius. Too many upgrades and details to list.Come see for yourself, you won't want to miss this opportunity."
$427,985
44024 COTTON TAIL CT, Leonardtown MD 20650
3
BEDS
3
BATHS
2,245
SQFT
$191
$/SQFT
0.28
ACRES
2019
BUILT
"The Dunkirk on a gorgeous FLAT lot! One of the last larger lots left in Meadows. There is still time to customize this beauty and choose the color scheme that is right for you! Located in Leonardtown, Maryland, The Meadows at Town Run offers 107 homesites and a variety of one and two-story floor plans to choose from. This community provides easy access to Pax River Naval Air Station, and is conveniently situated for commuters traveling Route 301, Route 4, and Route 5. A quaint wharf town with rich colonial history, Leonardtown has undergone a remarkable revitalization over the past two decades."
* PRICE INCREASED - $427,360 TO $427,985 
$425,000
44445 MEDLEYS NECK RD, Leonardtown MD 20650
3
BEDS
2
BATHS
2,261
SQFT
$188
$/SQFT
4.99
ACRES
1989
BUILT
"Nestled in the woods on 4.99 acres of land, this home could be your own retreat. It features a large stocked pond, fruit trees, pool, hot tub, sauna, 30x40 detached garage/workshop, shed, deck, whole-house generator, brand new lighting in the kitchen and living room, gorgeous handmade cabinets, and more. With a Geothermal heat pump, 6 inch walls, energy efficient windows, a central boiler, and a wood furnace, this home has several options for energy efficiency. The interior showcases an abundance of character and quality, making this beautiful home unlike any other. The property offers privacy while being conveniently located just off of Route 5. This home is sure to be loved! Come see it before it's gone!"
$419,900
43011 CHICKADEE ST, Leonardtown MD 20650
3
BEDS
2
BATHS
2,339
SQFT
$180
$/SQFT
0.21
ACRES
2019
BUILT
"**TO BE BUILT** Quality Built Homes' newest rambler to be featured in Meadows at Town Run! This is one leveling living at its' finest. Complete with a split bedroom floor plan...a large master suite on one side and the other 2 bedrooms on the other side of the house! Huge galley kitchen that opens to the family room. A sunroom like breakfast area that walks out to a covered porch. What more can you ask for? Get in soon while it's still pre-construction pricing!"
* LISTED OVER 120 DAYS 
$419,900
23589 ABRAHAM DR, Leonardtown MD 20650
4
BEDS
5
BATHS
2,474
SQFT
$170
$/SQFT
0.33
ACRES
2003
BUILT
"Besides Style and Charm, this Colonial has 4 Bedrooms, 4.5 Baths, living room, dining room, kitchen ope n to the family room, office, fully finished basement with a guest rm./workout room full bath and a wet bar. Step outside to the stamped concrete patio that features an outdoor kitchen, bar, hot tub, water feature and fireplace. Freshly painted, new carpet and new roof. This home will not disappoint you."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $422,900 TO $419,900 
$415,000
23611 GUNNELL DR, Leonardtown MD 20650
5
BEDS
4
BATHS
2,976
SQFT
$139
$/SQFT
0.29
ACRES
2005
BUILT
"Gorgeous Colonial in The Village At Leonardtown, ready for you to call home. This Spacious 5 bedroom, 4 full bath home has been nicely maintained. Stunning details throughout, ceramic tile foyer columns, formal separate dining and living room, crown molding, chair railings, and Wainscoting, nice kitchen w/breakfast bar, nice stainless Applainces, ceramic tile floor, large pantry, family room w/gas/propane fireplace with mantle, recess lights,bright Morning Room w/vaulted ceiling, french doors leads to large deck overlooking landscaped yard, library or office space, full bath with double vanity, separate shower, upper level has master suite with his/her walk-in closets, master bath w/soaking tub, double vanity, separate shower, three other bedrooms, hallway bath double vanity, hardwood floors throughout, fleshly painted, new roof, hot water heater, garbage disposal, A/C, finished basement with in-law suite, full bath, large family room, and exercise room, wet/dry bar, ceramic tile floor, and walk out basement."
$409,900
41408 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,660
SQFT
$154
$/SQFT
0.15
ACRES
2020
BUILT
"Soon to be started inventory home. The Elizabeth Elevation 2 Floorplan. Hardwood at the 1st Floor, Gas Fireplace, Stainless Steel Appliances, Upgraded Cabinetry, Granite Counters, Finished Rec. Room and Full Bath at Basement, 9' Poured Concrete Walls in the Basement, Upgraded Carpet and Padding throughout."
 
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