Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 07/15/2019 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! A Beautiful Southern Maryland Coastal Retreat. Gracious & Sophisticated. Elegant Details throughout this well appointed home. View the 3D video Tour at https://jpowell339.wixsite.com/website-177. The Custom 2-story Barrel Ceilings are truly Gorgeous. Stained Glass insert in the Foyer is Beautiful. 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. 30 Minutes to NAS Patuxent River and an hour to DC and VA."
* PRICE LOWERED - $1,499,750 TO $1,250,000 
$1,200,000
22559 BAYSIDE RD, Leonardtown MD 20650
4
BEDS
2
BATHS
1,514
SQFT
$793
$/SQFT
48.90
ACRES
1951
BUILT
"Such a UNIQUE piece of the property located in the quaint town of Leonardtown ** Water Front farm with 4 bedroom Cap Cod, barns, out buildings, small house, foundation for 3000 + sq ft house, already perced and ready to finish your dream home, pier ..all on over 48 ACRES !!!Beautiful location and just minutes from all your shopping and entertainmentProperty is situated on Cecil Creek..protected from the River ** over 1500 foot of water front..WOW !!!!Make some extra income leasing the property to farm or huntOR>>>>>> just enjoy yourself !"
* LISTED OVER 120 DAYS 
$1,095,000
42741 WAVERLY WAY, Leonardtown MD 20650
4
BEDS
3
BATHS
2,777
SQFT
$394
$/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 "
$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. Recently built cottage style home w/ 1st floor suite, open living areas, office, stacked stone fireplace & over sized garage. Plus a large 2 story center aisle barn w/ 2 bedroom apartment. A great place for family, friends or a business. The property offers several outbuildings, miles of board fencing, lighted riding ring & trails. Need help with the down payment? Ask about MARBIDCO"
* LISTED OVER 120 DAYS 
$795,000
41955 SWANS CT, Leonardtown MD 20650
6
BEDS
7
BATHS
7,160
SQFT
$111
$/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 it's 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. 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 automatic 17kw generator, and double hot water heaters. Enjoy dining, shopping, and entertainment just a few minutes away in "
$749,900
40125 ARMY WAY, Leonardtown MD 20650
5
BEDS
4
BATHS
3,395
SQFT
$221
$/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 - $775,000 TO $749,900 
$684,900
42403 RIVERWINDS DR, Leonardtown MD 20650
3
BEDS
3
BATHS
2,079
SQFT
$329
$/SQFT
0.63
ACRES
1953
BUILT
"2 Homes for 1! Unique opportunity to own 2 detached units on the same waterfront lot! 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."
$606,900
40090 GREENTREE DR, Leonardtown MD 20650
4
BEDS
3
BATHS
3,000
SQFT
$202
$/SQFT
2.27
ACRES
2019
BUILT
"TO BE BUILT on 2+ acre lot in up-scale community, with high speed Internet.main level master suite, and a two-story foyer and family room. Additional features include covered front porch, attached 2 car garage and unfinished basement Builder will build your dream home with your construction loan. Build your dream home on a private lot with your floorplans or ours, just outside of town."
* LISTED OVER 120 DAYS 
$584,000
40863 LARK WAY, Leonardtown MD 20650
5
BEDS
5
BATHS
6,388
SQFT
$91
$/SQFT
2.03
ACRES
1998
BUILT
"Gorgeous low-country style Cape Cod home nestled on 2.3 acres of wooded privacy and abundant landscaping in ever-popular Avenmar. Walk to pool/tennis/water access in the beautiful Leonardtown neighborhood. This is a custom-built home with 4500+ sf of living space above grade and another approx. 1800 sf of finished space on the lower level. This sensational home offers large room sizes and plenty of space to spread out! Most of the main level has Brazilian Cherry hardwoods, wonderful open Cook's Kitchen open to sizable Family Room with new gas fireplace, bright and cheerful Sunroom, formal Living and Dining Rooms and fabulous Laundry. First floor also offers the Owner's Suite which has a gas fireplace, large Owner's Bath with huge shower, and two large walk-in closets. Easy access to the ample screened porch from the Kitchen, Sunroom and Owner's Suite. The second floor features three enormous Bedrooms (one with enSuite Bath), two Baths, open Study/Reading area, and a great upper level Office/Study (currently used as bedroom #5). Dual staircases lead to the second floor. The lower level is tremendous fun! How about a Theater and Games Room, Hobby Room, Bath and Canadian-style cabin room which leads to the lower level stone paver patio. Both HVAC systems have been replace with high-efficiency units which keep electric bills very reasonable! Invisible fencing on entire yard. Rough-in on screened porch for hot tub. So much to offer new loving owners. Home Warranty."
* PRICE LOWERED - $599,900 TO $584,000 
$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 
$549,900
21265 HUNTING CT, Leonardtown MD 20650
5
BEDS
5
BATHS
4,779
SQFT
$115
$/SQFT
1.05
ACRES
2007
BUILT
"Beautiful one owner two story colonial, 5 bedroom 4.5 bath house on a 1.05 acre corner lot in the desired community of Leonardtown Farm. Beautiful oak hardwood floors and berber carpet downstairs, with a large custom kitchen with granite and cherry cabinets. Large master bedroom and fully tiled custom bathroom with a walk in shower and jetted jacuzzi. Finished basement with plenty of unfinished storage. Two car garage with a deep sink. Great neighborhood with plenty of areas to play, walk, run, or bike. Come see for yourself what this house has inside. You will not be disappointed."
$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. Main level Owners Suite with Spa leads to Deck. Gourmet Kitchen. Gas FPs. Hardwood and Ceramic Floors. Walk-out Basement with full Bath.Upper lvl 2nd Master & Library. Floor plans, location drawing and details available."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $549,900 TO $544,900 
$525,000
41505 REINS CT, Leonardtown MD 20650
4
BEDS
4
BATHS
4,508
SQFT
$116
$/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"
* PRICE LOWERED - $547,000 TO $525,000 
$499,999
40977 PIPITS LN, Leonardtown MD 20650
4
BEDS
4
BATHS
3,970
SQFT
$126
$/SQFT
2.84
ACRES
1997
BUILT
"Private lot in beautiful Avenmar Community. 4 Bedroom, 3.5 Bath nestled on a 2.84 acre Water privileged with club house, pool, tennis courts, boat ramp and dock with kayak storage, playground, horse trails, barn, riding. main level gleams with fresh paint. All new stainless steel appliances in the kitchen. Formal living room and dining room. Gourmet kitchen with granite counters, library/office, wood burning fireplace, wood floors on main level, master bath with separate shower, walk in closet, and sitting area. Basement with rec room. Multi level deck overlooks quiet backyard. New front door, new back door, Added molding in the office, new light fixtures, in entry, dining room and kitchen, new double oven, new granite counter tops, new carpet and flooring in family room, new shower in master bath, molding added to half bath on main floor."
* PRICE LOWERED - $529,000 TO $499,999 
$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. Custom home has Open floor plan w/ master suite on main level. Many standard upgrades include granite, wood on main level, upgraded trim package, stainless appliances, upgraded fixtures."
$499,000
40140 WATHEN RD, Leonardtown MD 20650
4
BEDS
3
BATHS
3,527
SQFT
$141
$/SQFT
3.00
ACRES
2000
BUILT
"Price Reduced!! 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 - $507,000 TO $499,000 
$484,500
23767 COVENTRY DR, Leonardtown MD 20650
6
BEDS
4
BATHS
4,209
SQFT
$115
$/SQFT
0.29
ACRES
2013
BUILT
"Look no further this house has all the bells and whistles.~ This Frederick Model has a nice open floor plan that provides lots of living space, with 6 bedrooms, 3 full baths & 1 half bath.~Freshly painted and new carpet.~Sun-room overlooks nice size back yard that overlooks that woods. Eat in kitchen with a separate formal dining room.~ Master bathroom has separate vanities, standing shower and full soaking tub. Master bedroom has a extra sitting room which could also be used for office. Basement is equipped with two bedrooms with a full bath and large rec room area for entertaining. Basement also has unfinished area space for storage. Right in the heart of Leonardtown, and with convenience to stores and schools. Motivated Sellers, 30 day closing and drastic price drop!!!"
* PRICE LOWERED - $499,900 TO $484,500 
$482,832
23056 TOWN RUN DR, Leonardtown MD 20650
4
BEDS
3
BATHS
3,072
SQFT
$157
$/SQFT
0.27
ACRES
2019
BUILT
"**TO BE BUILT** Quality Built Homes' Clarke to be featured in Meadows at Town Run! This home is a stunner!!"
* PRICE INCREASED - $428,900 TO $482,832 
$475,000
23603 MARGRAVE DR, Leonardtown MD 20650
5
BEDS
4
BATHS
4,271
SQFT
$111
$/SQFT
0.20
ACRES
2011
BUILT
"This Barstow model is located in desirable Leonard's Grant! Offering 5 bedrooms and 3.5 baths A gorgeous Kitchen with a large center island, stunning granite countertops, wall oven, a huge pantry. There is a separate formal dining room, an open family room with gas fireplace, and full finished basement. Beautiful hardwood floors, recessed lighting, ceiling fans and overhead lighting in all bedrooms.spacious Master suite with cathedral ceiling and a huge walk in closet. The Master bath features a soaking tub and very spacious separate walk-in shower with bench, and separate vanities.The finished basement offers a full bath and rec room. There is also a large unfinished storage room. The backyard yard is fenced and features a large deck for entertaining. Attached 2-car front load garage with openers. Leonard's Grant is a Master Planned Community with pool, clubhouse, open greens, sidewalks, playgrounds, tennis court, basketball court, and lots more to offer."
* NEW LISTING 
$469,000
21864 FAIRWAY DR, Leonardtown MD 20650
4
BEDS
5
BATHS
4,112
SQFT
$114
$/SQFT
0.64
ACRES
1997
BUILT
"Beautiful updated home on 4th Tee of Breton Bay Golf Course! This is a great home with extensive hardscape/mature landscape to enjoy the summer. The floor plan offers plenty of living space for everyone. Most rooms have custom window treatments or plantation shutters and the main level floors are mostly hardwood. The gorgeous kitchen design offers tons of custom cabinetry, SS appliances, granite counters, large island, updated tile floors and breakfast area. Kitchen opens to large family room with wood burning fireplace. Cheerful sunroom adds to your year-round enjoyment and has great view of the landscaped backyard. In addition, you'll find a nice private study with glass French doors, separate dining room and full laundry. The upper level features four sizable bedrooms with three full baths and plenty of closet space. In the basement you'll find an exercise room, large game room with outside access, office space and another full bath. The garage is over-sized and has lots of cabinets for storage. Some of the extras you'll get with this home: underground lawn sprinkler system, invisible fence, retractable awning at back patio, whole-house generator and gutter leaf guards. Walk to the community beach area (currently $50/yr), Breton Bay Golf & Country Club (pool requires membership), or a small private marina if you have a boat. This is a great lifestyle to enjoy all year!"
$468,900
22195 HANOVER DR, Leonardtown MD 20650
5
BEDS
4
BATHS
3,710
SQFT
$126
$/SQFT
0.74
ACRES
2007
BUILT
"Beautiful home located in much sought-after Hanover Farms neighborhood. A family centered home, this house is located central to Leonardtown public and parochial schools and offers plenty of space for the everyone. Upon entering the 2-story foyer, your eyes are led up the lovely staircase where you find a huge mater suite, 3 spacious bedrooms and a second-story laundry room. An open floor plan and paver patio downstairs offer plenty of room for entertaining both inside and out, and the home includes many technology upgrades including surround sound, multi-zone whole-house audio, internal WAP and outdoor speakers to keep everyone entertained and connected. There~s even an invisible fence for the furry members of your family on ~ acres of a dog approved yard! The first floor boasts solid oak hardwood throughout and includes kitchen/dining area open to the living room, and a first-floor office. The garage has been upgraded to provide ample storage including wall-to-wall cabinetry, workbench, and 3 large ceiling mounted storage racks. The fully finished basement has been recently remodeled with new high-grade laminate flooring, fresh paint, pellet stove, wet bar, full bath and is wired for 7.1 theater quality sound, making an excellent suite for mother-in-law, house guests, or hang-out for kids and their friends. Beautifully landscaped private yard, abuts an antique tobacco barn which provides a relaxing atmosphere for morning coffee, grilling out, or roasting marshmallows by the firepit, and the barn-style shed is large enough to house all of your outdoor toys! Community amenities in the rear of this intimate neighborhood include open area playground, large gazebo with firepit, kayak/canoe/boat storage, and pier providing opportunities to paddle your way all over Breton Bay including stops at the Leonardtown Wharf, or Winery for the days when you want to get out on the water. Located within walking distance of the St. Mary~s county fairgrounds, you won~t have "
* PRICE LOWERED - $480,000 TO $468,900 
$468,000
40502 PORT PL, Leonardtown MD 20650
3
BEDS
3
BATHS
1,952
SQFT
$240
$/SQFT
0.76
ACRES
1980
BUILT
"JUST REDUCED! Breton Bay Estates Waterfront home on Cherry Cove Creek with private pier and two electric boat lifts. 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 in the kitchen and entry level bedrooms."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $485,000 TO $468,000 
$465,427
44054 COTTON TAIL CT, Leonardtown MD 20650
3
BEDS
2
BATHS
2,339
SQFT
$199
$/SQFT
0.24
ACRES
2019
BUILT
"**Under Construction** Agent must accompany buyers** Meadows at Town Run FIRST Spec Home!! The desired Ashland floor plan will be completed just in time before school starts! There is still time to choose colors and make this home yours! Wide open floor plan with cathedral ceilings, galley kitchen, breakfast nook that feels like a sunroom, split bedroom floor plan & SO MUCH MORE! This home is one to impress!"
$459,873
41337 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
4
BATHS
0.15
ACRES
2019
BUILT
"Next Inventory Home: WICOMICO Floorplan: Summer 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."
* LISTED OVER 120 DAYS 
 
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