Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 12/08/2019 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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$1,080,000
41191 BRETON BEACH RD, Leonardtown MD 20650
4
BEDS
3
BATHS
3,941
SQFT
$274
$/SQFT
62.87
ACRES
2008
BUILT
"Live where you work. Successful horseback riding business. Property & business for sale. Step up and take over the reigns of this long time profitable business built from the ground up by the seller. All the pieces are in place to make money from day one. Helpful seller will get you started and show you how he did it for so many years. 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. Seller happy to share plans for an indoor too. Need help with the down payment? Ask about MARBIDCO. Serious inquiries only please and confidentially agreement must be signed prior to appointments."
* PRICE LOWERED - $1,100,000 TO $1,080,000 
$924,000
21500 ABELLS WHARF RD, Leonardtown MD 20650
7
BEDS
5
BATHS
10,276
SQFT
$90
$/SQFT
12.44
ACRES
1976
BUILT
"Fantastic Waterfront Opportunity! 12.44 acres zoned commercial marine on Breton Bay. Main house currently divided into 3 units but can easily be converted back to one house with an in law suite. Tenant house/cottage house has 2 BRs, 2 full BAs, kitchen, laundry & great room. Tenant house and in law suite have been renovated. Two car detached garage with walk up steps to attic storage or possible workshop. Open shed for boat storage, equipment & more. Private pier with deep water. Perfect for a large family needing an in law suite and a 2nd residence. Commercial uses such as Bed & Breakfast, Marina & Marine related sales, Boating clubs or associations, Special event location & so much more! Allows over 100 boat slips & land for a Boatel. The possibilities are endless with this gorgeous property."
$894,900
42741 WAVERLY WAY, Leonardtown MD 20650
4
BEDS
3
BATHS
2,777
SQFT
$322
$/SQFT
4.07
ACRES
1956
BUILT
"Rare Find!! 4 Bedrooms, 3 Baths, 4.07 Acres, 800 feet of pristine Potomac beachfront, as well as a beachfront Cabana with water and power, all within minutes of downtown Leonardtown! This large, traditional brick ranch home has been in the same family since first built, and offers possibly the most panoramic waterfront views anywhere in the area. This home features a full basement, perfect for a large workshop, or ready to be finished off for additional living space. Heating is oil-fired baseboard, the Cadillac of heating systems. Propane powers the gas cooktop and wall mounted oven. Wood burning fireplaces are found in both the formal living room and family room/study. Original hardwood floors cover over half of the house. A large concrete full length deck off of the rear of the home allows for a multitude of outdoor uses, all with a scenic view of Belvedere Creek. In recent years, improvements include a new roof, new deep well, and new septic drain field. That's a lot of money the new homeowners won't have to spend! With the amount of acreage, water everywhere, and a little bit of updating and customizing, this house has the potential to be the waterfront estate you've dreamed of!!"
* PRICE LOWERED - $949,900 TO $894,900 
$874,950
41191 BRETON BEACH RD, Leonardtown MD 20650
4
BEDS
4
BATHS
3,941
SQFT
$222
$/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. Seller happy to share plans for an indoor riding ring too! 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"
* PRICE LOWERED - $895,000 TO $874,950 
$639,900
21130 SOMEDAY FARM LN, Leonardtown MD 20650
4
BEDS
3
BATHS
3,194
SQFT
$200
$/SQFT
11.08
ACRES
2011
BUILT
"Beautiful custom built CAPE COD on over 11 acres. This home is truly a one level home with 3 Bedrooms, 2 1/2 baths on main level , with additional 4th Bedroom (bonus room), upstairs. Upgraded granite kitchen with Cords Cabinetry, hardwood floors, custom blinds, over sized laundry room, Hardscaping professionally done by Stepping Stone, Jacuzzi, and screened porch. The home is located in the highly desired Leonardtown School District and has been pet & smoke free. Outbuildings include a horse barn, storage shed and a huge (20'x40') workshop with concrete flooring and attic storage. Perfect for a farmette and your horses. A trail goes to St. Mary's State Park and over 7 miles of horse, biking and walking trails. Stocked lake for fishing too. NO HOA! Pool is possible as well."
$559,900
40624 BRETON OAKS LN, Leonardtown MD 20650
4
BEDS
4
BATHS
2,760
SQFT
$203
$/SQFT
1.49
ACRES
2019
BUILT
* PRICE INCREASED - $549,900 TO $559,900 
$475,900
41329 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
4
BATHS
3,878
SQFT
$123
$/SQFT
0.15
ACRES
2020
BUILT
"WICOMICO Inventory Home: Targeting a May 2020 Delivery 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, Double 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. 2x6 Construction with thicker insulation in walls/attic and Low E Windows."
$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 Early 2020 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. 2x6 Construction with thicker insulation in walls/attic and Low E Windows."
* PRICE INCREASED - $474,347 TO $475,900 
$474,100
25057 MEADOWLARK CT, Leonardtown MD 20650
3
BEDS
2
BATHS
2,339
SQFT
$203
$/SQFT
0.21
ACRES
2019
BUILT
"** TO BE BUILT ASHLAND MODEL WITH NEW ELEVATION ** 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!"
* PRICE INCREASED - $470,100 TO $474,100 
$471,657
25033 MEADOWLARK CT, Leonardtown MD 20650
4
BEDS
3
BATHS
3,046
SQFT
$155
$/SQFT
0.21
ACRES
2019
BUILT
"!! TO BE BUILT !! The very popular Lancaster floor plan located on a gorgeous flat lot in desired Leonardtown! This home has a little bit of everything for everyone - HUGE bedrooms so no one is fighting over who has the biggest room, a mudroom with drop zone, a grand kitchen with tons of cabinets and deluxe master bathroom. No worries about running out of hot water because there is a tank-less hot water heater STANDARD! There is still time to choose some options!"
* PRICE INCREASED - $466,657 TO $471,657 
$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."
$464,900
23630 HANSEL CT, Leonardtown MD 20650
5
BEDS
4
BATHS
4,765
SQFT
$98
$/SQFT
0.38
ACRES
2010
BUILT
"Leonards Grant community. Walking distance to Walter Francis Duke Elementary School and currently under construction, new county library. This community is known to attract even the most discerning buyers and this home will not disappoint. On a corner lot w/ 2 car side load garage and fully finished basement. 4 BR~s on the upper level and 2 FBA, main level with office/den and full bathroom, 2 story open family room with fireplace, living room, dining room, breakfast area, and grand kitchen with granite counters, island, stainless steel appliances and upgraded cabinetry. Breakfast area includes sliding glass door with access to deck and views of the backyard. Leonard~s Grant HOA includes pool, clubhouse, playground, sports area and community activities. Highly sought after school district!"
$462,000
23656 COVENTRY DR, Leonardtown MD 20650
5
BEDS
4
BATHS
3,812
SQFT
$121
$/SQFT
0.21
ACRES
2014
BUILT
"Beautiful upgraded Compton model located in desirable Leonard's Grant! Shows like a model home! This gorgeous home boasts upgraded gleaming hardwood floors, an open floor plan, spacious bedrooms, 2 foot bump-out, and perfect location! The large fenced rear yard make this home spacious and perfect for entertaining, a pool, and play equipment. Gourmet kitchen with owner upgraded stainless steel appliances! Double wall oven, granite counter tops, gas cooking and large refrigerator make this kitchen inviting for everyone. The family room is the perfect set up with in the wall Polk surround sound speakers and gas fireplace. Large dining room able to accommodate a table for 10+ people. An awesome tiled mudroom just off of the garage to stash your coats and bags. 4 spacious bedrooms upstairs with new carpeting and neutral colors. The master bedroom has a large walk-in closet, an ensuite bath room with huge tiled shower, separate soaking tub, his/hers vanities, and enclosed water closet. The upstairs laundry room comes with an LG washer and dryer! Fully finished basement with 5th bedroom, full bath, and large theatre area already wired for surround sound with in the wall speakers and movie projector hook up. This awesome home comes with a tankless hot water heater and has fresh landscaping! Located just steps away from the community pool, tot lots, club house, tennis courts, and basketball courts. Walk to the new library (coming fall 2019), Duke Elementary, and the popular Leonardtown Wharf! Well maintained and move in ready. Stop by to see this gorgeous home today!"
$459,900
23246 LINDSAY DR, Leonardtown MD 20650
5
BEDS
4
BATHS
3,876
SQFT
$119
$/SQFT
0.23
ACRES
2017
BUILT
"Beautiful Home located in highly-sought out Clark's Rest Community. Open-plan living provides you with the opportunity to host large numbers of friends and family, all while enjoying the stylish design and layout.Gourmet Kitchen with granite counters, stainless steel appliances, breakfast bar, huge pantry. Formal Dining and Living Room open into the Family Room Area. Owners Suite with large bedroom, 2 walk-in closets, bath with separate soaking tub & shower. Basement offers a Recreational Room, 5th bedroom, full bath, ample storage rooms, plus rough-in for kitchenette/wet bar. Equipped with Ring security system, solar panels, 2-car garage with epoxy flooring, paved side parking space, composite deck and fenced-in back-yard. Located on a premium lot, overlooking the nature trail and pond; one of the best lots and views within the community. Community Amenities include: Clubhouse, basketball and tennis court, oversized pool with separate kiddie pool, pond, walking trails and more! Schedule your showing today. This Beautiful Home Awaits You!"
* PRICE LOWERED - $469,900 TO $459,900 
$454,988
25052 MEADOWLARK CT, Leonardtown MD 20650
4
BEDS
3
BATHS
2,675
SQFT
$170
$/SQFT
0.19
ACRES
20
BUILT
"CURRENTLY UNDER CONSTRUCTION - STILL TIME TO CHOOSE COLORS! The NEW Adelinalocated on a gorgeous flat lot in desired Leonardtown! Walk into this home and watch your guests jaw drop at the stunning staircase. Tons of light will enter this home with all of the windows! Master suite is complete with 2 closets and a Deluxe master bathroom!! No worries about running out of hot water because there is a tank-less hot water heater STANDARD! There is still time to choose some options!"
* PRICE INCREASED - $449,998 TO $454,988 
$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! READY EARLY 2020!! One of the last larger lots left in Meadows. 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
40444 OLD BRETON BEACH RD, Leonardtown MD 20650
5
BEDS
4
BATHS
3,065
SQFT
$139
$/SQFT
1.00
ACRES
2004
BUILT
"Breathtaking water views and peaceful living in this gorgeous colonial featuring 5 bedrooms, 3 full baths situated on an acre! Refreshed throughout with new flooring, fresh paint, new hvac unit and more. Spend your afternoons sipping ice tea and taking in the expansive views of the Potomac River. Stroll down to the community waterfront area and enjoy the beach or kayak. Room for everyone with in law suite on the lower level. Garage, shed, storage room."
$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!"
$415,000
41815 CHELSEY FAYE, Leonardtown MD 20650
4
BEDS
3
BATHS
2,426
SQFT
$171
$/SQFT
0.84
ACRES
"Looking for a sizable lot to customize your LOCAL Quality Built home!! This location is ideal for anyone looking to have it all (retail, 'town' activities, local schools, libraries and of course employment) within minutes and not have an HOA regulating every move you make! Convenience, distance between your neighbors and valuable land ready for you to call home. Call today to inquire about all of the features for this price point! Multiple Floor Plan options available and customization possible."
$414,900
41404 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,807
SQFT
$148
$/SQFT
0.15
ACRES
2020
BUILT
"Elizabeth 3 Spec. To Be Built, Granite Counter, Stainless Steel Appliances, Upgraded Cabinetry, Finished Basement Rec. Room and Full Bath, Hardwood in Foyer, Powder Room, Dining Room, Kitchen and Family Room. Gas Fireplace. Deep Tray Ceiling at Owner's Suite and Walk-In Closet. Community amenities feature: Pool, Clubhouse, Tennis and Basketball Court, Playground, Walking Trails."
* PRICE INCREASED - $375,900 TO $414,900 
$409,900
21117 MARIGOLD ST, Leonardtown MD 20650
5
BEDS
4
BATHS
3,112
SQFT
$132
$/SQFT
1.17
ACRES
2001
BUILT
"Priced reduction! Check out this beautiful 5 bedroom, 3.5 bath colonial tucked away on over an acre in desirable Leonardtown location. Enjoy your privacy by sitting on the welcoming front porch or rear deck surrounded by mature trees! Home boasts over 3300 SF of living space and has a NEW roof! Kitchen features upgraded stainless steel appliances, including double oven with convection, granite countertops, breakfast bar, and space for kitchen table. Kitchen opens up into large living room with hardwood floors and wood burning fireplace with marble trim. Office/den with french doors and separate dining room have hardwood floors as well. 4 bedrooms and 2 full baths upstairs. Master has walk-in closet and huge soaking tub! Fully finished walk-out basement would be the perfect in law suite featuring a living room with wood stove, the 5th bedroom, full bath, and 2nd kitchen! Ceiling fans throughout, over-sized garage, composite deck, fenced in rear yard, and more! Washer & Dryer convey."
* PRICE LOWERED - $419,000 TO $409,900 
$409,900
41408 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,660
SQFT
$154
$/SQFT
0.15
ACRES
2020
BUILT
"INVENTORY HOME: Estimated early 2020 Delivery. 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. New Home Includes: 2x6 Construction, Low E Windows, Thicker Attic/Wall Insulation. Community Amenities: Clubhouse, Pool, Playground, Tennis Court, Basketball Court, Walking Trails, Volleyball Net, Sidewalks, Street Lights."
$399,999
43536 BAYBERRY CT, Leonardtown MD 20650
4
BEDS
4
BATHS
2,980
SQFT
$134
$/SQFT
2.45
ACRES
1990
BUILT
"Peaceful tranquility is finally here in Leonardtown. This beautiful 4 bedroom 3 1/2 bath has so much to explore..From an open concept kitchen and living area to a spacious partially finished basement. Step outside to a nice sized 2.45 acre lot with complete privacy. New septic was installed 5 years ago, along with a 1 year old water heater and AC unit."
* PRICE LOWERED - $415,000 TO $399,999 
 
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