Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 02/23/2020 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 
$884,900
42741 WAVERLY WAY, Leonardtown MD 20650
4
BEDS
3
BATHS
2,777
SQFT
$319
$/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!!(MOTIVATED SELLER)"
* PRICE LOWERED - $894,900 TO $884,900 
$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"
$636,000
40325 DRURY LN, Leonardtown MD 20650
3
BEDS
2
BATHS
2,260
SQFT
$281
$/SQFT
0.98
ACRES
1976
BUILT
"A home that tells its own story can be your dream home on the water! An architect and artist built this home in 1976 with inspiration from Frank Loyd Wright. The kitchen, pantry, office, laundry room and guest bath are inspired by a house boat with specialty-built drawers, cubbies and shelves galore! Views of the water can be seen from an endless wall of windows throughout the open-concept kitchen, dining and living room spaces. Architectural beams and beautifully incorporated stain glass blocks enrich the story of this home. The double fireplace in the living room area has a moving fire! This brilliant idea allows you to turn a crank and slide the fire from the living room into the master bedroom! Skylights are masterfully placed alongside high ceiling windows to allow natural light throughout the space. The amazing studio has cupboards galore to house all the supplies that nourish your inner artist. There is even a murphy bed in the wall for quick naps to keep the creative juices flowing. The studio opens to the carport and could easily be used as a home office. A beautiful deck surrounds a large portion of the property and leads out to overlook the water. A white brick hearth and patio, steps from the sun room and kitchen, are perfect for outdoor entertaining. This property also includes its own pier! Top it off with one enclosed garage and a double carport all in the same beautiful white brick. The large dry basement provides more storage than you could possibly need! This home begs for the perfect new creative family to continue its story! Could that be you?"
$624,900
22322 HANOVER DR, Leonardtown MD 20650
4
BEDS
5
BATHS
4,737
SQFT
$132
$/SQFT
1.04
ACRES
2005
BUILT
"Looking for lots of space? Here it is. This home has great space inside and out. Sitting at end of street in the culdesac on a little over and acre, backing to trees, in a water priviledged community. Welcoming two story foyer flanked by a formal living and formal ding area. Large Family room with gas fireplace is adjacent to the grand kitchen with custom cabinets, stainless steel kitchen aid appliances, granite counters , and huge center island. On rear of home you will find a second extra large family room. Master is also on main level with en-suite bath and extremely large walk in closet. Hardwood flooring throughout main level. Second story with second master suite, plus two additional bedrooms and full bath. Basement is partially finished with an 800 sq foot theater(all theater equipment will convey) plus a full bath. There is an additional 1700 sq ft of space for you to use as you desire. Did I mention the 1200 sq ft 3 car garage? Loft above is ready for heat and a/c. and your finishing touch. Paver patio out back and a nice level back yard. Community pier and access to Breton Bay. This is a great place to call home!!"
$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 
$549,900
43190 HERITAGE DR, Leonardtown MD 20650
4
BEDS
3
BATHS
3,472
SQFT
$158
$/SQFT
2.57
ACRES
2009
BUILT
"NEW NEW NEW! New roof, gutters and downspouts in 2019. New linoleum in the kitchen and new carpet in the family room. This beautiful one-owner two-story colonial offers plenty of privacy on an culdesac lot in sought-after Leonardtown Farms. Built with space in mind for everything, the dining room can seat the largest of gatherings, an ample kitchen with under-cabinet lighting is open to the family room to make daily interaction comfortable and functional. The kitchen / family room space opens to a large deck which extends the living area to the outdoors in fine weather. There is a library/office space on the main level for work or study and plenty of recreation space on the lower level with a theater room for movie-buffs and football fans alike. The lower level entertainment space is rounded out with a pool table and bar area for serving refreshments. When it~s time to rest, the upstairs offers comfortable bedrooms with plenty of closet space. The owner's suite is an oasis of comfort with a large sitting room and spa bath with walk-in shower and soaking tub. And there~s more! For car buffs and those who like to tinker, enjoy an attached 2-car garage AND an additional 3-car detached garage with storage above. Top everything off with an efficient solar system to keep the electric bills super low for a home this size! With a short commute to Pax River, Leonardtown government offices and the local hospital, this home is minutes from shopping, entertainment, entertainment and everything Southern Maryland has to offer. Come home to a great neighborhood with plenty of areas to play, walk, run, or bike."
* NEW LISTING 
$549,000
22103 PHILIP DR, Leonardtown MD 20650
5
BEDS
3
BATHS
3,222
SQFT
$170
$/SQFT
0.95
ACRES
1990
BUILT
"Welcome home to this spacious custom built colonial located in desirable WATERFRONT COMMUNITY of the Mulberrys of Breton Bay. Home has 5 bedrooms, 3 full baths with over 3200 sqft of living space. Three car attached garage and huge two level 14'x28' Amish built shed for all of your toys and tools. Nice level .95 acre lot with beautiful stamped concrete patio off the back of the home for entertaining and enjoying the outdoors. Newer HardiPlank siding. Generator hook up. Boat slip conveys at the community dock with 8000 lb boat lift! Other neighborhood amenities include tennis/basketball courts and winter boat, trailer and RV storage area. Convenient Leonardtown location and short distance to Breton Bay Golf and Country Club (memberships available) and Breton Bay Beach (memberships available). Home and property have been well maintained and is move in ready!"
* NEW LISTING 
$538,500
22520 LANDING WAY, Leonardtown MD 20650
3
BEDS
4
BATHS
2,752
SQFT
$196
$/SQFT
0.06
ACRES
2005
BUILT
"The first time on the market to own the best waterside townhouse in Leonardtown Landing and maybe the best townhouse in all of Southern Maryland! Enjoy the spectacular scenic water views from almost every room, where you can view the stunning sunrise and sunsets over Breton Bay. Renovated townhouse is filled with natural light and gourmet kitchen with granite counter tops, hardwood floors, a large deck and a nice size pantry. The family room has a fire place, hardwood floors and a large deck. The master bedroom has a 24-foot deck with panoramic views. Just off the master bedroom is an office with water views on three sides of the room. The game room has a large patio and full bath. The main level has nine-foot ceilings. This could be your forever home with an elevator that can take you to every level. You are a short distance from all that the Historic Leonardtown Arts and Entertainment District has to offer with restaurant~s, history, shopping, Leonardtown Warf Park and Leonardtown special events. Plenty of outdoor living with four large decks and a patio to take advantage of the perfect location next to Breton Bay. Biking, hiking and kayaking, are right out your front door. This your opportunity to live every day as an adventure in natures beauty."
$485,000
20770 DEER WOOD PARK DR, Leonardtown MD 20650
4
BEDS
4
BATHS
4,106
SQFT
$118
$/SQFT
4.75
ACRES
1995
BUILT
"Look no further. This well maintained colonial 4 bedroom 2.5 bath has 3256 sq ft plus bonus room is nestled on 4.75 acres in custom built Chestnut Hills. New roof. First floor HVAC is 3 years old, second floor HVAC is 1 year old. All new carpet on the second floor. Fresh paint throughout. home. First floor master bedroom or in-law Suite with a second master bedroom on the second floor. Hardwood floors on the first floor. Remodeled kitchen with new Sansung Flex Duo 5 burner. All bedrooms are large with a second room attached which could be used fora play room, office, or study area. Generous closets. Gas Fireplace, tankless hot water heater. Snow Blower, Lawn Mower, and 2 work benches convey. Come join this active community that sponsors many social and community activities throughout the year. Community has an active FACEBOOK page"
$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: Immediate Delivery, Hardwood Foyer/Dining Room/Kitchen/Breakfast Nook, SS Appliances w/Double Wall Ovens, Upgraded White Cabinetry at Kitchen, 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, Luxury Owner's Shower w/Tiled Floor and Frameless Glass Enclosure. 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 BRAND 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!! This new elevation gives a BIGGER front porch and the adorable look of a cape cod! There is a huge unfinished basement waiting for your personal touches! Contact us today to get your customized color scheme! There is still time to choose some options!"
* PRICE INCREASED - $470,100 TO $474,100 
$471,693
25033 MEADOWLARK CT, Leonardtown MD 20650
4
BEDS
3
BATHS
3,046
SQFT
$155
$/SQFT
0.21
ACRES
2019
BUILT
"LOCK IN NOW & TAKE ADVANTAGE OF THESE LOW RATES!! Under Construction NOW! 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!"
* PRICE INCREASED - $471,657 TO $471,693 
$468,283
23050 TOWN RUN DR, Leonardtown MD 20650
3
BEDS
3
BATHS
2,644
SQFT
$177
$/SQFT
0.24
ACRES
2020
BUILT
"Your chance to own the next Village Series home is NOW HERE! The Fenwick is making its appearance in Meadows at Town Run! Great floor plan for a great price with all of the amazing QBH quality upgrades! Granite gray siding with black accents will make this home stand out above the others. A tankless hot water heater to make sure that the hot water never runs out! Cinnamon random sized plank hardwood throughout the whole main level gives this home a warm and welcoming feeling. The Deluxe shower, tiled bathrooms & SO MUCH MORE! Builder gives $10K in closing when choosing one of their preferred lenders. There is still time to choose upgrades, lock in your interest rate & KNOW your payment NOW!"
$460,598
23044 TOWN RUN DR, Leonardtown MD 20650
3
BEDS
3
BATHS
2,536
SQFT
$182
$/SQFT
0.22
ACRES
2020
BUILT
"The *HAYDEN* now available in Meadows at Town Run! This home gives you all of the amazing QBH features at a price that you can afford! This lot only gives you ONE neighbor - not many like this in MTR! Our beautiful Grand kitchen is featured with slate appliances and amazing granite counter tops. Hardwood floors throughout the main living areas. A pantry - or maybe you want a butler pantry...we can do that! Huge laundry room upstairs, walk-in master closet, recessed lights and so much more!! Don't let the 3 bedrooms turn you away!! There is possibility to add a 4th bedroom and another bathroom! Still time for customization to make this house something that you can call home. 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. Shopping, dining, and recreation options abound in the Arts & Entertainment District, with numerous family-friendly events throughout the year."
* PRICE LOWERED - $461,663 TO $460,598 
$454,988
25052 MEADOWLARK CT, Leonardtown MD 20650
4
BEDS
3
BATHS
2,675
SQFT
$170
$/SQFT
0.19
ACRES
20
BUILT
"!! LOCK IN NOW AND TAKE ADVANTAGE OF THESE GOOD RATES !! 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 
$450,000
23681 MARGRAVE DR, Leonardtown MD 20650
4
BEDS
4
BATHS
3,603
SQFT
$125
$/SQFT
0.20
ACRES
2013
BUILT
"Lovely 4BR Leonards Grant Patuxent Model with Pond Views. Open Concept Floor Plan. Big Deck and Full Patio. Fenced back yard. Large Master Suite w/ 2 WI Closets and luxury Master Bathroom w/ 4' walk in shower, 2 sep. vanities and big soaking tub. Upstairs laundry room with front loading washer and dryer. 2nd and 3rd large bedrooms upstairs also have walk in closets. Fully finished WALK OUT basement with rec room, full bathroom and the 4th bedroom. Gourmet kitchen with granite, island, stainless, double ovens and gas cook top. Hardwood flooring. Large Family Room w/ Gas Fireplace. Formal DR or Office with French Doors. New Carpet in Basement and Fresh Paint. Turn Key and move-in Ready. Welcome Home!"
$450,000
40502 PORT PL, Leonardtown MD 20650
3
BEDS
3
BATHS
1,952
SQFT
$231
$/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."
$447,000
41457 CHARISMATIC WAY, Leonardtown MD 20650
4
BEDS
4
BATHS
3,276
SQFT
$136
$/SQFT
0.16
ACRES
2014
BUILT
"Step into this gorgeous, move- in ready and oh so popular Hayden Model! Located in the highly sought after community of Leonard's Grant. This home features gorgeous upgrades in an open concept floor plan with gleaming blonde hardwood floors. Immaculate and well maintained, this home is sure to please! The gourmet kitchen features upgraded stainless steel appliances, gas cooking, huge island and built-in desk. Many awesome features of this home include an office with French doors, formal dining room, huge family room with a fireplace and wired for surround sound. The fully finished basement features a theater area, bedroom, full bath and huge storage area for all of your extras. There are 3 spacious bedrooms upstairs, including a large 18x16 owners suite with a massive walk-in closet. The master bath features a soaking tub, separate tiled walk-in shower and his/her vanities. There is upgraded tile throughout all of the bathrooms. The house is situated on the perfect lot with gorgeous views of the farm across the street and the play ground. The backyard is fenced and features a stamped concert patio. the perfect spot for a fire pit and entertaining. They even installed a safety gate at the top of the exterior steps to help keep little ones safe. Just steps away from the playground and a short walk to the community pool and clubhouse. This home has all of the upgrades and extras including lawn irrigation, alarm system, tankless hot water heater, added trim work and a 2 car rear load garage. Sit on the front porch with a glass of tea and enjoy over looking the farm land. Walk to Duke Elementary School, the new library, or the Leonardtown Wharf. Enjoy the quaint shops, restaurants, markets, waterfront and exercise studios-just a short bike ride away!"
$432,985
44024 COTTON TAIL CT, Leonardtown MD 20650
3
BEDS
3
BATHS
2,245
SQFT
$193
$/SQFT
0.28
ACRES
2019
BUILT
"!! LOCK IN NOW AND TAKE ADVANTAGE OF THESE INTEREST RATES !! The Dunkirk on a gorgeous FLAT lot! IMMEDIATE DELIVERY! One of the last larger lots left in Meadows. All of the amazing QBH features at a GREAT price! 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 - $427,985 TO $432,985 
$432,000
23552 BELMAR DR, Leonardtown MD 20650
4
BEDS
3
BATHS
2,730
SQFT
$158
$/SQFT
0.20
ACRES
2009
BUILT
"Clean slate! This immaculate Leonard's Grant home looks like it's never been lived in. Beautiful, open, and airy, this home is ready for a buyer with just about any taste. This Quality Built Homes Newport model sits on a great lot that backs to trees and is just steps away from the popular Duke Elementary school. Featuring 4 bedrooms, 2.5 baths, and a huge unfinished basement; which is ready for a theatre room, workshop, exercise room, or whatever you can dream of. A neutral white color palette is a great option for any decorating style. The master bedroom features a huge walk-in closet, ensuite bath with dual vanities, separate soaking tub, and walk in shower. The additional 3 bedrooms upstairs are spacious enough to accommodate large furniture. A large deck off the back of the home is great for backyard bar-b-ques or entertaining. The spacious back yard is flat and useable and could easily be fenced in. Just a short walk to the new library (coming in fall 2020), local restaurants, the Leonardtown Wharf, shopping, and various sports fields. This awesome neighborhood features a community pool, tennis courts, various playgrounds, basketball courts, and community clubhouse. Come see for yourself why Leonard's Grant is one of the most requested neighborhoods in the area!"
* NEW LISTING 
$424,900
23246 CLARKS REST RD, Leonardtown MD 20650
5
BEDS
4
BATHS
3,024
SQFT
$141
$/SQFT
0.16
ACRES
2017
BUILT
"PRICE DROP !!!!!!!Already built and ready to go !!! Don't wait 6-8 months for a new one when you can buy this and move in 30 days or less. !!. Beautiful 5 bedroom 3.5 bath home only 2.5 years old. Has the bells and whistles that the new to be built ones offer. Full basement too!. Close to everything and just waiting for you to call it HOME Summer is coming..enjoy the pool and tennis courts or have a party at the clubhouse. Don't wait.... This will be gone !!! Interest rates are still very low so you can take advantage of it while it lasts. Call today to schedule your personal viewing."
* PRICE LOWERED - $430,000 TO $424,900 
$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! NEW ELEVATION AVAILABLE!!! 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?"
 
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