Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 12/16/2018 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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$894,950
41191 BRETON BEACH RD, Leonardtown MD 20650
4
BEDS
4
BATHS
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."
$640,000
44550 MONTANA WAY, Leonardtown MD 20650
3
BEDS
4
BATHS
3,270
SQFT
$196
$/SQFT
16.33
ACRES
1981
BUILT
"All Brick, single level living on 16+ acres, offers open floor plan to great room, dining and gourmet kitchen, Huge owner's wing w/sky-lighted cathedral ceiling; 2 walk-in closets, & over-sized shower. Relax alone or hold special gatherings on the large patio w/in-ground pool. 3-car garage with detached office space. Barn; equipment shed. Horses welcome. Grow your own veggies."
* LISTED OVER 120 DAYS 
$606,900
40090 GREENTREE DR, Leonardtown MD 20650
4
BEDS
3
BATHS
3,000
SQFT
$202
$/SQFT
2.27
ACRES
2018
BUILT
"TO BE BUILT on 2+ acre lot in up-scale community, with wireless 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."
$565,900
40624 BRETON OAKS LN, Leonardtown MD 20650
4
BEDS
4
BATHS
2,760
SQFT
$205
$/SQFT
1.49
ACRES
2019
BUILT
$560,400
40630 BRETON OAKS LN, Leonardtown MD 20650
4
BEDS
3
BATHS
2,450
SQFT
$229
$/SQFT
2.15
ACRES
2019
BUILT
$560,000
40099 ARMY WAY, Leonardtown MD 20650
2
BEDS
1
BATHS
2.63
ACRES
1961
BUILT
"UNIQUE PROPERTY. Beautiful private location on Combs Creek 300+ ft waterfront. 3 homes on 2.66 acre parcel. public sewer to all 3. Two wells (1 shared between 2 houses) Upscale neighboring homes. A DIAMOND IN THE ROUGH. What more could you want? Great potential to subdivide.Rent the 2 cottages while you build your dream home. Owner Financing considered."
* LISTED OVER 120 DAYS 
$559,900
21290 HUNTING CT, Leonardtown MD 20650
4
BEDS
4
BATHS
4,562
SQFT
$123
$/SQFT
1.90
ACRES
2007
BUILT
"Serenity awaits at this custom designed colonial in Leonardtown Farm! This immaculate home has plenty of privacy as it sits on a 1.9 acre corner lot. Over 5,600+ total sqft. Features new roof, hardwood floors, barrel ceilings, bullnose corners, eat-in kitchen, luxurious master bathroom and beautiful landscaping. Main floor master suite, three sided fireplace, cathedral ceilings and walk in closet."
* PRICE LOWERED - $569,900 TO $559,900 
$549,900
40559 PORT PL, Leonardtown MD 20650
4
BEDS
3
BATHS
3,300
SQFT
$167
$/SQFT
0.78
ACRES
1978
BUILT
"3300 sq ft home with spectacular water view on Breton Bay. Spacious kitchen/dining area,office,large family room with fireplace, Amazing second floor sunroom. 4 bedroom, 21/2 bath. Screened in porch. Located next to community beach and pier. All the joy of waterfront without the property taxes. Large 2 car garage with workshop space. Beautiful courtyard in the front yard. Outside storage."
$549,900
20480 CHESTNUT RIDGE DR, Leonardtown MD 20650
5
BEDS
5
BATHS
4,973
SQFT
$111
$/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 
$541,400
40636 BRETON OAKS LN, Leonardtown MD 20650
5
BEDS
3
BATHS
2,717
SQFT
$199
$/SQFT
2.87
ACRES
2019
BUILT
$499,900
40870 GREENWOOD LN, Leonardtown MD 20650
5
BEDS
5
BATHS
4,723
SQFT
$106
$/SQFT
0.89
ACRES
2012
BUILT
"SPECTACULAR BRICK FRONT COLONIAL ON PRIVATE STREET IN LEONARDTOWN. NO HOA! GREAT FLOOR PLAN WITH ALL THE BELLS AND WHISTLES, WHOLE HOUSE SOUND SYSTEM, SUNSETTER ROLL-OUT AWNING, FINISHED WALK-OUT BASEMENT, 3 CAR GARAGE, PAVED DRIVEWAY."
* PRICE LOWERED - $519,900 TO $499,900 
$499,900
22676 CHICKADEE LN, Leonardtown MD 20650
5
BEDS
4
BATHS
4,805
SQFT
$104
$/SQFT
4.11
ACRES
2001
BUILT
"Move right into this Majestic Colonial featuring an exceptional lifestyle! With a designers eye, every detail has been thought of, from the classic key stones making the curb appeal pop, to the upgrades found throughout the interior! You will love entertaining with this gourmet kit w/butlers pantry and tons of cabinets space, large well appointed rooms and full finished basement featuring a bedroom and full bath! 100% FHA FINANCING IS AVAILABLE! Check out the 3-D Virtual Tour!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $539,900 TO $499,900 
$485,000
40502 PORT PL, Leonardtown MD 20650
3
BEDS
3
BATHS
1,952
SQFT
$248
$/SQFT
0.76
ACRES
1980
BUILT
"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."
* PRICE LOWERED - $495,000 TO $485,000 
$469,900
41419 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
3
BATHS
3,408
SQFT
$138
$/SQFT
0.23
ACRES
2014
BUILT
"Price reduced! Modern open floor plan with large MBR & BR w/huge walk-in closets on the main level. Pristine St. Andrews features front porch and screen deck. Convenient kitchen layout w/ upgraded premium wood cabinets, granite countertops. Hardwood floors.Professionally managed garden/yard with automatic sprinkler system. Over $75,000+ worth of upgrades. You can't build this model for this price!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $474,900 TO $469,900 
$459,900
41325 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
4
BATHS
3,820
SQFT
$120
$/SQFT
0.15
ACRES
2019
BUILT
"Next Inventory Home: WICOMICO Floorplan: To-Be-Built, 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 - $457,930 TO $459,900 
$449,999
41488 PENSIVE ST, Leonardtown MD 20650
4
BEDS
4
BATHS
4,500
SQFT
$100
$/SQFT
0.23
ACRES
2008
BUILT
"Enter into an open foyer with high ceilings. Gleaming hardwoods cover the main floor. Gorgeous gourmet kitchen with granite countertops recessed lighting and tasteful backsplash. Large master with custom WIC. En-suite full bath with double vanity separate soaking tub and walk-in shower with glass doors. Basement fully finished with full bath, beautiful marble floors and wet bar. 2 car garage."
* PRICE LOWERED - $458,000 TO $449,999 
$449,900
23221 JENIFER CT, Leonardtown MD 20650
3
BEDS
3
BATHS
3,910
SQFT
$115
$/SQFT
0.37
ACRES
2004
BUILT
"This Beautiful Home Will Spoil You! 1st Floor Master Suite w/ luxury bath, bedroom with sitting area, 2 walk-in closets. Crown molding, 10 ft ceilings, plantation shutters, gorgeous flooring. Gourmet kitchen w/ granite counters, recessed lights. Family Room w/ gas fireplace. Formal Dining room with bay window. Huge secondary bedrooms. Screened-in porch, extensively landscaped yard, In-ground irrigation. Enormous basement w/ space for adding 4th bedroom and bath. Located in the sought-out Estates at Singletree Community. Close proximity to hospital, college, shopping, library, PAX River Base, and more."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $469,900 TO $449,900 
$449,000
23151 LUCKTON CT, Leonardtown MD 20650
4
BEDS
3
BATHS
2,574
SQFT
$174
$/SQFT
2.03
ACRES
1999
BUILT
"Awesome 4 bed 2.5 bath Colonial in wildly popular Forrest Farm neighborhood. 2.5 acre corner lot in spacious first phase of Forrest Farm. Large unfinished basement, hardwood floors throughout main floor, large kitchen, attached garage, updated HVAC, water heater and oil furnace. Great home under 450k, will not last long!"
$449,000
41406 WHIMSICAL CT, Leonardtown MD 20650
5
BEDS
4
BATHS
4,748
SQFT
$95
$/SQFT
0.31
ACRES
2010
BUILT
"Beautiful extended Hampton model in sought after Leonard' Grant community. Large flat corner lot. This home has over 5000 finished square feet to make your own. First floor has gourmet kitchen w/ ceramic tile & 2 story family room! Office or could be bedroom on the first floor & 4 large bedrooms upstairs w/ QBH deluxe master bath. Basement is fully finished w/ theater room, bedroom and full bath."
* PRICE LOWERED - $459,000 TO $449,000 
$445,000
22277 ORCHARD CT, Leonardtown MD 20650
4
BEDS
4
BATHS
2,655
SQFT
$168
$/SQFT
1.64
ACRES
2004
BUILT
"Tucked at the end of a cul de sac in a water access community, sits this beautiful 4 bedroom, 3.5 bath open concept Colonial. Enjoy the amenities of Hanover Farm at Breton Bay, a Leonardtown high school community, including community pier, playground, beach and pavilion. Plenty of space for everyone in the eat-in-kitchen w/gorgeous maple cabinetry, center island, corner window, double sink and pantry open to a spacious family room. Formal dining and living rm/office with french doors and stunning hardwood floors greet you. Chilly nights can be enjoyed in front of the gas fireplace or take a hot soak in the master bath tub. Master suite features 2 walk in closets, double sink in bath and separate shower. Dual zone HVAC keeps all levels comfortable including finished lower level with rec room, den office or guest room with full bath. And, plenty of room for storage. Cars can be kept in the 2-car attached garage while lawn equipment, bikes, etc. share space in the shed. Large, 1.64 acre partially-fenced yard backs to trees. Raised veggie garden, swing set, pergola and lots of room to spread out and play. Fresh paint. Super convenient location to PAX, DC"
$429,900
23577 ABRAHAM DR, Leonardtown MD 20650
4
BEDS
4
BATHS
3,266
SQFT
$132
$/SQFT
0.60
ACRES
2003
BUILT
"This beautiful brick 4 bedroom, 2.5 bath home has it all. Finished basement with full bath, level fenced in back yard with deck, eat in kitchen, 2 car garage."
* LISTED OVER 120 DAYS 
$429,900
41321 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
3
BATHS
2,515
SQFT
$171
$/SQFT
0.15
ACRES
2018
BUILT
"Brand New Lusby Floorplan! Marrick's newest Rambler has a Rear Load 2-Car Garage. It includes Granite at the Kitchen, Upgraded Cabinets, Stainless Steel Appliances, Finished Lower Level Rec. Room, Den and Full Bath, Hardwood at Foyer, Great Room, Kitchen. Includes a rear and front patio. 2' Owner's Suite Extension. Community Amenities: Pool, Clubhouse, Courts, Playground."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $419,900 TO $429,900 
$424,900
41455 OSBORNE LN, Leonardtown MD 20650
4
BEDS
4
BATHS
3,250
SQFT
$131
$/SQFT
0.15
ACRES
2019
BUILT
"PROJECTED MAY 2019 DELIVERY: Three Levels Finished. Hardwood at DR,Kitch&Foyer, SS Appliances w/Double Ovens & 30 Elect. Cooktop, Upgraded Cabinets throughout, Gas Fireplace, Front Porch, 3.5 Baths, 4 BR, Ceramic Tile at Owner's Bath Floor & Upgraded Tile at Owner's Shower Walls & Tub Surround, Finished Rec Room & Full Bath, Community Pool, Clubhouse, Tennis & Basketball Courts, Walking Trails."
* NEW LISTING 
$424,500
22216 HANOVER DR, Leonardtown MD 20650
5
BEDS
5
BATHS
4,206
SQFT
$101
$/SQFT
0.47
ACRES
2005
BUILT
"Beautiful Colonial on approx 1/2 acre lot. Hardwood floors main level, main level bedroom w/full bathroom, Formal liv & din rms, morning rm, fam rm w/fp & slider opens to deck perfect for entertaining. Master suite w/walk in closet, master bath w/soaking tub, sep shower & dual vanity. Fin basement w/wet bar/kitchenette, additional bdrm & full bath/inlaw suite. Community water access w/pier"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $434,300 TO $424,500 
 
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