Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 02/18/2019 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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$1,200,000
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 !"
$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."
* LISTED OVER 120 DAYS 
$799,900
40125 ARMY WAY, Leonardtown MD 20650
5
BEDS
4
BATHS
3,395
SQFT
$236
$/SQFT
1.29
ACRES
2004
BUILT
"Beautiful custom waterfront Cape Cod on 1.29 acres with private pier, 8000 lb boat lift, 2000 lb jet ski lift and sun deck. Enjoy outdoor living at its best including swimming, boating, fishing and many water activities. Grand foyer opens to a formal living room, dining room and office/den. The two story family room has a pellet stove and leads to the gourmet kitchen with upgraded stainless appliances, cooktop, wall oven and center island. There is a large pantry off kitchen, laundry room and mud room. Waterfront views from the family room, breakfast nook and master bedroom. First floor master bedroom with private entrance to outdoor patio overlooking the water. Two separate master closets. Master Bathroom with separate shower & clawfoot soaking tub. Built in safe, central vacuum and laundry shoot. Stamped concrete covered front porch and back patio overlooking the water. 2 car attached garage, 1 car detached garage with additional workshop space, pellet stove, & upstairs storage. Additional covered parking could be used for large motor home or boat storage. Close to downtown Leonardtown, schools, shopping and more. Call CSS to schedule an appointment today."
$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 
$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 w/dining and gourmet kitchen. Huge owners 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, equpment shed. Horses welcome. Grow your own veggies."
$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 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."
* LISTED OVER 120 DAYS 
$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
$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
$500,000
22535 WASHINGTON ST, Leonardtown MD 20650
5
BEDS
3
BATHS
3,205
SQFT
$156
$/SQFT
0.77
ACRES
1905
BUILT
"Wonderful Historic home in the heart of Leonardtown. Minutes to the wharf area and view of the water from many areas of the home including the screened in porch. Minutes to the town square and shopping and restaurants.The original home was on land of the Key family, (Stars Bangled Banner) and was either build by them or Captain Charles Norris, river boat captain, prior to the Civil War. The first historic record is a surveyor~s plot made by John F. Wathen in 1857. The house was significantly renovated on 1908 by D. B Johnson in 1908 by totally incorporating the originally the one and half story house into the present two story one. Owner has done many updates since his purchase in 1972.5 large bedrooms with 3 full baths. 2 staircases for easy use. Main level has office and beautiful foyer with formal living and dining areas.Hardwood floors through out all of the home. 2 car carport for parking. Sheds. Oil heat with wood burning stove as a back up system.Newer A/C system installed in last few years. Kitchen is large and has a great layout including a breakfast area and door to patio and fenced in yard. Double lot combined so lots of space!"
* NEW LISTING 
$499,000
40559 PORT PL, Leonardtown MD 20650
4
BEDS
3
BATHS
3,300
SQFT
$151
$/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. Yearly $50.00 fee gives you access to the beach, pier, fishing, playground, and picnic area. All the joy of waterfront without the property taxes. Large 2 car garage with workshop space. Beautiful courtyard in the front yard. Outside storage."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $549,900 TO $499,000 
$496,000
40099 ARMY WAY, Leonardtown MD 20650
2
BEDS
1
BATHS
2,100
SQFT
$236
$/SQFT
2.63
ACRES
1961
BUILT
"$64, 000 REDUCTION on this UNIQUE WATERFRONT PROPERTY. Private location and deep water on Combs Creek. 400+ ft waterfront with direct access to Breton Bay and Potomac River. Two piers. Two cottages and larger home in need of renovation on 2.66 acre parcel. Public sewer to all 3. Two wells (1 shared between 2 cottages) Upscale neighboring homes. A DIAMOND IN THE ROUGH. Combine the foot prints or renovate all three. Potential to subdivide. Rent the 2 cottages while you build your dream home. Owner Financing considered. All offers will be seriously considered.. Listing agent to accompany all showings."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $560,000 TO $496,000 
$489,900
40576 CANDELA PL, Leonardtown MD 20650
6
BEDS
5
BATHS
4,469
SQFT
$110
$/SQFT
0.29
ACRES
2003
BUILT
"Beautiful traditional move-in ready home with nearly 4,500 sq. ft. of finished living space. Main floor kitchen with center island, breakfast morning room, walk-in pantry, and hardwood floors. First floor open style living with beautiful archways for entertaining and a screened porch overlooking the beautiful in-ground, saltwater swimming pool. The clover-shaped, gunite swimming pool comes with a solar cover to start the swimming season early and extend it through the fall. The pool was constructed with a tanning ledge with umbrella sleeve as well as a diving board and shallow area with steps for ease of entry. It comes with a Loop-Loc mesh cover and the pool pump was replaced in 2018. There is plenty of social space on the exposed aggregate area surrounding the pool as well as an E. P. Henry retaining wall. Owners are including the 6 person hot tub for your enjoyment. Decorative fence surrounds the entire back yard. Work from home in the main level office and enjoy this 6 bedroom/4.5 bathroom home that has two master bedrooms, separate formal dining and living rooms, and a great room with gas fireplace. The spacious basement with 9 foot ceilings is a fully equipped, one bedroom apartment with its own eat-in kitchen, living room with gas fireplace, separate laundry room and pantry, and possesses handicap width doorways, low entry shower, and direct access onto the pool deck and hot tub. This lower level apartment comes with a separate entrance on the side of the home with a well-maintained exterior Acorn chair lift. The lower level apartment has windows on 3 sides due to the sloping lot so you do not feel like you are in a basement. The windows look out onto beautiful hardscape and landscaping with an underground lawn sprinkler system. All systems are maintained annually or semi-annually depending on the system and seller has purchased a 2-10 Home Buyers Warranty at the Supreme level. Great for a multi-generational family or rent the apartment for additi"
$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."
* LISTED OVER 120 DAYS  * 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 on main level. Professionally managed garden/yard with automatic sprinkler system. Over sized garage upgrade. Extended open family room( 6 ft ) and basement ( 6ft ). Double oven. Upgraded fixtures. 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 
$459,873
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."
* NEW LISTING 
$439,000
23151 LUCKTON CT, Leonardtown MD 20650
4
BEDS
3
BATHS
2,574
SQFT
$171
$/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!"
* PRICE LOWERED - $449,000 TO $439,000 
$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 
$429,900
43186 OAKWAY CT, Leonardtown MD 20650
4
BEDS
4
BATHS
2,910
SQFT
$148
$/SQFT
4.30
ACRES
1994
BUILT
"This beautiful home located in desirable Chestnut Ridge Community, with a low annual HOA of 155.00, is minutes from both PAX and LEONARDTOWN. Enjoy the amazing nature and quiet from the gorgeous deck and lower level area. End of cul de sac 4.3 acres allows for attitional garage, pool, your choice. Walk into a gorgeous foyer to your private living area, office, dining and walk through to a gourmet kitchen with double oven complete with built in microwave gas cooktop and custom granite. The lovely natural light will shock you from every room....still with total privacy. Walk a short distance to the master on the main level including an amazing walk in closet and en suite with soaking tub and shower. Once you have had a relaxing soak, curl up in front of the gorgeous fireplace. Want more? Perhaps a full finished basement with a full bath. Or upstairs to 3 additional bedrooms a great room perfect for a kids area as well as an additional storage room...do not miss the oversized garage with room for two plus more storage. Three levels of fresh paint, beautiful hardwoods and new carpet. Let us not forget a fabulous new high efficiency HVAC system! Why wouldn't you want to see your new home today!?"
$424,900
42079 STARLIGHT DR, Leonardtown MD 20650
4
BEDS
4
BATHS
2,692
SQFT
$158
$/SQFT
1.10
ACRES
2004
BUILT
"Click LINK for 3D tour. Private,~backs to tree conservation area. Cul-de-sac lot, The living area is quite generous, 9' ceilings, kitchen open to family room, walk out of massive screened in porch. Kitchen with 42 cabinets & granite, island, Sizeable bedrooms, Basement is partially finished has a~large storeage room and another roomwith full size window (no closet) As well as a full bath. True walkout level"
* NEW LISTING 
$420,000
23299 JENIFER CT, Leonardtown MD 20650
5
BEDS
3
BATHS
3,174
SQFT
$132
$/SQFT
0.45
ACRES
2005
BUILT
"Tranquil Leonardtown 5BR/3Bath Beauty. Over 3100 sf above Grade and almost a 1/2 acre lot. Lovely Hardwood Flooring! Main Floor Guest Suite w/bath and it's own laundry! Beautiful Kitchen w/ Stainless and Granite. Details abound. Spacious Family Room is Warm and Inviting. Large Master Suite w/ its own Fireplace. Large 15x11 Bonus Room upstairs. Use for another private Family Room or Recreation Room. All Bedrooms are spacious w/ large closets. Exterior Spaces are wonderful. A 10x10 screened porch. 2 patios. A fenced portion of the back yard for gardening or play! Backs to trees so some lovely shaded areas for outdoor dining too. Walk to Leonardtown Square, Shopping & Restaurants. 25 Minutes to Pax River. All Leonardtown Schools!"
$412,500
21716 FAIRWAY DR, Leonardtown MD 20650
5
BEDS
4
BATHS
2,752
SQFT
$150
$/SQFT
0.90
ACRES
1990
BUILT
"Very private, sought-after location on golf course. Lot is almost an acre. Wonderful open floorplan. One bedroom and bath are separate and at one end of the home; ideal for in-home office or live-in relative. Home shows well with lovely views over the golf course. Large private yard. No HOA; this is one of the only homes in neighborhood that does not belong to HOA. Local beach park, pool, tennis & golf course membership available which is optional."
$400,000
40361 OLD BRETON BEACH RD, Leonardtown MD 20650
3
BEDS
2
BATHS
1,344
SQFT
$298
$/SQFT
0.34
ACRES
2005
BUILT
"YOU CAN LIVE THE DREAM! Priced below assessed value. Beautiful Potomac River views, w/soothing sounds of waves on the shoreline & salty breezes. Protective rip-rap already in place & terrific pier: all set for you to crab, fish, raise oysters, boat, kayak, or simply sit and enjoy the views, watching the osprey, eagles & herons fly home in the evening sunset. Full length screened in porch looks out over the water all the way to VA. Custom built in '05 with an open floor plan, this home has many windows and sliding glass doors to take full advantage of the views. Other features include ceiling fans, hardwood floors, a large breakfast bar and laundry/utility room. Sturdy cement pilings are high enough to allow parking underneath, with room to host crab & oyster feasts on the cement pad, or just hang a hammock! Located near the end of the quiet road makes this a peaceful place. Perfect as a vacation, 2nd home or year round living! You don't want to let this one get away."
 
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