Leonardtown Real Estate, Homes and Condos for sale

All Leonardtown homes currently listed for sale in Leonardtown as of 03/23/2019 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.


Sort:
Show:
View:  
  Page 1 of 3  
 
$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. Need help with the down payment? Ask about MARBIDCO"
* LISTED OVER 120 DAYS 
$789,900
40125 ARMY WAY, Leonardtown MD 20650
5
BEDS
4
BATHS
3,395
SQFT
$233
$/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."
* PRICE LOWERED - $799,900 TO $789,900 
$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 
$565,000
40977 PIPITS LN, Leonardtown MD 20650
4
BEDS
4
BATHS
3,970
SQFT
$142
$/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. 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."
* NEW LISTING 
$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 
$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 
$540,400
40630 BRETON OAKS LN, Leonardtown MD 20650
4
BEDS
3
BATHS
2,450
SQFT
$221
$/SQFT
2.15
ACRES
2019
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $560,400 TO $540,400 
$521,400
40636 BRETON OAKS LN, Leonardtown MD 20650
5
BEDS
3
BATHS
2,717
SQFT
$192
$/SQFT
2.87
ACRES
2019
BUILT
* LISTED OVER 120 DAYS  * PRICE LOWERED - $541,400 TO $521,400 
$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 with park and facilities. View of the water from many areas of the home including the screened in porch, office, kitchen and bedrooms. Minutes to the town square and shopping and restaurants.The original home was on land of the Key family, (Star Spangled 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. Five 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! Near Breton Bay Golf Course too. Come and see today!"
$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 
$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 
$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."
$459,000
41470 PENSIVE ST, Leonardtown MD 20650
5
BEDS
4
BATHS
4,337
SQFT
$106
$/SQFT
0.25
ACRES
2008
BUILT
"WELCOME HOME! Beautiful Potomac Model in sought after Leonard's Grant. Dramatic 2-story Entry and Great Room with floor to ceiling windows. Main level Owner's Suite with luxury bath, 2 walk-in closets, a private walk-out onto rear deck to Hot Tub. Spacious Gourmet Kitchen with Upgraded Maple cabinets with soft close feature, granite countertops, backsplash, pantry, table space, and a separate formal Dining Room. Relax and unwind on your screened porch off the kitchen. Upper level offers 3 large bedrooms and a full bath. Finished lower level boasts a great place to hangout with friends and family. A Home Theatre and Rec Room, a 5th Bedroom and Full bath, along with a huge storage room. This home has an additional 2 ft. extension on all 3 levels along the complete rear of home for even more extra living space. The surrounding gardens have been freshly landscaped for Spring. Leonard's Grant is a Master Planned Community with pool, clubhouse, open greens, sidewalks, playgrounds, tennis court, basketball court, and walking paths. Close to Historic Leonardtown Square with the waterfront, quaint shops, restaurants, and parks. Children in the Leonard's Grant Community can walk and ride their bikes to Captain Walter Francis Duke Elementary School. Another convenience coming soon to the LG community is the Brand New Leonardtown Library which is currently under construction."
* PRICE LOWERED - $469,000 TO $459,000 
$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!"
* LISTED OVER 120 DAYS  * 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
2019
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
42079 STARLIGHT DR, Leonardtown MD 20650
5
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"
$419,999
41498 AFFIRMED WAY, Leonardtown MD 20650
4
BEDS
3
BATHS
2,734
SQFT
$154
$/SQFT
0.16
ACRES
2009
BUILT
"This is the one. Sought after Leonard's Grant will not last long. Mattingly model with hardwood floors, custom gourmet kitchen with stainless and granite. Master suite with optional dual show-head spa shower and soaking tub. Top rated schools and fantastic location."
* PRICE LOWERED - $429,999 TO $419,999 
$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."
* LISTED OVER 120 DAYS 
$398,900
41384 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,801
SQFT
$142
$/SQFT
0.15
ACRES
2019
BUILT
"IMMEDIATE Delivery! Elizabeth Floorplan w/Rear Load 2-Car Garage. Hardwood Floor at 1st Floor, SS Appliances, Upgraded Cabinetry, Granite Countertops, Gas Fireplace at Family Room, 4BR's & 3.5 Baths, Finished Lower Level Rec. Room, Deep Tray Ceilings at Owner's Suite, Walk-In Closet, Separate Shower & Soaking Tub, Water Closet, Cust. Trim at Dining Room & Foyer, Community Pool & Clubhouse, Courts."
* LISTED OVER 120 DAYS 
$395,900
41329 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
3
BATHS
2,515
SQFT
$157
$/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 and Full Bath, Hardwood at Foyer, Custom Trim at Foyer and Dining Room. Includes a rear and front patio. Community Amenities: Pool, Clubhouse, Courts, Playground"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $390,900 TO $395,900 
$375,000
20798 WATERSIDE DR, Leonardtown MD 20650
2
BEDS
1
BATHS
1,022
SQFT
$367
$/SQFT
0.18
ACRES
1950
BUILT
"This charming home located on the Potomac River is the perfect place to spend your time for a weekend getaway. Enjoy crabbing & fishing off your private pier equipped w/ boat lift. Home conveys fully furnished, walk in and relax! 2 Bedrooms, enclosed porch w/ amazing water view, recently renovated bathroom, hardwood floors, extremely low energy cost. Just 1 hour from DC Beltway. Great find!Five mile view over Potomac and historic St. Clement's Island. Fish and crab pier, reconditioned boat lift. Great fishing with easy run from your home or stay home and fill your cooler from your private pier.Pier, boat lift, picnic table on the pier for morning coffee, catch your breakfast fish and crab from the private pier. Large picnic table for crabfeasts at the water's edge. Boathouse. Great views and sunsets 365 days a year with a parade of ships, boats, and waterfowl every day. Private neighborhood at the end of the world and only 10 miles from Chesapeake Bay overlooking wide expanse of Potomac River."
$369,900
21302 BENNETT ESTATE LN, Leonardtown MD 20650
3
BEDS
2
BATHS
2,576
SQFT
$144
$/SQFT
4.79
ACRES
2004
BUILT
"Long rambler that offers so much. Family room with fireplace insert, cathedral ceiling, & surround sound. Long life metal roof.Extra large deck for entertaining. Extra large garage with added height as well. Spacious 2BR,1BA in-la apartment over garage for added income. Apartment has separate entrance. Convenient to Leonardtown, California, & Pax River."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $374,900 TO $369,900 
$368,900
41404 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,807
SQFT
$131
$/SQFT
0.15
ACRES
2019
BUILT
"Elizabeth 1. To Be Built, Granite Counter, Stainless Steel Appliances, Upgraded Cabinetry, Finished Basement Rec. Room and Full Bath, Hardwood in Foyer. Community amenities feature: Pool, Clubhouse, Tennis and Basketball Court, Playground, Walking Trails."
 
View:  
  Page 1 of 3  
 



One Moment Please..

Sign Up For A Free Account
We'll email you when we find properties that match your needs!
Receive notifications of New Listings & Price Changes.




Example: 801-111-2222
Search Smarter
  • New Listing Email Alerts
  • Price Change Alerts
  • All Detailed MLS Info
  • Photos, Tours & Videos
  • Save your Favorite Homes
  • Save Searches
  • Find Your Home Value
  • Agents Online to Answer Questions
  • Maps & Property Street View

Already Registered? Sign In.
By registering on our site you agree to our terms & privacy policy.