Leonardtown - MD Real Estate, Homes and Condos for sale

All Leonardtown - MD homes currently listed for sale in Leonardtown - MD as of 01/19/2019 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 - MD homes for sale or other Leonardtown - MD real estate, please contact us and one of our knowledgeable Leonardtown - MD 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 
$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
$560,000
40099 ARMY WAY, Leonardtown MD 20650
2
BEDS
1
BATHS
2,100
SQFT
$267
$/SQFT
2.63
ACRES
1961
BUILT
"UNIQUE PROPERTY. Beautiful private location on Combs Creek 400+ 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 
$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
$499,000
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. All the joy of waterfront without the property taxes. Large 2 car garage with workshop space. Beautiful courtyard in the front yard. Outside storage."
* PRICE LOWERED - $549,900 TO $499,000 
$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."
* 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 
$459,900
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 
$449,000
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!"
$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
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."
$419,900
41337 CHESTNUT HILL ST, Leonardtown MD 20650
4
BEDS
4
BATHS
3,573
SQFT
$118
$/SQFT
0.15
ACRES
2018
BUILT
"WICOMICO Floorplan: To-Be-Built, Hardwood Foyer, SS Appliances, Upgraded Cabinetry, Granite at Kitchen, Butlers Pantry, Mud Room, Walk-In Pantry, Sep. DR, Office, Front Porch, Oversized Garage, 2nd Floor Laundry. Community Amenities: Pool, Clubhouse, Tennis/Pickle Ball Court, Basketball Court, Playground, Walking Trails."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $414,900 TO $419,900 
$416,900
41447 OSBORNE LN, Leonardtown MD 20650
5
BEDS
4
BATHS
3,168
SQFT
$132
$/SQFT
0.15
ACRES
2017
BUILT
"Clarks Rest! To-Be-Built: The Lexington. 2-Car Rear Load Garage. Hardwood Foyer, Custom Trim at Foyer & Dining Room, Owner's Choice on main level (Make into a Guest Suite or Study), Granite Counters, Upgraded Cabinets at Kitchen & Baths, Stainless Steel Appliances, $10,000 towards closing costs w/using preferred lender and title company. Community will feature a Pool & Clubhouse!"
* LISTED OVER 120 DAYS  * PRICE INCREASED - $411,900 TO $416,900 
$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."
* NEW LISTING 
$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."
$399,000
22216 HANOVER DR, Leonardtown MD 20650
5
BEDS
5
BATHS
4,206
SQFT
$95
$/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 - $414,900 TO $399,000 
$398,900
41384 DOCTORS CROSSING RD, Leonardtown MD 20650
4
BEDS
4
BATHS
2,801
SQFT
$142
$/SQFT
0.15
ACRES
2019
BUILT
"FEBRUARY 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 
 
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