Pending Listings in Leonardtown, MD

23 homes

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UNDER CONTRACT

$475,000

3 beds2 baths2,458 sq ft

20697 Chingville Rd, Leonardtown, MD 20650

2.39 acre lot • 3 garage spots • Built 1948

(301) 862-2169

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Other lots in the area, call us to discuss TBB - Custom Home - Many other floor plans and locations - call to discuss

$772,000

4 beds4.5 baths3,000 sq ft

44798 Medleys Neck Rd, Leonardtown, MD 20650

4.42 acre lot • 3 garage spots

(301) 843-5100

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Nestled in the highly sought-after Clark's Rest community, this exceptional home offers the perfect blend of convenience and charm. Hardwood floors in the entryway set the tone for the quality finishes throughout the home - including the spacious living room, dining room, and kitchen - featuring luxury vinyl plank flooring, combining durability and style. The kitchen stands out as a true highlight, boasting quartz countertops, stainless steel appliances, a farmhouse sink with tile backsplash, and a convenient eat-at bar. This space is perfectly designed for both everyday living and entertaining, making meal preparation and gatherings effortless. Upstairs, the floor plan includes four bedroo

$525,000

4 beds3.5 baths2,827 sq ft

41467 Osborne Ln, Leonardtown, MD 20650

8,064 sq ft lot • 2 garage spots • Community pool

(301) 892-1131

UNDER CONTRACTVIDEO TOUR

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sought-after Leonard’s Grant. From the inviting covered porch to the thoughtfully designed open floor plan, this home offers both comfort and functionality. The gourmet kitchen seamlessly flows into the great room—perfect for entertaining. Step out onto the private patio just off the kitchen and savor your morning coffee in peace. The main-level primary suite features a sitting area and a large bathroom with dual vanities, offering a private retreat from the rest of the home. Upstairs, you’ll find a versatile loft area and three generously sized bedrooms. The fully finished basement adds

$639,000

5 beds3.5 baths4,500 sq ft

41430 Challedon Way, Leonardtown, MD 20650

Covered porch • Gourmet kitchen • Private patio

(443) 771-8009

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Welcome home to 41492 Charismatic Way, the stunning Fenwick model by Quality Built Homes in the highly sought-after Leonard’s Grant community in Leonardtown! With 4 spacious bedrooms, 3.5 baths, and nearly 4,000 finished sq ft, this well-appointed home blends elevated design, thoughtful functionality, and timeless comfort in every detail. A welcoming foyer opens to formal living and dining rooms, ideal for gatherings and entertaining. Continue into the expansive gourmet kitchen featuring granite countertops, a large center island, stainless steel appliances, abundant cabinetry, and a sun-lit breakfast area. The open layout flows seamlessly into the inviting family room complete with a

$639,900

4 beds3.5 baths3,322 sq ft

41492 Charismatic Way, Leonardtown, MD 20650

9,733 sq ft lot • 2 garage spots • Community pool

(443) 771-8009

Property at 21920 Newtowne Neck Rd, Leonardtown, MD 20650, 4 beds, 2.5 baths

$510,000

4 beds2.5 baths2,291 sq ft

21920 Newtowne Neck Rd, Leonardtown, MD 20650

(443) 771-8009

Property at 22626 Chickadee Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$614,900

4 beds3.5 baths3,048 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

(240) 925-2224

Property at 41402 Silver Charm Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$650,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 298-2892

Property at 21039 Woodmere Dr, Leonardtown, MD 20650, 5 beds, 2.5 baths

$580,000

5 beds2.5 baths4,112 sq ft

21039 Woodmere Dr, Leonardtown, MD 20650

(301) 884-9493

Property at 41536 Fairwood Ct, Leonardtown, MD 20650, 4 beds, 3.5 baths

$569,000

4 beds3.5 baths3,308 sq ft

41536 Fairwood Ct, Leonardtown, MD 20650

(301) 843-5100

Property at 41535 Singletree Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$530,000

4 beds2.5 baths2,262 sq ft

41535 Singletree Dr, Leonardtown, MD 20650

(301) 684-4895

Property at 22362 Armstrong Dr, Leonardtown, MD 20650, 3 beds, 3 baths

$429,900

3 beds3 baths2,028 sq ft

22362 Armstrong Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 40533 Breton Knolls Ct, Leonardtown, MD 20650

$180,000

— beds— baths— sq ft

40533 Breton Knolls Ct, Leonardtown, MD 20650

(301) 705-5000

Property at 19921 Tower Hill Rd, Leonardtown, MD 20650

$130,000

— beds— baths— sq ft

19921 Tower Hill Rd, Leonardtown, MD 20650

(301) 884-9493

Property at Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths— sq ft

Lot 96-23724 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 23264 Lindsay Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$599,000

3 beds2 baths2,824 sq ft

23264 Lindsay Dr, Leonardtown, MD 20650

(301) 884-9493

Property at 23098 Town Run Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$685,000

5 beds3.5 baths3,642 sq ft

23098 Town Run Dr, Leonardtown, MD 20650

(301) 702-4200

Property at Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths— sq ft

Lot 107-23677 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$445,900

4 beds3.5 baths— sq ft

Lot 92-23700 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Cedar Lane Rd, Leonardtown, MD 20650

$3,800,000

— beds— baths— sq ft

Cedar Lane Rd, Leonardtown, MD 20650

(301) 862-2169

Property at Kiskadee Ln, Leonardtown, MD 20650

$200,000

— beds— baths— sq ft

Kiskadee Ln, Leonardtown, MD 20650

(410) 535-6291

Property at 25845 Point Lookout Rd, Leonardtown, MD 20650

$1,740,000

— beds— baths— sq ft

25845 Point Lookout Rd, Leonardtown, MD 20650

(703) 753-7910

Property at Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$447,400

4 beds3.5 baths2,604 sq ft

Lot 88-23676 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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Pending Listings in Leonardtown

There are currently 23 pending listings for sale in Leonardtown at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Leonardtown stay on the market for 56 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 7 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 7 townhouses, and 0 multi-family units for sale in Leonardtown last month. Find your dream home in Leonardtown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Leonardtown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Leonardtown. Our Leonardtown real estate stats and trends will give you more information about home buying and selling trends in Leonardtown. If you're looking to sell your home in the Leonardtown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Leonardtown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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