Pending Listings in Leonardtown, MD

30 homes

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Charming 4 bedroom 2 full bath Cape Cod on a 5.27 acre lot in Leonardtown! This adorable home is ready for a new owner just in time for the holidays. As you drive up to the house the expansive lot opens up to the beautiful front porch and entry into the home. Hard wood floors throughout the main level. The living room is spacious and has a brick fireplace with a wood insert. Perfect for cozy evenings. The updated kitchen includes stainless steel appliances, granite counters with peninsula seating and dining area. The sliders open to the back covered deck. This is definitely a show stopper with its rough sawn kiln dried poplar ceiling. The views from the back covered deck are amazing. Peace

$485,000

4 beds2 baths1,848 sq ft

21515 Our Drive Way, Leonardtown, MD 20650

5.27 acre lot • 2 garage spots • Car-dependent

(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 • Car-dependent

(301) 843-5100

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
Welcome to 41474 Charismatic Way in the highly sought-after Leonard’s Grant community of Leonardtown, Maryland. This beautifully maintained 5-bedroom, 3.5-bath home offers over 3,600 square feet of finished living space and combines elegance, comfort, and function in every detail. From the charming large front porch to the professionally landscaped yard, the curb appeal is undeniable. Step inside to find hardwood flooring and crown molding throughout the main level, an open-concept family room and gourmet kitchen featuring stainless steel appliances, granite countertops, 42” cabinetry, and a spacious island perfect for gatherings. Upstairs, you’ll find four generously size

$639,000

5 beds3.5 baths3,647 sq ft

41474 Charismatic Way, Leonardtown, MD 20650

7,150 sq ft lot • $80 HOA • 2 garage spots

(443) 771-8009

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
OPEN HOUSE CANCELED DUE TO ACCEPTED CONTRACT. Desirable Breton Bay Brick Colonial with a NEW ROOF! Enter the soaring two-story foyer of this 4-bedroom, 2.5 bath home, and take note of the refinished hardwood floors, wide staircase with wrought iron railings, and Palladian window that allows for lots of natural light. Head past the shiplap wall treatment into the eat-in kitchen that features tall white cabinets, newer appliances, beautiful Quartz counters, tile backsplash, updated flooring, and pantry closet. For elegant gatherings, a formal living room w/ crown molding, and dining room w/ bump out, make the perfect setting. The family room with a floor-to-ceiling stone hearth, and French do

$605,000

4 beds2.5 baths2,860 sq ft

21745 Pinehurst Ct, Leonardtown, MD 20650

0.58 acre lot • $25 HOA • 2 garage spots

(301) 862-2169

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Leonardtown, MD:
This property is back on the market. This is your gain. A rare opportunity on the shores of Breton Bay, presents a canvas for transformation. This expansive 1.05 acre waterfront boast 164 feet of private shoreline and delivers breathtaking sunset panoramas. This classic 1955 construction offers endless renovation potential. With 1468 square feet of main living space and a 1247 square foot basement, this 3 bedroom 2 bathroom home shows potential for amazing views and waterfront living. The well has a recent water quality certification. The owner has repaired the septic system including replacing the tank with a BAT septic system and replacing the distribution box due to its age and repla

$550,000

3 beds2 baths1,488 sq ft

41130 Cryer Ct, Leonardtown, MD 20650

1.05 acre lot • Garage • Car-dependent

(301) 862-2169

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 41435 Osborne Ln, Leonardtown, MD 20650, 6 beds, 4.5 baths

$665,000

6 beds4.5 baths4,145 sq ft

41435 Osborne Ln, Leonardtown, MD 20650

(301) 702-4200

Property at 20591 Chestnut Ridge Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$599,900

5 beds3.5 baths3,061 sq ft

20591 Chestnut Ridge Dr, Leonardtown, MD 20650

(888) 860-7369

Property at 41900 Nazareth Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$470,000

4 beds2.5 baths2,528 sq ft

41900 Nazareth Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 20919 Ridge Path Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$549,000

4 beds3.5 baths3,465 sq ft

20919 Ridge Path Way, Leonardtown, MD 20650

(240) 925-2224

Property at 23242 Clarks Rest Rd, Leonardtown, MD 20650, 5 beds, 3.5 baths

$589,000

5 beds3.5 baths3,296 sq ft

23242 Clarks Rest Rd, Leonardtown, MD 20650

(240) 925-2224

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 23155 Greenstone, Leonardtown, MD 20650, 6 beds, 3.5 baths

$1,300,000

6 beds3.5 baths5,888 sq ft

23155 Greenstone, Leonardtown, MD 20650

(301) 884-9493

Property at 23730 Hicks Dr, Leonardtown, MD 20650, 3 beds, 2 baths

$415,000

3 beds2 baths1,992 sq ft

23730 Hicks Dr, Leonardtown, MD 20650

(833) 335-7433

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 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 22216 Hanover Dr, Leonardtown, MD 20650, 5 beds, 4.5 baths

$640,000

5 beds4.5 baths4,206 sq ft

22216 Hanover Dr, Leonardtown, MD 20650

(443) 771-8009

Property at 20413 Scarlet Tanager Way, Leonardtown, MD 20650, 4 beds, 3 baths

$575,000

4 beds3 baths3,094 sq ft

20413 Scarlet Tanager Way, Leonardtown, MD 20650

(301) 862-2169

Property at 23745 Bayside Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$399,900

3 beds2 baths1,344 sq ft

23745 Bayside Rd, Leonardtown, MD 20650

(301) 702-4200

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 22305 Hanover Dr, Leonardtown, MD 20650, 4 beds, 3 baths

$639,900

4 beds3 baths3,404 sq ft

22305 Hanover Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 23534 Belmar Dr, Leonardtown, MD 20650, 5 beds, 3.5 baths

$639,000

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 21983 Point Lookout Rd, Leonardtown, MD 20650, 2 beds, 1 bath

$70,000

2 beds1 bath1,144 sq ft

21983 Point Lookout Rd, Leonardtown, MD 20650

(410) 488-3124

Property at Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths2,966 sq ft

Lot 93-23706 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths— sq ft

Lot 97-23730 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

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

Property at 40534 Miss Ettas Way, Leonardtown, MD 20650, 3 beds, 2.5 baths

$470,000

3 beds2.5 baths1,770 sq ft

40534 Miss Ettas Way, Leonardtown, MD 20650

(410) 535-6291

Property at Lot 94 - 23712 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$479,900

4 beds3.5 baths— sq ft

Lot 94 - 23712 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 90 - 23688 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$469,900

4 beds3.5 baths— sq ft

Lot 90 - 23688 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

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Pending Listings in Leonardtown

There are currently 30 pending listings for sale in Leonardtown at a median listing price of $540K. 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 58 days and receive 2 offers. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 9 homes have been sold in Leonardtown. In addition to houses in Leonardtown, there was also 1 condo, 11 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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