Homes with Parking for Sale in Leonardtown, MD

20 homes

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ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Seller is offering a flooring credit for the first floor with Clarke's Flooring.

$495,000

4 beds2.5 baths1,952 sq ft

21738 Pinehurst Ct, Leonardtown, MD 20650

0.37 acre lot • 2 garage spots • Built 1992

(410) 394-0990

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Contemporary-style home offering exceptional flexibility as a single-family residence or an income-producing property with a private apartment. The freshly painted interior features 5 bedrooms and 3 full baths, including a 2BR/1BA apartment with its own entrance—ideal for multigenerational living, guests, or rental income. The main living level showcases hardwood floors, an open living/dining layout with a fireplace and eat-in kitchen. Multiple sliding doors flood the home with natural light and open to a front deck—perfect for enjoying morning sun and neighborhood views. The kitchen offers charming cottage-style cabinetry, vintage appliances, a wine storage closet, and built-in

$650,000

5 beds3 baths3,464 sq ft

40855 Spring House Ln, Leonardtown, MD 20650

Private owners suite • Vintage appliances • Built in features

(410) 394-0990

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Stunning Dunleigh model by Marrick Homes, tucked away at the end of a quiet cul-de-sac on over 1 full acre in desirable Leonardtown Farm! Offering nearly 3,400 sq ft of finished living space, this beautifully maintained 4BR/2.5BA home features a spacious, gourmet kitchen with large center island, upgraded cabinets and granite countertops, and stainless steel appliances – perfect for entertaining. Enjoy formal living and dining rooms, plus a comfortable family room with fireplace just off the kitchen. A private office/study on the main level is ideal for remote work or flex space. The full, unfinished basement provides endless potential for future expansion and/or storage. Step outsid

$699,900

4 beds2.5 baths3,372 sq ft

42975 Baywood Pl, Leonardtown, MD 20650

1.08 acre lot • 3 garage spots • Built 2010

(888) 860-7369

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this move-in-ready home in the desirable Leonardtown Farms community offers space, layout, and functionality. With 5 bedrooms on the upper level, 3.5 bathrooms, and generous living spaces on every level, there is room to grow, gather, and truly settle in. Beautiful landscaping welcomes you to the covered front porch and into an open foyer, flanked by a formal sitting room and dining room. A dedicated office provides an ideal work-from-home space and flows into the large family room. The updated kitchen features new Zellige tile backsplash, granite countertops, updated stainless steel appliances, an island wi

$699,900

5 beds3.5 baths4,080 sq ft

21345 Fairwood Ct, Leonardtown, MD 20650

Soaking tub • Fire pit • Updated kitchen

(443) 771-8009

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Welcome to your new home! This impressive 5-bedroom, 3.5-bathroom residence is a masterpiece of design, offering a spacious and well-thought-out layout. Nestled in a prime location with access to top-rated schools, this property caters to both practicality and beauty. Both HVAC systems have been replaced, roof is only 5 years old, new paint throughout and a new BEAUTIFUL patio!! Key Features: * * 5 Bedrooms * * : Generously sized bedrooms provide comfort and privacy for every family member or guest. * * 3.5 Bathrooms * * : Stylishly designed bathrooms with modern fixtures and finishes add a touch of elegance. * * Prime Location * * : Conveniently located near essential amenities, sh

$580,000

5 beds3.5 baths2,940 sq ft

23593 Mitchell Dr, Leonardtown, MD 20650

0.32 acre lot • 2 garage spots • Built 2004

(443) 771-8009

Property at 22547 Landing Way, Leonardtown, MD 20650, 3 beds, 3.5 baths

$520,000

3 beds3.5 baths2,764 sq ft

22547 Landing Way, Leonardtown, MD 20650

(888) 860-7369

Property at 23581 Gallent Fox Way, Leonardtown, MD 20650, 4 beds, 3.5 baths

$645,900

4 beds3.5 baths3,736 sq ft

23581 Gallent Fox Way, Leonardtown, MD 20650

(443) 771-8009

Property at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650, 4 beds, 2.5 baths

$574,900

4 beds2.5 baths2,594 sq ft

20753 Chestnut Ridge Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 42043 Starlight Dr, Leonardtown, MD 20650, 4 beds, 3.5 baths

$539,900

4 beds3.5 baths2,472 sq ft

42043 Starlight Dr, Leonardtown, MD 20650

(443) 771-8009

Property at 40461 Old Breton Beach Rd, Leonardtown, MD 20650, 2 beds, 2.5 baths

$679,900

2 beds2.5 baths2,040 sq ft

40461 Old Breton Beach Rd, Leonardtown, MD 20650

(855) 450-0442

Property at 41635 Ferber Ct, Leonardtown, MD 20650, 4 beds, 2.5 baths

$565,000

4 beds2.5 baths2,222 sq ft

41635 Ferber Ct, Leonardtown, MD 20650

(301) 862-4000

Property at 21117 Catnip Ct, Leonardtown, MD 20650, 5 beds, 3.5 baths

$610,000

5 beds3.5 baths3,526 sq ft

21117 Catnip Ct, Leonardtown, MD 20650

(443) 771-8009

Property at 20959 Redgate Ln, Leonardtown, MD 20650, 3 beds, 1 bath

$209,000

3 beds1 bath1,026 sq ft

20959 Redgate Ln, Leonardtown, MD 20650

(443) 660-9229

Property at Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 105 - 23689 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 43018 Bluejay Ln, Leonardtown, MD 20650, 4 beds, 2.5 baths

$645,900

4 beds2.5 baths2,888 sq ft

43018 Bluejay Ln, Leonardtown, MD 20650

(443) 771-8009

Property at Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

Lot 104 - 23695 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths— sq ft

lot 106 - 23683 Dragonfly Ln, Leonardtown, MD 20650

(443) 771-8009

Property at 18937 Hodges Ln, Leonardtown, MD 20650, 3 beds, 2 baths

$659,000

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

(301) 609-9000

Property at 41810 Chelsey Faye Ln, Leonardtown, MD 20650, 4 beds, 3 baths

$720,000

4 beds3 baths2,650 sq ft

41810 Chelsey Faye Ln, Leonardtown, MD 20650

(301) 684-4895

Property at 42520 Riverwinds Dr, Leonardtown, MD 20650, 4 beds, 2 baths

$1,999,999

4 beds2 baths2,744 sq ft

42520 Riverwinds Dr, Leonardtown, MD 20650

(301) 862-2169

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COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Beautifully maintained home in Hollywood, offering privacy and modern updates. New quartz countertops in kitchen, Laminate flooring, new interior doors, replacement windows and a 2015 roof with owned solar panels on the back side. The HVAC system (heat pump with oil backup) was replaced in 2016 for year-round efficiency. The lower level includes a 4th bedroom, full bath, and a spacious family/game room, with a walk-out basement leading to a serene, wooded backyard. Designed for entertaining, enjoy cookouts on the upper deck, relaxation on the lower deck, or gatherings on the newly built custom patio with a built-in firepit. A newly paved driveway (2024) leads to an oversized 23' x 24' garag

$459,900

4 beds3 baths2,312 sq ft

44699 Emma Ln, Hollywood, MD 20636

1.02 acre lot • 2 garage spots • Built 1977

(301) 862-2169

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Coming Soon!!!!!!! Welcome Home to Wildewood! This spacious townhome offers a 1 car garage, Large entry level room that can be used as a 4th bedroom, office, or another family/entertainment room with a full bath. The second floor offers your kitchen and living areas with a half bath. The 3rd level offers 3 bedrooms and 2 full bath.

$375,000

4 beds3.5 baths2,100 sq ft

44535 River Otter Dr, California, MD 20619

$89 HOA • Garage • Community pool

(301) 862-2169

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Welcome home to a place where Southern charm meets everyday ease, set on nearly two acres of peaceful privacy with no homeowners association. This inviting rambler offers the freedom to spread out, unwind, and truly enjoy your surroundings while still being close to everything you need. Inside, the home is designed for both connection and comfort. Three well-appointed bedrooms and two full baths on the main level provide effortless living, while the full basement, workshop, and garage open the door to endless possibilities—whether you’re creating, storing, or planning for the future. The open kitchen flows naturally into the living space, where hardwood floors set a warm tone fo

$399,999

3 beds2 baths2,442 sq ft

44620 Saint Andrews Church Rd, California, MD 20619

1.97 acre lot • Garage • Built 1955

(443) 295-6123

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
This property is located in a rapidly developing area of central St. Mary’s County very close to the expanding county airport, offering strong potential for future growth and investment. The parcel is currently zoned RL (Residential Low Density), which allows for one dwelling unit per acre, with the potential for up to five homes per acre under the current zoning ordinance. Additionally, neighboring properties reflect varying zoning classifications, which may present an opportunity for rezoning or future development alignment, subject to county approval. All zoning, density, and development possibilities should be independently verified through St. Mary’s County Land Use &

$950,000

4 beds2 baths3,744 sq ft

23660 Pine View Ln, Hollywood, MD 20636

21.05 acre lot • 2 garage spots • Pool

(443) 771-8009

SHORT SALE

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Enjoy a comfortable, lock-and-leave lifestyle in Westmeath with sidewalks, a community pool, playground, and sports courts, all close to shopping, dining, and entertainment. This updated 1-bedroom, 1.5-bath condo offers protected, covered basement garage parking with secure elevator access—no stairs required. The open-concept living area features new flooring, a gas fireplace, and a private balcony. The well-appointed kitchen includes granite counters, stainless steel appliances, a gas stove, and a defined dining area. The bedroom suite provides two walk-in closets, a dual-sink vanity, and a garden soaking tub. A tankless water heater, private secure storage, and a convenient half bat

$175,000

1 bed1 bath879 sq ft

45472 Westmeath Way Unit I 12, Great Mills, MD 20634

Community pool • Private balcony • Gas stove

(301) 862-4000

ABOUT THIS HOME
Home with Parking for sale in Leonardtown, MD:
Located on a quiet cul-de-sac in the sought-after Forrest Farm community, this beautifully maintained ranch-style home offers exceptional space, flexibility, and thoughtful design throughout. Inside, an open and airy floor plan is highlighted by hardwood and ceramic tile flooring, crown molding, and chair rail accents. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by stainless steel appliances, a large center island and pantry, and seamless flow into the family room, where a gas fireplace creates a warm gathering space. The main level offers true one-level living, including two generously sized bedrooms and a spacious primary suite with a soaking tub

$715,000

6 beds4.5 baths4,913 sq ft

43336 Lillian Way, Hollywood, MD 20636

0.74 acre lot • 3 garage spots • Community pool

(443) 771-8009

Property at 24931 Sotterley Rd, Hollywood, MD 20636, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths1,631 sq ft

24931 Sotterley Rd, Hollywood, MD 20636

(443) 295-6123

Property at 23370 Town Creek Dr, Lexington Park, MD 20653, 4 beds, 2.5 baths

$359,000

4 beds2.5 baths1,762 sq ft

23370 Town Creek Dr, Lexington Park, MD 20653

(301) 862-2169

Property at 42470 Helen Ct, Hollywood, MD 20636, 6 beds, 2.5 baths

$399,999

6 beds2.5 baths1,716 sq ft

42470 Helen Ct, Hollywood, MD 20636

(888) 838-9044

Property at TBD Lot 28 South Glebe Rd, Montross, VA 22520, 3 beds, 2 baths

$475,000

3 beds2 baths1,555 sq ft

TBD Lot 28 South Glebe Rd, Montross, VA 22520

(540) 373-2000

Property at 45575 Catalina Ln, California, MD 20619, 3 beds, 3 baths

$339,900

3 beds3 baths1,948 sq ft

45575 Catalina Ln, California, MD 20619

(443) 771-8009

Property at 653 Blackbeard Pond, Hague, VA 22469, 4 beds, 2 baths

$234,900

4 beds2 baths1,458 sq ft

653 Blackbeard Pond, Hague, VA 22469

(804) 493-1888

Property at 43526 Marguerite Way, California, MD 20619, 4 beds, 3.5 baths

$380,000

4 beds3.5 baths2,080 sq ft

43526 Marguerite Way, California, MD 20619

(301) 862-2169

Property at 43913 Eucalyptus Way, California, MD 20619, 3 beds, 3.5 baths

$425,000

3 beds3.5 baths2,240 sq ft

43913 Eucalyptus Way, California, MD 20619

(301) 855-8600

Property at 25294 Vista Rd, Hollywood, MD 20636, 4 beds, 3.5 baths

$450,000

4 beds3.5 baths2,450 sq ft

25294 Vista Rd, Hollywood, MD 20636

(301) 355-6104

Property at TBD LOT 256 Armed Forces, Montross, VA 22520, 3 beds, 2.5 baths

$369,900

3 beds2.5 baths1,556 sq ft

TBD LOT 256 Armed Forces, Montross, VA 22520

(540) 373-2000

Property at 78 Cypress Dr, Montross, VA 22520, 4 beds, 2.5 baths

$419,900

4 beds2.5 baths2,400 sq ft

78 Cypress Dr, Montross, VA 22520

(540) 371-5220

Property at 45655 Centerview Ln, Great Mills, MD 20634, 4 beds, 2.5 baths

$419,900

4 beds2.5 baths2,088 sq ft

45655 Centerview Ln, Great Mills, MD 20634

(540) 662-4500

Property at 43998 Swift Fox Dr, California, MD 20619, 4 beds, 3.5 baths

$540,000

4 beds3.5 baths3,413 sq ft

43998 Swift Fox Dr, California, MD 20619

Property at 23175 Whistlewood Ln, California, MD 20619, 4 beds, 2.5 baths

$489,900

4 beds2.5 baths2,169 sq ft

23175 Whistlewood Ln, California, MD 20619

Homes with Parking for Sale in Leonardtown

There are currently 20 homes with parking homes for sale in Leonardtown at a median listing price of $530K. 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 67 days. This map is refreshed with the newest listings in Leonardtown every 15 minutes.

In the past month, 12 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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