20627, MD homes for sale & real estate

12 homes

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41699 Courthouse Dr, Leonardtown, MD 20650
41699 Courthouse Dr, Leonardtown, MD 20650
41699 Courthouse Dr, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Welcome to 41699 Courthouse Drive, a well-maintained home tucked away on a private lot in the heart of historic Leonardtown. Offering comfort, space, and small-town charm, this property is perfectly positioned with no HOA, public water and sewer, and easy access to everything Leonardtown has to offer. Inside, you’ll find a bright kitchen with plenty of cabinetry, an inviting dining area, and a spacious living room — freshly updated with new carpet and ready for entertaining. The home has been lovingly cared for, with the original stove, refrigerator, HVAC, and roof all in working condition. For added peace of mind, a Home Warranty will be included. Upstairs, the primary suite of

$525,000

5 beds3 baths2,420 sq ft

41699 Courthouse Dr, Leonardtown, MD 20650

0.38 acre lot • 2 garage spots • Somewhat walkable

(301) 862-2169

41535 Fairwood Ct, Leonardtown, MD 20650
41535 Fairwood Ct, Leonardtown, MD 20650
41535 Fairwood Ct, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Stunning 4 Bed / 4 Bath Ranch Rambler in Sought-After Clark’s Rest Community Welcome to your dream home! Nestled in the highly desirable Clark’s Rest community, this stunning 4-bedroom, 4-bath Ranch Rambler is only one year old and loaded with upgrades with exceptional curb appeal and luxurious features throughout, this is a rare find that won’t last long. This modern home blends comfort, style, and convenience—all just minutes from downtown Leonardtown's shopping, dining, waterfront activities and entertainment. Enjoy main-level living at its finest with a spacious FIRST FLOOR MASTER complete with ensuite with soaking tub and walk in shower and additional nice sized

$750,000

4 beds4 baths4,829 sq ft

41535 Fairwood Ct, Leonardtown, MD 20650

8,100 sq ft lot • $69 HOA • 2 garage spots

(888) 860-7369

VIDEO TOUR

41430 Challedon Way, Leonardtown, MD 20650
41430 Challedon Way, Leonardtown, MD 20650
41430 Challedon Way, Leonardtown, MD 20650

$650,000

5 beds3.5 baths4,500 sq ft

41430 Challedon Way, Leonardtown, MD 20650

9,733 sq ft lot • $81 HOA • 2 garage spots

(443) 771-8009

COMING SOON

23242 Clarks Rest Rd, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Welcome to this beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Clark’s Rest community of Leonardtown! Boasting an open floor plan filled with natural light, this home offers a perfect blend of comfort and functionality. The main level features spacious living and dining areas that flow effortlessly into a modern kitchen—ideal for entertaining and everyday living. Upstairs, you’ll find generously sized bedrooms, including a well-appointed primary suite. The fully finished basement provides additional living space perfect for a home theater, playroom, gym, or guest suite. Enjoy all the amenities Clark’s Rest has to offer, including a

$599,000

5 beds3.5 baths2,296 sq ft

23242 Clarks Rest Rd, Leonardtown, MD 20650

6,673 sq ft lot • $42 HOA • 2 garage spots

(240) 925-2224

41430 Whimsical Ct, Leonardtown, MD 20650
41430 Whimsical Ct, Leonardtown, MD 20650
41430 Whimsical Ct, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Price Improvement!!!! This home is a MUST SEE!!!! Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for growing families, multi-generational living, or anyone seeking flexible, functional space. Step inside to find a warm, welcoming layout , a spacious eat-in kitchen, and a cozy family room ideal for relaxing or entertaining. One of the standout features is the highly desirable first-floor large primary suite wi

$634,999

5 beds3.5 baths3,907 sq ft

41430 Whimsical Ct, Leonardtown, MD 20650

8,750 sq ft lot • $81 HOA • 2 garage spots

(443) 256-3773

Property at 23275 Jenifer Ct, Leonardtown, MD 20650, 5 beds, 4.5 baths

$625,000

5 beds4.5 baths6,311 sq ft

23275 Jenifer Ct, Leonardtown, MD 20650

(301) 862-2169

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

$655,000

5 beds3.5 baths4,046 sq ft

41402 Silver Charm Ct, Leonardtown, MD 20650

(301) 862-2169

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

$659,000

5 beds3.5 baths4,738 sq ft

23534 Belmar Dr, Leonardtown, MD 20650

(301) 862-2169

Property at 23348 Lindsay Dr, Leonardtown, MD 20650, 5 beds, 4 baths

$599,900

5 beds4 baths3,540 sq ft

23348 Lindsay Dr, Leonardtown, MD 20650

(301) 439-9500

Property at 25365 Point Lookout Rd, Leonardtown, MD 20650, 3 beds, 2 baths

$497,500

3 beds2 baths2,952 sq ft

25365 Point Lookout Rd, Leonardtown, MD 20650

(301) 862-2169

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

$675,000

4 beds3 baths2,650 sq ft

41810 Chelsey Faye Ln, Leonardtown, MD 20650

(301) 684-4895

Property at 41815 Chelsey Faye, Leonardtown, MD 20650

$95,000

— beds— baths— sq ft

41815 Chelsey Faye, Leonardtown, MD 20650

(301) 684-4895

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Nearby homes that match your criteria

COMING SOON

$529,900

4 beds2.5 baths2,328 sq ft

22338 White Oak Rd, Leonardtown, MD 20650

0.66 acre lot • 2 garage spots • Pool

(301) 862-2169

40801 Kiskadee Ln, Leonardtown, MD 20650
40801 Kiskadee Ln, Leonardtown, MD 20650
40801 Kiskadee Ln, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Welcome to 40801 Kiskadee Lane — a truly exceptional residence nestled on over 3 private acres in the prestigious waterfront community of Avenmar. This grand colonial home is an entertainer’s dream, offering over 6,000 square feet of beautifully designed living space, and is specially offered with the last available building lot in the community — an additional 3.5+ acre parcel for $200,000, giving you over 6.5 acres of tranquil privacy and future investment potential. (Seller prefers to sell together) As you enter this elegant home, you are immediately welcomed by the soaring ceilings and abundant natural light of the two-story family room, creating an open and inviting a

$785,000

5 beds3 baths6,064 sq ft

40801 Kiskadee Ln, Leonardtown, MD 20650

3.18 acre lot • $200 HOA • 2 garage spots

(410) 535-6291

22626 Chickadee Ln, Leonardtown, MD 20650
22626 Chickadee Ln, Leonardtown, MD 20650
22626 Chickadee Ln, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Welcome to your new home in the lovely Avenmar Community! Upon entering your new home you’re greeted by a stunningly adorned 2 story foyer. As you make your way around the lower level you will find a formal living and dining room with a timeless trim work design. Walking into the kitchen you have an open concept flowing seamlessly into your family room where you will find a gas fireplace to keep you and your family cozy all winter long. As you go out the back door to your beautiful stamped concrete patio that was made for entertaining and you’ll find a walkway to your outdoor fire pit and be able to take in the views of your wooded 2 acre lot. Heading back inside and moving upst

$649,900

4 beds3.5 baths2,948 sq ft

22626 Chickadee Ln, Leonardtown, MD 20650

2 acre lot • $200 HOA • 2 garage spots

(301) 684-4895

22362 Armstrong Dr, Leonardtown, MD 20650
22362 Armstrong Dr, Leonardtown, MD 20650
22362 Armstrong Dr, Leonardtown, MD 20650
ABOUT THIS HOME
20627, MD Homes for Sale
Charming Home with a Rare Double Lot in Society Hill, Leonardtown, MD Nestled in the desirable Society Hill neighborhood of Leonardtown, this one-of-a-kind property offers a rare opportunity with its expansive double lot—a true gem in the community. While the home retains a timeless charm, it presents an exciting chance to add your personal touch and modern updates. Inside, you'll find character-filled spaces, including spacious living areas, and an inviting layout that exudes warmth. The home’s unique charm shines through in its craftsmanship, offering a perfect blend of nostalgia and potential. The large lot provides endless possibilities—expand the home, create an outd

$434,900

3 beds3 baths2,028 sq ft

22362 Armstrong Dr, Leonardtown, MD 20650

1.06 acre lot • 2 garage spots • Community pool

(301) 862-2169

Average home prices near 20627, MD

Cities

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$455,000
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$470,000
Leonardtown homes for sale
$634,999
Solomons homes for sale
$599,900
Colonial Beach homes for sale
$375,000
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$627,500
St. Leonard homes for sale
$742,479
California homes for sale
$450,000

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