12

Leonardtown, MD Homes for Sale with Pool

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  • 41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    41480 Whimsical Ct, Leonardtown, MD 20650
    /53

    $699,900

    • 5 Beds
    • 4 Baths
    • 3,825 Sq Ft

    41480 Whimsical Ct, Leonardtown, MD 20650

    Welcome home to this stunning and spacious colonial in sought after Leonards Grant. This home enjoys over 3,800 square feet and is situated on .46 acre at the end of the cul-de-sac making it a private oasis. Upon entering, you're greeted by a two story foyer that is filled with natural sunlight. You'll instantly notice the pristine hard wood floors that flow throughout the home, along with the

    Fran Slade Compass

    41480 Whimsical Ct, Leonardtown, MD 20650
  • 22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    22626 Chickadee Ln, Leonardtown, MD 20650
    /65

    $649,000

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    22626 Chickadee Ln, Leonardtown, MD 20650

    Welcome to 22626 Chickadee Lane—an exceptional 4-bedroom, 3.5-bath home nestled on a serene 2-acre lot in the highly sought-after Avenmar neighborhood of Leonardtown. This elegant property offers the perfect blend of privacy, space, and convenience with an open-concept layout that is flooded with natural light and designed for comfortable living and entertaining.Inside, you'll find

    Matthew Burgan Infinitas Realty Group

    22626 Chickadee Ln, Leonardtown, MD 20650
  • 41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    41402 Silver Charm Ct, Leonardtown, MD 20650
    /99

    $635,000

    • 5 Beds
    • 3.5 Baths
    • 4,046 Sq Ft

    41402 Silver Charm Ct, Leonardtown, MD 20650

    Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field. Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches.

    Kelly Padgett CENTURY 21 New Millennium

    41402 Silver Charm Ct, Leonardtown, MD 20650
  • 23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    23246 Lindsay Dr, Leonardtown, MD 20650
    /42

    $639,900

    • 5 Beds
    • 3.5 Baths
    • 3,876 Sq Ft

    23246 Lindsay Dr, Leonardtown, MD 20650

    Clark's Rest Community:Welcome to this stunning 5-bedroom, 3.5-bath home with over 3,800 square feet of finished living space.Fully owned solar panels—no lease, no monthly payments—drastically reducing electric bills and increasing your home’s efficiency and value. Additional features include convenient attic access located above the 2-car garage, ideal for extra

    Wanda White CENTURY 21 New Millennium

    23246 Lindsay Dr, Leonardtown, MD 20650
  • 41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    41430 Challedon Way, Leonardtown, MD 20650
    /79

    $650,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    41430 Challedon Way, Leonardtown, MD 20650

    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

    Heather Foster RE/MAX One

    41430 Challedon Way, Leonardtown, MD 20650
  • 23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    23264 Lindsay Dr, Leonardtown, MD 20650
    /59

    $629,900

    • 3 Beds
    • 2 Baths
    • 2,824 Sq Ft

    23264 Lindsay Dr, Leonardtown, MD 20650

    Main Level living at its finest in the heart of Leonardtown! Built on an oversized premium corner lot. Customized Lusby model built in 2020 in the highly desirable Clarks Rest Community. This home has the builders 2-10 home warranty which transfers to the new homeowner. VA assumable loan available (to veteran only) at 2.75%. This exquisite home boasts an open floorplan that flows

    Wayne & Christine Floyd RE/MAX Realty Group

    23264 Lindsay Dr, Leonardtown, MD 20650
  • 41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    41412 Doctors Crossing Rd, Leonardtown, MD 20650
    /50

    $540,000

    • 4 Beds
    • 3.5 Baths
    • 2,686 Sq Ft

    41412 Doctors Crossing Rd, Leonardtown, MD 20650

    Welcome to your dream home in highly sought-after Clarks Rest, just minutes from all the charm and dining of Leonardtown Square. This vibrant community features sidewalks, a community pool, and that perfect neighborhood feel you’ve been looking for. Step inside to find real hardwood floors in the entryway and luxury vinyl plank flooring throughout the main living areas, including the spacious

    Delaney Burgess RE/MAX United Real Estate

    41412 Doctors Crossing Rd, Leonardtown, MD 20650
  • 0 Kiskadee Ln, Leonardtown, MD 20650
    0 Kiskadee Ln, Leonardtown, MD 20650
    0 Kiskadee Ln, Leonardtown, MD 20650
    /18

    $200,000

    • Land
    • 3.53 Acres
    • $56,657 per Acre

    0 Kiskadee Ln, Leonardtown, MD 20650

    The LAST BUILDING SITE in Avenmar! You won't want to miss this opportunity to purchase the last builder developed parcel in one of Leonardtown's most sought after communities! With over 3.5 wooded acres, this property offers a flat, private, wooded setting like no other. Community features pier, boat ramp, stables, pool, community center and so much more! Contact us for more info, or to set up a

    Pattee McInerney Scott McInerney RE/MAX One

    0 Kiskadee Ln, Leonardtown, MD 20650
  • 41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    41505 Knight Rd, Leonardtown, MD 20650
    /126

    $5,950,000

    • 5 Beds
    • 8 Baths
    • 12,113 Sq Ft

    41505 Knight Rd, Leonardtown, MD 20650

    Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along the tranquil waters off of the Potomac River, this custom-built four level waterfront estate on almost 18 acres, is a testament to architectural brilliance and sophisticated design. As you approach the grand entrance, you are greeted by a circular driveway, detached 3-car garage, attached 2-car garage,

    Travis Gray Engel & Völkers Annapolis

    41505 Knight Rd, Leonardtown, MD 20650
  • Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650
    /6

    $459,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft

    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650

    Unit 89 Oakley D1New Construction – Oakley D1 End Unit at Meadows at Town Run II2,966 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Oakley D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland. This expansive 2,966 sq ft home offers generous living areas, abundant natural light, and the perfect

    Laura Bernth RE/MAX One

    Lot 89 23676 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650
    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650
    /5

    $439,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650

    Unit 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage Welcome to the Madison D2, a spacious and thoughtfully designed townhome by Quality Built Homes located in the vibrant new community of Meadows at Town Run II in Leonardtown, MD. This 3-level, 2,604 sq ft interior unit offers flexible living space, starting with a

    Laura Bernth RE/MAX One

    Lot 88 23676 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650
    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650
    /10

    $439,900 Open Mon 10AM - 12PM

    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650

    Unit 87 Madison D3: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D3 Interior Unit, a thoughtfully designed 3-level townhome offering 2,604 sq ft of beautifully finished living space. This interior unit features an oversized one-car garage and an entry-level flex space that includes built-in cubbies and coat hooks, plus

    Laura Bernth RE/MAX One

    Lot 87 23670 Dragonfly Ln, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Homes for Sale with Pool in Leonardtown, MD

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 29 days on the market compared to the national average of 52 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $547,450, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$547,450
Median Single Family Sale Price
$589,900
Median Townhouse Sale Price
$439,900
Median 2 Bedroom Sale Price
$279,000
Average Price Per Sq Ft
$191
Number of Homes for Sale
29
Last 12 months Home Sales
136
Months of Supply
2.60
Median List Price
$549,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Leonardtown, there are currently 12 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Leonardtown, MD and discover your ideal residence.

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