15

Colonial Homes for Sale in Leonardtown, MD

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  • /33

    $459,900

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    41923 Sara Ann Ct, Leonardtown, MD 20650

    Sellers have outgrown this great Leonardtown location without the hustle and bustle of being in down town. Also offered at less than typical Leonardtown homes where the median sold price is $547,500. This 3 bedroom home has been upgraded with new deck/screened porch in 2023, upstairs vinyl flooring, kitchen quartz and new appliances in 2025 & backsplash & new roof. Be in and settled in this one

    Agent Photo

    Jimmy Hayden

    RE/MAX One

    (227) 238-1072

    41923 Sara Ann Ct, Leonardtown, MD 20650
  • /34

    $449,900 Open Thu 11AM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650

    ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's preferred lender and title co*** (special is for this Homesite #101 Madison D3 only). ***IMMEDIATE DELIVERY***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

    Laura Bernth RE/MAX One

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
  • /64

    $635,000

    • 5 Beds
    • 3 Baths
    • 3,030 Sq Ft

    41585 Austin Ct, Leonardtown, MD 20650

    Welcome to the completely unforgettable curb appeal of this home situated in the only culdesac of custom homes in the Estates at Singletree! Loved and beautifully maintained from the start by its current owners, they have personally curated, creative florals that surround this Southern Living traditional build, all the way to the perimeters of the property which provide abundant blueberries,

    Drema Ballengee-grunst EXP Realty, LLC

    41585 Austin Ct, Leonardtown, MD 20650
  • /45

    $449,900 Open Thu 11AM - 3:45PM

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

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650

    ***Mid-May Delivery*** Builder Incentive, Receive $12,500 in Builder Closing Help with use of Preferred Lender & Title company. Homesite 135 - 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

    Laura Bernth RE/MAX One

    Lot 135 - 23679 Weeping Willow Way, Leonardtown, MD 20650
  • /57

    $600,000

    • 5 Beds
    • 4 Baths
    • 3,724 Sq Ft

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    NOW offered at $600,000 — a compelling opportunity in CLARK'S REST. *Get up to $3,000 with use of preferred lender for CLOSING COST assistance or use funds for a rate buy-down. Recently reintroduced with improved pricing, this is your chance to own one of the largest homes in the community, offering space, flexibility, and a lifestyle buyers are actively searching for. Welcome to 41377 Doctors

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • /34

    $449,900 New Construction

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

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650

    ****Mid May Delivery*** Homesite # 136 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 2,554 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

    Laura Bernth RE/MAX One

    Lot 136 - 23673 Weeping Willow Way, Leonardtown, MD 20650
  • /35

    $449,900 Open Thu 11AM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's preferred lender and title co*** (special is for this Homesite #99 Madison D3 only). ***Available NOW*** Homesite #99 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

    Laura Bernth RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • /47

    $629,000

    • 5 Beds
    • 5 Baths
    • 2,756 Sq Ft

    43430 Browns Ln, Leonardtown, MD 20650

    Sellers are motivated and have found their home of choice. This unique property has so much to offer and has been a great family home providing many warm memories. Well cared for 4 BR 2.5 BA home has 2,116 sq. ft, and features an open floor plan for comfortable living. The welcoming kitchen has classic granite counters and maple cabinets, while a custom-made stainless steel top island borders the

    Juliet Brown Residential Plus Real Estate Services

    43430 Browns Ln, Leonardtown, MD 20650
  • /75

    $574,900

    • 5 Beds
    • 3.5 Baths
    • 4,300 Sq Ft

    41482 Pensive St, Leonardtown, MD 20650

    Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, boasting over 4500SQFT located in Sought After Neighborhood of Leonard's Grant! Homes with this SQFT at this price point are almost non-existent. Similar homes have sold in this neighborhood for $625,000-$675,000! This home will need some cosmetic repair but is ready to shine again! From the street you are

    Mark Frisco CENTURY 21 New Millennium

    41482 Pensive St, Leonardtown, MD 20650
  • /41

    $479,900 New Construction

    • 4 Beds
    • 3.5 Baths

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650

    **TO BE BUILT**** Homesite 141 - Oakley D1 End Unit ***October Delivery**** ***Choose your color scheme from of our available options** 2,966 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

    Laura Bernth RE/MAX One

    Lot 141 - 23653 Dragonfly Ln, Leonardtown, MD 20650
  • /69

    $599,900 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    40704 Chance Way, Leonardtown, MD 20650

    Beautiful 4 bedroom, 2 1/2 bathroom colonial located in Leonardtown. Just mins from downtown Leonardtown amenities, shopping, restaurants, schools and more. This home has hardwood floors throughout. Spacious formal living and dining rooms. Kitchen with lots of cabinets and island with seating. Breakfast area and sliding doors that open to the back yard and patio. Family room w/gas fireplace off

    Kelly Padgett Century 21 Redwood Realty

    40704 Chance Way, Leonardtown, MD 20650
  • /42

    $449,900 Open Thu 11AM - 4PM

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

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650

    Homesite #111 Madison D3: ****May Delivery***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

    Laura Bernth RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
  • /57

    $649,900

    • 5 Beds
    • 3.5 Baths
    • 4,340 Sq Ft

    42032 Starlight Dr, Leonardtown, MD 20650

    PROFESSIONAL PICTURES COMING NEXT WEEK! Welcome to 42032 Starlight Drive in Leonardtown, MD, a spacious and beautifully updated home offering comfort, flexibility, and thoughtful upgrades throughout. This beautiful property backs to woods, providing a peaceful and private setting to enjoy year-round. Inside, fresh new paint throughout, new carpet upstairs, and new vinyl plank flooring in the

    Bill Oosterink CENTURY 21 New Millennium

    42032 Starlight Dr, Leonardtown, MD 20650
  • /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 ac of fertile land with a mile-long view of the Potomac River’s white sand shoreline, truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • /46

    $489,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,095 Sq Ft

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

    ***TO BE BUILT*** ***November Delivery*** ***Choose your color scheme from of our available options*** Home Site 142 New Construction – Cumberland D1 End Unit at Meadows at Town Run II 3095 Sq Ft | 4 Bedrooms | 3.5 Baths | 1-Car Garage. Discover the spacious Cumberland D1 end-unit townhome at Meadows at Town Run II, crafted by Quality Built Homes and located in the heart of Leonardtown, Maryland.

    Laura Bernth RE/MAX One

    Lot 142 - 23647 Dragonfly Ln, Leonardtown, MD 20650

Home Trends in Leonardtown, MD

Housing Trends

Median Sale Price
$536,250
Median Single Family Sale Price
$592,000
Median Townhouse Sale Price
$449,900
Average Price Per Sq Ft
$196
Number of Homes for Sale
29
Last 12 months Home Sales
176
Months of Supply
2.00
Median List Price
$537,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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