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Colonial Homes for Sale in Leonardtown, MD

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  • 21749 Pinehurst Ct, Leonardtown, MD 20650
    21749 Pinehurst Ct, Leonardtown, MD 20650
    21749 Pinehurst Ct, Leonardtown, MD 20650
    /86

    $570,000

    • 4 Beds
    • 3.5 Baths
    • 3,410 Sq Ft

    21749 Pinehurst Ct, Leonardtown, MD 20650

    Gorgeous Colonial in Breton Bay! This welcoming home is nestled on a quiet cul-de-sac, steps away from the great amenities this desirable community has to offer. Start your tour of this 4-bedroom, 3.5-bath home by opening the attractive glass front door, and stepping across stunning hardwood floors, refinished just last year. Pass the formal living room, perfect for conversations, or a good book.

    Agent Photo

    Patrick Deighan

    CENTURY 21 New Millennium

    (227) 232-1113

    21749 Pinehurst Ct, Leonardtown, MD 20650
  • 41982 Satchel Paige Way, Hollywood, MD 20636
    41982 Satchel Paige Way, Hollywood, MD 20636
    41982 Satchel Paige Way, Hollywood, MD 20636
    /24

    $255,000

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    41982 Satchel Paige Way, Hollywood, MD 20636

    Nestled in the charming Holland Forrest Landing community, this delightful Colonial townhouse offers a perfect blend of comfort and convenience. With three spacious bedrooms and two full bathrooms, this home is designed for easy living. The inviting interior features a mix of carpet and stylish laminate plank flooring, creating a warm atmosphere throughout. Ready for your vision, finishing

    Agent Photo

    Ben Antkowiak

    Epique Realty

    (227) 238-1671

    41982 Satchel Paige Way, Hollywood, MD 20636
  • 41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    41488 Pensive St, Leonardtown, MD 20650
    /50

    $680,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,992 Sq Ft

    41488 Pensive St, Leonardtown, MD 20650

    Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard’s Grant, offering a spacious layout and thoughtful design throughout. As you enter the home, you’re welcomed by hardwood floors, a grand entryway, and a beautiful staircase that creates an inviting first impression.To the right, French doors open to a large room that works well as a home office or additional

    Heather Foster RE/MAX One

    41488 Pensive St, Leonardtown, MD 20650
  • 41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    41377 Doctors Crossing Rd, Leonardtown, MD 20650
    /63

    $639,999

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

    41377 Doctors Crossing Rd, Leonardtown, MD 20650

    Welcome Home!41377 Doctors Crossing Rd is a well-maintained home located in the sought-after Clark’s Rest community — where comfortable living meets a vibrant neighborhood lifestyle, with a pond just steps away and walking distance to the clubhouse. Offering 5,538 total square feet, including 3,724 finished square feet above grade, this home provides the space and flexibility. As you step

    Minh Lofaso Keller Williams Realty/Lee Beaver & Assoc.

    41377 Doctors Crossing Rd, Leonardtown, MD 20650
  • Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
    /35

    $449,900 Open Fri 2PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #99 Madison D3: ****ALMOST READY FOR MARCH 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

    Laura Bernth RE/MAX One

    Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650
  • Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
    /34

    $449,900 Open Fri 2PM - 4PM

    • 4 Beds
    • 3.5 Baths

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650

    Homesite #101 Madison D3: ***ALMOST READY FOR MARCH 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

    Laura Bernth RE/MAX One

    Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650
  • 41497 Affirmed Way, Leonardtown, MD 20650
    41497 Affirmed Way, Leonardtown, MD 20650
    41497 Affirmed Way, Leonardtown, MD 20650
    /83

    $655,000

    • 5 Beds
    • 3.5 Baths
    • 3,934 Sq Ft

    41497 Affirmed Way, Leonardtown, MD 20650

    Beautiful inside and out, this impeccably maintained home offers exceptional curb appeal with professionally landscaped grounds, a fenced backyard, and a partially covered paver patio—an ideal space for outdoor dining, relaxing, and entertaining.Inside, the thoughtfully designed floor plan includes a private home office and a dedicated dining room, perfect for both everyday living and special

    Heather Foster RE/MAX One

    41497 Affirmed Way, Leonardtown, MD 20650
  • 41516 Marwood Cir, Leonardtown, MD 20650
    41516 Marwood Cir, Leonardtown, MD 20650
    41516 Marwood Cir, Leonardtown, MD 20650
    /55

    $437,000

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft

    41516 Marwood Cir, Leonardtown, MD 20650

    Professional photos coming soon. Welcome home to Marwood Circle in the desirable Clark's Rest Neighborhood of Leonardtown. This nearly new townhome built in 2020 has over 2400 square feet of living space and is in move in condition. Nice open concept on the main level includes an updated kitchen with granite countertops and island, stainless appliances and pantry, large family room, separate

    Cynthia Ballard CENTURY 21 New Millennium

    41516 Marwood Cir, Leonardtown, MD 20650
  • 40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    40737 Bobwhite Ln, Leonardtown, MD 20650
    /101

    $809,900

    • 4 Beds
    • 3.5 Baths
    • 5,454 Sq Ft

    40737 Bobwhite Ln, Leonardtown, MD 20650

    Avenmar beauty situated on over 3.5 acres, offering exceptional space and privacy. The custom kitchen features top-of-the-line appliances, custom cabinetry, solid-surface countertops, and stunning light fixtures. The main level includes formal dining and living rooms, a dedicated office space, and a two-story family room with an overlook from above. Floor-to-ceiling windows showcase peaceful

    Jennifer Goddard CENTURY 21 New Millennium

    40737 Bobwhite Ln, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, 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
  • 23299 Jenifer Ct, Leonardtown, MD 20650
    23299 Jenifer Ct, Leonardtown, MD 20650
    23299 Jenifer Ct, Leonardtown, MD 20650
    /57

    $550,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 3,482 Sq Ft

    23299 Jenifer Ct, Leonardtown, MD 20650

    Beautiful 5BR, 3BA home with over 3,100 sq ft above grade tucked away on a peaceful 1⁄2-acre flag lot backing to trees in the heart of Leonardtown. Inside you’ll find hardwood flooring, spacious living areas, and a warm, inviting family room perfect for everyday living or entertaining. The kitchen features granite countertops, stainless steel appliances, and plenty of workspace. The main level

    Conor Loughran CENTURY 21 New Millennium

    23299 Jenifer Ct, Leonardtown, MD 20650
  • 23563 Belmar Dr, Leonardtown, MD 20650
    23563 Belmar Dr, Leonardtown, MD 20650
    23563 Belmar Dr, Leonardtown, MD 20650
    /3

    $650,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 3,299 Sq Ft

    23563 Belmar Dr, Leonardtown, MD 20650

    Heather Foster RE/MAX One

    23563 Belmar Dr, Leonardtown, MD 20650
  • 20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    20260 Hawks Way, Leonardtown, MD 20650
    /28

    $579,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    20260 Hawks Way, Leonardtown, MD 20650

    IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new construction home situated on 1.34 flat acres in rural Leonardtown. This 4-bedroom, 2.5-bath residence showcases a modern design with thoughtful details and high-end finishes throughout. The main level features luxury vinyl plank flooring and a bright, open-concept layout perfect for both everyday living and

    Mark Frisco CENTURY 21 New Millennium

    20260 Hawks Way, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Real Estate & Homes for Sale in Leonardtown, MD

Home Trends in Leonardtown, MD

On average, homes in Leonardtown, MD sell after 43 days on the market compared to the national average of 54 days. The median sale price for homes in Leonardtown, MD over the last 12 months is $542,500, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$542,500
Median Single Family Sale Price
$582,000
Median Townhouse Sale Price
$454,225
Average Price Per Sq Ft
$198
Number of Homes for Sale
28
Last 12 months Home Sales
164
Months of Supply
2.00
Median List Price
$542,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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