27

Leonardtown, MD Homes for Sale with Garage

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  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    /19

    $449,900

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

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ***Estimated Late October Delivery****Under Construction*** 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 main-level entry that opens into a finished rec room or 4th bedroom with a

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 41400 Real Quiet Dr, Leonardtown, MD 20650
    41400 Real Quiet Dr, Leonardtown, MD 20650
    41400 Real Quiet Dr, Leonardtown, MD 20650
    /4

    $769,000

    Coming Soon
    • 6 Beds
    • 4 Baths
    • 5,569 Sq Ft

    41400 Real Quiet Dr, Leonardtown, MD 20650

    Welcome to your peaceful sanctuary at 41400 Real Quiet Drive! This exceptional property perfectly blends interior comfort with an extraordinary outdoor living experience. The highlight of this home is a $40,000 outdoor transformation featuring an expansive, premium patio designed for ultimate entertaining and a fully enclosed black aluminum fence. Inside, you will find a bright, open-concept

    James Dick Long & Foster Real Estate, Inc.

    41400 Real Quiet Dr, Leonardtown, MD 20650
  • Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    /12

    $454,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    Hurry in! Secure your new home now and personalize it with your choice of interior colors. Expected December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! Homesite 157 Madison D1: Welcome to Meadows at Town Run.... Leonardtown’s Newest Townhome Community by Quality Built Homes! Discover the Madison-D1 Interior Unit, a thoughtfully designed 3-level

    Laura Hefley RE/MAX One

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
  • 23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    /85

    $649,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Step inside to find gorgeous hardwood floors flowing seamlessly across the main level. The mostly finished basement is an entertainer's dream, featuring a dedicated theater area ready for your custom equipment, a spacious

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    /77

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in the highly desirable Breton Bay Golf Community, this beautifully maintained home offers the perfect blend of comfort, convenience, and Southern Maryland living. Enjoy a peaceful setting with virtually no through traffic, while still being just minutes from the community beach, pier, waterfront access,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. **** Homesite #116 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

    Laura Hefley RE/MAX One

    Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    /2

    $645,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Photos coming soon

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • 22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    22856 White Swan Way, Leonardtown, MD 20650
    /49

    $1,100,000

    • 5 Beds
    • 5 Baths
    • 5,410 Sq Ft

    22856 White Swan Way, Leonardtown, MD 20650

    This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane in Avenmar; a water oriented community on Breton Bay. Its elegant facade overlooks the lovely landscaped yard. From the gourmet kitchen, wander on to the custom covered rear screened porch where the morning sun dances across the private backyard and patio. Each spacious bedroom is filled with natural light

    Barbara Stellway KW Metro Center

    22856 White Swan Way, Leonardtown, MD 20650
  • 40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    40115 Combs Creek Way, Leonardtown, MD 20650
    /89

    $1,700,000

    • 5 Beds
    • 3.5 Baths
    • 2,993 Sq Ft

    40115 Combs Creek Way, Leonardtown, MD 20650

    Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown, where panoramic views of Breton Bay, a private sandy beach peninsula, deep-water boating access, and comfort-inspired amenities create one of St. Mary’s County’s remarkable waterfront offerings this year. Perfectly positioned to capture breathtaking water views, this exceptional property offers a rare

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    /74

    $670,000

    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this well-maintained Belmont model in the desirable Leonard's Grant community, tucked toward the back of the neighborhood and featuring a large fenced backyard and composite deck—perfect for outdoor entertaining and everyday enjoyment.Upon entering, you're greeted by a grand staircase and a front living room with built-in bookshelves that flows seamlessly into the formal dining

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • 21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    21983 Point Lookout Rd, Leonardtown, MD 20650
    /30

    $379,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21983 Point Lookout Rd, Leonardtown, MD 20650

    OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler located in the highly desirable Leonardtown School District, offering the perfect blend of modern updates and peaceful living on almost 1-acre lot.This move-in ready home features 3 bedrooms and 2 full bathrooms, along with a 1-car garage as well as man cave, workshop, or bonus space. The home has been

    Natalya Ford RE/MAX One

    21983 Point Lookout Rd, Leonardtown, MD 20650
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $515,000

    • 4 Beds
    • 2.5 Baths
    • 2,774 Sq Ft

    40659 Klear Ct, Leonardtown, MD 20650

    This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's bathroom shower has a leak and will probably need to be replaced. As you can see, it's listed well below market value. If you're looking for something to build equity, this could be the one for you. This Colonial features 4 bedrooms and 2 full baths and the laundry room on the upper level. The main level

    Christopher Blondin Baldus Real Estate, Inc.

    40659 Klear Ct, Leonardtown, MD 20650
  • Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
    /43

    $449,900

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

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

    BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's Preferred Lender and Title. ****Available Now***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

    Laura Hefley RE/MAX One

    Lot 111 - 23684 Weeping Willow Way, Leonardtown, MD 20650
  • 42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    42195 White Point Beach Rd, Leonardtown, MD 20650
    /57

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    42195 White Point Beach Rd, Leonardtown, MD 20650

    Enjoy peaceful mornings in the 11’ x 26’ sunroom with wall of windows offering unobstructed views of the Potomac River from Piney Point, Virginia shoreline and west to St. Clements Island. End your day with majestic sunsets. A perfect waterfront escape but minutes to Leonardtown! Vintage 1920’s Cottage with all mechanicals, roof, windows, doors updated within the last 10 years but still

    Carl Franzen Franzen Realtors, Inc.

    42195 White Point Beach Rd, Leonardtown, MD 20650
  • 41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    41620 Church St, Leonardtown, MD 20650
    /70

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    41620 Church St, Leonardtown, MD 20650

    Fully renovated. Move-in ready. Prime downtown location.Welcome to 41620 Church St — a rare opportunity to own a completely updated home in the heart of Leonardtown at an exceptional value.Step inside to discover brand new vinyl flooring throughout, a stunning kitchen featuring quartz countertops, and beautifully refreshed bathrooms that bring a modern, clean aesthetic to every corner of

    Chanel Li Evergreen Properties

    41620 Church St, Leonardtown, MD 20650
  • 23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    23636 Gunnell Dr, Leonardtown, MD 20650
    /37

    $599,500

    • 4 Beds
    • 2.5 Baths
    • 2,948 Sq Ft

    23636 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial offers nearly 3,000 square feet of comfortable living space on a beautifully maintained 0.51-acre lot.Step inside to discover fresh updates, including new carpet and luxury vinyl plank flooring, creating a move-in ready home with a modern feel. The thoughtfully designed floor plan provides ample room for

    Marie Hankinson EXP Realty, LLC

    23636 Gunnell Dr, Leonardtown, MD 20650
  • 22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    22332 Cedar St, Leonardtown, MD 20650
    /12

    $329,900

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    22332 Cedar St, Leonardtown, MD 20650

    Quaint All-Brick Rambler in a Water-Oriented Community This well-built, all-brick rambler offers timeless charm and solid construction. Features include a gas furnace, central air conditioning, and hardwood floors beneath the carpeting. The interior has been freshly painted and includes a bright eat-in kitchen. Oversized two car garage with large workshop area & pull down stairs to attic storage.

    Carol Kalmus-Choporis Century 21 Redwood Realty

    22332 Cedar St, Leonardtown, MD 20650
  • 42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    42084 Wildflower Dr, Leonardtown, MD 20650
    /33

    $629,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42084 Wildflower Dr, Leonardtown, MD 20650

    To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Built Homes’ Clarke Model ... a beautifully designed single-family home offering spacious living, timeless curb appeal, located on a corner lot and the opportunity to personalize your new home from the start. This thoughtfully planned home features 4 bedrooms, 2.5 baths, a rear-entry garage, and an inviting

    Laura Hefley RE/MAX One

    42084 Wildflower Dr, Leonardtown, MD 20650
  • Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
    /44

    $449,900

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

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650

    ***Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ** Homesite #114 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

    Laura Hefley RE/MAX One

    Lot 114 - 23702 Weeping Willow Way, Leonardtown, MD 20650
  • 42970 Heritage Dr, Leonardtown, MD 20650
    42970 Heritage Dr, Leonardtown, MD 20650
    42970 Heritage Dr, Leonardtown, MD 20650
    /94

    $829,900

    Open Sun 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 5,082 Sq Ft

    42970 Heritage Dr, Leonardtown, MD 20650

    Welcome home to this stunning luxury residence in the sought-after Leonardtown Farms neighborhood, offering over 5000 finished square feet! Built and impeccably maintained by its original owners, this home feels brand new; not a detail has been overlooked. A detailed record of every upgrade and maintenance item from 2012 through 2026 is available, giving buyers complete peace of mind and a clear

    Sarah Mulford-Martin EXP Realty, LLC

    42970 Heritage Dr, Leonardtown, MD 20650
  • 42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    42096 Wildflower Dr, Leonardtown, MD 20650
    /45

    $619,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,976 Sq Ft

    42096 Wildflower Dr, Leonardtown, MD 20650

    Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Quality Built Homes’ Bell Floorplan ... a 4-bedroom, 2.5-bath single-family home with a smart layout, rear-load garage, and flexible living space. This floorplan offers the convenience of a main-level primary bedroom with a private en suite bath, plus three additional bedrooms upstairs. The main level is

    Laura Hefley RE/MAX One

    42096 Wildflower Dr, Leonardtown, MD 20650
  • 42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    42102 Wildflower Dr, Leonardtown, MD 20650
    /72

    $609,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,701 Sq Ft

    42102 Wildflower Dr, Leonardtown, MD 20650

    New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality Built Homes’ Mattingly Model ... a 4-bedroom, 2.5-bath single-family home with timeless curb appeal, smart design, and room to grow. The main level offers an open and comfortable layout with a spacious family room, kitchen, breakfast area, formal dining room, and living room. Upstairs, the owner’s suite

    Laura Hefley RE/MAX One

    42102 Wildflower Dr, Leonardtown, MD 20650
  • 40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    /29

    $365,000

    • 4 Beds
    • 2 Baths
    • 2,474 Sq Ft

    40743 Magee Dr, Leonardtown, MD 20650

    Unlock the potential in this 4-bedroom, 2-bath handyman special located in the highly desirable Brenton Bay community of Leonardtown! Perfect for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features a functional layout with a kitchen, separate dining room, spacious living room, two bedrooms, and a full bathroom. The finished

    Liam Coonahan Real of Pennsylvania

    40743 Magee Dr, Leonardtown, MD 20650
  • Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
    /7

    $454,900

    New Construction $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ***** Hurry in! Secure your new home now and personalize it with your choice of interior colors. December delivery, with a beautiful lot backing to trees for added privacy and a peaceful setting! ***** Homesite #156 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

    Laura Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • 23628 Belmar Dr, Leonardtown, MD 20650
    23628 Belmar Dr, Leonardtown, MD 20650
    /2

    $730,000

    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    PROFESSIONAL PHOTOS COMING!

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • 42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    42108 Wildflower Dr, Leonardtown, MD 20650
    /31

    $614,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft

    42108 Wildflower Dr, Leonardtown, MD 20650

    New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring Quality Built Homes’ Fenwick Model ... a beautifully designed to-be-built home offering 3 bedrooms, 2.5 baths, and the chance to get in early and personalize select interior finishes, fixtures, and colors depending on construction timing. The Fenwick offers a smart, comfortable layout with a spacious family

    Laura Hefley RE/MAX One

    42108 Wildflower Dr, Leonardtown, MD 20650
  • 41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    41444 Osborne Ln, Leonardtown, MD 20650
    /47

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 3,690 Sq Ft

    41444 Osborne Ln, Leonardtown, MD 20650

    Charming Home in Prime Leonardtown LocationThis inviting home sits in the heart of historic Leonardtown— a highly sought-after community with easy access to schools, the hospital, parks, restaurants, and shops. Inside, an open floor plan with abundant natural light creates a welcoming feel. A flexible main-level room works perfectly as a bedroom, office, or playroom. The separate dining room

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Homes for Sale with Garage in Leonardtown, MD

Home Prices in Leonardtown, MD

The median home sale price in Leonardtown, MD is $540,000, down 2% year-over-year. Homes in Leonardtown sell in 43 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$540,000
Median Single Family Sale Price
$599,700
Median Townhouse Sale Price
$449,900
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$192
Number of Homes for Sale
29
Last 12 months Home Sales
195
Months of Supply
1.80
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-2%
How to Buy a Home How to Finance a Home How to Sell a Home

In Leonardtown, there are currently 27 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Leonardtown, MD and find the perfect place to call home.

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