36

Leonardtown, MD Homes for Sale with Pool

Section Image Section Image Section Image
  • /44

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 2,601 Sq Ft

    40751 Merlin Way, Leonardtown, MD 20650

    Welcome to this beautiful brick-front home in the highly sought-after Avenmar Community of historic Leonardtown, Maryland. Situated on over 3 private acres and tucked away on a secluded road shared by only three other homes, this property offers the perfect balance of privacy, nature, and convenience.Freshly updated with a new roof, new carpet throughout, and fresh paint, this

    Agent Photo

    Tracy Trammell

    Metro City Realty

    40751 Merlin Way, Leonardtown, MD 20650
  • /21

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650

    ALMOST READY***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

    Laura Lee Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • /41

    $449,900

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

    23684 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersNatural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe Shower

    Quality Built Homes Builder
    23684 Dragonfly Ln, Leonardtown, MD 20650
  • /13

    $454,900

    New Construction Open Thu 11:30AM - 3:30PM
    • 4 Beds
    • 3.5 Baths
    • 2,571 Sq Ft

    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650

    **** 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 townhome offering 2,571 sq ft of beautifully finished living space. This interior unit

    Laura Lee Hefley RE/MAX One

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

    $619,500

    $60K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    NEW 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 office

    John Kreamer Taylor Properties

    23636 Hansel Ct, Leonardtown, MD 20650
  • /40

    $449,900

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

    23672 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSandstone Beige Carolina Bead SidingMusket Brown ShuttersBronze Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsWhite Ice Granite CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23672 Weeping Willow Way, Leonardtown, MD 20650
  • /42

    $449,900

    New Construction Open Thu 11AM - 4PM
    • 4 Beds
    • 3.5 Baths

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650

    ***** October Delivery *********** Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #139 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.

    Laura Lee Hefley RE/MAX One

    Lot 139 - 23665 Dragonfly Ln, Leonardtown, MD 20650
  • /77

    $524,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,370 Sq Ft

    40777 Center 40 Cir, Leonardtown, MD 20650

    NEW PRICE — $524,900! If you’ve been waiting for the right opportunity to make your move to Breton Bay, this could be the one.There’s something special about living in Breton Bay. It’s the kind of neighborhood where you can come home at the end of the day, leave the traffic behind, and actually enjoy where you live. Tucked away on a quiet cul-de-sac with virtually no through traffic, this

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • /64

    $690,000

    Open Sat 9:30AM - 12PM $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,066 Sq Ft

    21395 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 acres in one of Leonardtown’s most desirable neighborhoods. Tucked near the end of a quiet street by the cul-de-sac, this 4-bedroom, 3.5-bath home offers more than 3,500 square feet of finished living space, a fully finished basement, and an expansive backyard designed to be enjoyed.Step inside to a

    Lauren Garner EXP Realty, LLC

    21395 Fairwood Ct, Leonardtown, MD 20650
  • /73

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    40579 Port Place, Leonardtown, MD 20650

    Experience breathtaking panoramic views of Breton Bay and unforgettable sunsets! Cape Cod-style home featuring 3 bedrooms plus a spacious loft.Designed to maximize the water views, the home offers hardwood floors throughout and an inviting floor plan with a living room, family room, dining room, and breakfast room—all overlooking the bay. Enjoy the expansive 37' x 8' front porch or the

    Carol Kalmus-Choporis Century 21 Redwood Realty

    40579 Port Place, Leonardtown, MD 20650
  • /75

    $635,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,314 Sq Ft

    41462 Culpepper Way, Leonardtown, MD 20650

    Welcome home to this beautifully refreshed home in the sought-after Leonard’s Grant community! Ideally located on Leonard’s Grant Parkway, this move-in ready home features fresh paint and brand-new carpet throughout, offering a clean, updated feel from the moment you step inside.The thoughtfully designed floor plan showcases beautiful hardwood floors, a gourmet kitchen with abundant

    Heather Foster RE/MAX One

    41462 Culpepper Way, Leonardtown, MD 20650
  • /28

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,691 Sq Ft

    43954 Main Way Rd, Leonardtown, MD 20650

    Set on a level, open corner lot with a small view of the Potomac River—and best of all, **NO HOA**—this well-maintained split-foyer offers comfortable living, thoughtful updates, and a backyard designed for entertaining. A blacktop driveway provides a clean, finished approach to the oversized two-car garage, which accommodates two vehicles with plenty of additional room. The main level features

    Danny Martin Keller Williams Flagship

    43954 Main Way Rd, Leonardtown, MD 20650
  • /45

    $575,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3 Baths
    • 2,730 Sq Ft

    22010 Society Hill Rd, Leonardtown, MD 20650

    Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appreciate the landscaping leading to the home, which was completed in the fall of 2025. Upon entering, you're greeted with wood floors and sunlight that floods the space thanks to the large windows across the front of the home. The open floor plan allows the living room to flow seamlessly into the dining area

    Fran Slade Compass

    22010 Society Hill Rd, Leonardtown, MD 20650
  • /89

    $1,590,000

    $110K PRICE DROP
    • 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

    Diana Washabaugh CENTURY 21 New Millennium

    40115 Combs Creek Way, Leonardtown, MD 20650
  • /58

    $624,990

    • 4 Beds
    • 3.5 Baths
    • 2,562 Sq Ft

    40611 Merion Ct, Leonardtown, MD 20650

    Welcome to 40611 Merion Court, Leonardtown, MD 20650! This stunning three-level Colonial offers the perfect blend of elegance, comfort, and resort-style living, ideally positioned with beautiful views backing directly to Breton Bay golf course. Featuring 4 bedrooms, 3.5 baths, and a fully finished basement, this home provides exceptional space for both everyday living and entertaining. The

    Kalee Kelly Infinitas Realty Group

    40611 Merion Ct, Leonardtown, MD 20650
  • /74

    $649,000

    $21K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,051 Sq Ft

    23591 Margrave Dr, Leonardtown, MD 20650

    Welcome to this home 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 room and kitchen. The

    Heather Foster RE/MAX One

    23591 Margrave Dr, Leonardtown, MD 20650
  • /43

    $695,000

    Open Sat 11AM - 2PM
    • 5 Beds
    • 3.5 Baths
    • 4,084 Sq Ft

    23214 Dairy Barn Dr, Leonardtown, MD 20650

    Located in Clark's Rest, this home features Marrick's Kensington floor plan, with a covered front entry and separate covered sitting porch. Inside, a two-story foyer features hardwood flooring and elegant moldings that continue into the dining room. To the left, a versatile room offers flexibility for a home office, library, study, or playroom. The dining room connects through the butler's pantry

    Wanda White CENTURY 21 New Millennium

    23214 Dairy Barn Dr, Leonardtown, MD 20650
  • /4

    $749,900

    Coming Soon Sep 1
    • 5 Beds
    • 4 Baths
    • 4,873 Sq Ft

    41402 Omaha Ct, Leonardtown, MD 20650

    2.25% Assumable VA loan & one of the largest lots in Leonard's Grant at .64 acres! This brilliant Leonardtown residence perfectly blends modern upgrades with unique features you won't find anywhere else. Lots of fruit trees (Fig, Apple, Mulberry, Dwarf Peach, Pear, Strawberry and Persimmon). Enter to find gorgeous exotic hardwood tigerwood floors flowing seamlessly across the main level into the

    Jonathan Powell Real Broker, LLC

    41402 Omaha Ct, Leonardtown, MD 20650
  • /41

    $449,900

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

    23679 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D2 Natural Clay Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Taj Quartz CountertopsSplendur Cream BacksplashDeluxe Shower in Primary

    Quality Built Homes Builder
    23679 Weeping Willow Way, Leonardtown, MD 20650
  • /42

    $449,900

    New Construction
    • 4 Beds
    • 3.5 Baths

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650

    *** November Delivery ******Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ****Homesite #143 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.

    Laura Lee Hefley RE/MAX One

    Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD 20650
  • /36

    $449,900

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

    23714 Weeping Willow Way, Leonardtown, MD 20650

    Interior Elevation D3 with DormersSavannah Wicker Carolina Bead SidingMusket Brown ShuttersSunbrook Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorCeramic Tile in BathroomsUpgraded Maple Kitchen CabinetsIvory Coast Quartz CountertopsSplendur Cream BacksplashDeluxe

    Quality Built Homes Builder
    23714 Weeping Willow Way, Leonardtown, MD 20650
  • /2

    $600,000

    Open Sat 11AM - 1PM Coming Soon Aug 28
    • 4 Beds
    • 3 Baths
    • 3,793 Sq Ft

    41524 Fairwood Ct, Leonardtown, MD 20650

    Welcome to 41524 Fairwood Ct, Leonardtown, MD 20650! This inviting ranch-style home offers comfortable one-level living with a spacious, open-concept great room, dining area, and kitchen designed for everyday living and entertaining. The kitchen features a generous island and built-in pantry, while the convenient mudroom and first-floor laundry add functionality.The thoughtful layout

    Billy Rabbitt The Southside Group Real Estate

    41524 Fairwood Ct, Leonardtown, MD 20650
  • /65

    $714,900

    • 5 Beds
    • 3.5 Baths
    • 4,744 Sq Ft

    23760 Coventry Dr, Leonardtown, MD 20650

    Welcome home to the Hampton model, featuring fresh paint, newer flooring, and updated carpet throughout! The main level showcases a welcoming two-story foyer and a soaring two-story family room flooded with natural light, along with dedicated formal living and dining room, a private study, and a chef-inspired grand kitchen with an expansive center island. Upstairs, you’ll find four spacious

    Tracey Summers CENTURY 21 New Millennium

    23760 Coventry Dr, Leonardtown, MD 20650
  • /9

    $454,900

    New Construction Open Thu 11:15AM - 3:30PM $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 2,554 Sq Ft

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650

    ****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 townhome offering 2,554 sq ft of beautifully finished living space. This interior unit

    Laura Lee Hefley RE/MAX One

    Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD 20650
  • /39

    $449,900

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

    23725 Dragonfly Ln, Leonardtown, MD 20650

    Interior Elevation D3 with DormersHerringbone Carolina Bead SidingMusket Brown ShuttersSedona Summit Ledge4 bedrooms w/3.5 Baths1.5 Car Garage9' Ceilings 1st and 2nd FloorsDropzone Bench w/CubbiesLVP Flooring 1st FloorLVT in Bathrooms and Laundry RoomUpgraded Maple Kitchen CabinetsRoccoco Quartz CountertopsSplendur White BacksplashDeluxe Shower

    Quality Built Homes Builder
    23725 Dragonfly Ln, Leonardtown, MD 20650
  • /90

    $715,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    23628 Belmar Dr, Leonardtown, MD 20650

    Welcome to this exceptional home in the sought-after Leonard’s Grant community, where timeless design, quality finishes, and incredible indoor and outdoor living come together. From the inviting front porch to the private, tree-lined backyard, every space has been thoughtfully designed for comfortable living and effortless entertaining. Inside, stunning Tigerwood floors flow throughout much of

    Heather Foster RE/MAX One

    23628 Belmar Dr, Leonardtown, MD 20650
  • /47

    $599,900

    $50K PRICE DROP
    • 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

    Tracey Summers CENTURY 21 New Millennium

    41444 Osborne Ln, Leonardtown, MD 20650

Home Price Trends

Median Sale Price
$530,000
Median Single Family Sale Price
$580,000
Median Townhouse Sale Price
$452,450
Median 2 Bedroom Sale Price
$315,000
Average Price Per Sq Ft
$190
Number of Homes for Sale
54
Last 12 months Home Sales
195
Months of Supply
3.30
Median List Price
$537,500
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