72

Homes for Sale near Leonardtown Middle School

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  • 20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    20798 Waterside Dr, Leonardtown, MD 20650
    /33

    $450,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft

    20798 Waterside Dr, Leonardtown, MD 20650

    Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s crabbing,

    Agent Photo

    Connie Fitzgerald

    RE/MAX One

    20798 Waterside Dr, Leonardtown, MD 20650
  • 23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    23801 Mcintosh Rd, Hollywood, MD 20636
    /31

    $439,900

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,634 Sq Ft

    23801 Mcintosh Rd, Hollywood, MD 20636

    BIG PRICE IMPROVEMENT – Now Offered at $439,900. Pool is open and ready for summer. Welcome to this well-maintained split foyer home situated on a 1.25-acre lot in Hollywood, MD, offering the perfect blend of space, comfort, and convenience. Located in the sought-after Leonardtown school district—Duke Elementary, Leonardtown Middle, and Leonardtown High School—this home offers NO HOA and no

    Agent Photo

    Deanna Rothstein

    RE/MAX One

    23801 Mcintosh Rd, Hollywood, MD 20636
  • 42625 Richly Ln, Hollywood, MD 20636
    42625 Richly Ln, Hollywood, MD 20636
    42625 Richly Ln, Hollywood, MD 20636
    /50

    $900,000

    $50K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 5,179 Sq Ft

    42625 Richly Ln, Hollywood, MD 20636

    PRICE REDUCED!!! Welcome to refined living in this exceptional QBHI Fairfax model, perfectly situated on nearly two private acres and just 16 months young. Located in the highly sought-after Broyhill community of Leonardtown, this beautifully crafted home blends luxury, comfort, and thoughtful design at every turn. From the moment you arrive, you’ll appreciate the expansive, mostly flat

    Dorothy Bistransin Redfin Corp

    42625 Richly Ln, Hollywood, MD 20636
  • 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****To Be Built*** 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 full

    Laura Hefley RE/MAX One

    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
  • 42161 Patuxent Dr, Mechanicsville, MD 20659
    42161 Patuxent Dr, Mechanicsville, MD 20659
    42161 Patuxent Dr, Mechanicsville, MD 20659
    /58

    $465,000

    $80K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    42161 Patuxent Dr, Mechanicsville, MD 20659

    Welcome to 42161 Patuxent Drive, a stunning waterview home that blends comfort, character, and thoughtful upgrades in a truly unique split-level layout. This 3-bedroom, 2.5-bathroom residence offers beautiful water views of the Patuxent River, spacious living areas, and exceptional functionality, both inside and out! The main level features an open-concept kitchen flowing into the dining area,

    Tim Farr Samson Properties

    42161 Patuxent Dr, Mechanicsville, MD 20659
  • 00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, Leonardtown, MD 20650
    00 Saint Andrews Church Rd, Leonardtown, MD 20650
    /36

    $93,500

    • Land
    • 4.11 Acres
    • $22,749 per Acre

    00 Saint Andrews Church Rd, Leonardtown, MD 20650

    Tucked away in Leonardtown in St. Mary's County, this 4.11 acre wooded parcel on St. Andrews Church Road is a rare chance to build, invest, or settle into your own recreational retreat. The property already has a previous perc site in place for a conventional septic system. Soil stability testing will be required, but preliminary work points to favorable conditions. Buyers are encouraged to

    Casey Kennedy Whitetail Properties Real Estate

    00 Saint Andrews Church Rd, Leonardtown, MD 20650
  • 42204 Ridge Rd, Mechanicsville, MD 20659
    42204 Ridge Rd, Mechanicsville, MD 20659
    /2

    $425,000

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 2,006 Sq Ft

    42204 Ridge Rd, Mechanicsville, MD 20659

    Samara Dinnius JPAR Real Estate Professionals

    42204 Ridge Rd, Mechanicsville, MD 20659
  • 44481 Boxwood Dr, Callaway, MD 20620
    44481 Boxwood Dr, Callaway, MD 20620
    44481 Boxwood Dr, Callaway, MD 20620
    /13

    $749,999

    Coming Soon
    • 5 Beds
    • 4 Baths
    • 4,764 Sq Ft

    44481 Boxwood Dr, Callaway, MD 20620

    Welcome to your own private retreat! Nestled on 2.2 beautifully landscaped acres, this stunning 5-bedroom, 4-bathroom brick-front home offers the perfect combination of space, comfort, and outdoor living. From the moment you arrive, you'll appreciate the home's impressive curb appeal, complete with a side-load 2-car attached garage and a setting that provides exceptional privacy. Inside, you'll

    Mariah Riedell O'Brien Realty ERA Powered

    44481 Boxwood Dr, Callaway, MD 20620
  • 22755 Deerhaven Ln, California, MD 20619
    22755 Deerhaven Ln, California, MD 20619
    22755 Deerhaven Ln, California, MD 20619
    /33

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    22755 Deerhaven Ln, California, MD 20619

    Rare opportunity to enjoy the perfect blend of country living and everyday convenience! Nestled on 3 private acres in California, Maryland, this charming farmette is just minutes from schools, shopping, restaurants, and PAX Naval Air Station, yet offers the peaceful setting you've been dreaming of. The 1,824 sq ft rambler features 3 bedrooms, 2 full baths, and a spacious floor plan designed for

    Mary Chambers JPAR Real Estate Professionals

    22755 Deerhaven Ln, California, MD 20619
  • 0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650
    /6

    $175,000

    • Land
    • 6.24 Acres
    • $28,045 per Acre

    0 St Andrews Church Rd Unit MDSM2029070, Leonardtown, MD 20650

    6+ acre lot zoned RPD in a prime location with approximately 600 ft of road frontage and high visibility potential. This is NOT currently a residential building lot because it failed a perc test in April 2005. However, the current Comprehensive Zoning Ordinance lists other “potential” uses that may not require on-site sewage disposal. The list includes but is not limited to: Construction

    Lewie Aldridge III Berkshire Hathaway HomeServices PenFed Realty

    0 St Andrews Church Rd Unit MDSM2029070, 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
    /2

    $679,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 4,836 Sq Ft

    23636 Hansel Ct, Leonardtown, MD 20650

    COMING SOON! 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
  • 43979 Drum Cliff Rd, Hollywood, MD 20636
    43979 Drum Cliff Rd, Hollywood, MD 20636
    43979 Drum Cliff Rd, Hollywood, MD 20636
    /58

    $499,900

    • 2 Beds
    • 2 Baths
    • 3,140 Sq Ft

    43979 Drum Cliff Rd, Hollywood, MD 20636

    Enjoy waterfront living with this cottage style home offering breathtaking views of the Patuxent River and St. Thomas Creek. The open main-level floor plan of this 2BR 2FB home captures water views from most areas of the home, as does the rear of the fully finished walkout-level basement. The spacious walk-up attic could potentially offer future expansion into a third floor, perhaps maybe with

    Ken Phipps CENTURY 21 New Millennium

    43979 Drum Cliff Rd, Hollywood, MD 20636
  • 26188 Skyview Dr, Hollywood, MD 20636
    26188 Skyview Dr, Hollywood, MD 20636
    26188 Skyview Dr, Hollywood, MD 20636
    /9

    $399,000

    $181K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,150 Sq Ft

    26188 Skyview Dr, Hollywood, MD 20636

    JUST REDUCED $100,000.00 WHAT A DEAL = HOME NEEDS SOME WORK = IT'S AN INVESTORS DREAM REMODLE AND SELL IT AND MAKE SOME MONEY= VACANT = WATERFRONT ON COLES CREEK.

    Glen Elrod Elrod & Associates Real Estate, Inc

    26188 Skyview Dr, Hollywood, MD 20636
  • 25826 S Sandgates Rd, Mechanicsville, MD 20659
    25826 S Sandgates Rd, Mechanicsville, MD 20659
    25826 S Sandgates Rd, Mechanicsville, MD 20659
    /26

    $489,900

    New Construction $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,576 Sq Ft

    25826 S Sandgates Rd, Mechanicsville, MD 20659

    New construction, ready and completed in desirable Mechanicsville! This beautiful home offers an open-concept floor plan with the living room, kitchen, and dining area flowing seamlessly together, making it perfect for everyday living and entertaining. The kitchen is a standout with a center island, gorgeous granite countertops, custom cabinetry with plenty of storage, and stainless steel

    Billy Rabbitt The Southside Group Real Estate

    25826 S Sandgates Rd, Mechanicsville, MD 20659
  • 24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    24040 Hollywood Rd, Hollywood, MD 20636
    /5

    $335,000

    $15K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    24040 Hollywood Rd, Hollywood, MD 20636

    3BR / 1B Rambler on an acre of land w/garage (storage), Detached carport and outbuildings. Paved driveway just off Hollywood/Leonardtown Road. Hardwood floors throughout Living Room, Hall and bedrooms. Level rear yard bordered by trees. Oil Furnace, water heater, utility sink and washer hook-up are located in the (walk-in) storage area under the home.

    Sheila Milburn Coldwell Banker Premier

    24040 Hollywood Rd, Hollywood, MD 20636
  • 22405 Hood Ln, Leonardtown, MD 20650
    22405 Hood Ln, Leonardtown, MD 20650
    22405 Hood Ln, Leonardtown, MD 20650
    /73

    $715,000

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    22405 Hood Ln, Leonardtown, MD 20650

    **Professional photography was delayed due to weather and will be uploaded as soon as possible** Welcome to 22405 Hood Lane - a custom home nestled on 11 acres. Built in 2024, you get all the benefits of new construction, without the wait and hassle of building. The drive along Hood Lane feels so private and serene, it is easy to forget that you are just minutes from both Downtown Leonardtown and

    Jaymie Lewis O'Brien Realty ERA Powered

    22405 Hood Ln, Leonardtown, MD 20650
  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    /70

    $539,900

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

    40777 Center 40 Cir, Leonardtown, MD 20650

    Coming Soon 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, Leonardtown Square, restaurants,

    Bill Oosterink CENTURY 21 New Millennium

    40777 Center 40 Cir, Leonardtown, MD 20650
  • 42205 Ridge Rd, Mechanicsville, MD 20659
    42205 Ridge Rd, Mechanicsville, MD 20659
    42205 Ridge Rd, Mechanicsville, MD 20659
    /59

    $415,000

    $15K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    42205 Ridge Rd, Mechanicsville, MD 20659

    Welcome to 42205 Ridge Road in Mechanicsville, a move-in ready Colonial located in the established St. Mary's Beach community. Renovated in 2018, this 4 bedroom, 3 full bathroom home offers a comfortable and functional layout. The main level features a welcoming foyer, kitchen and dining area, breakfast nook, crown molding, and a full bathroom. Upstairs, you'll find all four bedrooms, including

    Ashley Frazier Five Star Real Estate

    42205 Ridge Rd, Mechanicsville, MD 20659
  • 0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    0 Saint Johns Rd, Hollywood, MD 20636
    /8

    $200,000

    $50K PRICE DROP
    • Land
    • 1.2 Acres
    • $166,667 per Acre

    0 Saint Johns Rd, Hollywood, MD 20636

    Rare opportunity to own prime land in Hollywood, MD! This vacant, flat, and open parcel sits at the high-visibility intersection of Three Notch Road and St. John’s Road, offering exceptional exposure and accessibility. Public water and sewer are adjacent to the property, creating outstanding development potential. Ideal for a variety of uses—including a farmers market, roadside produce stand,

    John Gatton CENTURY 21 New Millennium

    0 Saint Johns Rd, Hollywood, MD 20636
  • 41531 Kalitan Ln, Leonardtown, MD 20650
    41531 Kalitan Ln, Leonardtown, MD 20650
    41531 Kalitan Ln, Leonardtown, MD 20650
    /83

    $665,000

    • 5 Beds
    • 3.5 Baths
    • 3,570 Sq Ft

    41531 Kalitan Ln, Leonardtown, MD 20650

    Welcome to this beautiful Wingate model in the highly desirable Leonard’s Grant community! Situated in the front of the neighborhood, this home offers charming curb appeal with a welcoming front porch, side-load garage, and a large fenced backyard complete with a composite deck—perfect for entertaining and outdoor enjoyment. Inside, the main level features new carpet, a spacious formal dining

    Heather Foster RE/MAX One

    41531 Kalitan Ln, 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
  • 27075 Widow Ln, Mechanicsville, MD 20659
    27075 Widow Ln, Mechanicsville, MD 20659
    /2

    $760,000

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    27075 Widow Ln, Mechanicsville, MD 20659

    Coming soon! This expansive Cape Cod style home is a once in a lifetime find. Perfect for a farmette or luxurious retreat on 4.51 acres and no HOA. Enjoy a delicious nectarine from one of the many fruit trees while relaxing by your inground pool. The back yard features extensive hardscaping, mature landscaping and a fully fenced in yard. A gas fire feature and full shaded pergola set the scene

    Brittany Bahen JPAR Real Estate Professionals

    27075 Widow Ln, Mechanicsville, MD 20659
  • 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
  • 24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    24645 Springhill Ln, Leonardtown, MD 20650
    /3

    $175,000

    • Land
    • 4.83 Acres
    • $36,232 per Acre

    24645 Springhill Ln, Leonardtown, MD 20650

    Breton Knolls is a 24-lot subdivision, conveniently located in Leonardtown, featuring lot sizes from 1 - 7 acres. Bring your own builder or ask us about one of our preferred builders. Breton Knolls HOA is $300 annually with an initial capital contribution of $500 per lot. Please contact us for additional information or to schedule a private showing.

    Mark Posey Greenmark Real Estate

    24645 Springhill Ln, Leonardtown, MD 20650
  • 22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    22501 Bull Rd, Leonardtown, MD 20650
    /3

    $175,000

    $50K PRICE DROP
    • Land
    • 7.58 Acres
    • $23,087 per Acre

    22501 Bull Rd, Leonardtown, MD 20650

    Price Reduction! Only 5 lots left! Breton Knolls is a 24 lot subdivision in Leonardtown of 1-7.5 acre lots. HOA of $300 annually with a $500 initial capital contribution

    Mark Posey Greenmark Real Estate

    22501 Bull Rd, Leonardtown, MD 20650
  • 24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    /6

    $515,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,365 Sq Ft

    24301 Old Hollywood Rd, Hollywood, MD 20636

    One owner for almost 60 years! Home recently had new roof, new windows, new doors, and appliances. If you desire no subdivision, 1+ acres, detached garage/workshop, extra outside storage, secluded area, centrally located, and ONE level, this may be what you're looking for. Unfinished walk up/out basement centrally located in Hollywood close to park. Close to downtown Leonardtown, hospital,

    Jimmy Hayden RE/MAX One

    24301 Old Hollywood Rd, Hollywood, MD 20636
  • 24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    24249 Mcintosh Rd, Hollywood, MD 20636
    /65

    $950,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    24249 Mcintosh Rd, Hollywood, MD 20636

    Rare opportunity to own a breathtaking Horse Farm that features an exquisite custom farmhouse on 21.95 breathtaking acres just 2 miles from downtown Leonardtown! This unbelievable location offers the perfect balance of privacy and convenience with easy access to schools, shopping, restaurants, coffee shops, and commuter routes while enjoying the peace and tranquility of country living. The

    Mary Chambers JPAR Real Estate Professionals

    24249 Mcintosh Rd, Hollywood, MD 20636
  • 27020 Cat Creek Rd, Mechanicsville, MD 20659
    27020 Cat Creek Rd, Mechanicsville, MD 20659
    27020 Cat Creek Rd, Mechanicsville, MD 20659
    /28

    $375,000

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,556 Sq Ft

    27020 Cat Creek Rd, Mechanicsville, MD 20659

    Rambler on nearly 5 private acres - bring your vision! Discover the ease of one-level living nestled in the heart of Mechanicsville. Offering 4 bedrooms and 2 bathrooms, this property provides plenty of space both inside and out. Enjoy the peace and privacy of the expansive lot, where you can relax, listen to the birds, and truly unwind. Detached garage included for additional storage, hobbies,

    Billy Rabbitt The Southside Group Real Estate

    27020 Cat Creek Rd, Mechanicsville, MD 20659
  • 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
  • 0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    0 Whirlwind Rd, Leonardtown, MD 20650
    /17

    $288,900

    • Land
    • 23.44 Acres
    • $12,325 per Acre

    0 Whirlwind Rd, Leonardtown, MD 20650

    Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or

    Brooke Matthews RE/MAX One

    0 Whirlwind Rd, 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
  • 26407 Hillendale Rd, Hollywood, MD 20636
    26407 Hillendale Rd, Hollywood, MD 20636
    26407 Hillendale Rd, Hollywood, MD 20636
    /22

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    26407 Hillendale Rd, Hollywood, MD 20636

    IMMACULATE!! Welcome to this beautifully renovated 3-bedroom, 2-bath rancher offering stylish, move-in-ready, one-level living in the heart of Hollywood. From the moment you arrive, you'll appreciate the fresh curb appeal, new landscaping, and welcoming front entry. Inside, the bright open layout features luxury vinyl plank flooring, recessed lighting, and abundant natural light throughout. The

    Mark Frisco CENTURY 21 New Millennium

    26407 Hillendale Rd, Hollywood, MD 20636
  • 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
  • 26864 Oak Ridge Dr, Mechanicsville, MD 20659
    26864 Oak Ridge Dr, Mechanicsville, MD 20659
    26864 Oak Ridge Dr, Mechanicsville, MD 20659
    /25

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft

    26864 Oak Ridge Dr, Mechanicsville, MD 20659

    --------------------------- SELLER OFFERING CLOSING HELP- CONTACT FOR DETAILS-------------------------- PRICED TO SELL MANY RECENT UPDATES INCLUDING ROOF AND NEW HVAC 1200 Sq foot unfinished basement offers potential investmentWELCOME TO SAINT MARY’S BEACH! Nestled on a beautifully wooded 0.78-acre lot on a quiet cul-de-sac, 26864 Oak Ridge Drive in Mechanicsville, Maryland offers tremendous

    Mark Levenson Samson Properties

    26864 Oak Ridge Dr, Mechanicsville, MD 20659
  • 40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    40412 B Somerville Ln, Leonardtown, MD 20650
    /28

    $99,000

    • Land
    • 2.28 Acres
    • $43,421 per Acre

    40412 B Somerville Ln, Leonardtown, MD 20650

    Discover 2.28 acres of level, open land offering a great opportunity to build your dream home or investment property. This property includes an existing septic system and nearby power supply. Enjoy privacy and space while still being within easy reach of local amenities and major routes. Buyer to verify all feasibility, utility connections, and intended use with the county.

    Renee Thomas Topside Realty

    40412 B Somerville Ln, Leonardtown, MD 20650
  • 40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    40659 Klear Ct, Leonardtown, MD 20650
    /54

    $515,000

    Coming Soon
    • 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
  • 42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    42249 Saint Johns Rd, Leonardtown, MD 20650
    /15

    $384,900

    $15K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,161 Sq Ft

    42249 Saint Johns Rd, Leonardtown, MD 20650

    The required verbiage below shall take the place of the MLS Advisory Task verbiage in res.net. This Property was previously financed by a mortgage loan that was insured by the U.S. Department of Housing and Urban Development (“HUD”) and will require disclosure on the MLS. You may use the disclosure language below in lieu of the MLS task requirements issued through RESNET. Disclosure language must

    Jason Gregg CENTURY 21 New Millennium

    42249 Saint Johns Rd, 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

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