100

Homes for Sale near Leonardtown Middle School

Section Image Section Image Section Image
  • 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
  • 40751 Merlin Way, Leonardtown, MD 20650
    40751 Merlin Way, Leonardtown, MD 20650
    40751 Merlin Way, Leonardtown, MD 20650
    /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
  • 42204 Ridge Rd, Mechanicsville, MD 20659
    42204 Ridge Rd, Mechanicsville, MD 20659
    42204 Ridge Rd, Mechanicsville, MD 20659
    /41

    $415,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,006 Sq Ft

    42204 Ridge Rd, Mechanicsville, MD 20659

    Welcome home to this beautifully updated rambler in the heart of Mechanicsville! Offering 3 bedrooms, 3 full bathrooms, and a finished basement, this home provides the flexible living space today's buyers are looking for. Need a fourth bedroom, home office, gym, or playroom? The spacious bonus room gives you the versatility to make it your own. Freshly painted throughout and featuring new luxury

    Samara Dinnius JPAR Real Estate Professionals

    42204 Ridge Rd, Mechanicsville, MD 20659
  • Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, Leonardtown, MD 20650
    Lot 140 - 23659 Dragonfly Ln, 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
  • 42161 Patuxent Dr, Mechanicsville, MD 20659
    42161 Patuxent Dr, Mechanicsville, MD 20659
    42161 Patuxent Dr, Mechanicsville, MD 20659
    /54

    $449,500

    • 3 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    42161 Patuxent Dr, Mechanicsville, MD 20659

    Set on the Patuxent River in the sought-after St. Mary's Beach community, 42161 Patuxent Drive is a 3-bedroom, 2.5-bath split-level offering water views, flexible living space across four distinct levels, and a list of upgrades that's hard to match at this price point.Step inside to an open kitchen and dining area made for entertaining, plus a bonus living room near the entry - ideal as a

    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
  • 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
  • 23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 Dragonfly Ln, Leonardtown, MD 20650
    23684 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
  • Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 Dragonfly Ln, Leonardtown, MD 20650
    Lot 157 - 23640 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
  • 23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, Leonardtown, MD 20650
    23636 Hansel Ct, 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
  • 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
  • 41160 Living Water Ln, Mechanicsville, MD 20659
    41160 Living Water Ln, Mechanicsville, MD 20659
    41160 Living Water Ln, Mechanicsville, MD 20659
    /5

    $175,000

    • Land
    • 3.05 Acres
    • $57,377 per Acre

    41160 Living Water Ln, Mechanicsville, MD 20659

    Tucked away in the peaceful wooded landscape of Mechanicsville, Maryland, this 3.05-acre perced lot on Living Water Lane offers an ideal setting for a private single-family home. Surrounded by mature trees and gently rolling terrain, the property provides a natural retreat with plenty of space to build, grow, and enjoy the outdoors. Approved for a septic system and well-suited for residential

    Ralph Harvey ListWithFreedom.com

    41160 Living Water Ln, Mechanicsville, MD 20659
  • 43410 Old Wharf Ln, Hollywood, MD 20636
    43410 Old Wharf Ln, Hollywood, MD 20636
    43410 Old Wharf Ln, Hollywood, MD 20636
    /43

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 2,748 Sq Ft

    43410 Old Wharf Ln, Hollywood, MD 20636

    Nestled along the shores of the Patuxent River is this very private, custom-built, all brick home with beautiful hardwood flooring throughout, modern kitchen and baths situated on 5 sprawling acres. Riprapped shoreline, professionally landscaped yard w/ sprinkler system, 4 stall horse barn, dog run and more. Enjoy nature's beauty on the water; conveniently located for a D.C. commute. A great

    Barbara Stellway KW Metro Center

    43410 Old Wharf Ln, Hollywood, MD 20636
  • 18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    18937 Hodges Ln, Leonardtown, MD 20650
    /19

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    18937 Hodges Ln, Leonardtown, MD 20650

    If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boating, fishing, crabbing, or simply relaxing while taking in breathtaking water views, this beautifully renovated home has it all. Step inside to discover a spacious, open-concept kitchen and family room designed for gathering and everyday living. The stunning backyard provides the perfect setting for

    Ingrid Butler CENTURY 21 New Millennium

    18937 Hodges Ln, Leonardtown, MD 20650
  • 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, Hollywood, MD 20636
    25826 S Sandgates Rd, Hollywood, MD 20636
    25826 S Sandgates Rd, Hollywood, MD 20636
    /23

    $475,000

    Open Sat 10AM - 12PM $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    25826 S Sandgates Rd, Hollywood, MD 20636

    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, Hollywood, MD 20636
  • 40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    40743 Magee Dr, Leonardtown, MD 20650
    /29

    $359,777

    • 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
  • 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
  • 23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, Leonardtown, MD 20650
    23672 Weeping Willow Way, 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
  • 40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, Leonardtown, MD 20650
    40777 Center 40 Cir, 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
  • 42205 Ridge Rd, Mechanicsville, MD 20659
    42205 Ridge Rd, Mechanicsville, MD 20659
    42205 Ridge Rd, Mechanicsville, MD 20659
    /59

    $399,000

    $1K PRICE DROP
    • 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.Fully 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

    Ashley Frazier Five Star Real Estate

    42205 Ridge Rd, Mechanicsville, MD 20659
  • 21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    21395 Fairwood Ct, Leonardtown, MD 20650
    /64

    $700,000

    • 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
  • 26457 Peninsular Dr, Hollywood, MD 20636
    26457 Peninsular Dr, Hollywood, MD 20636
    26457 Peninsular Dr, Hollywood, MD 20636
    /3

    $29,900

    • Land
    • 10,454 Sq Ft
    • $124,583 per Acre

    26457 Peninsular Dr, Hollywood, MD 20636

    Vacant parcel around 1/4 acre in size in Hollywood Shores. Call Listing Agent with questions. Photos to be posted soon.

    Gloria Abell Coldwell Banker Premier

    26457 Peninsular Dr, Hollywood, MD 20636
  • 40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    40579 Port Place, Leonardtown, MD 20650
    /17

    $750,000

    Coming Soon
    • 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
  • 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
  • 27075 Widow Ln, Mechanicsville, MD 20659
    27075 Widow Ln, Mechanicsville, MD 20659
    27075 Widow Ln, Mechanicsville, MD 20659
    /63

    $760,000

    Open Sun 12PM - 3PM
    • 5 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    27075 Widow Ln, Mechanicsville, MD 20659

    Here is your chance! Available for showing starting on 7/31/26! 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

    Brittany Bahen JPAR Real Estate Professionals

    27075 Widow Ln, Mechanicsville, MD 20659
  • 41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, Leonardtown, MD 20650
    41462 Culpepper Way, 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
  • 23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    23620 Gunnell Dr, Leonardtown, MD 20650
    /56

    $615,000

    • 5 Beds
    • 4 Baths
    • 4,346 Sq Ft

    23620 Gunnell Dr, Leonardtown, MD 20650

    Welcome to 23620 Gunnell Dr., a beautiful, large colonial style home built by Marrick Homes in 2005. Pride of ownership shows with this home as it has been wonderfully maintained and upgraded since it was built. This home features 5 bedrooms, 4 full bathrooms, a fully finished basement, multiple bump outs, multiple entertaining areas, an oversize double car garage, a bar in the basement and so

    Tyler Mattingly Coldwell Banker Premier

    23620 Gunnell Dr, Leonardtown, MD 20650
  • 24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    24301 Old Hollywood Rd, Hollywood, MD 20636
    /22

    $475,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,365 Sq Ft

    24301 Old Hollywood Rd, Hollywood, MD 20636

    Motivated seller! 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 with french drains, centrally located in Hollywood close to park. Close to

    Jimmy Hayden RE/MAX One

    24301 Old Hollywood Rd, Hollywood, MD 20636
  • 43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, Leonardtown, MD 20650
    43954 Main Way Rd, 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
  • 22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    22010 Society Hill Rd, Leonardtown, MD 20650
    /45

    $575,000

    • 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
  • 23655 Daniel Farm Ln, Hollywood, MD 20636
    23655 Daniel Farm Ln, Hollywood, MD 20636
    /2

    $500,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 1,804 Sq Ft

    23655 Daniel Farm Ln, Hollywood, MD 20636

    Welcome to 23655 Daniel Farm Lane, situated on a spacious 1-acre lot in Hollywood, Maryland! This well-maintained home offers generous living space, thoughtful updates, and a flexible layout designed to accommodate a variety of lifestyles.Step inside to a freshly painted interior and beautiful hardwood floors throughout the main living area. The updated kitchen features stainless steel

    DJ Hayes RLAH @properties

    23655 Daniel Farm Ln, Hollywood, MD 20636
  • 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

    $1,590,000

    $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
  • 40611 Merion Ct, Leonardtown, MD 20650
    40611 Merion Ct, Leonardtown, MD 20650
    40611 Merion Ct, 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
  • 44015 Drum Cliff Rd, Hollywood, MD 20636
    44015 Drum Cliff Rd, Hollywood, MD 20636
    44015 Drum Cliff Rd, Hollywood, MD 20636
    /114

    $825,000

    • 2 Beds
    • 2 Baths
    • 1,783 Sq Ft

    44015 Drum Cliff Rd, Hollywood, MD 20636

    Escape to your own private waterfront retreat! Stunning panoramic views of the Patuxent River will greet you each day at this hilltop property where the water is visible from almost every window. Aptly named "Turtle Watch," this almost 2-acre slice of serenity is tucked away from the hustle and bustle of daily life. With great spaces for entertaining or quiet contemplation, this desirable

    Andrew Shemeta CENTURY 21 New Millennium

    44015 Drum Cliff Rd, Hollywood, MD 20636
  • 23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, Leonardtown, MD 20650
    23591 Margrave Dr, 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

Showing Results 1 - 40, Page 1 of 3

Maryland St Marys County Leonardtown

Real Estate & Homes for Sale near Leonardtown Middle School

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group