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Homes for Sale near Leonardtown Middle School

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  • 42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    42043 Starlight Dr, Leonardtown, MD 20650
    /50

    $539,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    42043 Starlight Dr, Leonardtown, MD 20650

    Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has a bright and cheery interior with four spacious bedrooms on the upper level. Generous closets. Convenient upper level laundry. The main floor features an oversized great room, a kitchen with solid surface counters, and a garden window over the kitchen sink to grow fresh herbs. A front sitting room makes for a

    Kimberly St. Laurent RE/MAX One

    42043 Starlight Dr, Leonardtown, MD 20650
  • 43361 Quail St, Hollywood, MD 20636
    43361 Quail St, Hollywood, MD 20636
    43361 Quail St, Hollywood, MD 20636
    /70

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 3,769 Sq Ft

    43361 Quail St, Hollywood, MD 20636

    Motivated Sellers!!!!SOLAR PANELS ARE FULLY PAID FOR AND YOUR ELECTRIC BILLS ARE PRACTICALLY NONEXISTENT!!This beautifully maintained and upgraded Preston model by Quality Built Homes, built in 2015, has been lovingly cared for by the original owners and is completely move-in ready. The grand kitchen features Maple cabinets, granite countertops, and top-notch appliances, including a LG INSTA VIEW

    Boyd Grainger Pearson Smith Realty, LLC

    43361 Quail St, Hollywood, MD 20636
  • 0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
    /6

    $24,900

    • Land
    • 0.18 Acre
    • $138,333 per Acre

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650

    These wooded lots are almost across the street from the St. Clements Shores Community Park! Invest in undeveloped land now, for future building lot. Public sewer hook up planned to be available, as system expansion is slated to occur within a few years per MetCom. Currently could possibly be used for storage building or similar.

    Juliet Brown Residential Plus Real Estate Services

    0 Long Leaf Ln Unit MDSM2026482, Leonardtown, MD 20650
  • 21738 Pinehurst Ct, Leonardtown, MD 20650
    21738 Pinehurst Ct, Leonardtown, MD 20650
    21738 Pinehurst Ct, Leonardtown, MD 20650
    /59

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    21738 Pinehurst Ct, Leonardtown, MD 20650

    Seller is offering a flooring credit for the first floor with Clarke's Flooring.

    Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    21738 Pinehurst Ct, Leonardtown, MD 20650
  • 42975 Baywood Place, Leonardtown, MD 20650
    42975 Baywood Place, Leonardtown, MD 20650
    42975 Baywood Place, Leonardtown, MD 20650
    /65

    $699,900

    • 4 Beds
    • 2.5 Baths
    • 3,372 Sq Ft

    42975 Baywood Place, Leonardtown, MD 20650

    Stunning Dunleigh model by Marrick Homes, tucked away at the end of a quiet cul-de-sac on over 1 full acre in desirable Leonardtown Farm! Offering nearly 3,400 sq ft of finished living space, this beautifully maintained 4BR/2.5BA home features a spacious, gourmet kitchen with large center island, upgraded cabinets and granite countertops, and stainless steel appliances – perfect for entertaining.

    Erika Yowell EXP Realty, LLC

    42975 Baywood Place, Leonardtown, MD 20650
  • 44180 Cross Bow Ln, California, MD 20619
    44180 Cross Bow Ln, California, MD 20619
    44180 Cross Bow Ln, California, MD 20619
    /61

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 2,655 Sq Ft

    44180 Cross Bow Ln, California, MD 20619

    Start out the New Year in a new home! Welcome Home to 44180 Cross Bow Lane centrally located in the highly desirable Arrowhead neighborhood in California, MD. The home has been well maintained and is move in ready. Beautiful hardwood floors throughout were recently refinished in 2024. Fresh paint, new carpet, updated lighting/ceiling fans and new Levolor blinds. Newer heat pump, new gutters and

    Cynthia Ballard CENTURY 21 New Millennium

    44180 Cross Bow Ln, California, MD 20619
  • 26350 Three Notch Rd, Mechanicsville, MD 20659
    26350 Three Notch Rd, Mechanicsville, MD 20659
    26350 Three Notch Rd, Mechanicsville, MD 20659
    /7

    $200,000

    • Land
    • 2.56 Acres
    • $78,125 per Acre

    26350 Three Notch Rd, Mechanicsville, MD 20659

    **Prime Commercial Opportunity on 2.56 Acres with Excellent Visibility!**This **corner lot** boasts approximately 750 feet of road frontage on busy Route 235 northbound, offering fantastic visibility and accessibility for your business. Zoned **RCL**, this property provides a wide range of commercial possibilities (county verification required), making it a flexible choice for

    Jessica Raley CENTURY 21 New Millennium

    26350 Three Notch Rd, Mechanicsville, MD 20659
  • 25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    /5

    $497,500

    • 3 Beds
    • 3 Baths
    • 2,952 Sq Ft

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one bath, replaced furnace, window AC units, storage, partial unfinished basement. Needs updating. The former Doctor's office has had some updating recently. New heat pump last year. Both are on separate electric meters, heating and cooling systems. Ample parking behind building for both units. Showings by

    Jan Barnes CENTURY 21 New Millennium

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • 19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    19700 Mulberry Fields Rd, Leonardtown, MD 20650
    /139

    $20,000,000

    • 6 Beds
    • 4.5 Baths
    • 13,458 Sq Ft

    19700 Mulberry Fields Rd, Leonardtown, MD 20650

    Welcome to Historic Mulberry Fields, situated on just under 500 acres of fertile land with a mile-long view of the Potomac River’s white sand shoreline, is truly one of a kind. As you drive along the cedar-lined driveway, you are transported back in time as the magnificent manor house appears in front of you. It is the only remaining Georgian manor house in St. Mary’s County today. From the south

    Kornelia Stuphan Long & Foster Real Estate, Inc.

    19700 Mulberry Fields Rd, Leonardtown, MD 20650
  • 40624 Breton Oaks Ln, Leonardtown, MD 20650
    40624 Breton Oaks Ln, Leonardtown, MD 20650
    40624 Breton Oaks Ln, Leonardtown, MD 20650
    /6

    $159,900

    • Land
    • 1.49 Acres
    • $107,315 per Acre

    40624 Breton Oaks Ln, Leonardtown, MD 20650

    Charming Cul-de-Sac Lot in Breton Oaks – No HOA!Discover the perfect place to build your dream home on this beautiful, private lot located in the peaceful cul-de-sac of Breton Oaks. This small, custom-built subdivision offers a tranquil setting, with all homes in the neighborhood uniquely designed by St. Maries Builders. You can choose to build with them or bring your own builder to bring

    Carol Kalmus-Choporis CENTURY 21 New Millennium

    40624 Breton Oaks Ln, Leonardtown, MD 20650
  • 43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    43488 Medleys Neck Rd, Leonardtown, MD 20650
    /10

    $215,000

    • Land
    • 5 Acres
    • $43,000 per Acre

    43488 Medleys Neck Rd, Leonardtown, MD 20650

    PRICE IMPROVEMENT!Discover the potential of this beautiful parcel in the heart of Southern Maryland. Located on Medleys Neck Road in Leonardtown, this property offers the perfect opportunity to build your dream home or investment project in a highly desirable location. The lot features three active perc approvals, making it an attractive option for builders, developers, or anyone seeking

    Bill Oosterink CENTURY 21 New Millennium

    43488 Medleys Neck Rd, Leonardtown, MD 20650
  • 43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    43018 Bluejay Ln, Leonardtown, MD 20650
    /61

    $645,900

    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    43018 Bluejay Ln, Leonardtown, MD 20650

    Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in Leonardtown. This home has large 6 ft. windows on the entire main level to allow tons of natural light! A beautiful front porch is a great place to sit and chat with your neighbors and enjoy the peaceful community. The upstairs has 4 large bedrooms, the laundry room, and two bathrooms. The main bedroom suite

    Diane Fenwick RE/MAX One

    43018 Bluejay Ln, Leonardtown, MD 20650
  • 43063 Hugh Dr, Hollywood, MD 20636
    43063 Hugh Dr, Hollywood, MD 20636
    43063 Hugh Dr, Hollywood, MD 20636
    /33

    $689,900

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

    43063 Hugh Dr, Hollywood, MD 20636

    Welcome to this extraordinary 29.5-acre wooded estate offering the perfect blend of craftsmanship, updates, and endless possibilities. Step inside the 2,700+ sq ft home and immediately admire the fine details, including the striking cedar beam accent and dual stairways that set the tone for its timeless character. At the heart of the home, the expansive kitchen impresses with sleek tile flooring,

    Billy Rabbitt The Southside Group Real Estate

    43063 Hugh Dr, Hollywood, MD 20636
  • 0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
    /6

    $5,000

    • Land
    • 0.14 Acre
    • $35,714 per Acre

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650

    Fully Available!Wonderful opportunity with a buyer that has vision. Nice lot to possibly build on. Call St Mary's county for details and confirm if suitable for your needs.

    Jan Kleponis O'Brien Realty ERA Powered

    0 Long Leaf Ln Unit MDSM2026514, Leonardtown, MD 20650
  • 43336 Lillian Way, Hollywood, MD 20636
    43336 Lillian Way, Hollywood, MD 20636
    43336 Lillian Way, Hollywood, MD 20636
    /47

    $715,000 Open Sat 11AM - 1PM

    • 6 Beds
    • 4.5 Baths
    • 4,913 Sq Ft

    43336 Lillian Way, Hollywood, MD 20636

    Located on a quiet cul-de-sac in the sought-after Forrest Farm community, this beautifully maintained ranch-style home offers exceptional space, flexibility, and thoughtful design throughout. Inside, an open and airy floor plan is highlighted by hardwood and ceramic tile flooring, crown molding, and chair rail accents. The gourmet kitchen is designed for both everyday living and entertaining,

    Cynthia Lisa RE/MAX One

    43336 Lillian Way, Hollywood, MD 20636
  • 39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    39645 Sweetpea Ln, Leonardtown, MD 20650
    /67

    $799,900

    • Land
    • 3.56 Acres
    • $224,691 per Acre

    39645 Sweetpea Ln, Leonardtown, MD 20650

    UNIQUE BEAUTIFUL OPPORTUNITY to Unlock the potential of a lifetime with this rare and spectacular waterfront property! This stunning PENINSULA boasts approximately 1200 feet of waterfront, with its prime location fronting St. Clements Bay with protected coves/creeks on either side. There is some sandy beach on property in one section. This property offers breathtaking views and endless

    Sandi Denny CENTURY 21 New Millennium

    39645 Sweetpea Ln, Leonardtown, MD 20650
  • 44646 Medleys Neck Rd, Leonardtown, MD 20650
    44646 Medleys Neck Rd, Leonardtown, MD 20650
    /2

    $80,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    44646 Medleys Neck Rd, Leonardtown, MD 20650

    Presenting an opportunity for creative redevelopment: a level lot equipped with a septic system and a driveway easement, along with a trailer that has microbiological growth. The property will require the removal of the existing trailer, with the option to proceed with new construction or secure a trailer replacement. Qualified buyers looking to customize and reimagine the site are encouraged to

    Ron Lord Home Towne Real Estate

    44646 Medleys Neck Rd, Leonardtown, MD 20650
  • 41635 Ferber Ct, Leonardtown, MD 20650
    41635 Ferber Ct, Leonardtown, MD 20650
    /2

    $565,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    41635 Ferber Ct, Leonardtown, MD 20650

    Beautiful 2 story home situated on a professionally landscaped level lot with fully fenced back yard. Home is freshly painted and has newly installed carpet throughout main and upper levels. Roof and gutters were recently replaced in 2025. HVAC has been serviced annually. Upper level has 4bedrooms; 2 full bathrooms and laundry room. Main level consists of living room, dining room, family room

    Alvin Frazier Home Towne Real Estate

    41635 Ferber Ct, Leonardtown, MD 20650

Showing Results 41 - 58, Page 2 of 2

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