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Homes for Rent near Leonardtown Middle School

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  • 44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
    44980 Hamptons Blvd, Leonardtown, MD 20650
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    $2,150 - $2,750 per month

    The Hamptons at Leonardtown

    2 - 3 Beds

    44980 Hamptons Blvd, Leonardtown, MD 20650

    The Newest Apartment Community Serving Pax River. Luxury apartment homes in Leonardtown, MD. A Gated Community within walking distance to the town square, which features many restaurants, shops, entertainment venues and the Wharf Waterfront. Short drive to NAVAIR - Pax River Naval Air Station. 2 and 3 bedroom apartments...all with 2 bathrooms, gourmet kitchens, FREE CLIMATE CONTROLLED STORAGE

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • 42544 Keith Ct, Hollywood, MD 20636
    42544 Keith Ct, Hollywood, MD 20636
    42544 Keith Ct, Hollywood, MD 20636
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    $2,400 per month

    • 4 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • House for Rent

    42544 Keith Ct, Hollywood, MD 20636

    This beautifully renovated 4-bedroom, 2-bathroom ranch-style home offers the perfect balance of modern updates and peaceful, rural living. Set on a spacious lot, the open and airy floorplan is ideal for anyone seeking comfortable, one-level living.At the heart of the home is a gorgeous kitchen featuring a butcher block island, white quartz countertops, stainless steel appliances, a

    Mark Frisco CENTURY 21 New Millennium

    42544 Keith Ct, Hollywood, MD 20636
  • 41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
    41665 Tudor Hall Rd, Leonardtown, MD 20650
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    $2,100 per month

    • 4 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • House for Rent

    41665 Tudor Hall Rd, Leonardtown, MD 20650

    Please fill out application And make sure to include all tenants who are 18 and older also For an application fee.

    41665 Tudor Hall Rd, Leonardtown, MD 20650
  • 25180 Pappys Way, Hollywood, MD 20636
    25180 Pappys Way, Hollywood, MD 20636
    25180 Pappys Way, Hollywood, MD 20636
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    $3,900 per month

    • 4 Beds
    • 2.5 Baths
    • 3,321 Sq Ft
    • House for Rent

    25180 Pappys Way, Hollywood, MD 20636

    Space for everyone. Entry floor has formal dining room, 2 story family room, sunroom, Primary Bedroom with full bath... Upstairs you will find 3 good sized bedrooms with full bath.. Basement level, walk out with partial daylight.. Ready for all of your hobbies or just plenty of storage

    Pamela Young RE/MAX One

    25180 Pappys Way, Hollywood, MD 20636
  • 18858 McKays Beach Rd, Leonardtown, MD 20650
    18858 McKays Beach Rd, Leonardtown, MD 20650
    18858 McKays Beach Rd, Leonardtown, MD 20650
    /20

    $2,500 per month

    • 4 Beds
    • 2 Baths
    • 2,682 Sq Ft
    • House for Rent

    18858 McKays Beach Rd, Leonardtown, MD 20650

    Experience waterfront living in this beautifully furnished 4-bedroom, 2-bath home, available for lease from November 11, 2025 through May 1, 2026. Flexible lease terms: minimum 2 months, preferred up to 5.5 months. As this is our part-time residence, only furnished, short-term leases are available. No exceptions to our no-pet policy, as other animal scents upset our cats.Property

    18858 McKays Beach Rd, Leonardtown, MD 20650
  • 23591 Gunnell Dr, Leonardtown, MD 20650
    23591 Gunnell Dr, Leonardtown, MD 20650
    23591 Gunnell Dr, Leonardtown, MD 20650
    /20

    $3,300 per month

    • 5 Beds
    • 3 Baths
    • 2,666 Sq Ft
    • House for Rent

    23591 Gunnell Dr, Leonardtown, MD 20650

    Excellent Leonardtown location, close to Saint Mary’s Hospital, easy commute to NAVAIR. This home features five generously sized bedrooms including bedroom and full bath on main level. Traditional colonial floor plan, entry level two story foyer, office/flex room, formal dining room, spacious family room open to kitchen, full bath and that main level bedroom off kitchen as well. Upper level

    Becky King Home Towne Real Estate

    23591 Gunnell Dr, Leonardtown, MD 20650
  • 22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
    22645 Washington St, Leonardtown, MD 20650
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    $1,550 - $1,750 per month

    Seymour Apartments

    1 Bed

    22645 Washington St, Leonardtown, MD 20650

    Introducing Seymour Apartments, in the heart of Historic Downtown Leonardtown! Come live in town just up the hill from the Warf while being steps away from the shops and restaurants on the square. Apartments in the Seymour Apartment building. Access to unit is from a common stairwell with private entrance. Units have new ductless heat pumps, onsite laundry is in common basement area,

    22645 Washington St, Leonardtown, MD 20650
  • 22425 Point Lookout Rd, Leonardtown, MD 20650
    22425 Point Lookout Rd, Leonardtown, MD 20650
    22425 Point Lookout Rd, Leonardtown, MD 20650
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    $1,650 per month

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • House for Rent

    22425 Point Lookout Rd, Leonardtown, MD 20650

    Great Opportunity in Leonardtown!Discover this unique property featuring a spacious garage with a 3-bedroom, 1-bath private residence situated on nearly an acre of land. The home is in excellent condition and has been thoughtfully updated in recent years. Improvements include heat pumps, cabinetry, hot water heater, and more — offering both comfort and peace of mind. The property is serviced

    Conor Loughran CENTURY 21 New Millennium

    22425 Point Lookout Rd, Leonardtown, MD 20650
  • 23063 Pembrook Dr, Hollywood, MD 20636
    23063 Pembrook Dr, Hollywood, MD 20636
    23063 Pembrook Dr, Hollywood, MD 20636
    /58

    $3,700 per month

    • 5 Beds
    • 2.5 Baths
    • 3,427 Sq Ft
    • House for Rent

    23063 Pembrook Dr, Hollywood, MD 20636

    Spacious and inviting, this large 4-bedroom Colonial home is located in a sought-after neighborhood and offers over 3,400 square feet of living space plus a full unfinished basement for ample storage or flexible use. Situated on over 2 acres, the fully fenced, level backyard provides privacy and room to roam. Inside, you’ll find a light-filled layout with an updated kitchen, fresh flooring,

    Tracey Summers CENTURY 21 New Millennium

    23063 Pembrook Dr, Hollywood, MD 20636
  • 22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
    22695 Washington St Unit 2, Leonardtown, MD 20650
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    $1,400 per month

    • 1 Bed
    • 1 Bath
    • 11,686 Sq Ft
    • Condo for Rent

    22695 Washington St Unit 2, Leonardtown, MD 20650

    Welcome to your charming new home in the heart of historic Leonardtown! This delightful 1-bedroom, 1-bathroom apartment boasts fresh paint and brand-new luxury vinyl plank (LVP) flooring, providing a modern and comfortable living space. Nestled in an amazing location, you'll enjoy the convenience of being within walking distance to an array of fantastic restaurants, shops, and local attractions.

    Natalya Ford EXP Realty, LLC

    22695 Washington St Unit 2, Leonardtown, MD 20650
  • 22680 Washington St Unit 1, Leonardtown, MD 20650
    22680 Washington St Unit 1, Leonardtown, MD 20650
    22680 Washington St Unit 1, Leonardtown, MD 20650
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    $2,300 per month

    • 2 Beds
    • 2.5 Baths
    • 900 Sq Ft
    • House for Rent

    22680 Washington St Unit 1, Leonardtown, MD 20650

    Apartments in beautifully renovated Seymour Building on the square in Leonardtown! 2 bedrooms and 2.5 baths along with all stainless steel appliances. Washer and dryer included. Rent includes water, sewer, trash . Apartment # 1.

    Karen Alford-Brooks CENTURY 21 New Millennium

    22680 Washington St Unit 1, Leonardtown, MD 20650
  • 23293 Nicholson St, Hollywood, MD 20636
    23293 Nicholson St, Hollywood, MD 20636
    23293 Nicholson St, Hollywood, MD 20636
    /25

    $4,500 per month

    • 5 Beds
    • 3 Baths
    • 3,036 Sq Ft
    • House for Rent

    23293 Nicholson St, Hollywood, MD 20636

    *** Rent with the option to buy. ***Welcome to this stunning, well-maintained 3-bedroom, 2-bathroom rancher nestled on a private, wooded lot in Hollywood, MD. This home offers peaceful living with modern upgrades and spacious living areas throughout. Features Include:• Spacious open-concept living room with vaulted ceilings, ceiling fan, and a cozy fireplace• Stylish

    Pamela Portillo Samson Properties

    23293 Nicholson St, Hollywood, MD 20636
  • 39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, Leonardtown, MD 20650
    39870 Lady Baltimore Ave, Leonardtown, MD 20650
    /15

    $2,350 per month

    • 4 Beds
    • 2.5 Baths
    • 1,380 Sq Ft
    • House for Rent

    39870 Lady Baltimore Ave, Leonardtown, MD 20650

    Charming Rambler in Water-Access Community – Available Now!Enjoy easy one-level living in this adorable 4-bedroom, 2.5-bath rambler nestled in the St. Clements Shores community. With access to St. Clements Bay, you'll love spending time outdoors in the spacious yard with mature trees, a large deck, and peaceful surroundings.Inside, the open-concept layout offers great flow for

    Lesa Clark Redfin Corp

    39870 Lady Baltimore Ave, Leonardtown, MD 20650
  • 25150 Gallant Man Dr, Hollywood, MD 20636
    25150 Gallant Man Dr, Hollywood, MD 20636
    25150 Gallant Man Dr, Hollywood, MD 20636
    /35

    $2,600 per month

    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft
    • House for Rent

    25150 Gallant Man Dr, Hollywood, MD 20636

    *New floors installed on the lower-level as of 08/01/2025*. They are beautiful!!!Welcome to your new retreat on Gallant Man Drive in Hollywood, Maryland. This home offers a beautifully manicured yard that provides both charm and exceptional privacy, perfect for enjoying peaceful moments outdoors. Lawn care and trash service are included, making everyday living even more convenient.

    Diana Washabaugh CENTURY 21 New Millennium

    25150 Gallant Man Dr, Hollywood, MD 20636
  • 24676 Broad Creek Dr, Hollywood, MD 20636
    24676 Broad Creek Dr, Hollywood, MD 20636
    24676 Broad Creek Dr, Hollywood, MD 20636
    /59

    $3,100 per month

    • 4 Beds
    • 3.5 Baths
    • 3,325 Sq Ft
    • House for Rent

    24676 Broad Creek Dr, Hollywood, MD 20636

    This spacious 4-bedroom single family home offers the perfect blend of comfort and functionality. Featuring generously sized rooms, an open-concept layout, plenty of natural light and a finished basement. This home is professionally managed by Granson Property Management, LLC. Application fee is $65 per adult and is non-refundable. All adults 18 years of age or older MUST submit a

    Jesieryl Hartzer CENTURY 21 New Millennium

    24676 Broad Creek Dr, Hollywood, MD 20636
Maryland St Marys County Leonardtown Leonardtown Middle School

Homes for Rent near Leonardtown Middle School

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