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Leonardtown, MD Houses for Rent

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  • 25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
    25365 Point Lookout Rd, Leonardtown, MD 20650
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    $2,050 Per Month

    • 3 Beds
    • 1 Bath
    • 2,952 Sq Ft
    • House for Rent

    25365 Point Lookout Rd, Leonardtown, MD 20650

    Charming Home !!!Welcome to in-town Leonardtown living—where everything you love is just a short walk away. ***Located just minutes from Leonardtown Wharf, award-winning restaurants, charming boutique shops, local wineries, and scenic parks, you’ll experience the best of what St. Mary’s County has to offer. Commuting is easy with quick access to major routes and PAX River Naval Air Station. This

    Robin Lower Residential Plus Real Estate Services

    25365 Point Lookout Rd, Leonardtown, MD 20650
  • 21113 Arbor Ct, Leonardtown, MD 20650
    21113 Arbor Ct, Leonardtown, MD 20650
    21113 Arbor Ct, Leonardtown, MD 20650
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    $2,450 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,684 Sq Ft
    • House for Rent

    21113 Arbor Ct, Leonardtown, MD 20650

    Beautifully kept home nestled cozily off Rt. 5. Minutes away from local schools as well as downtown Leonardtown. Home was well kept and shows nicely. Lots of room at this property!Tenant pays METCOM, SMECO,Trash and lawncare are not included in the rental price

    Roland Mellies O'Brien Realty ERA Powered

    21113 Arbor Ct, Leonardtown, MD 20650
  • 23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
    23687 Coventry Dr, Leonardtown, MD 20650
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    $4,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,961 Sq Ft
    • House for Rent

    23687 Coventry Dr, Leonardtown, MD 20650

    Spacious rental home in the sought-after Leonard’s Grant community! This 6-bedroom, 4.5-bath home offers over 5,500 finished square feet with plenty of room to live, work, relax, and entertain. The main level features a gourmet kitchen with granite countertops, oversized island, double ovens, gas cooking, butler’s pantry, and breakfast room. The private main-level primary suite includes dual

    Robin Errington CENTURY 21 New Millennium

    23687 Coventry Dr, Leonardtown, MD 20650
  • 22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
    /74

    $3,200 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    22373 Enoch Rd, Leonardtown, MD 20650

    Gorgeous, Classy, Completely Remodeled Colonial on a Beautiful Premium Lot Backing to Trees in the Sought After Neighborhood of Breton Bay/Society Hill. A Welcoming Covered Front Porch is the perfect spot for enjoying the array of birds that live around the property. Open Floor Plan with Upgraded, Luxury Vinyl Plank (LVP) Flooring. Stylish Living Room with Wood Burning Fireplace, Charming Dining

    Jenny Norris EXP Realty, LLC

    22373 Enoch Rd, Leonardtown, MD 20650
  • 22397 Armstrong Dr, Leonardtown, MD 20650
    22397 Armstrong Dr, Leonardtown, MD 20650
    22397 Armstrong Dr, Leonardtown, MD 20650
    /43

    $2,850 Per Month

    • 3 Beds
    • 3 Baths
    • 2,331 Sq Ft
    • House for Rent

    22397 Armstrong Dr, Leonardtown, MD 20650

    Just 7 minutes from the Leonardtown Square & Wharf, St. Mary's Hospital. 10 minutes from the beaches & trails of Newtowne Neck State Park. Armstrong Drive is located in the charming Breton Bay community. This delightful split-level home offers a perfect blend of comfort and convenience. Students are served by Benjamin Banneker Elementary School and Leonardtown Middle & High School. If you would

    Jonathan Powell Real Broker, LLC

    22397 Armstrong Dr, Leonardtown, MD 20650
  • 23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
    /54

    $2,490 Per Month

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    23581 Belmar Dr, Leonardtown, MD 20650

    Recently Renovated Cabin on Over 2 Acres in Leonardtown! 3 Spacious Bedrooms; 2 Full Baths; Fully Renovated Kitchen with New Cabinets, Countertops, Appliances; New Flooring! See it Today! Walking Distance to Duke Elementary and Minutes to Leonardtown Middle School and Leonardtown High School! Close to Leonardtown Square, Shopping, Restaurants, Schools, and More! Application fee is $65 per adult

    Erika Yowell EXP Realty, LLC

    23581 Belmar Dr, Leonardtown, MD 20650
Maryland St Marys County Leonardtown

Houses for Rent in Leonardtown, MD

Frequently Asked Questions

How much does it cost to rent a single-family home in Leonardtown, MD?
The median rent for a single-family home in Leonardtown, MD is $2,700 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while single-family homes and townhouses are currently more expensive.
How much do you need to make to afford rent in Leonardtown, MD?
To comfortably afford the median rent in Leonardtown, MD, a household needs to earn roughly $99,600 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,490 per month in Leonardtown, MD, renters typically need to show $7,470 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Leonardtown, MD?
In Leonardtown, MD, the price-to-rent ratio is 18.2, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Leonardtown, MD are best for renting a single-family home?
The best neighborhood for renting in Leonardtown, MD depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include Piney Point and Newburg, each with its own character and price range.

Rental Home Trends in Leonardtown, MD

There are currently 6 single-family homes available for rent in Leonardtown, MD. The median rent is $2,700 per month, with 3-bedroom houses renting at $2,598, 4-bedroom houses at $2,900 and 5-bedroom houses at $3,225.

Rental Home Trends

Number of Houses for Rent
6
Median Single Family Home Rent
$2,700
Median 3 Bedroom Single Family Home Rent
$2,598
Median 4 Bedroom Single Family Home Rent
$2,900
Median 5 Bedroom Single Family Home Rent
$3,225
How to Rent a Home

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