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Leonardtown, MD Homes for Rent

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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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    Starting at $2,250 Per Month

    • 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

    The Hamptons at Leonardtown

    (443) 342-9476

    44980 Hamptons Blvd, Leonardtown, MD 20650
  • 41515 Singletree Dr, Leonardtown, MD 20650
    41515 Singletree Dr, Leonardtown, MD 20650
    41515 Singletree Dr, Leonardtown, MD 20650
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    $900

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • House for Rent

    41515 Singletree Dr, Leonardtown, MD 20650

    Large bedroom with walk in closet, can be furnished or unfinished and I can provide any other items needed for your comfort.Access to whole house with high speed internet House is walking distance to college of southern Maryland and St. Mary’s hospital in a very safe and quiet neighborhood.

    41515 Singletree Dr, Leonardtown, MD 20650
  • 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
    • 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!

    21113 Arbor Ct, 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
  • 41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650
    41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650
    41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650
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    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,113 Sq Ft
    • Condo for Rent

    41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650

    Beautiful condo for lease in the heart of Leonardtown...walk to everything downtown has to offer. Shopping, Restaurants, Ice Cream, Bars, and history! 2 Bedroom 2 bath and very well appointed with everything needed to live that condo life...This one won't last long so don't wait to come see!!

    Steven Carroll Berkshire Hathaway HomeServices PenFed Realty

    41820 Eastwick Ln Unit 3201, Leonardtown, MD 20650
  • 18937 McKays Cove Ln, Leonardtown, MD 20650
    18937 McKays Cove Ln, Leonardtown, MD 20650
    18937 McKays Cove Ln, Leonardtown, MD 20650
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    $2,100 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,583 Sq Ft
    • House for Rent

    18937 McKays Cove Ln, Leonardtown, MD 20650

    Welcome to this charming water-access rambler! This inviting 3-bedroom, 1.5-bath home offers comfortable single-level living in a peaceful coastal setting.Inside, you’ll find an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinet space, perfect for everyday living and entertaining. The functional open floor plan provides bright living areas, well-sized

    Erika Yowell EXP Realty, LLC

    18937 McKays Cove Ln, Leonardtown, MD 20650
  • 22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
    22373 Enoch Rd, Leonardtown, MD 20650
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    $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
  • 20503 Chestnut Ridge Dr, Leonardtown, MD 20650
    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
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    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • House for Rent

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650

    Located in the Chestnut Ridge Subdivision where peace and tranquility exist. 3 Bedroom 2 1/2 Bath, 2 Car Garage Cape Cod-style residence. Home has been Freshly painted and new carpet installed in all of the bedroom areas. Equipped with a new washer and dryer. Enjoy the country setting and sit on the Front porch or family gatherings on the rear large deck which is perfect for grilling. Any

    Jay Camp Coldwell Banker Premier

    20503 Chestnut Ridge Dr, Leonardtown, MD 20650
  • 23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
    23581 Belmar Dr, Leonardtown, MD 20650
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    $2,695 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

Homes for Rent in Leonardtown, MD

Why Live in Leonardtown

Leonardtown, Maryland, is a rapidly growing community in Southern Maryland, with its population nearly doubling between 2010 and 2020. Located on a peninsula surrounded by the Potomac River, Patuxent River, and Chesapeake Bay, Leonardtown is home to around 19,000 residents. The town's appeal includes a revitalized downtown, water access, and proximity to Naval Air Station Patuxent River, the county's top employer. Leonardtown is approximately 60 miles south of Washington, D.C., making it a viable option for commuters. The town boasts above-average schools, including Leonardtown Elementary, Leonardtown Middle, Leonardtown High, and St. Mary's Ryken High. Housing in Leonardtown has seen significant development, with new subdivisions like Clark’s Rest featuring Colonial Revival-inspired homes and waterfront properties available in areas like Breton Bay. The town's historic downtown has been rejuvenated with new businesses, restaurants, and community-funded murals. Leonardtown is known for its freshly caught seafood, particularly at local restaurants such as T&Js Cove. The town earned the distinction of being the region’s first Arts & Entertainment District in 2013, with a thriving art scene and events like the annual Leonardtown Art Walk. The United States National Oyster Festival, held every October, is a major attraction, celebrating oysters with various activities and competitions. Outdoor recreation is abundant, with parks like Leonardtown Wharf Park and Newtowne Neck State Park offering boating, fishing, and hiking opportunities. Leonardtown is accessible via STS Transit and several state highways, with three major airports within 90 miles. Healthcare needs are met by MedStar St. Mary's Hospital.

Learn more about living in Leonardtown

Frequently Asked Questions

How much does it cost to rent a home in Leonardtown, MD?
The median rent for a home in Leonardtown, MD is $2,450 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 $98,000 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 $2,450 per month in Leonardtown, MD, renters typically need to show $7,350 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 18.5, 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.

Rental Trends in Leonardtown, MD

There are currently 10 homes available for rent in Leonardtown, MD. The median rent is $2,450 per month, with single-family homes renting at $2,600, townhouses at $2,900 and condos at $2,350.

Rental Home Trends

Number of Homes for Rent
10
Median Rent
$2,450
Median Single Family Home Rent
$2,600
Median Townhouse Rent
$2,900
Median Condo Rent
$2,350
How to Rent a Home

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