Real Estate Investment Properties for Sale in Leonardtown, MD

Looking for investment property in Leonardtown, MD with high ROI ?

Explore a variety of short-term homes & houses in Leonardtown, MD. Invest wisely with VRBO & Leonardtown, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Leonardtown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21955 BUDDS CREEK RD Leonardtown, MD Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,930 sq.ft.	$384,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 4.72% Airbnb Rental Income: $1330 Traditional Rental Income: $2371 Airbnb ROI: 0.69% Traditional ROI: 4.72%
41535 SINGLETREE Drive Leonardtown, MD Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 bat...	4 beds \| 3 baths \| 2,262 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $2986 Airbnb ROI: N/A Traditional ROI: 3.98%
23261 JENIFER Court Leonardtown, MD This Colonial in the sought-after Estates at Singletree offers 5 bedrooms, 3.5 baths, and ...	5 beds \| 4 baths \| 3,575 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.76% Airbnb Rental Income: $null Traditional Rental Income: $3728 Airbnb ROI: N/A Traditional ROI: 4.76%
21920 NEWTOWNE NECK Road Leonardtown, MD Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,29...	4 beds \| 3 baths \| 2,291 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $2987 Airbnb ROI: N/A Traditional ROI: 4.18%
42520 RIVERWINDS Drive Leonardtown, MD Seller is entertaining offers now. Looking for elbow room? Look no further-this property o...	4 beds \| 2 baths \| 2,744 sq.ft.	$1,999,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 0.27%
20240 BIG OAK LN Leonardtown, MD Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,935 sq.ft.	$505,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.38% Airbnb Rental Income: $1330 Traditional Rental Income: $2345 Airbnb ROI: 0.36% Traditional ROI: 3.38%
40533 BRETON KNOLLS CT Leonardtown, MD TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spann...	4 beds \| 3 baths \| N/A	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $3042 Airbnb ROI: N/A Traditional ROI: 2.57%
18937 HODGES Lane Leonardtown, MD Are you dreaming of living on the water? This is your perfect opportunity! Well maintained...	3 beds \| 2 baths \| 1,834 sq.ft.	$659,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.51% Airbnb Rental Income: $1330 Traditional Rental Income: $2686 Airbnb ROI: -0.36% Traditional ROI: 2.51%
41810 CHELSEY FAYE Lane Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 4 baths \| 2,650 sq.ft.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.37% Airbnb Rental Income: $null Traditional Rental Income: $3064 Airbnb ROI: N/A Traditional ROI: 3.37%
25365 POINT LOOKOUT Road Leonardtown, MD Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one ba...	3 beds \| 3 baths \| 2,952 sq.ft.	$497,500	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.58% Airbnb Rental Income: $1330 Traditional Rental Income: $3021 Airbnb ROI: 0.06% Traditional ROI: 4.58%
20959 REDGATE Lane Leonardtown, MD A True Hidden Gem just a few miles South of Downtown Leonardtown. Leonardtown, Maryland of...	3 beds \| 1 baths \| 1,026 sq.ft.	$229,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 5.82% Airbnb Rental Income: $1330 Traditional Rental Income: $1744 Airbnb ROI: 2.01% Traditional ROI: 5.82%
23534 BELMAR Drive Leonardtown, MD Back on the market after buyer failed to perform. **Price reduced and now below recent...	5 beds \| 4 baths \| 4,738 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3852 Airbnb ROI: N/A Traditional ROI: 4.32%
41430 CHALLEDON Way Leonardtown, MD Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sou...	5 beds \| 4 baths \| 4,500 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $3818 Airbnb ROI: N/A Traditional ROI: 4.06%
40461 OLD BRETON BEACH Road Leonardtown, MD Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with ...	2 beds \| 3 baths \| 2,040 sq.ft.	$689,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 2.67% Airbnb Rental Income: $2283 Traditional Rental Income: $2941 Airbnb ROI: 0.76% Traditional ROI: 2.67%
23264 LINDSAY Drive Leonardtown, MD Custom Floorplan Front Load Garage with expanded guest parking on driveway, Upgraded c...	3 beds \| 2 baths \| 2,824 sq.ft.	$599,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.5% Airbnb Rental Income: $1330 Traditional Rental Income: $2636 Airbnb ROI: -0.57% Traditional ROI: 2.5%
21056 WOODMERE Drive Leonardtown, MD Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front...	4 beds \| 3 baths \| 2,205 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 3.94%
39825 SWEETPEA Lane Leonardtown, MD Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 fe...	4 beds \| 4 baths \| 2,442 sq.ft.	$790,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $3921 Airbnb ROI: N/A Traditional ROI: 3.61%
DRAGONFLY Lane lot: 88-23676 Leonardtown, MD *MOVE IN READY*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credit plu...	4 beds \| 4 baths \| 2,604 sq.ft.	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.23% Airbnb Rental Income: $null Traditional Rental Income: $3204 Airbnb ROI: N/A Traditional ROI: 6.23%
41650 MATTHEW Court Leonardtown, MD This home features 4 spacious Bedrooms, an open Kitchen & great room w/built-in TV Niche o...	4 beds \| 3 baths \| 2,230 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $2873 Airbnb ROI: N/A Traditional ROI: 3.75%
42043 STARLIGHT Drive Leonardtown, MD Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has a...	4 beds \| 4 baths \| 2,472 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $3165 Airbnb ROI: N/A Traditional ROI: 4.11%
DRAGONFLY Lane lot: 93-23706 Leonardtown, MD ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,...	4 beds \| 4 baths \| 2,966 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $3472 Airbnb ROI: N/A Traditional ROI: 6.47%
DRAGONFLY Lane lot: 103-23701 Leonardtown, MD *Under Construction*Builder Incentive, Settle in 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.56% Airbnb Rental Income: $null Traditional Rental Income: $3580 Airbnb ROI: N/A Traditional ROI: 6.56%
21039 WOODMERE Drive Leonardtown, MD Situated on a beautiful lot in the lovely Leonardtown neighborhood of Wilderness Run. Roof...	5 beds \| 3 baths \| 4,112 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $3456 Airbnb ROI: N/A Traditional ROI: 4.51%
DRAGONFLY Lane lot: 107-23677 Leonardtown, MD ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,...	4 beds \| 4 baths \| N/A	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.68% Airbnb Rental Income: $null Traditional Rental Income: $3562 Airbnb ROI: N/A Traditional ROI: 6.68%
DRAGONFLY Lane lot: 91-23694 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credi...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $3561 Airbnb ROI: N/A Traditional ROI: 7.09%
DRAGONFLY Lane lot: 95-23718 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credi...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $3561 Airbnb ROI: N/A Traditional ROI: 7.09%
23098 TOWN RUN Drive Leonardtown, MD Built in 2022, this stunning QBH Adelina floor plan shows like brand new, complete with ev...	5 beds \| 4 baths \| 3,642 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 4.28%
DRAGONFLY Lane lot: 92-23700 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credi...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $2653 Airbnb ROI: N/A Traditional ROI: 5.1%
DRAGONFLY Lane lot: 97-23730 Leonardtown, MD ***QUICK DELIVERY INCENTIVE....Settle in 2025 and receive $10,000 Builder Credit plus $12,...	4 beds \| 4 baths \| N/A	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2658 Airbnb ROI: N/A Traditional ROI: 4.8%
40171 LITTLE WOODS Lane Leonardtown, MD Waterfront Retreat with Spectacular Sunsets Waterfront Retreat with Spectacular Sunsets. W...	4 beds \| 2 baths \| 2,586 sq.ft.	$880,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 1.96%
21117 CATNIP Court Leonardtown, MD Absolutely stunning home in Leonardtown's sought-after Kingston Subdivision! Perched on a ...	5 beds \| 4 baths \| 3,526 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $3778 Airbnb ROI: N/A Traditional ROI: 4.5%
21925 BUDDS CREEK Road Leonardtown, MD This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family ...	3 beds \| 2 baths \| 2,527 sq.ft.	$479,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.78% Airbnb Rental Income: $1330 Traditional Rental Income: $2511 Airbnb ROI: 0.22% Traditional ROI: 3.78%
45474 MEDLEYS NECK Road Leonardtown, MD Welcome Home to your peaceful retreat in the Valley! This home has been impeccably maintai...	3 beds \| 3 baths \| 2,653 sq.ft.	$650,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.43% Airbnb Rental Income: $1330 Traditional Rental Income: $3201 Airbnb ROI: -0.33% Traditional ROI: 3.43%
22305 HANOVER Drive Leonardtown, MD Welcome to your ideal home in the sought-after Hanover at Breton Bay! This beautiful, spac...	4 beds \| 3 baths \| 3,404 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $3147 Airbnb ROI: N/A Traditional ROI: 3.41%

Real Estate investment in Leonardtown, MD

There are 34 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $554,900 and the average price per square foot is $201. In October 2025, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $3,053.

Leonardtown, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 34 investment properties available for sale in Leonardtown.

In 2025, the best neighborhood to buy investment property is Leonardtown.

The ROI for Short-Term is higher than the Long-Term in Leonardtown with average rental income of $1,330.

Your search for investment property begins and ends here

Investment Property for Sale in Leonardtown, MD

21955 BUDDS CREEK RD

Leonardtown, MD

3 beds | 2 baths | 1,930 sq.ft.

$384,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1330

Traditional Rental Income: $2371

Airbnb ROI: 0.69%

Traditional ROI: 4.72%

41535 SINGLETREE Drive

Leonardtown, MD

4 beds | 3 baths | 2,262 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2986

Airbnb ROI: N/A

Traditional ROI: 3.98%

23261 JENIFER Court

Leonardtown, MD

5 beds | 4 baths | 3,575 sq.ft.

$590,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.76%

Airbnb Rental Income: $null

Traditional Rental Income: $3728

Airbnb ROI: N/A

Traditional ROI: 4.76%

21920 NEWTOWNE NECK Road

Leonardtown, MD

4 beds | 3 baths | 2,291 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2987

Airbnb ROI: N/A

Traditional ROI: 4.18%

42520 RIVERWINDS Drive

Leonardtown, MD

4 beds | 2 baths | 2,744 sq.ft.

$1,999,999

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $2964

Airbnb ROI: N/A

Traditional ROI: 0.27%

20240 BIG OAK LN

Leonardtown, MD

3 beds | 2 baths | 1,935 sq.ft.

$505,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1330

Traditional Rental Income: $2345

Airbnb ROI: 0.36%

Traditional ROI: 3.38%

40533 BRETON KNOLLS CT

Leonardtown, MD

4 beds | 3 baths | N/A

$859,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $3042

Airbnb ROI: N/A

Traditional ROI: 2.57%

18937 HODGES Lane

Leonardtown, MD

3 beds | 2 baths | 1,834 sq.ft.

$659,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1330

Traditional Rental Income: $2686

Airbnb ROI: -0.36%