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: 1.02% Traditional cash on cash: 4.72% Airbnb Rental Income: $1473 Traditional Rental Income: $2371 Airbnb ROI: 1.02% Traditional ROI: 4.72%
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: 0.61% Traditional cash on cash: 3.38% Airbnb Rental Income: $1473 Traditional Rental Income: $2345 Airbnb ROI: 0.61% Traditional ROI: 3.38%
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: -0.17% Traditional cash on cash: 2.51% Airbnb Rental Income: $1473 Traditional Rental Income: $2686 Airbnb ROI: -0.17% 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: 0.32% Traditional cash on cash: 4.58% Airbnb Rental Income: $1473 Traditional Rental Income: $3021 Airbnb ROI: 0.32% 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.	$219,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 6.12% Airbnb Rental Income: $1473 Traditional Rental Income: $1744 Airbnb ROI: 2.72% Traditional ROI: 6.12%
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: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $2941 Airbnb ROI: N/A Traditional ROI: 2.67%
22338 WHITE OAK Road Leonardtown, MD COMING SOON! Beautiful 4 bedroom, 2 1/2 bathroom colonial on over half an acre lot in Bret...	4 beds \| 3 baths \| 2,328 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.71% Airbnb Rental Income: $null Traditional Rental Income: $3344 Airbnb ROI: N/A Traditional ROI: 4.71%
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: 103 - 23701 Leonardtown, MD *** HOME IN TIME FOR THE HOLIDAYS, Receive $10,000 in Builder Credit plus $12,500 in Closi...	4 beds \| 4 baths \| N/A	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $3580 Airbnb ROI: N/A Traditional ROI: 6.41%
DRAGONFLY Lane lot: 95 - 23718 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.01% Airbnb Rental Income: $null Traditional Rental Income: $3561 Airbnb ROI: N/A Traditional ROI: 7.01%
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.	$859,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.04% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 2.04%
21117 CATNIP Court Leonardtown, MD Seller is offering a $4,000 concession with an accepted full-price offer! Use it for an in...	5 beds \| 4 baths \| 3,526 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.85% Airbnb Rental Income: $null Traditional Rental Income: $3778 Airbnb ROI: N/A Traditional ROI: 4.85%
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.	$465,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.92% Airbnb Rental Income: $1473 Traditional Rental Income: $2511 Airbnb ROI: 0.53% Traditional ROI: 3.92%
41832 FOXWELL POINT Lane Leonardtown, MD Discover this stunning cedar siding contemporary waterfront home offering a perfect blend ...	3 beds \| 4 baths \| 3,683 sq.ft.	$800,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.4% Airbnb Rental Income: $1473 Traditional Rental Income: $3967 Airbnb ROI: -0.53% Traditional ROI: 3.4%
43018 BLUEJAY Lane Leonardtown, MD Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in L...	4 beds \| 3 baths \| 2,888 sq.ft.	$645,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $3256 Airbnb ROI: N/A Traditional ROI: 3.5%
DRAGONFLY Lane lot: 104 - 23695 Leonardtown, MD *Immediate Delivery*Builder Incentive, SETTLE in 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2699 Airbnb ROI: N/A Traditional ROI: 5.15%
DRAGONFLY Lane lot: 106 - 23683 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.25% Airbnb Rental Income: $null Traditional Rental Income: $3582 Airbnb ROI: N/A Traditional ROI: 7.25%
DRAGONFLY Lane lot: 105 - 23689 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2699 Airbnb ROI: N/A Traditional ROI: 5.15%
20753 CHESTNUT RIDGE Drive Leonardtown, MD Nestled within one of the most desirable subdivisions, this classic two-story Colonial wel...	4 beds \| 3 baths \| 2,594 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $3094 Airbnb ROI: N/A Traditional ROI: 3.82%
23581 GALLENT FOX Way Leonardtown, MD Welcome to 23581 Gallent Fox Way, a beautifully maintained and thoughtfully upgraded home ...	4 beds \| 4 baths \| 3,736 sq.ft.	$645,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $3638 Airbnb ROI: N/A Traditional ROI: 4.04%
20260 HAWKS Way Leonardtown, MD IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new co...	4 beds \| 3 baths \| 2,500 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 3.53%
43543 BAYBERRY Court Leonardtown, MD Welcome to this charming single-family rambler nestled in the peaceful Chestnut Ridge subd...	3 beds \| 2 baths \| 1,732 sq.ft.	$440,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.36% Airbnb Rental Income: $1473 Traditional Rental Income: $2319 Airbnb ROI: 1.25% Traditional ROI: 4.36%
20250 HAWKS Way Leonardtown, MD IMMEDIATE DELIVERY! Brand-New Leonardtown Rambler on 1.37 Acres Welcome to a beautifully c...	3 beds \| 2 baths \| 1,557 sq.ft.	$519,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.4% Airbnb Rental Income: $1473 Traditional Rental Income: $2316 Airbnb ROI: 0.77% Traditional ROI: 3.4%

Real Estate investment in Leonardtown, MD

There are 25 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $550,000 and the average price per square foot is $223. In December 2025, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $3,021.

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

There are 25 investment properties available for sale in Leonardtown.

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

The ROI for Long-Term is higher than the Short-Term in Leonardtown with average rental income of $3,021.

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: 1.02%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1473

Traditional Rental Income: $2371

Airbnb ROI: 1.02%

Traditional ROI: 4.72%

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: 0.61%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1473

Traditional Rental Income: $2345

Airbnb ROI: 0.61%

Traditional ROI: 3.38%

18937 HODGES Lane

Leonardtown, MD

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

$659,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1473

Traditional Rental Income: $2686

Airbnb ROI: -0.17%

Traditional ROI: 2.51%

41810 CHELSEY FAYE Lane

Leonardtown, MD

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

3 beds | 3 baths | 2,952 sq.ft.

$497,500

Airbnb cash on cash: 0.32%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $1473

Traditional Rental Income: $3021

Airbnb ROI: 0.32%

Traditional ROI: 4.58%

20959 REDGATE Lane

Leonardtown, MD

3 beds | 1 baths | 1,026 sq.ft.

$219,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 6.12%

Airbnb Rental Income: $1473

Traditional Rental Income: $1744

Airbnb ROI: 2.72%

Traditional ROI: 6.12%

40461 OLD BRETON BEACH Road

Leonardtown, MD

2 beds | 3 baths | 2,040 sq.ft.

$689,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.67%

Airbnb Rental Income: $null

Traditional Rental Income: $2941

Airbnb ROI: N/A