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.

Single Family Homes for Sale in Leonardtown, MD

Search for Single Family Residential for Sale in Leonardtown, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 31 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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 Dr 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%
Bayside Rd Leonardtown, MD Welcome to Bayside Road. Residents of Leonardtown believe this is THE place to live. This ...	4 beds \| 2 baths \| 2,130 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.29% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 0.29%
22204 Nomoni St Leonardtown, MD Welcome Home to this charming and beautifully updated home in the desirable Saint Clements...	2 beds \| 2 baths \| 1,008 sq.ft.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $1738 Airbnb ROI: N/A Traditional ROI: 3.93%
41810 Chelsey Faye Ln Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 2 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%
20959 Redgate Ln 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.	$189,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 7.22% Airbnb Rental Income: $1473 Traditional Rental Income: $1744 Airbnb ROI: 3.3% Traditional ROI: 7.22%
40461 Old Breton Beach Rd Leonardtown, MD Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with ...	2 beds \| 2 baths \| 2,040 sq.ft.	$679,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $2941 Airbnb ROI: N/A Traditional ROI: 2.72%
43018 Bluejay Ln Leonardtown, MD Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in L...	4 beds \| 2 baths \| 2,888 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $3256 Airbnb ROI: N/A Traditional ROI: 3.49%
20260 Hawks Way Leonardtown, MD IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new co...	4 beds \| 2 baths \| 2,500 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 4.35%
21345 Fairwood Ct Leonardtown, MD Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this mo...	5 beds \| 3 baths \| 4,080 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $3808 Airbnb ROI: N/A Traditional ROI: 3.87%
22615 Washington St Leonardtown, MD 22615 Washington St, Leonardtown, MD 20650 \| Single Family Residential	N/A beds \| N/A baths \| 1,691 sq.ft.	$599,950	Airbnb cash on cash: N/A Traditional cash on cash: -0.06% Airbnb Rental Income: $null Traditional Rental Income: $1226 Airbnb ROI: N/A Traditional ROI: -0.06%
22393 Saint Clements Ave Leonardtown, MD Experience refined waterfront living in this completely renovated rancher overlooking Sain...	4 beds \| 2 baths \| 2,097 sq.ft.	$778,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $2063 Airbnb ROI: N/A Traditional ROI: 1.11%
41438 Silver Charm Ct Leonardtown, MD	5 beds \| 3 baths \| 4,180 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $2618 Airbnb ROI: N/A Traditional ROI: 1.69%
22343 Newtowne Neck Rd Leonardtown, MD 22343 Newtowne Neck Rd, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 2,114 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 4.54%
44545 Brewer Ln Leonardtown, MD 44545 Brewer Ln, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 3 baths \| 3,243 sq.ft.	$674,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.53% Airbnb Rental Income: $null Traditional Rental Income: $2369 Airbnb ROI: N/A Traditional ROI: 1.53%
41377 Doctors Crossing Rd Leonardtown, MD 41377 Doctors Crossing Rd, Leonardtown, MD 20650 \| Single Family Residential	5 beds \| 4 baths \| 3,724 sq.ft.	$639,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $3038 Airbnb ROI: N/A Traditional ROI: 2.72%

Your search for investment property begins and ends here

Single Family Homes 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 Dr

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%

Bayside Rd

Leonardtown, MD

4 beds | 2 baths | 2,130 sq.ft.

$1,750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2785

Airbnb ROI: N/A

Traditional ROI: 0.29%

22204 Nomoni St

Leonardtown, MD

2 beds | 2 baths | 1,008 sq.ft.

$315,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.93%

Airbnb Rental Income: $null

Traditional Rental Income: $1738

Airbnb ROI: N/A

Traditional ROI: 3.93%

41810 Chelsey Faye Ln

Leonardtown, MD

4 beds | 2 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%

20959 Redgate Ln

Leonardtown, MD

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

$189,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 7.22%

Airbnb Rental Income: $1473

Traditional Rental Income: $1744

Airbnb ROI: 3.3%

Traditional ROI: 7.22%

40461 Old Breton Beach Rd

Leonardtown, MD

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

$679,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2941

Airbnb ROI: N/A