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 30 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
21395 Fairwood Ct Leonardtown, MD Beautiful home on almost 1 acre, 4 bed, 3.5 bath home. Large kitchen with 42 in. cabinets,...	4 beds \| 3 baths \| 4,066 sq.ft.	$700,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 1.94% Airbnb Rental Income: $1824 Traditional Rental Income: $2434 Airbnb ROI: 0.25% Traditional ROI: 1.94%
20798 Waterside Dr Leonardtown, MD Stunning Waterfront Opportunity on the Potomac River. Discover the perfect cottage waterfr...	2 beds \| 1 baths \| 1,018 sq.ft.	$450,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.17% Airbnb Rental Income: $1123 Traditional Rental Income: $1726 Airbnb ROI: -0.16% Traditional ROI: 2.17%
41444 Osborne Ln Leonardtown, MD Charming Home in Prime Leonardtown Location This inviting home sits in the heart of histor...	4 beds \| 3 baths \| 3,690 sq.ft.	$639,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.32% Airbnb Rental Income: $1824 Traditional Rental Income: $2818 Airbnb ROI: 0.83% Traditional ROI: 3.32%
41620 Church St Leonardtown, MD Fully renovated. Move-in ready. Prime downtown location. Welcome to 41620 Church St - a ra...	3 beds \| 2 baths \| 1,728 sq.ft.	$399,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.57% Airbnb Rental Income: $1634 Traditional Rental Income: $2111 Airbnb ROI: 1.06% Traditional ROI: 3.57%
23898 Speith Rd Leonardtown, MD Step into this ONE level, completely renovated home that was stripped down to the studs an...	3 beds \| 2 baths \| 1,632 sq.ft.	$429,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.48% Airbnb Rental Income: $1634 Traditional Rental Income: $2225 Airbnb ROI: 0.86% Traditional ROI: 3.48%
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: -0.61% Traditional cash on cash: 0.29% Airbnb Rental Income: $1824 Traditional Rental Income: $2785 Airbnb ROI: -0.61% Traditional ROI: 0.29%
23636 Hansel Ct Leonardtown, MD New Lower Price!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence p...	4 beds \| 2 baths \| 4,836 sq.ft.	$649,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 2.93% Airbnb Rental Income: $1824 Traditional Rental Income: $3072 Airbnb ROI: 0.05% Traditional ROI: 2.93%
19700 Mulberry Fields Rd Leonardtown, MD 19700 Mulberry Fields Rd, Leonardtown, MD 20650 \| Single Family Residential	6 beds \| 4 baths \| 5,500 sq.ft.	$20,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.85% Airbnb Rental Income: $null Traditional Rental Income: $4446 Airbnb ROI: N/A Traditional ROI: -1.85%
22393 Saint Clements Ave Leonardtown, MD Experience waterfront living at its finest in this beautifully renovated home overlooking ...	4 beds \| 2 baths \| 2,097 sq.ft.	$774,900	Airbnb cash on cash: 0.1% Traditional cash on cash: 1.12% Airbnb Rental Income: $1824 Traditional Rental Income: $2063 Airbnb ROI: 0.1% Traditional ROI: 1.12%
42249 Saint Johns Rd Leonardtown, MD The required verbiage below shall take the place of the MLS Advisory Task verbiage. This P...	3 beds \| 1 baths \| 1,161 sq.ft.	$384,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.59% Airbnb Rental Income: $1634 Traditional Rental Income: $1946 Airbnb ROI: 1.45% Traditional ROI: 3.59%
42195 White Point Beach Rd Leonardtown, MD 42195 White Point Beach Rd, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,636 sq.ft.	$699,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 0.72% Airbnb Rental Income: $1634 Traditional Rental Income: $1922 Airbnb ROI: -0.43% Traditional ROI: 0.72%
21983 Point Lookout Rd Leonardtown, MD OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler locat...	3 beds \| 2 baths \| 1,144 sq.ft.	$369,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.07% Airbnb Rental Income: $1634 Traditional Rental Income: $1675 Airbnb ROI: 1.62% Traditional ROI: 3.07%
40743 Magee Dr Leonardtown, MD 40743 Magee Dr, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 2,474 sq.ft.	$359,777	Airbnb cash on cash: 1.58% Traditional cash on cash: 4.08% Airbnb Rental Income: $1824 Traditional Rental Income: $2173 Airbnb ROI: 1.58% Traditional ROI: 4.08%
23636 Gunnell Dr Leonardtown, MD Welcome to 23636 Gunnell Drive in Leonardtown! This spacious 4-bedroom, 2.5-bath colonial ...	4 beds \| 2 baths \| 2,948 sq.ft.	$590,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 2.06% Airbnb Rental Income: $1824 Traditional Rental Income: $2206 Airbnb ROI: 0.48% Traditional ROI: 2.06%
22856 White Swan Way Leonardtown, MD This stunning 5 bedroom home sits gracefully at the end of a cul-de-sac on a private lane ...	5 beds \| 5 baths \| 5,810 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.96% Airbnb Rental Income: $null Traditional Rental Income: $4996 Airbnb ROI: N/A Traditional ROI: 2.96%
40115 Combs Creek Way Leonardtown, MD Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown...	5 beds \| 3 baths \| 2,993 sq.ft.	$1,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $5003 Airbnb ROI: N/A Traditional ROI: 1.63%
42108 Wildflower Dr Leonardtown, MD New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring ...	4 beds \| 2 baths \| 3,072 sq.ft.	$614,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.7% Airbnb Rental Income: $1824 Traditional Rental Income: $2342 Airbnb ROI: -0.06% Traditional ROI: 1.7%
40777 Center 40 Cir Leonardtown, MD Here's your chance to make your new home in Breton Bay! Nestled on a quiet cul-de-sac in t...	4 beds \| 2 baths \| 2,370 sq.ft.	$539,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.58% Airbnb Rental Income: $1824 Traditional Rental Income: $2217 Airbnb ROI: 0.82% Traditional ROI: 2.58%
18800 Mckays Beach Rd Leonardtown, MD This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal ret...	3 beds \| 2 baths \| 1,667 sq.ft.	$465,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.37% Airbnb Rental Income: $1634 Traditional Rental Income: $1932 Airbnb ROI: 0.63% Traditional ROI: 2.37%
40659 Klear Ct Leonardtown, MD This is an estate sale being sold AS-IS. The Estate will not make any repairs. The owner's...	4 beds \| 2 baths \| 2,774 sq.ft.	$515,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.58% Airbnb Rental Income: $1824 Traditional Rental Income: $2222 Airbnb ROI: 0.73% Traditional ROI: 2.58%
42084 Wildflower Dr Leonardtown, MD To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Bui...	4 beds \| 2 baths \| 3,072 sq.ft.	$629,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.61% Airbnb Rental Income: $1824 Traditional Rental Income: $2342 Airbnb ROI: -0.11% Traditional ROI: 1.61%
42096 Wildflower Dr Leonardtown, MD Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Q...	4 beds \| 2 baths \| 2,976 sq.ft.	$619,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.67% Airbnb Rental Income: $1824 Traditional Rental Income: $2342 Airbnb ROI: -0.08% Traditional ROI: 1.67%
42102 Wildflower Dr Leonardtown, MD New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality B...	4 beds \| 2 baths \| 2,701 sq.ft.	$609,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.63% Airbnb Rental Income: $1824 Traditional Rental Income: $2288 Airbnb ROI: -0.05% Traditional ROI: 1.63%
23591 Margrave Dr Leonardtown, MD Welcome to this well-maintained Belmont model in the desirable Leonard's Grant community, ...	5 beds \| 3 baths \| 4,051 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.22% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 2.22%
23628 Belmar Dr Leonardtown, MD PROFESSIONAL PHOTOS COMING!	5 beds \| 3 baths \| 4,834 sq.ft.	$730,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.75% Airbnb Rental Income: $null Traditional Rental Income: $2680 Airbnb ROI: N/A Traditional ROI: 1.75%
42970 Heritage Dr Leonardtown, MD Welcome home to this stunning luxury residence in the sought-after Leonardtown Farms neigh...	5 beds \| 4 baths \| 5,082 sq.ft.	$829,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $3023 Airbnb ROI: N/A Traditional ROI: 1.89%
40111 Army Way Leonardtown, MD 40111 Army Way, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 4 baths \| 7,679 sq.ft.	$2,500,000	Airbnb cash on cash: -1.55% Traditional cash on cash: -0.9% Airbnb Rental Income: $1824 Traditional Rental Income: $2848 Airbnb ROI: -1.55% Traditional ROI: -0.9%
43954 Main Way Rd Leonardtown, MD 43954 Main Way Rd, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 3 baths \| 1,691 sq.ft.	$469,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.23% Airbnb Rental Income: $1634 Traditional Rental Income: $1989 Airbnb ROI: 0.37% Traditional ROI: 2.23%
22332 Cedar St Leonardtown, MD 22332 Cedar St, Leonardtown, MD 20650 \| Single Family Residential	2 beds \| 1 baths \| 1,000 sq.ft.	$329,900	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.72% Airbnb Rental Income: $1123 Traditional Rental Income: $1276 Airbnb ROI: 0.01% Traditional ROI: 1.72%
41462 Culpepper Way Leonardtown, MD 41462 Culpepper Way, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 3 baths \| 3,314 sq.ft.	$645,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.83% Airbnb Rental Income: $1824 Traditional Rental Income: $2454 Airbnb ROI: -0.04% Traditional ROI: 1.83%

Your search for investment property begins and ends here

Single Family Homes for Sale in Leonardtown, MD

21395 Fairwood Ct

Leonardtown, MD

4 beds | 3 baths | 4,066 sq.ft.

$700,000

Airbnb cash on cash: 0.25%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $1824

Traditional Rental Income: $2434

Airbnb ROI: 0.25%

Traditional ROI: 1.94%

20798 Waterside Dr

Leonardtown, MD

2 beds | 1 baths | 1,018 sq.ft.

$450,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1123

Traditional Rental Income: $1726

Airbnb ROI: -0.16%

Traditional ROI: 2.17%

41444 Osborne Ln

Leonardtown, MD

4 beds | 3 baths | 3,690 sq.ft.

$639,900

Airbnb cash on cash: 0.83%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1824

Traditional Rental Income: $2818

Airbnb ROI: 0.83%

Traditional ROI: 3.32%

41620 Church St

Leonardtown, MD

3 beds | 2 baths | 1,728 sq.ft.

$399,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1634

Traditional Rental Income: $2111

Airbnb ROI: 1.06%

Traditional ROI: 3.57%

23898 Speith Rd

Leonardtown, MD

3 beds | 2 baths | 1,632 sq.ft.

$429,000

Airbnb cash on cash: 0.86%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $1634

Traditional Rental Income: $2225

Airbnb ROI: 0.86%

Traditional ROI: 3.48%

Bayside Rd

Leonardtown, MD

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

$1,750,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $1824

Traditional Rental Income: $2785

Airbnb ROI: -0.61%

Traditional ROI: 0.29%

23636 Hansel Ct

Leonardtown, MD

4 beds | 2 baths | 4,836 sq.ft.

$649,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $1824

Traditional Rental Income: $3072

Airbnb ROI: 0.05%

Traditional ROI: 2.93%

19700 Mulberry Fields Rd

Leonardtown, MD

6 beds | 4 baths | 5,500 sq.ft.

$20,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.85%

Airbnb Rental Income: $null

Traditional Rental Income: $4446

Airbnb ROI: N/A