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
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.	$649,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.25% Airbnb Rental Income: $1824 Traditional Rental Income: $2818 Airbnb ROI: 0.8% Traditional ROI: 3.25%
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%
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%
43488 Medleys Neck Rd Leonardtown, MD 43488 Medleys Neck Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 0.73%
20265 Hawks Way Leonardtown, MD 20265 Hawks Way, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 1.46%
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%
St. Andrews Church Rd Leonardtown, MD St. Andrews Church Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| 2,188 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 0.97%
Ferny Hills Ln Leonardtown, MD Ferny Hills Ln, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$840,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.34% Airbnb Rental Income: $null Traditional Rental Income: $674 Airbnb ROI: N/A Traditional ROI: -1.34%
Lot 111 - 23684 Weeping Willow Way Leonardtown, MD BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's P...	4 beds \| 3 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 6.24% Airbnb Rental Income: $1824 Traditional Rental Income: $3237 Airbnb ROI: 1.72% Traditional ROI: 6.24%
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%
41708 Fenwick St Leonardtown, MD 41708 Fenwick St, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: 0.02%
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.	$379,900	Airbnb cash on cash: 1.55% Traditional cash on cash: 2.96% Airbnb Rental Income: $1634 Traditional Rental Income: $1675 Airbnb ROI: 1.55% Traditional ROI: 2.96%
Lot 140 - 23659 Dragonfly Ln Leonardtown, MD *Estimated Late October DeliveryUnder Construction* Welcome to the Madison D2, a s...	4 beds \| 3 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 6.22% Airbnb Rental Income: $1824 Traditional Rental Income: $3226 Airbnb ROI: 1.72% Traditional ROI: 6.22%
Lot 156 - 23634 Dragonfly Ln Leonardtown, MD ***** Hurry in! Secure your new home now and personalize it with your choice of interior c...	4 beds \| 3 baths \| 2,554 sq.ft.	$454,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.13% Airbnb Rental Income: $1824 Traditional Rental Income: $3221 Airbnb ROI: 1.69% Traditional ROI: 6.13%
Whirlwind Rd Leonardtown, MD Whirlwind Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$288,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: 0.11%
39645 Sweetpea Ln Leonardtown, MD 39645 Sweetpea Ln, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: -1.29% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: -1.29%
Lot 157 - 23640 Dragonfly Ln Leonardtown, MD Hurry in! Secure your new home now and personalize it with your choice of interior colors....	4 beds \| 3 baths \| 2,571 sq.ft.	$454,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 6.12% Airbnb Rental Income: $1824 Traditional Rental Income: $3217 Airbnb ROI: 1.69% Traditional ROI: 6.12%
40743 Magee Dr Leonardtown, MD 40743 Magee Dr, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 2,474 sq.ft.	$365,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.99% Airbnb Rental Income: $1824 Traditional Rental Income: $2173 Airbnb ROI: 1.53% Traditional ROI: 3.99%
WEEPING WILLOW Way lot: 116 - 23714 Leonardtown, MD *Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ...	4 beds \| 4 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.55% Airbnb Rental Income: $1824 Traditional Rental Income: $2524 Airbnb ROI: 1.72% Traditional ROI: 4.55%
Lot 116 - 23714 Weeping Willow Way Leonardtown, MD Lot 116 - 23714 Weeping Willow Way, Leonardtown, MD 20650 \| Townhouse	4 beds \| 3 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.5% Airbnb Rental Income: $1824 Traditional Rental Income: $2524 Airbnb ROI: 0.67% Traditional ROI: 3.5%
Lot 114 - 23702 Weeping Willow Way Leonardtown, MD *Builder Incentive $12,500 in Closing Help with use of both Preferred Lender & Title. ...	4 beds \| 3 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.55% Airbnb Rental Income: $1824 Traditional Rental Income: $2524 Airbnb ROI: 1.72% Traditional ROI: 4.55%
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.	$599,500	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.02% Airbnb Rental Income: $1824 Traditional Rental Income: $2206 Airbnb ROI: 0.45% Traditional ROI: 2.02%
42700 Moll Dyer Rd Leonardtown, MD 42700 Moll Dyer Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.01% Airbnb Rental Income: $null Traditional Rental Income: $684 Airbnb ROI: N/A Traditional ROI: 0.01%
22405 HOOD Lane Leonardtown, MD **Professional photography was delayed due to weather and will be uploaded as soon as poss...	3 beds \| 2 baths \| 2,400 sq.ft.	$715,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.92% Airbnb Rental Income: $1634 Traditional Rental Income: $2429 Airbnb ROI: 0.04% Traditional ROI: 1.92%
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 \| 5,410 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.	$670,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.12% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 2.12%
Parcel 323 Tract 2 Washington St Leonardtown, MD Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.49% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: -0.49%
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%

Real Estate investment in Leonardtown, MD

There are 44 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $498,352 and the average price per square foot is $175. In July 2026, the average monthly cash on cash return in Leonardtown is 2.00%. The average monthly rental income in Leonardtown is $2,429.

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

There are 44 investment properties available for sale in Leonardtown.

In 2026, 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 $2,429.

Your search for investment property begins and ends here

Investment Property for Sale in Leonardtown, MD

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.

$649,900

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1824

Traditional Rental Income: $2818

Airbnb ROI: 0.8%

Traditional ROI: 3.25%

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%

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

Traditional ROI: -1.85%

43488 Medleys Neck Rd

Leonardtown, MD

N/A beds | N/A baths | N/A

$190,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.73%

Airbnb Rental Income: $null

Traditional Rental Income: $600

Airbnb ROI: N/A

Traditional ROI: 0.73%

20265 Hawks Way

Leonardtown, MD

N/A beds | N/A baths | N/A

$149,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.46%

Airbnb Rental Income: $null

Traditional Rental Income: $600

Airbnb ROI: N/A