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: -0.48% Traditional cash on cash: 4.72% Airbnb Rental Income: $824 Traditional Rental Income: $2371 Airbnb ROI: -0.48% Traditional ROI: 4.72%
20798 WATERSIDE Drive 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: -0.68% Traditional cash on cash: 2.17% Airbnb Rental Income: $859 Traditional Rental Income: $1726 Airbnb ROI: -0.68% Traditional ROI: 2.17%
41620 CHURCH Street 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: -0.74% Traditional cash on cash: 3.57% Airbnb Rental Income: $824 Traditional Rental Income: $2111 Airbnb ROI: -0.74% Traditional ROI: 3.57%
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: -1.02% Traditional cash on cash: 0.27% Airbnb Rental Income: $909 Traditional Rental Income: $2964 Airbnb ROI: -1.02% 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: -0.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $824 Traditional Rental Income: $2345 Airbnb ROI: -0.54% Traditional ROI: 3.38%
BAYSIDE Road 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: -1.08% Traditional cash on cash: 0.29% Airbnb Rental Income: $909 Traditional Rental Income: $2785 Airbnb ROI: -1.08% Traditional ROI: 0.29%
40461 Old Breton Beach Rd Leonardtown, MD MOTIVATED SELLER! COME FALL IN LOVE WITH THE VIEW AND MAKE AN OFFER! Discover waterfront l...	2 beds \| 2 baths \| 2,040 sq.ft.	$650,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 2.89% Airbnb Rental Income: $859 Traditional Rental Income: $2941 Airbnb ROI: -1.09% Traditional ROI: 2.89%
19700 Mulberry Fields Rd Leonardtown, MD 19700 Mulberry Fields Rd, Leonardtown, MD 20650 \| Single Family Residential	6 beds \| 4 baths \| 13,458 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 Avenue Leonardtown, MD Back on the market with even more improvements and a new price! The sellers invested in ad...	4 beds \| 4 baths \| 2,097 sq.ft.	$774,900	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.12% Airbnb Rental Income: $909 Traditional Rental Income: $2063 Airbnb ROI: -0.95% 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%
DRAGONFLY Lane lot: 99 - 23725 Leonardtown, MD ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's prefer...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.02% Airbnb Rental Income: $909 Traditional Rental Income: $2300 Airbnb ROI: -0.09% Traditional ROI: 4.02%
DRAGONFLY Lane lot: 101 - 23713 Leonardtown, MD ***SPRING SPECIAL $5,000 Builder Credit Plus $12,500 in Closing Help with Builder's prefer...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.02% Airbnb Rental Income: $909 Traditional Rental Income: $2300 Airbnb ROI: -0.09% Traditional ROI: 4.02%
41377 DOCTORS CROSSING Road Leonardtown, MD NOW offered at $600,000 HUGE Price Adjustment!- a compelling opportunity in CLARK'S REST. ...	5 beds \| 4 baths \| 3,724 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.06% Airbnb Rental Income: $null Traditional Rental Income: $3038 Airbnb ROI: N/A Traditional ROI: 3.06%
0 Saint Andrews Church Rd Leonardtown, MD 0 Saint Andrews Church Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$98,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $620 Airbnb ROI: N/A Traditional ROI: 3.41%
22394 WHITE OAK Road Leonardtown, MD Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-b...	4 beds \| 3 baths \| 2,507 sq.ft.	$485,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 4.81% Airbnb Rental Income: $909 Traditional Rental Income: $3041 Airbnb ROI: -0.64% Traditional ROI: 4.81%
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%
WEEPING WILLOW Way lot: 135 - 23679 Leonardtown, MD *Mid-May Delivery* Builder Incentive, Receive $12,500 in Builder Closing Help with use...	4 beds \| 4 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 6.03% Airbnb Rental Income: $909 Traditional Rental Income: $3145 Airbnb ROI: -0.09% Traditional ROI: 6.03%
DRAGONFLY Lane lot: 141 - 23653 Leonardtown, MD TO BE BUILT Homesite 141 - Oakley D1 End Unit October Delivery* *Choose your...	4 beds \| 4 baths \| N/A	$479,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 4.46% Airbnb Rental Income: $909 Traditional Rental Income: $2638 Airbnb ROI: -0.15% Traditional ROI: 4.46%
18866 RUSSELL Road Leonardtown, MD *Rare Waterfront Opportunity* Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD...	3 beds \| 2 baths \| 1,128 sq.ft.	$450,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.4% Airbnb Rental Income: $824 Traditional Rental Income: $1897 Airbnb ROI: -0.93% Traditional ROI: 2.4%
DRAGONFLY Lane lot: 142 - 23647 Leonardtown, MD *TO BE BUILT* *November Delivery* ***Choose your color scheme from of our availabl...	4 beds \| 4 baths \| 3,095 sq.ft.	$489,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 6.27% Airbnb Rental Income: $909 Traditional Rental Income: $3519 Airbnb ROI: -0.17% Traditional ROI: 6.27%
43430 BROWNS Lane Leonardtown, MD Sellers are motivated and have found their home of choice. This unique property has so muc...	5 beds \| 5 baths \| 2,756 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.29% Airbnb Rental Income: $null Traditional Rental Income: $4722 Airbnb ROI: N/A Traditional ROI: 6.29%
WEEPING WILLOW Way lot: 111 - 23684 Leonardtown, MD Homesite #111 Madison D3: **May Delivery*Welcome to Meadows at Town Run.... Leonardtow...	4 beds \| 4 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 6.24% Airbnb Rental Income: $909 Traditional Rental Income: $3237 Airbnb ROI: -0.09% Traditional ROI: 6.24%
39577 POTOMAC Avenue Leonardtown, MD There are waterfront homes-and then there are waterfront escapes with million-dollar views...	4 beds \| 3 baths \| 3,412 sq.ft.	$839,900	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.78% Airbnb Rental Income: $909 Traditional Rental Income: $2021 Airbnb ROI: -1.07% Traditional ROI: 0.78%
22281 Nomoni St Leonardtown, MD 22281 Nomoni St, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,152 sq.ft.	$355,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 2.8% Airbnb Rental Income: $824 Traditional Rental Income: $1718 Airbnb ROI: -0.86% Traditional ROI: 2.8%
41249 BRENDA Court Leonardtown, MD Meticulously cared for rambler, fully updated and move in ready, on nearly one private , p...	3 beds \| 3 baths \| 3,098 sq.ft.	$669,900	Airbnb cash on cash: -1.08% Traditional cash on cash: 1.42% Airbnb Rental Income: $824 Traditional Rental Income: $2060 Airbnb ROI: -1.08% Traditional ROI: 1.42%
41585 AUSTIN Court Leonardtown, MD Welcome to the completely unforgettable curb appeal of this home situated in the only culd...	5 beds \| 3 baths \| 3,030 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 2.55%
41482 PENSIVE Street Leonardtown, MD Instant Equity! 5 Bed 3.5 Bath Colonial w/ a fully finished basement and a 2-car garage, b...	5 beds \| 4 baths \| 4,300 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $3843 Airbnb ROI: N/A Traditional ROI: 4.87%
42249 SAINT JOHNS Road Leonardtown, MD Charming and beautifully updated brick rancher located in the heart of Leonardtown! This s...	3 beds \| 2 baths \| 1,161 sq.ft.	$399,900	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.42% Airbnb Rental Income: $824 Traditional Rental Income: $1946 Airbnb ROI: -0.44% Traditional ROI: 3.42%
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: -1.46% Traditional cash on cash: 0.72% Airbnb Rental Income: $824 Traditional Rental Income: $1922 Airbnb ROI: -1.46% Traditional ROI: 0.72%
WEEPING WILLOW Way lot: 136 - 23673 Leonardtown, MD **Mid May Delivery* Homesite # 136 Madison D3: Welcome to Meadows at Town Run.... Leon...	4 beds \| 4 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 6% Airbnb Rental Income: $909 Traditional Rental Income: $3136 Airbnb ROI: -0.09% Traditional ROI: 6%
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 Road Leonardtown, MD Beautifully renovated rambler located in the highly desirable Leonardtown School District,...	3 beds \| 2 baths \| 1,144 sq.ft.	$399,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.76% Airbnb Rental Income: $824 Traditional Rental Income: $1675 Airbnb ROI: -0.38% Traditional ROI: 2.76%
42032 STARLIGHT Drive Leonardtown, MD PROFESSIONAL PICTURES COMING NEXT WEEK! Welcome to 42032 Starlight Drive in Leonardtown, M...	5 beds \| 4 baths \| 4,340 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3812 Airbnb ROI: N/A Traditional ROI: 4.35%

Real Estate investment in Leonardtown, MD

There are 42 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $479,900 and the average price per square foot is $170. In May 2026, the average monthly cash on cash return in Leonardtown is 3.00%. The average monthly rental income in Leonardtown is $2,469.

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

There are 42 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 $2,469.

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: -0.48%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $824

Traditional Rental Income: $2371

Airbnb ROI: -0.48%

Traditional ROI: 4.72%

20798 WATERSIDE Drive

Leonardtown, MD

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

$450,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $859

Traditional Rental Income: $1726

Airbnb ROI: -0.68%

Traditional ROI: 2.17%

41620 CHURCH Street

Leonardtown, MD

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

$399,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $824

Traditional Rental Income: $2111

Airbnb ROI: -0.74%

Traditional ROI: 3.57%

42520 RIVERWINDS Drive

Leonardtown, MD

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

$1,999,999

Airbnb cash on cash: -1.02%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $909

Traditional Rental Income: $2964

Airbnb ROI: -1.02%

Traditional ROI: 0.27%

20240 BIG OAK LN

Leonardtown, MD

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

$505,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $824

Traditional Rental Income: $2345

Airbnb ROI: -0.54%

Traditional ROI: 3.38%

BAYSIDE Road

Leonardtown, MD

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

$1,750,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $909

Traditional Rental Income: $2785

Airbnb ROI: -1.08%

Traditional ROI: 0.29%

40461 Old Breton Beach Rd

Leonardtown, MD

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

$650,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $859

Traditional Rental Income: $2941

Airbnb ROI: -1.09%

Traditional ROI: 2.89%

19700 Mulberry Fields Rd

Leonardtown, MD

6 beds | 4 baths | 13,458 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