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: 1.71% Traditional cash on cash: 4.72% Airbnb Rental Income: $1770 Traditional Rental Income: $2371 Airbnb ROI: 1.71% 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: -0.32% Traditional cash on cash: 2.17% Airbnb Rental Income: $1041 Traditional Rental Income: $1726 Airbnb ROI: -0.32% Traditional ROI: 2.17%
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: 1.13% Traditional cash on cash: 3.38% Airbnb Rental Income: $1770 Traditional Rental Income: $2345 Airbnb ROI: 1.13% 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: -0.83% Traditional cash on cash: 0.29% Airbnb Rental Income: $1388 Traditional Rental Income: $2785 Airbnb ROI: -0.83% 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: -0.84% Traditional cash on cash: 2.89% Airbnb Rental Income: $1041 Traditional Rental Income: $2941 Airbnb ROI: -0.84% 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 Experience waterfront living at its finest in this beautifully renovated home overlooking ...	4 beds \| 4 baths \| 2,097 sq.ft.	$774,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.12% Airbnb Rental Income: $1388 Traditional Rental Income: $2063 Airbnb ROI: -0.4% 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%
WEEPING WILLOW Way lot: 135 - 23679 Leonardtown, MD *Available Now* Builder Incentive, Receive $12,500 in Builder Closing Help with use of...	4 beds \| 4 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.03% Airbnb Rental Income: $1388 Traditional Rental Income: $3145 Airbnb ROI: 0.86% Traditional ROI: 6.03%
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: 0.95% Traditional cash on cash: 2.4% Airbnb Rental Income: $1770 Traditional Rental Income: $1897 Airbnb ROI: 0.95% Traditional ROI: 2.4%
WEEPING WILLOW Way lot: 111 - 23684 Leonardtown, MD BUILDER INCENTIVE: Receive $12,500 in Closing Help or Rate Buydown with use of Builder's P...	4 beds \| 4 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.24% Airbnb Rental Income: $1388 Traditional Rental Income: $3237 Airbnb ROI: 0.86% Traditional ROI: 6.24%
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: 1.5% Traditional cash on cash: 2.8% Airbnb Rental Income: $1770 Traditional Rental Income: $1718 Airbnb ROI: 1.5% Traditional ROI: 2.8%
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.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $3843 Airbnb ROI: N/A Traditional ROI: 5.02%
42249 SAINT JOHNS Road Leonardtown, MD The required verbiage below shall take the place of the MLS Advisory Task verbiage. This P...	3 beds \| 2 baths \| 1,161 sq.ft.	$384,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 3.59% Airbnb Rental Income: $1770 Traditional Rental Income: $1946 Airbnb ROI: 1.76% 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: -0.26% Traditional cash on cash: 0.72% Airbnb Rental Income: $1770 Traditional Rental Income: $1922 Airbnb ROI: -0.26% 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 Road Leonardtown, MD OWNER FINANCING AVAILABLE, no banks, call for details. Beautifully renovated rambler locat...	3 beds \| 2 baths \| 1,144 sq.ft.	$395,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.8% Airbnb Rental Income: $1770 Traditional Rental Income: $1675 Airbnb ROI: 1.75% Traditional ROI: 2.8%
DRAGONFLY Lane lot: 140 - 23659 Leonardtown, MD *Estimated Late October DeliveryTo Be Built* Welcome to the Madison D2, a spacious...	4 beds \| 4 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 6.22% Airbnb Rental Income: $1388 Traditional Rental Income: $3226 Airbnb ROI: 0.86% Traditional ROI: 6.22%
DRAGONFLY Lane lot: 156 - 23634 Leonardtown, MD ***** Hurry in! Secure your new home now and personalize it with your choice of interior c...	4 beds \| 4 baths \| 2,554 sq.ft.	$454,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 6.13% Airbnb Rental Income: $1388 Traditional Rental Income: $3221 Airbnb ROI: 0.84% Traditional ROI: 6.13%
41600 MISS BESSIE DR Leonardtown, MD Brick-front one-level rambler featuring 3 bedrooms, 2 full bathrooms, and over 1,900 finis...	3 beds \| 2 baths \| N/A	$428,799	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.42% Airbnb Rental Income: $1770 Traditional Rental Income: $2231 Airbnb ROI: 1.06% Traditional ROI: 3.42%
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%
DRAGONFLY Lane lot: 157 - 23640 Leonardtown, MD Hurry in! Secure your new home now and personalize it with your choice of interior colors....	4 beds \| 4 baths \| 2,571 sq.ft.	$454,900	Airbnb cash on cash: 0.84% Traditional cash on cash: 6.12% Airbnb Rental Income: $1388 Traditional Rental Income: $3217 Airbnb ROI: 0.84% 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: 0.47% Traditional cash on cash: 3.99% Airbnb Rental Income: $1388 Traditional Rental Income: $2173 Airbnb ROI: 0.47% 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: 0.86% Traditional cash on cash: 4.55% Airbnb Rental Income: $1388 Traditional Rental Income: $2524 Airbnb ROI: 0.86% 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: -0.19% Traditional cash on cash: 3.5% Airbnb Rental Income: $1388 Traditional Rental Income: $2524 Airbnb ROI: -0.19% Traditional ROI: 3.5%
WEEPING WILLOW Way lot: 114 - 23702 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: 0.86% Traditional cash on cash: 4.55% Airbnb Rental Income: $1388 Traditional Rental Income: $2524 Airbnb ROI: 0.86% Traditional ROI: 4.55%
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%

Real Estate investment in Leonardtown, MD

There are 43 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $499,642 and the average price per square foot is $180. In June 2026, the average monthly cash on cash return in Leonardtown is 3.00%. The average monthly rental income in Leonardtown is $2,517.

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

There are 43 investment properties available for sale in Leonardtown.

In 2026, the best neighborhood to buy investment property is Leonardtown.

The ROI for Short-Term is higher than the Long-Term in Leonardtown with average rental income of $1,388.

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: 1.71%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1770

Traditional Rental Income: $2371

Airbnb ROI: 1.71%

Traditional ROI: 4.72%

20798 WATERSIDE Drive

Leonardtown, MD

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

$450,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1041

Traditional Rental Income: $1726

Airbnb ROI: -0.32%

Traditional ROI: 2.17%

20240 BIG OAK LN

Leonardtown, MD

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

$505,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1770

Traditional Rental Income: $2345

Airbnb ROI: 1.13%

Traditional ROI: 3.38%

BAYSIDE Road

Leonardtown, MD

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

$1,750,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $1388

Traditional Rental Income: $2785

Airbnb ROI: -0.83%

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: -0.84%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $1041

Traditional Rental Income: $2941

Airbnb ROI: -0.84%

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

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