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: 0.69% Traditional cash on cash: 4.72% Airbnb Rental Income: $1330 Traditional Rental Income: $2371 Airbnb ROI: 0.69% Traditional ROI: 4.72%
20798 WATERSIDE Drive Leonardtown, MD Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect...	2 beds \| 1 baths \| 1,018 sq.ft.	$450,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.17% Airbnb Rental Income: $2283 Traditional Rental Income: $1726 Airbnb ROI: 2.14% Traditional ROI: 2.17%
41535 SINGLETREE Drive Leonardtown, MD Welcome home to 41535 Singletree Dr. This beautiful colonial offers 4 bedrooms and 2.5 bat...	4 beds \| 3 baths \| 2,262 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $2986 Airbnb ROI: N/A Traditional ROI: 3.98%
23261 JENIFER Court Leonardtown, MD This Colonial in the sought-after Estates at Singletree offers 5 bedrooms, 3.5 baths, and ...	5 beds \| 4 baths \| 3,575 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $3728 Airbnb ROI: N/A Traditional ROI: 4.86%
21920 NEWTOWNE NECK Road Leonardtown, MD Welcome to 21920 Newtowne Neck Road! Step inside this inviting Colonial home offering 2,29...	4 beds \| 3 baths \| 2,291 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $2987 Airbnb ROI: N/A Traditional ROI: 4.18%
44504 WATSON Lane Leonardtown, MD This 3 bed, 2 bath Cape Cod in the Leonardtown district offers a comfortable secluded sett...	3 beds \| 2 baths \| 2,304 sq.ft.	$465,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.67% Airbnb Rental Income: $1330 Traditional Rental Income: $2514 Airbnb ROI: 0.01% Traditional ROI: 3.67%
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: 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: 0.36% Traditional cash on cash: 3.38% Airbnb Rental Income: $1330 Traditional Rental Income: $2345 Airbnb ROI: 0.36% Traditional ROI: 3.38%
40533 BRETON KNOLLS CT Leonardtown, MD TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spann...	4 beds \| 3 baths \| N/A	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $3042 Airbnb ROI: N/A Traditional ROI: 2.57%
18937 HODGES Lane Leonardtown, MD Are you dreaming of living on the water? This is your perfect opportunity! Well maintained...	3 beds \| 2 baths \| 1,834 sq.ft.	$659,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.51% Airbnb Rental Income: $1330 Traditional Rental Income: $2686 Airbnb ROI: -0.36% Traditional ROI: 2.51%
41810 CHELSEY FAYE Lane Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 4 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%
25365 POINT LOOKOUT Road Leonardtown, MD Unique property : Residential AND Commercial !!! The two story home has 3 bedrooms, one ba...	3 beds \| 3 baths \| 2,952 sq.ft.	$497,500	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.58% Airbnb Rental Income: $1330 Traditional Rental Income: $3021 Airbnb ROI: 0.06% Traditional ROI: 4.58%
20959 REDGATE Lane 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.	$229,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 5.82% Airbnb Rental Income: $1330 Traditional Rental Income: $1744 Airbnb ROI: 2.01% Traditional ROI: 5.82%
41430 CHALLEDON Way Leonardtown, MD Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sou...	5 beds \| 4 baths \| 4,500 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $3818 Airbnb ROI: N/A Traditional ROI: 4.06%
40461 OLD BRETON BEACH Road Leonardtown, MD Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with ...	2 beds \| 3 baths \| 2,040 sq.ft.	$689,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 2.67% Airbnb Rental Income: $2283 Traditional Rental Income: $2941 Airbnb ROI: 0.76% Traditional ROI: 2.67%
23264 LINDSAY Drive Leonardtown, MD Custom Floorplan Front Load Garage with expanded guest parking on driveway, Upgraded c...	3 beds \| 2 baths \| 2,824 sq.ft.	$599,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.5% Airbnb Rental Income: $1330 Traditional Rental Income: $2636 Airbnb ROI: -0.57% Traditional ROI: 2.5%
39825 SWEETPEA Lane Leonardtown, MD Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 fe...	4 beds \| 4 baths \| 2,442 sq.ft.	$730,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $3921 Airbnb ROI: N/A Traditional ROI: 3.98%
41650 MATTHEW Court Leonardtown, MD This home features 4 spacious Bedrooms, an open Kitchen & great room w/built-in TV Niche o...	4 beds \| 3 baths \| 2,230 sq.ft.	$520,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2873 Airbnb ROI: N/A Traditional ROI: 3.93%
42043 STARLIGHT Drive Leonardtown, MD Great opportunity to live in the coveted Kingston Subdivision! This classic Colonial has a...	4 beds \| 4 baths \| 2,472 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $3165 Airbnb ROI: N/A Traditional ROI: 4.11%
DRAGONFLY Lane lot: 103-23701 Leonardtown, MD *Under Construction*Builder Incentive, SETTLE IN 2025, Receive $10,000 in Builder Cred...	4 beds \| 4 baths \| N/A	$489,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $3580 Airbnb ROI: N/A Traditional ROI: 6.41%
21039 WOODMERE Drive Leonardtown, MD Nestled on a beautiful 1.17 acre lot in the Leonardtown neighborhood of Wilderness Run. Th...	5 beds \| 3 baths \| 4,112 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $3456 Airbnb ROI: N/A Traditional ROI: 4.51%
DRAGONFLY Lane lot: 107-23677 Leonardtown, MD ***QUICK DELIVERY INCENTIVE....SETTLE IN 2025 and receive $10,000 Builder Credit plus $12,...	4 beds \| 4 baths \| N/A	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.52% Airbnb Rental Income: $null Traditional Rental Income: $3562 Airbnb ROI: N/A Traditional ROI: 6.52%
DRAGONFLY Lane lot: 91-23694 Leonardtown, MD *Immediate Delivery*BUILDER SPECIAL: SETTLE IN 2025, Receive $6,000 in Builder Credit ...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $3561 Airbnb ROI: N/A Traditional ROI: 7.09%
DRAGONFLY Lane lot: 95-23718 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credi...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $3561 Airbnb ROI: N/A Traditional ROI: 7.09%
23098 TOWN RUN Drive Leonardtown, MD Built in 2022, this stunning QBH Adelina floor plan shows like brand new, complete with ev...	5 beds \| 4 baths \| 3,642 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 4.28%
DRAGONFLY Lane lot: 92-23700 Leonardtown, MD *Immediate Delivery*Builder Incentive, Settle in 2025, Receive $6,000 in Builder Credi...	4 beds \| 4 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $2653 Airbnb ROI: N/A Traditional ROI: 5.1%
40171 LITTLE WOODS Lane Leonardtown, MD Waterfront Retreat with Spectacular Sunsets Waterfront Retreat with Spectacular Sunsets. W...	4 beds \| 2 baths \| 2,586 sq.ft.	$880,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $2988 Airbnb ROI: N/A Traditional ROI: 1.96%
21117 CATNIP Court Leonardtown, MD Located on a quiet, no-through street in the desirable Kingston Estates community of Leona...	5 beds \| 4 baths \| 3,526 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $3778 Airbnb ROI: N/A Traditional ROI: 4.5%
21925 BUDDS CREEK Road Leonardtown, MD This is a large 3 bedrooms, 2 bath, and large sunroom on 2nd level home with large family ...	3 beds \| 2 baths \| 2,527 sq.ft.	$479,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.78% Airbnb Rental Income: $1330 Traditional Rental Income: $2511 Airbnb ROI: 0.22% Traditional ROI: 3.78%
45474 MEDLEYS NECK Road Leonardtown, MD Welcome to your retreat in The Valley, where every day feels like vacation! This gorgeous ...	3 beds \| 3 baths \| 2,653 sq.ft.	$650,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.43% Airbnb Rental Income: $1330 Traditional Rental Income: $3201 Airbnb ROI: -0.33% Traditional ROI: 3.43%
22539 LANDING Way Leonardtown, MD Live in this lovely waterfront community. Enjoy Kayaking, Paddle boarding whatever your ho...	3 beds \| 4 baths \| 2,764 sq.ft.	$520,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 4.22% Airbnb Rental Income: $1330 Traditional Rental Income: $3037 Airbnb ROI: -0.13% Traditional ROI: 4.22%
41832 FOXWELL POINT Lane Leonardtown, MD Professional Photos Coming Soon! OPEN HOUSE:SATURDAY, November 1st from 1:00-3:00 PM! Disc...	3 beds \| 4 baths \| 3,683 sq.ft.	$825,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 3.26% Airbnb Rental Income: $1330 Traditional Rental Income: $3967 Airbnb ROI: -0.7% Traditional ROI: 3.26%
43107 GUM SPRING Drive Leonardtown, MD Nestled in prestigious Chestnut Ridge, this exquisite Colonial home offers a harmonious bl...	3 beds \| 3 baths \| 2,742 sq.ft.	$625,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.2% Airbnb Rental Income: $1330 Traditional Rental Income: $2973 Airbnb ROI: -0.33% Traditional ROI: 3.2%

Real Estate investment in Leonardtown, MD

There are 33 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $559,900 and the average price per square foot is $212. In October 2025, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $3,021.

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

There are 33 investment properties available for sale in Leonardtown.

In 2025, 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 $1,330.

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: 0.69%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1330

Traditional Rental Income: $2371

Airbnb ROI: 0.69%

Traditional ROI: 4.72%

20798 WATERSIDE Drive

Leonardtown, MD

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

$450,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2283

Traditional Rental Income: $1726

Airbnb ROI: 2.14%

Traditional ROI: 2.17%

41535 SINGLETREE Drive

Leonardtown, MD

4 beds | 3 baths | 2,262 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2986

Airbnb ROI: N/A

Traditional ROI: 3.98%

23261 JENIFER Court

Leonardtown, MD

5 beds | 4 baths | 3,575 sq.ft.

$580,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3728

Airbnb ROI: N/A

Traditional ROI: 4.86%

21920 NEWTOWNE NECK Road

Leonardtown, MD

4 beds | 3 baths | 2,291 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2987

Airbnb ROI: N/A

Traditional ROI: 4.18%

44504 WATSON Lane

Leonardtown, MD

3 beds | 2 baths | 2,304 sq.ft.

$465,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1330

Traditional Rental Income: $2514

Airbnb ROI: 0.01%

Traditional ROI: 3.67%

42520 RIVERWINDS Drive

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: 0.36%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1330

Traditional Rental Income: $2345

Airbnb ROI: 0.36%