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

separator

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: 1.02% Traditional cash on cash: 4.72% Airbnb Rental Income: $1473 Traditional Rental Income: $2371 Airbnb ROI: 1.02% Traditional ROI: 4.72%
40624 Breton Oaks Ln Leonardtown, MD	N/A beds \| N/A baths \| N/A	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.31% Airbnb Rental Income: $null Traditional Rental Income: $1609 Airbnb ROI: N/A Traditional ROI: 8.31%
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: 0.61% Traditional cash on cash: 3.38% Airbnb Rental Income: $1473 Traditional Rental Income: $2345 Airbnb ROI: 0.61% 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: N/A Traditional cash on cash: 0.29% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 0.29%
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: -0.17% Traditional cash on cash: 2.51% Airbnb Rental Income: $1473 Traditional Rental Income: $2686 Airbnb ROI: -0.17% 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: 0.32% Traditional cash on cash: 4.58% Airbnb Rental Income: $1473 Traditional Rental Income: $3021 Airbnb ROI: 0.32% 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.	$199,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 6.82% Airbnb Rental Income: $1473 Traditional Rental Income: $1744 Airbnb ROI: 3.09% Traditional ROI: 6.82%
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.	$679,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $2941 Airbnb ROI: N/A Traditional ROI: 2.72%
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.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $3165 Airbnb ROI: N/A Traditional ROI: 4.3%
21117 CATNIP Court Leonardtown, MD Seller is offering a $4,000 concession with an accepted full-price offer! Use it for an in...	5 beds \| 4 baths \| 3,526 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.93% Airbnb Rental Income: $null Traditional Rental Income: $3778 Airbnb ROI: N/A Traditional ROI: 4.93%
43018 BLUEJAY Lane Leonardtown, MD Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in L...	4 beds \| 3 baths \| 2,888 sq.ft.	$640,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $3256 Airbnb ROI: N/A Traditional ROI: 3.45%
DRAGONFLY Lane lot: 104 - 23695 Leonardtown, MD *Immediate Delivery*Builder Incentive, READY- NOW Incentive, Receive $10,000 in Builde...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.97% Airbnb Rental Income: $null Traditional Rental Income: $2699 Airbnb ROI: N/A Traditional ROI: 4.97%
DRAGONFLY Lane lot: 106 - 23683 Leonardtown, MD *Immediate Delivery*READY-NOW Builder Incentive, Receive $10,000 in Builder Credit plu...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.06% Airbnb Rental Income: $null Traditional Rental Income: $3582 Airbnb ROI: N/A Traditional ROI: 7.06%
DRAGONFLY Lane lot: 105 - 23689 Leonardtown, MD *Immediate Delivery*READY-NOW Builder Incentive, Receive $10,000 in Builder Credit plu...	4 beds \| 4 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $2699 Airbnb ROI: N/A Traditional ROI: 4.78%
20753 CHESTNUT RIDGE Drive Leonardtown, MD Nestled within one of the most desirable subdivisions, this classic two-story Colonial wel...	4 beds \| 3 baths \| 2,594 sq.ft.	$564,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $3094 Airbnb ROI: N/A Traditional ROI: 3.88%
20260 HAWKS Way Leonardtown, MD IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new co...	4 beds \| 3 baths \| 2,500 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 4.18%
22547 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: -0.1% Traditional cash on cash: 4.01% Airbnb Rental Income: $1473 Traditional Rental Income: $3035 Airbnb ROI: -0.1% Traditional ROI: 4.01%
21345 FAIRWOOD Court Leonardtown, MD Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this mo...	5 beds \| 4 baths \| 4,080 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.87% Airbnb Rental Income: $null Traditional Rental Income: $3808 Airbnb ROI: N/A Traditional ROI: 3.87%
40736 CENTER 40 Circle Leonardtown, MD Charming Split Level home on just over 1/2 an acre in Breton Bay. As you enter the front d...	3 beds \| 3 baths \| 1,829 sq.ft.	$425,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 4.3% Airbnb Rental Income: $1473 Traditional Rental Income: $2501 Airbnb ROI: 0.63% Traditional ROI: 4.3%
23369 MARVIEW Court Leonardtown, MD Beautiful Clark's Rest townhome offering three finished levels, a two-car garage, and over...	3 beds \| 4 baths \| 2,308 sq.ft.	$435,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.77% Airbnb Rental Income: $1473 Traditional Rental Income: $2905 Airbnb ROI: 0.19% Traditional ROI: 4.77%

Real Estate investment in Leonardtown, MD

There are 27 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $449,900 and the average price per square foot is $180. In January 2026, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $2,796.

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

There are 27 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 $2,796.

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: 1.02%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $1473

Traditional Rental Income: $2371

Airbnb ROI: 1.02%

Traditional ROI: 4.72%

40624 Breton Oaks Ln

Leonardtown, MD

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

$159,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.31%

Airbnb Rental Income: $null

Traditional Rental Income: $1609

Airbnb ROI: N/A

Traditional ROI: 8.31%

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: 0.61%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1473

Traditional Rental Income: $2345

Airbnb ROI: 0.61%

Traditional ROI: 3.38%

BAYSIDE Road

Leonardtown, MD

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

$1,750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2785

Airbnb ROI: N/A

Traditional ROI: 0.29%

18937 HODGES Lane

Leonardtown, MD

3 beds | 2 baths | 1,834 sq.ft.

$659,000

Airbnb cash on cash: -0.17%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $1473

Traditional Rental Income: $2686

Airbnb ROI: -0.17%

Traditional ROI: 2.51%

41810 CHELSEY FAYE Lane

Leonardtown, MD

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

3 beds | 3 baths | 2,952 sq.ft.

$497,500

Airbnb cash on cash: 0.32%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $1473

Traditional Rental Income: $3021

Airbnb ROI: 0.32%