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: 1.02% Traditional cash on cash: 4.72% Airbnb Rental Income: $1473 Traditional Rental Income: $2371 Airbnb ROI: 1.02% Traditional ROI: 4.72%
41516 Marwood Cir Leonardtown, MD Welcome to this stunning better than new 2-year young town home located in the highly soug...	3 beds \| 3 baths \| 2,402 sq.ft.	$437,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.9% Airbnb Rental Income: $1473 Traditional Rental Income: $2479 Airbnb ROI: 0.38% Traditional ROI: 3.9%
42520 Riverwinds Dr 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 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: N/A Traditional cash on cash: 0.29% Airbnb Rental Income: $null Traditional Rental Income: $2785 Airbnb ROI: N/A Traditional ROI: 0.29%
41810 Chelsey Faye Ln Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 2 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%
20959 Redgate Ln 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.	$189,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 7.22% Airbnb Rental Income: $1473 Traditional Rental Income: $1744 Airbnb ROI: 3.3% Traditional ROI: 7.22%
40461 Old Breton Beach Rd Leonardtown, MD Discover waterfront living at its finest with this charming 2-bedroom, 2.5-bath home with ...	2 beds \| 2 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%
43018 Bluejay Ln Leonardtown, MD Price Reduced on this beautiful colonial home in the Meadows of Town Run neighborhood in L...	4 beds \| 2 baths \| 2,888 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $3256 Airbnb ROI: N/A Traditional ROI: 3.49%
Lot 104 - 23695 Dragonfly Ln Leonardtown, MD *Immediate Delivery*Builder Incentive, READY- NOW Incentive, Receive $10,000 in Builde...	4 beds \| 3 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%
lot 106 - 23683 Dragonfly Ln Leonardtown, MD *Immediate Delivery*READY-NOW Builder Incentive, Receive $10,000 in Builder Credit plu...	4 beds \| 3 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%
Lot 105 - 23689 Dragonfly Ln Leonardtown, MD *Immediate Delivery*READY-NOW Builder Incentive, Receive $10,000 in Builder Credit plu...	4 beds \| 3 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%
20260 Hawks Way Leonardtown, MD IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new co...	4 beds \| 2 baths \| 2,500 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $3070 Airbnb ROI: N/A Traditional ROI: 4.35%
21345 Fairwood Ct Leonardtown, MD Welcome to 21345 Fairwood Court! Thoughtfully updated and meticulously maintained, this mo...	5 beds \| 3 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%
22615 Washington St Leonardtown, MD 22615 Washington St, Leonardtown, MD 20650 \| Single Family Residential	N/A beds \| N/A baths \| 1,691 sq.ft.	$599,950	Airbnb cash on cash: N/A Traditional cash on cash: -0.06% Airbnb Rental Income: $null Traditional Rental Income: $1226 Airbnb ROI: N/A Traditional ROI: -0.06%
22393 Saint Clements Ave Leonardtown, MD Experience refined waterfront living in this completely renovated rancher overlooking Sain...	4 beds \| 2 baths \| 2,097 sq.ft.	$778,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $2063 Airbnb ROI: N/A Traditional ROI: 1.11%
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%
Lot 102 - 23707 Dragonfly Ln Leonardtown, MD Lot 102- 23707 Dragonfly Ln, Leonardtown, MD 20650 \| Townhouse	4 beds \| 3 baths \| N/A	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.66% Airbnb Rental Income: $null Traditional Rental Income: $2300 Airbnb ROI: N/A Traditional ROI: 2.66%
Lot 100 - 23719 Dragonfly Ln Leonardtown, MD Lot 100 - 23719 Dragonfly Ln, Leonardtown, MD 20650 \| Townhouse	4 beds \| 3 baths \| 2,571 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.32% Airbnb Rental Income: $null Traditional Rental Income: $2447 Airbnb ROI: N/A Traditional ROI: 3.32%
41438 Silver Charm Ct Leonardtown, MD	5 beds \| 3 baths \| 4,180 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $2618 Airbnb ROI: N/A Traditional ROI: 1.69%
Lot 99 - 23725 Dragonfly Ln Leonardtown, MD Lot 99 - 23725 Dragonfly Ln, Leonardtown, MD 20650 \| Townhouse	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $2300 Airbnb ROI: N/A Traditional ROI: 2.97%
Lot 101 - 23713 Dragonfly Ln Leonardtown, MD Lot 101 - 23713 Dragonfly Ln, Leonardtown, MD 20650 \| Townhouse	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $2300 Airbnb ROI: N/A Traditional ROI: 2.97%

Real Estate investment in Leonardtown, MD

There are 39 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 $183. In March 2026, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $2,598.

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

There are 39 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 $2,598.

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%

41516 Marwood Cir

Leonardtown, MD

3 beds | 3 baths | 2,402 sq.ft.

$437,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1473

Traditional Rental Income: $2479

Airbnb ROI: 0.38%

Traditional ROI: 3.9%

42520 Riverwinds Dr

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 Rd

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%

41810 Chelsey Faye Ln

Leonardtown, MD

4 beds | 2 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%

20959 Redgate Ln

Leonardtown, MD

3 beds | 1 baths | 1,026 sq.ft.

$189,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 7.22%

Airbnb Rental Income: $1473

Traditional Rental Income: $1744

Airbnb ROI: 3.3%

Traditional ROI: 7.22%

40461 Old Breton Beach Rd

Leonardtown, MD

2 beds | 2 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