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
21395 Fairwood Ct Leonardtown, MD Welcome to 21395 Fairwood Ct., where space, comfort, and community come together on 0.85 a...	4 beds \| 3 baths \| 4,066 sq.ft.	$690,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 1.87% Airbnb Rental Income: $1859 Traditional Rental Income: $2434 Airbnb ROI: 0.2% Traditional ROI: 1.87%
20798 Waterside Dr 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: -0.09% Traditional cash on cash: 2.17% Airbnb Rental Income: $1155 Traditional Rental Income: $1726 Airbnb ROI: -0.09% Traditional ROI: 2.17%
23354 Lindsay Dr Leonardtown, MD Under contract to be built Lusby #2 home at Clarks Rest by Marrick Homes in Leonardtown. T...	4 beds \| 3 baths \| 2,736 sq.ft.	$609,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.49% Airbnb Rental Income: $1859 Traditional Rental Income: $2798 Airbnb ROI: 0.97% Traditional ROI: 3.49%
41620 Church St 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.	$389,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.69% Airbnb Rental Income: $1487 Traditional Rental Income: $2111 Airbnb ROI: 0.78% Traditional ROI: 3.69%
40751 Merlin Way Leonardtown, MD Welcome to this beautiful brick-front home in the highly sought-after Avenmar Community of...	5 beds \| 2 baths \| 2,601 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $3345 Airbnb ROI: N/A Traditional ROI: 3.31%
23011 Newtowne Neck Rd Leonardtown, MD Attention Developers or Land Loving Owner Occupants!! Welcome to 23011 Newtowne Neck Road ...	5 beds \| 2 baths \| 1,552 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $2011 Airbnb ROI: N/A Traditional ROI: 4.13%
41524 Fairwood Ct Leonardtown, MD Looking for a ranch-style floor plan? Put the Arlington at the top of your list! This smar...	4 beds \| 3 baths \| 3,793 sq.ft.	$600,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 3.08% Airbnb Rental Income: $1859 Traditional Rental Income: $3063 Airbnb ROI: 0.04% Traditional ROI: 3.08%
23444 Lindsay Dr Leonardtown, MD ASK ABOUT SPECIAL FINANCING! Discover this notable Hemingway home, ready for quick move-i...	4 beds \| 3 baths \| 3,340 sq.ft.	$639,900	Airbnb cash on cash: 0.06% Traditional cash on cash: 2.6% Airbnb Rental Income: $1859 Traditional Rental Income: $2880 Airbnb ROI: 0.06% Traditional ROI: 2.6%
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: -0.59% Traditional cash on cash: 0.29% Airbnb Rental Income: $1859 Traditional Rental Income: $2785 Airbnb ROI: -0.59% Traditional ROI: 0.29%
18937 Hodges Ln Leonardtown, MD If you've been dreaming of waterfront living, now is your chance. Whether you enjoy boatin...	3 beds \| 2 baths \| 1,834 sq.ft.	$699,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.28% Airbnb Rental Income: $1487 Traditional Rental Income: $2686 Airbnb ROI: -0.22% Traditional ROI: 2.28%
23636 Hansel Ct Leonardtown, MD NEW PRICE!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfect...	4 beds \| 2 baths \| 4,836 sq.ft.	$610,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 3.18% Airbnb Rental Income: $1859 Traditional Rental Income: $3072 Airbnb ROI: 0.17% Traditional ROI: 3.18%
19700 Mulberry Fields Rd Leonardtown, MD 19700 Mulberry Fields Rd, Leonardtown, MD 20650 \| Single Family Residential	6 beds \| 4 baths \| 5,500 sq.ft.	$15,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.77% Airbnb Rental Income: $null Traditional Rental Income: $4446 Airbnb ROI: N/A Traditional ROI: -1.77%
43488 Medleys Neck Rd Leonardtown, MD 43488 Medleys Neck Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$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%
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 Ave Leonardtown, MD Experience waterfront living at its finest in this beautifully renovated home overlooking ...	4 beds \| 2 baths \| 2,097 sq.ft.	$738,997	Airbnb cash on cash: 0.2% Traditional cash on cash: 1.22% Airbnb Rental Income: $1859 Traditional Rental Income: $2063 Airbnb ROI: 0.2% Traditional ROI: 1.22%
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%
42249 Saint Johns Rd Leonardtown, MD THIS PROPERTY IS FOR SALE ONLY AND IS NOT FOR RENT. BEWARE OF SCAMMERS-ANY RENTAL ADVERTIS...	3 beds \| 1 baths \| 1,161 sq.ft.	$374,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.71% Airbnb Rental Income: $1487 Traditional Rental Income: $1946 Airbnb ROI: 1.17% Traditional ROI: 3.71%
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%
Lot 140 - 23659 Dragonfly Ln Leonardtown, MD ALMOST READY*Estimated Late October DeliveryUnder Construction* Welcome to the Mad...	4 beds \| 3 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: 1.79% Traditional cash on cash: 6.22% Airbnb Rental Income: $1859 Traditional Rental Income: $3226 Airbnb ROI: 1.79% Traditional ROI: 6.22%
Lot 156 - 23634 Dragonfly Ln Leonardtown, MD ****December delivery, with a beautiful lot backing to trees for added privacy and a peace...	4 beds \| 3 baths \| 2,554 sq.ft.	$454,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 6.13% Airbnb Rental Income: $1859 Traditional Rental Income: $3221 Airbnb ROI: 1.76% Traditional ROI: 6.13%
Whirlwind Rd Leonardtown, MD Whirlwind Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$288,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.11% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: 0.11%
Lot 157 - 23640 Dragonfly Ln Leonardtown, MD **** December delivery, with a beautiful lot backing to trees for added privacy and a peac...	4 beds \| 3 baths \| 2,571 sq.ft.	$454,900	Airbnb cash on cash: 1.76% Traditional cash on cash: 6.12% Airbnb Rental Income: $1859 Traditional Rental Income: $3217 Airbnb ROI: 1.76% Traditional ROI: 6.12%
42700 Moll Dyer Rd Leonardtown, MD 42700 Moll Dyer Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $684 Airbnb ROI: N/A Traditional ROI: 0.09%
40115 Combs Creek Way Leonardtown, MD Welcome to an extraordinary waterfront experience in the Rosebank community of Leonardtown...	5 beds \| 3 baths \| 2,993 sq.ft.	$1,590,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $5003 Airbnb ROI: N/A Traditional ROI: 1.81%
42108 Wildflower Dr Leonardtown, MD New Single-Family Home Opportunity in Meadows at Town Run II! Welcome to Lot 3, featuring ...	4 beds \| 2 baths \| 3,072 sq.ft.	$614,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.7% Airbnb Rental Income: $1859 Traditional Rental Income: $2342 Airbnb ROI: -0.01% Traditional ROI: 1.7%
40777 CENTER 40 Circle Leonardtown, MD NEW PRICE - $524,900! If you've been waiting for the right opportunity to make your move t...	4 beds \| 3 baths \| 2,370 sq.ft.	$524,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 2.68% Airbnb Rental Income: $1859 Traditional Rental Income: $2217 Airbnb ROI: 0.93% Traditional ROI: 2.68%
18800 Mckays Beach Rd Leonardtown, MD This 1,600+ square foot cottage offers the ultimate foundation for your custom coastal ret...	3 beds \| 2 baths \| 1,667 sq.ft.	$350,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.46% Airbnb Rental Income: $1487 Traditional Rental Income: $1932 Airbnb ROI: 0.78% Traditional ROI: 3.46%
40659 Klear Ct Leonardtown, MD Buyers, come take a look. The estate just dropped the price by $10,000 . This is an estate...	4 beds \| 2 baths \| 2,774 sq.ft.	$449,500	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.1% Airbnb Rental Income: $1859 Traditional Rental Income: $2222 Airbnb ROI: 1.05% Traditional ROI: 3.1%
42084 Wildflower Dr Leonardtown, MD To-Be-Built Opportunity in Meadows at Town Run II! Welcome to Lot 7, featuring Quality Bui...	4 beds \| 2 baths \| 3,072 sq.ft.	$629,900	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.61% Airbnb Rental Income: $1859 Traditional Rental Income: $2342 Airbnb ROI: -0.06% Traditional ROI: 1.61%
42096 Wildflower Dr Leonardtown, MD Limited New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 5, featuring Q...	4 beds \| 2 baths \| 2,976 sq.ft.	$619,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.67% Airbnb Rental Income: $1859 Traditional Rental Income: $2342 Airbnb ROI: -0.03% Traditional ROI: 1.67%
42102 Wildflower Dr Leonardtown, MD New Home Opportunity in Meadows at Town Run II! Welcome to Homesite 4, featuring Quality B...	4 beds \| 2 baths \| 2,701 sq.ft.	$609,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $1859 Traditional Rental Income: $2288 Airbnb ROI: N/A Traditional ROI: 1.63%
23591 Margrave Dr Leonardtown, MD Welcome to this home in the desirable Leonard's Grant community, tucked toward the back of...	5 beds \| 3 baths \| 4,051 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.22% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 2.22%
Parcel 323 Tract 2 Washington St Leonardtown, MD Parcel 323 Tract 2 Washington St, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.49% Airbnb Rental Income: $null Traditional Rental Income: $687 Airbnb ROI: N/A Traditional ROI: -0.49%
23628 Belmar Dr Leonardtown, MD Welcome to this exceptional home in the sought-after Leonard's Grant community, where time...	5 beds \| 3 baths \| 4,834 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $2680 Airbnb ROI: N/A Traditional ROI: 1.81%
43954 Main Way Rd Leonardtown, MD Set on a level, open corner lot with a small view of the Potomac River-and best of all, **...	3 beds \| 3 baths \| 1,691 sq.ft.	$469,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 2.64% Airbnb Rental Income: $1487 Traditional Rental Income: $1989 Airbnb ROI: 0.51% Traditional ROI: 2.64%
41462 Culpepper Way Leonardtown, MD Welcome home to this beautifully refreshed home in the sought-after Leonard's Grant commun...	4 beds \| 3 baths \| 3,314 sq.ft.	$624,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 2.22% Airbnb Rental Income: $1859 Traditional Rental Income: $2454 Airbnb ROI: 0.35% Traditional ROI: 2.22%
41650 Miss Bessie Dr Leonardtown, MD 41650 Miss Bessie Dr, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $685 Airbnb ROI: N/A Traditional ROI: 1.92%
23620 Gunnell Dr Leonardtown, MD 23620 Gunnell Dr, Leonardtown, MD 20650 \| Single Family Residential	5 beds \| 4 baths \| 4,346 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $3013 Airbnb ROI: N/A Traditional ROI: 2.97%
22010 Society Hill Rd Leonardtown, MD Welcome to this beautifully updated home in popular Breton Bay! As you arrive, you'll appr...	4 beds \| 3 baths \| 2,730 sq.ft.	$575,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.22% Airbnb Rental Income: $1859 Traditional Rental Income: $2667 Airbnb ROI: 0.79% Traditional ROI: 3.22%
21365 Bogies Ln Leonardtown, MD 21365 Bogies Ln, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.02% Airbnb Rental Income: $null Traditional Rental Income: $684 Airbnb ROI: N/A Traditional ROI: 0.02%

Real Estate investment in Leonardtown, MD

There are 66 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $498,352 and the average price per square foot is $166. In September 2026, the average monthly cash on cash return in Leonardtown is 2.00%. The average monthly rental income in Leonardtown is $2,454.

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

There are 66 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 $2,454.

Your search for investment property begins and ends here

Investment Property for Sale in Leonardtown, MD

21395 Fairwood Ct

Leonardtown, MD

4 beds | 3 baths | 4,066 sq.ft.

$690,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $1859

Traditional Rental Income: $2434

Airbnb ROI: 0.2%

Traditional ROI: 1.87%

20798 Waterside Dr

Leonardtown, MD

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

$450,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1155

Traditional Rental Income: $1726

Airbnb ROI: -0.09%

Traditional ROI: 2.17%

23354 Lindsay Dr

Leonardtown, MD

4 beds | 3 baths | 2,736 sq.ft.

$609,900

Airbnb cash on cash: 0.97%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1859

Traditional Rental Income: $2798

Airbnb ROI: 0.97%

Traditional ROI: 3.49%

41620 Church St

Leonardtown, MD

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

$389,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $1487

Traditional Rental Income: $2111

Airbnb ROI: 0.78%

Traditional ROI: 3.69%

40751 Merlin Way

Leonardtown, MD

5 beds | 2 baths | 2,601 sq.ft.

$635,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3345

Airbnb ROI: N/A

Traditional ROI: 3.31%

23011 Newtowne Neck Rd

Leonardtown, MD

5 beds | 2 baths | 1,552 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2011

Airbnb ROI: N/A

Traditional ROI: 4.13%

41524 Fairwood Ct

Leonardtown, MD

4 beds | 3 baths | 3,793 sq.ft.

$600,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $1859

Traditional Rental Income: $3063

Airbnb ROI: 0.04%

Traditional ROI: 3.08%

23444 Lindsay Dr

Leonardtown, MD

4 beds | 3 baths | 3,340 sq.ft.

$639,900

Airbnb cash on cash: 0.06%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $1859

Traditional Rental Income: $2880

Airbnb ROI: 0.06%