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.

Single Family Homes for Sale in Leonardtown, MD

Search for Single Family Residential for Sale in Leonardtown, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 53 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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.	$680,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.91% Airbnb Rental Income: $1823 Traditional Rental Income: $2434 Airbnb ROI: 0.17% Traditional ROI: 1.91%
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: 0.35% Traditional cash on cash: 2.17% Airbnb Rental Income: $1378 Traditional Rental Income: $1726 Airbnb ROI: 0.35% Traditional ROI: 2.17%
41427 Osborne Ln Leonardtown, MD AUGUST DELIVERY: Three Levels Finished. Hardwood at DR,Kitch&Foyer, SS Appliances w/Double...	4 beds \| 3 baths \| 3,264 sq.ft.	$650,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.06% Airbnb Rental Income: $1823 Traditional Rental Income: $2724 Airbnb ROI: 0.76% Traditional ROI: 3.06%
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.	$599,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.57% Airbnb Rental Income: $1823 Traditional Rental Income: $2798 Airbnb ROI: 0.95% Traditional ROI: 3.57%
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: 1.3% Traditional cash on cash: 3.69% Airbnb Rental Income: $1714 Traditional Rental Income: $2111 Airbnb ROI: 1.3% 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.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $3345 Airbnb ROI: N/A Traditional ROI: 3.45%
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.	$590,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 3.17% Airbnb Rental Income: $1823 Traditional Rental Income: $3063 Airbnb ROI: 0.02% Traditional ROI: 3.17%
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.	$629,900	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.66% Airbnb Rental Income: $1823 Traditional Rental Income: $2880 Airbnb ROI: 0.02% Traditional ROI: 2.66%
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: -0.61% Traditional cash on cash: 0.29% Airbnb Rental Income: $1823 Traditional Rental Income: $2785 Airbnb ROI: -0.61% Traditional ROI: 0.29%
40533 Breton Knolls Ct Leonardtown, MD TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spann...	4 beds \| 2 baths \| 3,460 sq.ft.	$739,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.14% Airbnb Rental Income: $1823 Traditional Rental Income: $3042 Airbnb ROI: 0.66% Traditional ROI: 3.14%
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.	$675,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.4% Airbnb Rental Income: $1714 Traditional Rental Income: $2686 Airbnb ROI: 0.11% Traditional ROI: 2.4%
23636 Hansel Ct Leonardtown, MD NEW PRICE!!Welcome home to 23636 Hansel Court! This stunning Leonardtown residence perfect...	5 beds \| 2 baths \| 4,836 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.11% Airbnb Rental Income: $null Traditional Rental Income: $3072 Airbnb ROI: N/A Traditional ROI: 3.11%
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%
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.	$723,997	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.26% Airbnb Rental Income: $1823 Traditional Rental Income: $2063 Airbnb ROI: 0.18% Traditional ROI: 1.26%
20270 Beauvue Ct Leonardtown, MD 20270 Beauvue Ct, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 4 baths \| 2,666 sq.ft.	$444,500	Airbnb cash on cash: 0.89% Traditional cash on cash: 4.22% Airbnb Rental Income: $1823 Traditional Rental Income: $2714 Airbnb ROI: 0.89% Traditional ROI: 4.22%
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.	$364,900	Airbnb cash on cash: 1.78% Traditional cash on cash: 3.84% Airbnb Rental Income: $1714 Traditional Rental Income: $1946 Airbnb ROI: 1.78% Traditional ROI: 3.84%
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%
Lot 3 - 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: -0.07% Traditional cash on cash: 1.7% Airbnb Rental Income: $1823 Traditional Rental Income: $2342 Airbnb ROI: -0.07% Traditional ROI: 1.7%
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.	$439,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.2% Airbnb Rental Income: $1823 Traditional Rental Income: $2222 Airbnb ROI: 1.03% Traditional ROI: 3.2%
Lot 7 - 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: -0.11% Traditional cash on cash: 1.61% Airbnb Rental Income: $1823 Traditional Rental Income: $2342 Airbnb ROI: -0.11% Traditional ROI: 1.61%
Lot 5 - 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: -0.08% Traditional cash on cash: 1.67% Airbnb Rental Income: $1823 Traditional Rental Income: $2342 Airbnb ROI: -0.08% Traditional ROI: 1.67%
Lot 4 - 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: -0.05% Traditional cash on cash: 1.63% Airbnb Rental Income: $1823 Traditional Rental Income: $2288 Airbnb ROI: -0.05% Traditional ROI: 1.63%
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.	$449,900	Airbnb cash on cash: 1.02% Traditional cash on cash: 2.8% Airbnb Rental Income: $1714 Traditional Rental Income: $1989 Airbnb ROI: 1.02% Traditional ROI: 2.8%
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: 0.3% Traditional cash on cash: 2.22% Airbnb Rental Income: $1823 Traditional Rental Income: $2454 Airbnb ROI: 0.3% Traditional ROI: 2.22%
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.	$560,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.33% Airbnb Rental Income: $1823 Traditional Rental Income: $2667 Airbnb ROI: 0.78% Traditional ROI: 3.33%
23214 Dairy Barn Dr Leonardtown, MD Located in Clark's Rest, this home features Marrick's Kensington floor plan, with a covere...	5 beds \| 3 baths \| 4,084 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $2724 Airbnb ROI: N/A Traditional ROI: 2.06%
42163 Blacksmith Shop Rd Leonardtown, MD Over 1/2 Acre \| No HOA \| One-Level Living: Set on a level 0.60-acre lot, this home offers ...	3 beds \| 1 baths \| 1,218 sq.ft.	$299,500	Airbnb cash on cash: 2.37% Traditional cash on cash: 3.48% Airbnb Rental Income: $1714 Traditional Rental Income: $1553 Airbnb ROI: 2.37% Traditional ROI: 3.48%
41402 Omaha Ct Leonardtown, MD 41402 Omaha Ct, Leonardtown, MD 20650 \| Single Family Residential	5 beds \| 4 baths \| 4,873 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $3044 Airbnb ROI: N/A Traditional ROI: 1.92%
40579 Port Pl Leonardtown, MD 40579 Port Pl, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 2,304 sq.ft.	$750,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 0.73% Airbnb Rental Income: $1714 Traditional Rental Income: $2062 Airbnb ROI: -0.44% Traditional ROI: 0.73%
44450 Schumann Way Leonardtown, MD 44450 Schumann Way, Leonardtown, MD 20650 \| Single Family Residential	5 beds \| 2 baths \| 2,953 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.57% Airbnb Rental Income: $null Traditional Rental Income: $2391 Airbnb ROI: N/A Traditional ROI: 1.57%
41888 Jenkins Ct Leonardtown, MD 41888 Jenkins Ct, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 3 baths \| 2,562 sq.ft.	$535,000	Airbnb cash on cash: 0.35% Traditional cash on cash: 2.71% Airbnb Rental Income: $1823 Traditional Rental Income: $2508 Airbnb ROI: 0.35% Traditional ROI: 2.71%
22601 Avenmar Dr Leonardtown, MD 22601 Avenmar Dr, Leonardtown, MD 20650 \| Single Family Residential	5 beds \| 4 baths \| 5,484 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 2.23%
40611 Merion Ct Leonardtown, MD 40611 Merion Ct, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 3 baths \| 2,562 sq.ft.	$624,990	Airbnb cash on cash: -0.01% Traditional cash on cash: 2.27% Airbnb Rental Income: $1823 Traditional Rental Income: $2661 Airbnb ROI: -0.01% Traditional ROI: 2.27%
The Clarke Plan Leonardtown, MD The Clarke Plan, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 3,072 sq.ft.	$629,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.44% Airbnb Rental Income: $1823 Traditional Rental Income: $2244 Airbnb ROI: -0.11% Traditional ROI: 1.44%
The Bell Plan Leonardtown, MD The Bell Plan, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 2,878 sq.ft.	$619,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.49% Airbnb Rental Income: $1823 Traditional Rental Income: $2238 Airbnb ROI: -0.08% Traditional ROI: 1.49%
The Mattingly Plan Leonardtown, MD The Mattingly Plan, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 2,701 sq.ft.	$609,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.48% Airbnb Rental Income: $1823 Traditional Rental Income: $2200 Airbnb ROI: -0.05% Traditional ROI: 1.48%
The Fenwick Plan Leonardtown, MD The Fenwick Plan, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 2,595 sq.ft.	$614,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.17% Airbnb Rental Income: $1714 Traditional Rental Income: $2040 Airbnb ROI: -0.22% Traditional ROI: 1.17%

Your search for investment property begins and ends here

Single Family Homes for Sale in Leonardtown, MD

21395 Fairwood Ct

Leonardtown, MD

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

$680,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $1823

Traditional Rental Income: $2434

Airbnb ROI: 0.17%

Traditional ROI: 1.91%

20798 Waterside Dr

Leonardtown, MD

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

$450,000

Airbnb cash on cash: 0.35%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1378

Traditional Rental Income: $1726

Airbnb ROI: 0.35%

Traditional ROI: 2.17%

41427 Osborne Ln

Leonardtown, MD

4 beds | 3 baths | 3,264 sq.ft.

$650,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $1823

Traditional Rental Income: $2724

Airbnb ROI: 0.76%

Traditional ROI: 3.06%

23354 Lindsay Dr

Leonardtown, MD

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

$599,900

Airbnb cash on cash: 0.95%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1823

Traditional Rental Income: $2798

Airbnb ROI: 0.95%

Traditional ROI: 3.57%

41620 Church St

Leonardtown, MD

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

$389,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $1714

Traditional Rental Income: $2111

Airbnb ROI: 1.3%

Traditional ROI: 3.69%

40751 Merlin Way

Leonardtown, MD

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

$615,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3345

Airbnb ROI: N/A

Traditional ROI: 3.45%

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.

$590,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $1823

Traditional Rental Income: $3063

Airbnb ROI: 0.02%