Real Estate Investments for Sale in Leonardtown, MD With High ROI

Are you looking for a vacation rental in Leonardtown, MD? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $2177 Airbnb ROI: N/A Traditional ROI: 4.18%
41815 CHELSEY FAYE Leonardtown, MD Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home is a modestly sized one...	3 beds \| 2 baths \| 1,627 sq.ft.	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2340 Airbnb ROI: N/A Traditional ROI: 3.38%
42520 RIVERWINDS DRIVE Leonardtown, MD Looking for elbow room? Look no further. LOTS of land here! Property borders Potomac Ri...	4 beds \| 2 baths \| 2,744 sq.ft.	$2,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.18% Airbnb Rental Income: $null Traditional Rental Income: $3061 Airbnb ROI: N/A Traditional ROI: 0.18%
44798 MEDLEYS NECK ROAD Leonardtown, MD Other lots in the area, call us to discuss TBB - Custom Home - Many other floor plans and ...	4 beds \| 5 baths \| 3,000 sq.ft.	$772,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.73% Airbnb Rental Income: $null Traditional Rental Income: $2886 Airbnb ROI: N/A Traditional ROI: 2.73%
40481 OLD BRETON BEACH ROAD Leonardtown, MD This Dream Waterfront Home is being sold as a Turn-Key Home. Upgraded, Updated, new A/C an...	2 beds \| 2 baths \| 1,144 sq.ft.	$650,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 1.86% Airbnb Rental Income: $2153 Traditional Rental Income: $2151 Airbnb ROI: 0.96% Traditional ROI: 1.86%
23220 BRANDON COURT Leonardtown, MD Back on the market and fully available! Buyers got cold feet. Discover this beautifully ma...	3 beds \| 2 baths \| 2,102 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $2513 Airbnb ROI: N/A Traditional ROI: 2.97%
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: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $2144 Airbnb ROI: N/A Traditional ROI: 2.95%
41541 FAIRWOOD COURT Leonardtown, MD MARRICK HOMES' PINEHURST IN CLARKS REST! MOVE IN NOW! Includes: Quartz Kitchen Counterto...	4 beds \| 4 baths \| 3,080 sq.ft.	$642,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $3531 Airbnb ROI: N/A Traditional ROI: 4.44%
23492 WATERVALE DRIVE Leonardtown, MD Hereâs your chance to own a stunning, spacious and LESS THAN A YEAR OLD home in the high...	5 beds \| 5 baths \| 4,441 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $4651 Airbnb ROI: N/A Traditional ROI: 4.39%
40443 BRETON VIEW DRIVE Leonardtown, MD Why settle for a typical subdivision when you can enjoy the beauty and lifestyle of Breton...	3 beds \| 4 baths \| 2,604 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $2412 Airbnb ROI: N/A Traditional ROI: 4.46%
40552 BRETON KNOLLS CT Leonardtown, MD To Be Built - A Breton Knolls exclusive offering. Be the first to call this to-be-built cu...	5 beds \| 3 baths \| 3,127 sq.ft.	$884,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $3389 Airbnb ROI: N/A Traditional ROI: 2.88%
40624 BRETON KNOLLS CT Leonardtown, MD To Be Built, Be the first to call this house your home! Make custom selections, update the...	5 beds \| 4 baths \| N/A	$824,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $3756 Airbnb ROI: N/A Traditional ROI: 3.64%
40533 BRETON KNOLLS CT Leonardtown, MD Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spanning 4,058 squa...	4 beds \| 3 baths \| N/A	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $3080 Airbnb ROI: N/A Traditional ROI: 2.61%
41505 KNIGHT ROAD Leonardtown, MD Stunning. Welcome to a world of unparalleled luxury and breathtaking beauty. Nestled along...	5 beds \| 8 baths \| 12,113 sq.ft.	$6,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.1% Airbnb Rental Income: $null Traditional Rental Income: $7564 Airbnb ROI: N/A Traditional ROI: -0.1%
40222 BRETON BEACH ROAD Leonardtown, MD This dreamy waterfront getaway is the perfect spot for you to fully unwind and relax. Loca...	2 beds \| 1 baths \| 1,296 sq.ft.	$594,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 1.63% Airbnb Rental Income: $2153 Traditional Rental Income: $2003 Airbnb ROI: 0.91% Traditional ROI: 1.63%
39834 BIG PINE TRAIL Leonardtown, MD 3 Bedroom 2 Full Bath Rancher all one level with open floor plan, front porch, rear deck, ...	3 beds \| 2 baths \| 1,344 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.36% Airbnb Rental Income: $null Traditional Rental Income: $2050 Airbnb ROI: N/A Traditional ROI: 4.36%
18937 HODGES LANE Leonardtown, MD Are you dreaming of life on the water? Here is your chance! Well maintained rambler featur...	3 beds \| 2 baths \| 1,834 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.31% Airbnb Rental Income: $null Traditional Rental Income: $2761 Airbnb ROI: N/A Traditional ROI: 2.31%
22876 WHITE SWAN WAY Leonardtown, MD Welcome to your new home in the Avenmar neighborhood of Breton Bay where there is somethin...	5 beds \| 4 baths \| 4,984 sq.ft.	$709,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $3591 Airbnb ROI: N/A Traditional ROI: 3.24%
23636 HANSEL COURT Leonardtown, MD Welcome to your dream home in Leonardtown, MD! Nestled in the charming community of Leona...	4 beds \| 3 baths \| 3,129 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3173 Airbnb ROI: N/A Traditional ROI: 3.44%
22536 LANDING WAY Leonardtown, MD Leonardtown Landing , Key West Flare in Leonardtown. Walk to town and enjoy Waterside liv...	3 beds \| 4 baths \| 2,764 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $3026 Airbnb ROI: N/A Traditional ROI: 4.26%
23730 HICKS DRIVE Leonardtown, MD This immaculate beauty boasts a newly renovated kitchen with quartz countertops, stainless...	3 beds \| 2 baths \| 1,992 sq.ft.	$429,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.15% Airbnb Rental Income: $null Traditional Rental Income: $2485 Airbnb ROI: N/A Traditional ROI: 4.15%
23244 JENIFER COURT Leonardtown, MD Look no further, this well-maintained and upgraded home ideally situated in the desired Es...	4 beds \| 3 baths \| 3,357 sq.ft.	$569,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $3174 Airbnb ROI: N/A Traditional ROI: 3.91%
40907 COOPER DRIVE Leonardtown, MD Nestled in one of the most sought-after neighborhoods, this charming residence offers an i...	3 beds \| 3 baths \| 2,226 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $2491 Airbnb ROI: N/A Traditional ROI: 3.81%
40407 BRETON VIEW DRIVE Leonardtown, MD Why settle for a view of your neighbors when you can relax on your deck and take in the se...	3 beds \| 4 baths \| 2,640 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A Traditional ROI: 6.04%

Real Estate investment in Leonardtown, MD

There are 24 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $602,000 and the average price per square foot is $202. In October 2024, the average monthly cash on cash return in Leonardtown is 3.00%. The average monthly rental income in Leonardtown is $2,952.

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

There are 24 investment properties available for sale in Leonardtown.

In 2024, 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 $2,952.

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: N/A

Traditional cash on cash: 4.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2177

Airbnb ROI: N/A

Traditional ROI: 4.18%

41815 CHELSEY FAYE

Leonardtown, MD

3 beds | 2 baths | 1,627 sq.ft.

$530,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2340

Airbnb ROI: N/A

Traditional ROI: 3.38%

42520 RIVERWINDS DRIVE

Leonardtown, MD

4 beds | 2 baths | 2,744 sq.ft.

$2,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3061

Airbnb ROI: N/A

Traditional ROI: 0.18%

44798 MEDLEYS NECK ROAD

Leonardtown, MD

4 beds | 5 baths | 3,000 sq.ft.

$772,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2886

Airbnb ROI: N/A

Traditional ROI: 2.73%

40481 OLD BRETON BEACH ROAD

Leonardtown, MD

2 beds | 2 baths | 1,144 sq.ft.

$650,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $2153

Traditional Rental Income: $2151

Airbnb ROI: 0.96%

Traditional ROI: 1.86%

23220 BRANDON COURT

Leonardtown, MD

3 beds | 2 baths | 2,102 sq.ft.

$535,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.97%

Airbnb Rental Income: $null

Traditional Rental Income: $2513

Airbnb ROI: N/A

Traditional ROI: 2.97%

20240 BIG OAK LN

Leonardtown, MD

3 beds | 2 baths | 1,935 sq.ft.

$505,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2144

Airbnb ROI: N/A

Traditional ROI: 2.95%

41541 FAIRWOOD COURT

Leonardtown, MD

4 beds | 4 baths | 3,080 sq.ft.

$642,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.44%

Airbnb Rental Income: $null

Traditional Rental Income: $3531

Airbnb ROI: N/A