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: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 4.72%
22380 WHITE OAK ROAD Leonardtown, MD Welcome to your dream home in the highly sought-after Breton Bay community of Leonardtown,...	4 beds \| 3 baths \| 2,680 sq.ft.	$455,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.56% Airbnb Rental Income: $null Traditional Rental Income: $3202 Airbnb ROI: N/A Traditional ROI: 5.56%
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: $2343 Airbnb ROI: N/A Traditional ROI: 3.38%
22395 HOOD LANE Leonardtown, MD Over the creek and through the woods to your new house we go!! Welcome to ultimate privac...	4 beds \| 4 baths \| 3,120 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $3461 Airbnb ROI: N/A Traditional ROI: 4.33%
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.	$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%
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 TWO Separate deeded LOTS! TWO PIERS!!! One New Sectic. This Dream Waterfront Home is being...	2 beds \| 2 baths \| 1,144 sq.ft.	$650,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 2.3% Airbnb Rental Income: $2153 Traditional Rental Income: $2419 Airbnb ROI: 0.96% Traditional ROI: 2.3%
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: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2345 Airbnb ROI: N/A Traditional ROI: 3.38%
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: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $3304 Airbnb ROI: N/A Traditional ROI: 2.78%
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: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $3833 Airbnb ROI: N/A Traditional ROI: 3.74%
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: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $3042 Airbnb ROI: N/A Traditional ROI: 2.57%
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.	$582,500	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.86% Airbnb Rental Income: $2153 Traditional Rental Income: $2051 Airbnb ROI: 1.04% Traditional ROI: 1.86%
41810 CHELSEY FAYE LANE Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 3 baths \| 2,566 sq.ft.	$639,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $3064 Airbnb ROI: N/A Traditional ROI: 3.92%
23255 LINDSAY DRIVE Leonardtown, MD Discover modern living at its finest in this stunning, fully finished three-level townhous...	3 beds \| 4 baths \| 2,896 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $3092 Airbnb ROI: N/A Traditional ROI: 5.45%
22540 LANDING WAY Leonardtown, MD Walk ability in Saint Marys Count how amazing! This home is right next to Leonardtown Wha...	3 beds \| 4 baths \| 2,764 sq.ft.	$499,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $3024 Airbnb ROI: N/A Traditional ROI: 4.24%
23246 CLARKS REST ROAD Leonardtown, MD Welcome to this beautiful home nestled in the highly sought-after Clark Rest Subdivision i...	5 beds \| 4 baths \| 3,024 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $3519 Airbnb ROI: N/A Traditional ROI: 4.38%
40778 S 40 DRIVE Leonardtown, MD Welcome to this beautiful Cape Cod home, offering 4 spacious bedrooms, 2 full baths, and a...	4 beds \| 2 baths \| 1,560 sq.ft.	$414,980	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $2394 Airbnb ROI: N/A Traditional ROI: 4.22%
22321 LEONARD STREET Leonardtown, MD Charming Cottage in Water-Privileged St. Clements Bay Discover the serenity of life in thi...	2 beds \| 1 baths \| 768 sq.ft.	$250,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 5.17% Airbnb Rental Income: $2153 Traditional Rental Income: $1714 Airbnb ROI: 4.71% Traditional ROI: 5.17%
42151 BLACKSMITH SHOP ROAD Leonardtown, MD	2 beds \| 1 baths \| 798 sq.ft.	$210,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 5.82% Airbnb Rental Income: $2153 Traditional Rental Income: $1600 Airbnb ROI: 5.84% Traditional ROI: 5.82%

Real Estate investment in Leonardtown, MD

There are 19 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $580,000 and the average price per square foot is $267. In December 2024, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $2,964.

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

There are 19 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 $2,964.

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: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2371

Airbnb ROI: N/A

Traditional ROI: 4.72%

22380 WHITE OAK ROAD

Leonardtown, MD

4 beds | 3 baths | 2,680 sq.ft.

$455,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.56%

Airbnb Rental Income: $null

Traditional Rental Income: $3202

Airbnb ROI: N/A

Traditional ROI: 5.56%

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: $2343

Airbnb ROI: N/A

Traditional ROI: 3.38%

22395 HOOD LANE

Leonardtown, MD

4 beds | 4 baths | 3,120 sq.ft.

$595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3461

Airbnb ROI: N/A

Traditional ROI: 4.33%

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%

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: 2.3%

Airbnb Rental Income: $2153

Traditional Rental Income: $2419

Airbnb ROI: 0.96%

Traditional ROI: 2.3%

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: 3.38%

Airbnb Rental Income: $null

Traditional Rental Income: $2345

Airbnb ROI: N/A