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: 7.48% Traditional cash on cash: 4.72% Airbnb Rental Income: $4265 Traditional Rental Income: $2371 Airbnb ROI: 7.48% Traditional ROI: 4.72%
20798 WATERSIDE DRIVE Leonardtown, MD Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect...	2 beds \| 1 baths \| 1,018 sq.ft.	$450,000	Airbnb cash on cash: 5.31% Traditional cash on cash: 2.17% Airbnb Rental Income: $3881 Traditional Rental Income: $1726 Airbnb ROI: 5.31% Traditional ROI: 2.17%
41412 DOCTORS CROSSING ROAD Leonardtown, MD Welcome to your dream home in highly sought-after Clarks Rest, just minutes from all the c...	4 beds \| 4 baths \| 2,686 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $2792 Airbnb ROI: N/A Traditional ROI: 3.45%
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: 5.45% Traditional cash on cash: 3.38% Airbnb Rental Income: $4265 Traditional Rental Income: $2343 Airbnb ROI: 5.45% Traditional ROI: 3.38%
42520 RIVERWINDS DRIVE Leonardtown, MD Seller is entertaining offers now. Looking for elbow room? Look no furtherthis property of...	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%
41900 NAZARETH COURT Leonardtown, MD Welcome to the Academy Hills of Leonardtown. The main level features a traditional floor p...	4 beds \| 3 baths \| 2,528 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.85% Airbnb Rental Income: $null Traditional Rental Income: $3081 Airbnb ROI: N/A Traditional ROI: 4.85%
23080 TOWN RUN DRIVE Leonardtown, MD Welcome to this exceptionally upgraded Quality Built Homes Adelina model in the highly des...	5 beds \| 4 baths \| 3,794 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $3646 Airbnb ROI: N/A Traditional ROI: 3.49%
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: 5.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $4265 Traditional Rental Income: $2345 Airbnb ROI: 5.54% 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%
40533 BRETON KNOLLS CT Leonardtown, MD TO BE BUILT - Introducing the "Patriot," a magnificent 4-bedroom, 2.5-bathroom abode spann...	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%
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.	$5,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.21% Airbnb Rental Income: $null Traditional Rental Income: $6502 Airbnb ROI: N/A Traditional ROI: -0.21%
41810 CHELSEY FAYE LANE Leonardtown, MD Introducing a stunning 4-bedroom, 2.5-bathroom detached home to be built with exceptional ...	4 beds \| 4 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%
41402 SILVER CHARM COURT Leonardtown, MD Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuri...	5 beds \| 4 baths \| 4,046 sq.ft.	$635,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.22% Airbnb Rental Income: $null Traditional Rental Income: $3788 Airbnb ROI: N/A Traditional ROI: 4.22%
41430 CHALLEDON WAY Leonardtown, MD Welcome to this spacious 5-bedroom, 3.5-bath home nestled on a beautiful corner lot in sou...	5 beds \| 4 baths \| 4,500 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $3818 Airbnb ROI: N/A Traditional ROI: 4.06%
40461 OLD BRETON BEACH ROAD Leonardtown, MD Welcome to 40461 Old Breton Beach Roada breathtaking waterfront retreat on the shores of t...	3 beds \| 3 baths \| 2,040 sq.ft.	$700,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.62% Airbnb Rental Income: $4265 Traditional Rental Income: $2941 Airbnb ROI: 3.27% Traditional ROI: 2.62%
23264 LINDSAY DRIVE Leonardtown, MD Main Level living at its finest in the heart of Leonardtown! Built on an oversized premium...	3 beds \| 2 baths \| 2,824 sq.ft.	$629,900	Airbnb cash on cash: 3.57% Traditional cash on cash: 2.33% Airbnb Rental Income: $4265 Traditional Rental Income: $2636 Airbnb ROI: 3.57% Traditional ROI: 2.33%
23674 JM GOUGH COURT Leonardtown, MD Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardt...	4 beds \| 3 baths \| 2,697 sq.ft.	$537,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $2990 Airbnb ROI: N/A Traditional ROI: 4.02%
20814 DEER WOOD PARK DRIVE Leonardtown, MD This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy o...	4 beds \| 3 baths \| 3,412 sq.ft.	$589,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $3142 Airbnb ROI: N/A Traditional ROI: 3.79%
20591 CHESTNUT RIDGE DRIVE Leonardtown, MD Welcome to this well-built colonial on a corner lot in the picturesque corner Chestnut Rid...	5 beds \| 4 baths \| 3,061 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $3645 Airbnb ROI: N/A Traditional ROI: 4.54%
21056 WOODMERE DRIVE Leonardtown, MD Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front...	4 beds \| 3 baths \| 2,205 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $2964 Airbnb ROI: N/A Traditional ROI: 3.94%
23246 LINDSAY DRIVE Leonardtown, MD Clark's Rest Community: Welcome to this stunning 5-bedroom, 3.5-bath home with over 3,800...	5 beds \| 4 baths \| 3,876 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $3806 Airbnb ROI: N/A Traditional ROI: 4.2%
39825 SWEETPEA LANE Leonardtown, MD Waterfront serenity awaits! Nestled on 3.59 private acres along Tennyson Creek with 300 fe...	4 beds \| 4 baths \| 2,442 sq.ft.	$790,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $3921 Airbnb ROI: N/A Traditional ROI: 3.61%
Lot 87 DRAGONFLY LANE Leonardtown, MD Unit 87 Madison D3: Welcome to Meadows at Town Run.... Leonardtowns Newest Townhome Commu...	4 beds \| 4 baths \| 2,554 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $3204 Airbnb ROI: N/A Traditional ROI: 6.33%
Lot 88 DRAGONFLY LANE Leonardtown, MD Unit 88 Madison D2: New Construction: Madison D2 at Meadows at Town Run II 2604 Sq Ft \| 4 ...	4 beds \| 4 baths \| 2,604 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.33% Airbnb Rental Income: $null Traditional Rental Income: $3204 Airbnb ROI: N/A Traditional ROI: 6.33%
Lot 89 DRAGONFLY LANE Leonardtown, MD Unit 89 Oakley D1 New Construction Oakley D1 End Unit at Meadows at Town Run II2,966 Sq Ft...	4 beds \| 4 baths \| 2,966 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.71% Airbnb Rental Income: $null Traditional Rental Income: $3505 Airbnb ROI: N/A Traditional ROI: 6.71%
40480 PARSONS MILL ROAD Leonardtown, MD Experience country living at its finest in this expansive rambler, nestled amidst pictures...	3 beds \| 1 baths \| 1,884 sq.ft.	$429,900	Airbnb cash on cash: 6.49% Traditional cash on cash: 2.63% Airbnb Rental Income: $4265 Traditional Rental Income: $1810 Airbnb ROI: 6.49% Traditional ROI: 2.63%
23092 TOWN RUN DRIVE Leonardtown, MD Welcome home to The Meadows of Town Run, and this Montross floorplan built by QBHI. The Mo...	5 beds \| 4 baths \| 3,806 sq.ft.	$619,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $3649 Airbnb ROI: N/A Traditional ROI: 4.2%
41480 WHIMSICAL COURT Leonardtown, MD Welcome home to this stunning and spacious colonial in sought after Leonards Grant. This h...	5 beds \| 4 baths \| 3,825 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.57% Airbnb Rental Income: $null Traditional Rental Income: $3707 Airbnb ROI: N/A Traditional ROI: 3.57%
40534 MISS ETTAS WAY Leonardtown, MD Welcome home to this beautifully maintained Cape Cod built by Hallmark Homes in 2016, situ...	3 beds \| 3 baths \| 1,770 sq.ft.	$480,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.94% Airbnb Rental Income: $4265 Traditional Rental Income: $2639 Airbnb ROI: 5.56% Traditional ROI: 3.94%

Real Estate investment in Leonardtown, MD

There are 29 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $589,000 and the average price per square foot is $199. In September 2025, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $3,064.

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

There are 29 investment properties available for sale in Leonardtown.

In 2025, the best neighborhood to buy investment property is Leonardtown.

The ROI for Short-Term is higher than the Long-Term in Leonardtown with average rental income of $4,265.

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: 7.48%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $4265

Traditional Rental Income: $2371

Airbnb ROI: 7.48%

Traditional ROI: 4.72%

20798 WATERSIDE DRIVE

Leonardtown, MD

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

$450,000

Airbnb cash on cash: 5.31%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $3881

Traditional Rental Income: $1726

Airbnb ROI: 5.31%

Traditional ROI: 2.17%

41412 DOCTORS CROSSING ROAD

Leonardtown, MD

4 beds | 4 baths | 2,686 sq.ft.

$540,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.45%

Airbnb Rental Income: $null

Traditional Rental Income: $2792

Airbnb ROI: N/A

Traditional ROI: 3.45%

41815 CHELSEY FAYE

Leonardtown, MD

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

$530,000

Airbnb cash on cash: 5.45%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $4265

Traditional Rental Income: $2343

Airbnb ROI: 5.45%

Traditional ROI: 3.38%

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%

41900 NAZARETH COURT

Leonardtown, MD

4 beds | 3 baths | 2,528 sq.ft.

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3081

Airbnb ROI: N/A

Traditional ROI: 4.85%

23080 TOWN RUN DRIVE

Leonardtown, MD

5 beds | 4 baths | 3,794 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3646

Airbnb ROI: N/A

Traditional ROI: 3.49%

20240 BIG OAK LN

Leonardtown, MD

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

$505,000

Airbnb cash on cash: 5.54%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $4265

Traditional Rental Income: $2345

Airbnb ROI: 5.54%