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: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 4.72%
23399 MARVIEW COURT Leonardtown, MD Gorgeous Townhomes "Compton" rear kitchen model. 2-Car Rear Load Garage, Open floor plan w...	3 beds \| 4 baths \| 2,320 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5% Airbnb Rental Income: $null Traditional Rental Income: $2916 Airbnb ROI: N/A Traditional ROI: 5%
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%
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%
41541 FAIRWOOD COURT Leonardtown, MD $20,000 SELLER CONCESSIONS TO BUYER!! MARRICK HOMES' PINEHURST IN CLARKS REST! MOVE IN NO...	4 beds \| 4 baths \| 3,080 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $3491 Airbnb ROI: N/A Traditional ROI: 4.4%
23492 WATERVALE DRIVE Leonardtown, MD SELLER'S ENTERTAINING BACK UP OFFERS. AVAILABLE FOR SHOWINGS Hereâs your chance to own...	5 beds \| 5 baths \| 4,441 sq.ft.	$759,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $4651 Airbnb ROI: N/A Traditional ROI: 4.32%
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.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.75% Airbnb Rental Income: $null Traditional Rental Income: $3167 Airbnb ROI: N/A Traditional ROI: 6.75%
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%
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: -0.28% Airbnb Rental Income: $null Traditional Rental Income: $6502 Airbnb ROI: N/A Traditional ROI: -0.28%
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: 0.95% Traditional cash on cash: 1.77% Airbnb Rental Income: $2153 Traditional Rental Income: $2051 Airbnb ROI: 0.95% Traditional ROI: 1.77%
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: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 2.19%
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.	$598,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $3072 Airbnb ROI: N/A Traditional ROI: 3.35%
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: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $2443 Airbnb ROI: N/A Traditional ROI: 4.04%
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.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $2748 Airbnb ROI: N/A Traditional ROI: 4.58%
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: 6.22% Airbnb Rental Income: $null Traditional Rental Income: $3082 Airbnb ROI: N/A Traditional ROI: 6.22%
20400 CHINGVILLE ROAD Leonardtown, MD Buyer got cold feet! BACK ON THE MARKET! Discover your future at this picturesque propert...	3 beds \| 2 baths \| 2,280 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $2407 Airbnb ROI: N/A Traditional ROI: 4.26%
20418 SCARLET TANAGER WAY Leonardtown, MD DIAMOND IN THE ROUGH - HANDYMAN SPECIAL! SPECâs: Ryan Modular Colonial Home, 2116 Sqf...	3 beds \| 3 baths \| 2,116 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.38% Airbnb Rental Income: $null Traditional Rental Income: $2782 Airbnb ROI: N/A Traditional ROI: 5.38%
23587 GUNNELL DRIVE Leonardtown, MD Welcome to this charming 5-bedroom, 3.5-bath Colonial in a highly sought-after community n...	5 beds \| 4 baths \| 3,712 sq.ft.	$560,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $4106 Airbnb ROI: N/A Traditional ROI: 5.86%
43610 DEER RUN COURT Leonardtown, MD Wonderful brick front colonial home sitting on over 6.5 acres in Chestnut Hills. This hom...	4 beds \| 3 baths \| 2,980 sq.ft.	$609,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $3263 Airbnb ROI: N/A Traditional ROI: 3.76%
41800 EASTWICK LANE #1303 Leonardtown, MD Experience the blend of comfort and convenience of the sought after "Foxwell Community" at...	2 beds \| 1 baths \| 1,056 sq.ft.	$272,900	Airbnb cash on cash: 3.99% Traditional cash on cash: 4.85% Airbnb Rental Income: $2153 Traditional Rental Income: $1827 Airbnb ROI: 3.99% Traditional ROI: 4.85%

Real Estate investment in Leonardtown, MD

There are 25 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $582,500 and the average price per square foot is $205. In November 2024, the average monthly cash on cash return in Leonardtown is 4.00%. The average monthly rental income in Leonardtown is $2,916.

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

There are 25 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 $2,916.

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%

23399 MARVIEW COURT

Leonardtown, MD

3 beds | 4 baths | 2,320 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5%

Airbnb Rental Income: $null

Traditional Rental Income: $2916

Airbnb ROI: N/A

Traditional ROI: 5%

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%

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

Traditional ROI: 3.38%

41541 FAIRWOOD COURT

Leonardtown, MD

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

$639,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.4%

Airbnb Rental Income: $null

Traditional Rental Income: $3491

Airbnb ROI: N/A