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: -0.45% Traditional cash on cash: 4.72% Airbnb Rental Income: $838 Traditional Rental Income: $2371 Airbnb ROI: -0.45% Traditional ROI: 4.72%
41488 Pensive St Leonardtown, MD Updated Photos coming in a couple weeks! Welcome to this Belmont model in Leonard's Grant,...	5 beds \| 3 baths \| 3,992 sq.ft.	$680,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $3741 Airbnb ROI: N/A Traditional ROI: 3.88%
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.	$500,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 1.85% Airbnb Rental Income: $986 Traditional Rental Income: $1726 Airbnb ROI: -0.48% Traditional ROI: 1.85%
41505 MARGROVE Circle Leonardtown, MD Welcome to this stunning end-unit townhome in the highly sought-after Clark's Rest communi...	3 beds \| 4 baths \| 2,306 sq.ft.	$435,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 4.95% Airbnb Rental Income: $838 Traditional Rental Income: $2961 Airbnb ROI: -1.07% Traditional ROI: 4.95%
41620 Church St Leonardtown, MD Charming Ramber privately situated in downtown Leonardtown. Turn-key home with new applian...	3 beds \| 2 baths \| 1,728 sq.ft.	$399,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.84% Airbnb Rental Income: $838 Traditional Rental Income: $2111 Airbnb ROI: -0.44% Traditional ROI: 3.84%
42520 Riverwinds Dr Leonardtown, MD Seller is entertaining offers now. Looking for elbow room? Look no further-this property o...	4 beds \| 2 baths \| 2,744 sq.ft.	$1,999,999	Airbnb cash on cash: -1.06% Traditional cash on cash: 0.27% Airbnb Rental Income: $818 Traditional Rental Income: $2964 Airbnb ROI: -1.06% Traditional ROI: 0.27%
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: -0.51% Traditional cash on cash: 3.38% Airbnb Rental Income: $838 Traditional Rental Income: $2345 Airbnb ROI: -0.51% Traditional ROI: 3.38%
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: -1.12% Traditional cash on cash: 0.29% Airbnb Rental Income: $818 Traditional Rental Income: $2785 Airbnb ROI: -1.12% Traditional ROI: 0.29%
20260 Hawks Way Leonardtown, MD IMMEDIATE DELIVERY! Welcome to 20260 Hawks Way, a stunning immediate delivery brand new co...	4 beds \| 2 baths \| 2,500 sq.ft.	$569,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.44% Airbnb Rental Income: $818 Traditional Rental Income: $3070 Airbnb ROI: -0.4% Traditional ROI: 4.44%
40736 CENTER 40 Circle Leonardtown, MD BACK ON MARKET. Charming Split Level home on just over 1/2 an acre in Breton Bay. As you e...	3 beds \| 3 baths \| 1,829 sq.ft.	$399,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.63% Airbnb Rental Income: $838 Traditional Rental Income: $2501 Airbnb ROI: -0.68% Traditional ROI: 4.63%
19700 Mulberry Fields Rd Leonardtown, MD 19700 Mulberry Fields Rd, Leonardtown, MD 20650 \| Single Family Residential	6 beds \| 4 baths \| 13,458 sq.ft.	$20,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.85% Airbnb Rental Income: $null Traditional Rental Income: $4446 Airbnb ROI: N/A Traditional ROI: -1.85%
43488 Medleys Neck Rd Leonardtown, MD 43488 Medleys Neck Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 0.73%
20265 Hawks Way Leonardtown, MD 20265 Hawks Way, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 1.46%
22393 Saint Clements Ave Leonardtown, MD BRAND NEW ROOF! Experience refined waterfront living in this fully renovated rancher o...	4 beds \| 2 baths \| 2,097 sq.ft.	$788,900	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.08% Airbnb Rental Income: $818 Traditional Rental Income: $2063 Airbnb ROI: -1.06% Traditional ROI: 1.08%
St. Andrews Church Rd Leonardtown, MD St. Andrews Church Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| 2,188 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $600 Airbnb ROI: N/A Traditional ROI: 0.97%
Lot 99 - 23725 Dragonfly Ln Leonardtown, MD Homesite #99 Madison D3: **ALMOST READY FOR SPRING DELIVERY*Welcome to Meadows at Town...	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.02% Airbnb Rental Income: $818 Traditional Rental Income: $2300 Airbnb ROI: -0.27% Traditional ROI: 4.02%
Lot 101 - 23713 Dragonfly Ln Leonardtown, MD Homesite #101 Madison D3: *ALMOST READY FOR MARCH DELIVERY*Welcome to Meadows at Town ...	4 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.02% Airbnb Rental Income: $818 Traditional Rental Income: $2300 Airbnb ROI: -0.27% Traditional ROI: 4.02%
22343 Newtowne Neck Rd Leonardtown, MD MOVE-IN READY!! Welcome to this beautifully maintained 4-bedroom, 2-bath rambler situated ...	4 beds \| 2 baths \| 2,114 sq.ft.	$464,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 2.69% Airbnb Rental Income: $818 Traditional Rental Income: $2015 Airbnb ROI: -0.81% Traditional ROI: 2.69%
41377 Doctors Crossing Rd Leonardtown, MD Price Improvement! This adjustment creates a fantastic opportunity for buyers to own a wel...	5 beds \| 4 baths \| 3,724 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $3038 Airbnb ROI: N/A Traditional ROI: 2.93%
0 Saint Andrews Church Rd Leonardtown, MD 0 Saint Andrews Church Rd, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$98,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $620 Airbnb ROI: N/A Traditional ROI: 3.41%
22394 White Oak Rd Leonardtown, MD Nestled in the coveted waterfront community of Breton Bay, this beautifully maintained 4-b...	4 beds \| 3 baths \| 2,507 sq.ft.	$495,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 4.69% Airbnb Rental Income: $818 Traditional Rental Income: $3041 Airbnb ROI: -0.81% Traditional ROI: 4.69%
Ferny Hills Ln Leonardtown, MD Ferny Hills Ln, Leonardtown, MD 20650 \| Other	N/A beds \| N/A baths \| N/A	$840,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.34% Airbnb Rental Income: $null Traditional Rental Income: $674 Airbnb ROI: N/A Traditional ROI: -1.34%
Lot 110 - 23678 Weeping Willow Way Leonardtown, MD Homesite 110 Madison D1: * May Delivery*Builder Incentive $12,500 in Closing Help with...	4 beds \| 3 baths \| 2,571 sq.ft.	$449,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 6.03% Airbnb Rental Income: $818 Traditional Rental Income: $3145 Airbnb ROI: -0.27% Traditional ROI: 6.03%
Lot 135 - 23679 Weeping Willow Way Leonardtown, MD *Mid-May Delivery* Builder Incentive, Receive $12,500 in Builder Closing Help with use...	4 beds \| 3 baths \| 2,604 sq.ft.	$449,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 6.03% Airbnb Rental Income: $818 Traditional Rental Income: $3145 Airbnb ROI: -0.27% Traditional ROI: 6.03%
40003 Tippit Rd Leonardtown, MD If you've been looking for Leonardtown waterfront, look no further! This exceptional .83-a...	3 beds \| 3 baths \| 2,490 sq.ft.	$995,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.64% Airbnb Rental Income: $838 Traditional Rental Income: $3109 Airbnb ROI: -1.16% Traditional ROI: 1.64%
Lot 141 - 23653 Dragonfly Ln Leonardtown, MD TO BE BUILT Homesite 141 - Oakley D1 End Unit October Delivery* *Choose your...	4 beds \| 3 baths \| N/A	$479,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.46% Airbnb Rental Income: $818 Traditional Rental Income: $2638 Airbnb ROI: -0.32% Traditional ROI: 4.46%
18866 Russell Rd Leonardtown, MD *Rare Waterfront Opportunity* Welcome to 18866 Russell Rd, Valley Lee /Leonardtown, MD...	3 beds \| 2 baths \| 1,128 sq.ft.	$450,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 2.4% Airbnb Rental Income: $838 Traditional Rental Income: $1897 Airbnb ROI: -0.9% Traditional ROI: 2.4%
Lot 142 - 23647 Dragonfly Ln Leonardtown, MD *TO BE BUILT* *November Delivery* ***Choose your color scheme from of our availabl...	4 beds \| 3 baths \| 3,095 sq.ft.	$489,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 6.27% Airbnb Rental Income: $818 Traditional Rental Income: $3519 Airbnb ROI: -0.33% Traditional ROI: 6.27%
43430 BROWNS Lane Leonardtown, MD This unique property has so much to offer and has been a great family home, however owners...	5 beds \| 5 baths \| 2,756 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $4722 Airbnb ROI: N/A Traditional ROI: 6.02%
Lot 111 - 23684 Weeping Willow Way Leonardtown, MD Homesite #111 Madison D3: **May Delivery*Welcome to Meadows at Town Run.... Leonardtow...	4 beds \| 3 baths \| 2,554 sq.ft.	$449,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 6.24% Airbnb Rental Income: $818 Traditional Rental Income: $3237 Airbnb ROI: -0.27% Traditional ROI: 6.24%
39577 Potomac Ave Leonardtown, MD	4 beds \| 2 baths \| 3,412 sq.ft.	$839,900	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.38% Airbnb Rental Income: $818 Traditional Rental Income: $2021 Airbnb ROI: -1.57% Traditional ROI: 0.38%
39577 Potomac Ave Leonardtown, MD	4 beds \| 2 baths \| 3,412 sq.ft.	$839,900	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.38% Airbnb Rental Income: $818 Traditional Rental Income: $2021 Airbnb ROI: -1.57% Traditional ROI: 0.38%
23207 Moakley St Leonardtown, MD 23207 Moakley St, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,926 sq.ft.	$520,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 1.75% Airbnb Rental Income: $838 Traditional Rental Income: $1956 Airbnb ROI: -1.22% Traditional ROI: 1.75%
23207 Moakley St Leonardtown, MD 23207 Moakley St, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,926 sq.ft.	$520,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 2.26% Airbnb Rental Income: $838 Traditional Rental Income: $2203 Airbnb ROI: -1.22% Traditional ROI: 2.26%
23592 Belmar Dr Leonardtown, MD 23592 Belmar Dr, Leonardtown, MD 20650 \| Single Family Residential	4 beds \| 2 baths \| 3,728 sq.ft.	$680,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 0.67% Airbnb Rental Income: $818 Traditional Rental Income: $1940 Airbnb ROI: -1.61% Traditional ROI: 0.67%
40810 Meadow Dr Leonardtown, MD 40810 Meadow Dr, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,368 sq.ft.	$459,900	Airbnb cash on cash: -1.11% Traditional cash on cash: 1.72% Airbnb Rental Income: $838 Traditional Rental Income: $1730 Airbnb ROI: -1.11% Traditional ROI: 1.72%
22281 Nomoni St Leonardtown, MD 22281 Nomoni St, Leonardtown, MD 20650 \| Single Family Residential	3 beds \| 2 baths \| 1,152 sq.ft.	$360,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 2.73% Airbnb Rental Income: $838 Traditional Rental Income: $1718 Airbnb ROI: -0.85% Traditional ROI: 2.73%

Real Estate investment in Leonardtown, MD

There are 50 properties for sale in the city of Leonardtown . The median list price in Leonardtown is $515,000 and the average price per square foot is $174. In April 2026, the average monthly cash on cash return in Leonardtown is 3.00%. The average monthly rental income in Leonardtown is $2,645.

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

There are 50 investment properties available for sale in Leonardtown.

In 2026, 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 $2,645.

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: -0.45%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $838

Traditional Rental Income: $2371

Airbnb ROI: -0.45%

Traditional ROI: 4.72%

41488 Pensive St

Leonardtown, MD

5 beds | 3 baths | 3,992 sq.ft.

$680,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.88%

Airbnb Rental Income: $null

Traditional Rental Income: $3741

Airbnb ROI: N/A

Traditional ROI: 3.88%

20798 Waterside Dr

Leonardtown, MD

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

$500,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 1.85%

Airbnb Rental Income: $986

Traditional Rental Income: $1726

Airbnb ROI: -0.48%

Traditional ROI: 1.85%

41505 MARGROVE Circle

Leonardtown, MD

3 beds | 4 baths | 2,306 sq.ft.

$435,000

Airbnb cash on cash: -1.07%

Traditional cash on cash: 4.95%

Airbnb Rental Income: $838

Traditional Rental Income: $2961

Airbnb ROI: -1.07%

Traditional ROI: 4.95%

41620 Church St

Leonardtown, MD

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

$399,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $838

Traditional Rental Income: $2111

Airbnb ROI: -0.44%

Traditional ROI: 3.84%

42520 Riverwinds Dr

Leonardtown, MD

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

$1,999,999

Airbnb cash on cash: -1.06%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $818

Traditional Rental Income: $2964

Airbnb ROI: -1.06%

Traditional ROI: 0.27%

20240 BIG OAK LN

Leonardtown, MD

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

$505,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $838

Traditional Rental Income: $2345

Airbnb ROI: -0.51%

Traditional ROI: 3.38%

Bayside Rd

Leonardtown, MD

4 beds | 2 baths | 2,130 sq.ft.

$1,750,000

Airbnb cash on cash: -1.12%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $818

Traditional Rental Income: $2785

Airbnb ROI: -1.12%