Real Estate Investment Properties for Sale in Hollywood, MD

Looking for investment property in Hollywood, MD with high ROI ?

Explore a variety of short-term homes & houses in Hollywood, MD. Invest wisely with VRBO & Hollywood, 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 Hollywood, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
44965 BLACKISTONE Circle Hollywood, MD Discover a captivating blend of comfort and nature in this stunning waterview home, nestle...	4 beds \| 4 baths \| 2,264 sq.ft.	$499,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.46% Airbnb Rental Income: $2063 Traditional Rental Income: $3043 Airbnb ROI: 1.22% Traditional ROI: 4.46%
24665 E MONTIEGO Road Hollywood, MD Welcome to 24665 E. Montiego Road in Hollywood, MD a split foyer home offering exceptional...	5 beds \| 3 baths \| 2,006 sq.ft.	$420,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.67% Airbnb Rental Income: $1995 Traditional Rental Income: $1801 Airbnb ROI: 1.84% Traditional ROI: 2.67%
43979 DRUM CLIFF Road Hollywood, MD Enjoy waterfront living with this cottage style home offering breathtaking views of the Pa...	2 beds \| 2 baths \| 3,140 sq.ft.	$499,900	Airbnb cash on cash: -1.12% Traditional cash on cash: 3.88% Airbnb Rental Income: $905 Traditional Rental Income: $2904 Airbnb ROI: -1.12% Traditional ROI: 3.88%
24065 PAPPYS Way Hollywood, MD Beautiful colonial situated on a 4.12 acre secluded lot backing to 28 acres of Forest Cons...	4 beds \| 4 baths \| 4,040 sq.ft.	$650,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.9% Airbnb Rental Income: $2063 Traditional Rental Income: $3578 Airbnb ROI: 0.52% Traditional ROI: 3.9%
23801 MCINTOSH Road Hollywood, MD OPEN HOUSE SUNDAY 1PM-3PM. Leonardtown schools, NO HOA or Leonardtown taxes! Welcome to th...	3 beds \| 3 baths \| 1,634 sq.ft.	$464,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.06% Airbnb Rental Income: $1156 Traditional Rental Income: $2557 Airbnb ROI: -0.04% Traditional ROI: 4.06%
43816 RASPBERRY Lane Hollywood, MD Coming soon. should be active next month. Call for more information	3 beds \| 4 baths \| 2,551 sq.ft.	$764,987	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.44% Airbnb Rental Income: $1156 Traditional Rental Income: $3887 Airbnb ROI: -0.92% Traditional ROI: 3.44%

Real Estate investment in Hollywood, MD

There are 11 properties for sale in the city of Hollywood . The median list price in Hollywood is $550,000 and the average price per square foot is $314. In May 2026, the average monthly cash on cash return in Hollywood is 4.00%. The average monthly rental income in Hollywood is $2,736.

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

There are 11 investment properties available for sale in Hollywood.

In 2026, the best neighborhood to buy investment property is Hollywood.

The ROI for Short-Term is higher than the Long-Term in Hollywood with average rental income of $1,156.

Your search for investment property begins and ends here

Investment Property for Sale in Hollywood, MD

44965 BLACKISTONE Circle

Hollywood, MD

4 beds | 4 baths | 2,264 sq.ft.

$499,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2063

Traditional Rental Income: $3043

Airbnb ROI: 1.22%

Traditional ROI: 4.46%

24665 E MONTIEGO Road

Hollywood, MD

5 beds | 3 baths | 2,006 sq.ft.

$420,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $1995

Traditional Rental Income: $1801

Airbnb ROI: 1.84%

Traditional ROI: 2.67%

43979 DRUM CLIFF Road

Hollywood, MD

2 beds | 2 baths | 3,140 sq.ft.

$499,900

Airbnb cash on cash: -1.12%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $905

Traditional Rental Income: $2904

Airbnb ROI: -1.12%

Traditional ROI: 3.88%

24065 PAPPYS Way

Hollywood, MD

4 beds | 4 baths | 4,040 sq.ft.

$650,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $2063

Traditional Rental Income: $3578

Airbnb ROI: 0.52%

Traditional ROI: 3.9%

23801 MCINTOSH Road

Hollywood, MD

3 beds | 3 baths | 1,634 sq.ft.

$464,900

Airbnb cash on cash: -0.04%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1156

Traditional Rental Income: $2557

Airbnb ROI: -0.04%

Traditional ROI: 4.06%

43816 RASPBERRY Lane

Hollywood, MD

3 beds | 4 baths | 2,551 sq.ft.

$764,987

Airbnb cash on cash: -0.92%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1156

Traditional Rental Income: $3887

Airbnb ROI: -0.92%

Traditional ROI: 3.44%

Real Estate investment in Hollywood, MD

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

How many investment properties are available for sale in Hollywood?

Which neighborhoods in Hollywood to invest in 2026?

Long-Term vs. Short-Term Rentals in Hollywood, Maryland: Which will earn the best returns?

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