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: 1.05% Traditional cash on cash: 4.46% Airbnb Rental Income: $1967 Traditional Rental Income: $3043 Airbnb ROI: 1.05% Traditional ROI: 4.46%
25033 THREE NOTCH Road Hollywood, MD Welcome to this 3-bedroom 2 bath extremely clean home. Everything in this house was put in...	3 beds \| 2 baths \| 1,248 sq.ft.	$350,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.09% Airbnb Rental Income: $1156 Traditional Rental Income: $1996 Airbnb ROI: 0.38% Traditional ROI: 4.09%
24665 E MONTIEGO Road Hollywood, MD Welcome to 24665 E. Montiego Road in Hollywood, MD a well-maintained split foyer home offe...	5 beds \| 3 baths \| 2,006 sq.ft.	$425,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 2.63% Airbnb Rental Income: $1995 Traditional Rental Income: $1801 Airbnb ROI: 1.81% Traditional ROI: 2.63%
26408 HILLENDALE Road Hollywood, MD Welcome to Hollywood Shores! This charming one-level home offers the perfect opportunity f...	3 beds \| 2 baths \| 1,012 sq.ft.	$264,900	Airbnb cash on cash: 0.92% Traditional cash on cash: 5.73% Airbnb Rental Income: $1156 Traditional Rental Income: $1975 Airbnb ROI: 0.92% Traditional ROI: 5.73%
43091 JOY Lane Hollywood, MD Welcome to this charming one-level 3 bedroom 1 bath home set on a beautiful 1.59-acre leve...	3 beds \| 1 baths \| 1,324 sq.ft.	$395,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 2.76% Airbnb Rental Income: $1156 Traditional Rental Income: $1763 Airbnb ROI: 0.09% Traditional ROI: 2.76%
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: -1.4% Traditional cash on cash: 3.88% Airbnb Rental Income: $752 Traditional Rental Income: $2904 Airbnb ROI: -1.4% 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.	$675,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.72% Airbnb Rental Income: $1967 Traditional Rental Income: $3578 Airbnb ROI: 0.34% Traditional ROI: 3.72%
44015 SANDY BOTTOM Road Hollywood, MD You want large? You want one level? You want some land? You want to be rural? You want to ...	5 beds \| 3 baths \| 1,752 sq.ft.	$475,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.17% Airbnb Rental Income: $1995 Traditional Rental Income: $2736 Airbnb ROI: 1.33% Traditional ROI: 4.17%
44760 JOY CHAPEL Road Hollywood, MD Hollywood waterfront on Cuckold Creek-custom-built, one-owner home offering space, quality...	5 beds \| 4 baths \| 3,408 sq.ft.	$959,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.3% Airbnb Rental Income: $1995 Traditional Rental Income: $4509 Airbnb ROI: -0.1% Traditional ROI: 3.3%
23801 MCINTOSH Road Hollywood, MD OPEN HOUSE- May 3rd, 2PM-4PM. Welcome to this well-maintained split foyer home situated on...	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%
43356 QUAIL Street Hollywood, MD Welcome to this beautifully maintained colonial in the sought-after Broad Creek neighborho...	5 beds \| 4 baths \| 3,248 sq.ft.	$610,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.73% Airbnb Rental Income: $1995 Traditional Rental Income: $3716 Airbnb ROI: 0.79% Traditional ROI: 4.73%

Real Estate investment in Hollywood, MD

There are 14 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 $311. In May 2026, the average monthly cash on cash return in Hollywood is 4.00%. The average monthly rental income in Hollywood is $2,974.

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

There are 14 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 $1,967.

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: 1.05%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $1967

Traditional Rental Income: $3043

Airbnb ROI: 1.05%

Traditional ROI: 4.46%

25033 THREE NOTCH Road

Hollywood, MD

3 beds | 2 baths | 1,248 sq.ft.

$350,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $1156

Traditional Rental Income: $1996

Airbnb ROI: 0.38%

Traditional ROI: 4.09%

24665 E MONTIEGO Road

Hollywood, MD

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

$425,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1995

Traditional Rental Income: $1801

Airbnb ROI: 1.81%

Traditional ROI: 2.63%

26408 HILLENDALE Road

Hollywood, MD

3 beds | 2 baths | 1,012 sq.ft.

$264,900

Airbnb cash on cash: 0.92%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $1156

Traditional Rental Income: $1975

Airbnb ROI: 0.92%

Traditional ROI: 5.73%

43091 JOY Lane

Hollywood, MD

3 beds | 1 baths | 1,324 sq.ft.

$395,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $1156

Traditional Rental Income: $1763

Airbnb ROI: 0.09%

Traditional ROI: 2.76%

43979 DRUM CLIFF Road

Hollywood, MD

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

$499,900

Airbnb cash on cash: -1.4%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $752

Traditional Rental Income: $2904

Airbnb ROI: -1.4%

Traditional ROI: 3.88%

24065 PAPPYS Way

Hollywood, MD

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

$675,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $1967

Traditional Rental Income: $3578

Airbnb ROI: 0.34%

Traditional ROI: 3.72%

44015 SANDY BOTTOM Road

Hollywood, MD

5 beds | 3 baths | 1,752 sq.ft.

$475,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $1995

Traditional Rental Income: $2736

Airbnb ROI: 1.33%