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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24730 HALF PONE POINT Road Hollywood, MD A legacy waterfront estate at the tip of coveted Half Pone Point. Commanding one of the mo...	4 beds \| 7 baths \| 13,665 sq.ft.	$4,595,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.04% Airbnb Rental Income: $3404 Traditional Rental Income: $7070 Airbnb ROI: -1% Traditional ROI: 0.04%
24439 BROAD CREEK Drive Hollywood, MD Don't miss this immaculate QBH Patuxent Model offering over 3,400 square feet of beautiful...	4 beds \| 4 baths \| 3,415 sq.ft.	$534,900	Airbnb cash on cash: 3.38% Traditional cash on cash: 5.22% Airbnb Rental Income: $3404 Traditional Rental Income: $3567 Airbnb ROI: 3.38% Traditional ROI: 5.22%
43732 RASPBERRY Lane Hollywood, MD Premier Waterfront Retreat with Unrivaled Patuxent River Views This extraordinary residenc...	2 beds \| 2 baths \| 1,226 sq.ft.	$598,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 1.21% Airbnb Rental Income: $1994 Traditional Rental Income: $1880 Airbnb ROI: 0.48% Traditional ROI: 1.21%
25263 SOTTERLEY Road Hollywood, MD Welcome to this beautifully renovated home in the heart of Hollywood! Completely updated i...	3 beds \| 2 baths \| 1,274 sq.ft.	$349,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.68% Airbnb Rental Income: $1280 Traditional Rental Income: $1823 Airbnb ROI: 0.8% Traditional ROI: 3.68%
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: 0.82% Traditional cash on cash: 3.88% Airbnb Rental Income: $1994 Traditional Rental Income: $2904 Airbnb ROI: 0.82% Traditional ROI: 3.88%
23801 MCINTOSH Road Hollywood, MD Now offered at new exceptional price! $424,900. Pool is Open & Summer Is Calling! The pool...	3 beds \| 3 baths \| 1,634 sq.ft.	$424,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 4.52% Airbnb Rental Income: $1280 Traditional Rental Income: $2557 Airbnb ROI: 0.31% Traditional ROI: 4.52%
43816 RASPBERRY Lane Hollywood, MD Experience timeless English Tudor character paired with sweeping, unobstructed views of th...	3 beds \| 3 baths \| 2,551 sq.ft.	$764,987	Airbnb cash on cash: -0.8% Traditional cash on cash: 3.43% Airbnb Rental Income: $1280 Traditional Rental Income: $3887 Airbnb ROI: -0.8% Traditional ROI: 3.43%
24814 HALF PONE POINT Road Hollywood, MD Welcome to this stunning custom waterfront home, situated high on Half Pone Point, offerin...	3 beds \| 4 baths \| 4,537 sq.ft.	$1,749,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 0.72% Airbnb Rental Income: $1280 Traditional Rental Income: $3797 Airbnb ROI: -1.08% Traditional ROI: 0.72%
25287 PINTO Drive Hollywood, MD Located on a beautiful corner lot in Hollywood, this charming ranch-style home is ready to...	3 beds \| 2 baths \| 1,344 sq.ft.	$355,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 4.31% Airbnb Rental Income: $1280 Traditional Rental Income: $2090 Airbnb ROI: 0.68% Traditional ROI: 4.31%
24301 OLD HOLLYWOOD Road Hollywood, MD One owner for almost 60 years! Home recently had new roof, new windows, new doors, and app...	3 beds \| 2 baths \| 2,365 sq.ft.	$499,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.15% Airbnb Rental Income: $1280 Traditional Rental Income: $2430 Airbnb ROI: -0.18% Traditional ROI: 3.15%
23017 Holloway Ct Hollywood, MD From its inviting curb appeal to its spacious, thoughtfully designed interior, this stunni...	5 beds \| 3 baths \| 4,238 sq.ft.	$679,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 4.05% Airbnb Rental Income: $3606 Traditional Rental Income: $3726 Airbnb ROI: 2.61% Traditional ROI: 4.05%
43410 OLD WHARF Lane Hollywood, MD Nestled along the shores of the Patuxent River is this very private, custom-built, all bri...	4 beds \| 3 baths \| 2,748 sq.ft.	$1,350,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.14% Airbnb Rental Income: $3404 Traditional Rental Income: $3457 Airbnb ROI: 0.49% Traditional ROI: 1.14%
24715 HALF PONE POINT Road Hollywood, MD A rare opportunity to own an extraordinary 11.83-acre wooded property in the prestigious H...	1 beds \| 1 baths \| 1,000 sq.ft.	$1,450,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.24% Airbnb Rental Income: $1040 Traditional Rental Income: $1983 Airbnb ROI: -0.73% Traditional ROI: 0.24%
44025 W LEOLA Court Hollywood, MD Welcome to this beautifully maintained home in the desirable Estates at Joy Chapel! Offeri...	5 beds \| 4 baths \| 4,152 sq.ft.	$615,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 5.45% Airbnb Rental Income: $3606 Traditional Rental Income: $3804 Airbnb ROI: 3.72% Traditional ROI: 5.45%

Real Estate investment in Hollywood, MD

There are 16 properties for sale in the city of Hollywood . The median list price in Hollywood is $565,000 and the average price per square foot is $310. In August 2026, the average monthly cash on cash return in Hollywood is 3.00%. The average monthly rental income in Hollywood is $3,512.

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

There are 16 investment properties available for sale in Hollywood.

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

The ROI for Long-Term is higher than the Short-Term in Hollywood with average rental income of $3,512.

Your search for investment property begins and ends here

Investment Property for Sale in Hollywood, MD

24730 HALF PONE POINT Road

Hollywood, MD

4 beds | 7 baths | 13,665 sq.ft.

$4,595,000

Airbnb cash on cash: -1%

Traditional cash on cash: 0.04%

Airbnb Rental Income: $3404

Traditional Rental Income: $7070

Airbnb ROI: -1%

Traditional ROI: 0.04%

24439 BROAD CREEK Drive

Hollywood, MD

4 beds | 4 baths | 3,415 sq.ft.

$534,900

Airbnb cash on cash: 3.38%

Traditional cash on cash: 5.22%

Airbnb Rental Income: $3404

Traditional Rental Income: $3567

Airbnb ROI: 3.38%

Traditional ROI: 5.22%

43732 RASPBERRY Lane

Hollywood, MD

2 beds | 2 baths | 1,226 sq.ft.

$598,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $1994

Traditional Rental Income: $1880

Airbnb ROI: 0.48%

Traditional ROI: 1.21%

25263 SOTTERLEY Road

Hollywood, MD

3 beds | 2 baths | 1,274 sq.ft.

$349,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1280

Traditional Rental Income: $1823

Airbnb ROI: 0.8%

Traditional ROI: 3.68%

43979 DRUM CLIFF Road

Hollywood, MD

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

$499,900

Airbnb cash on cash: 0.82%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1994

Traditional Rental Income: $2904

Airbnb ROI: 0.82%

Traditional ROI: 3.88%

23801 MCINTOSH Road

Hollywood, MD

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

$424,900

Airbnb cash on cash: 0.31%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $1280

Traditional Rental Income: $2557

Airbnb ROI: 0.31%

Traditional ROI: 4.52%

43816 RASPBERRY Lane

Hollywood, MD

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

$764,987

Airbnb cash on cash: -0.8%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $1280

Traditional Rental Income: $3887

Airbnb ROI: -0.8%

Traditional ROI: 3.43%

24814 HALF PONE POINT Road

Hollywood, MD

3 beds | 4 baths | 4,537 sq.ft.

$1,749,000

Airbnb cash on cash: -1.08%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $1280

Traditional Rental Income: $3797

Airbnb ROI: -1.08%