Real Estate Investment Properties for Sale in Shady Side, MD

Looking for investment property in Shady Side, MD with high ROI ?

Explore a variety of short-term homes & houses in Shady Side, MD. Invest wisely with VRBO & Shady Side, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Shady Side, MD

Search for Single Family Residential for Sale in Shady Side, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 18 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1197 POPLAR AVENUE Shady Side, MD Charming one-level home tucked away in the waterfront community of Cedarhurst! This proper...	3 beds \| 1 baths \| 1,088 sq.ft.	$340,000	Airbnb cash on cash: 7.77% Traditional cash on cash: 4.7% Airbnb Rental Income: $3981 Traditional Rental Income: $2146 Airbnb ROI: 7.77% Traditional ROI: 4.7%
1462 SNUG HARBOR ROAD Shady Side, MD 4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes ...	4 beds \| 2 baths \| 2,144 sq.ft.	$735,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 2.88% Airbnb Rental Income: $5433 Traditional Rental Income: $3065 Airbnb ROI: 4.74% Traditional ROI: 2.88%
1337 W RIVER RD Shady Side, MD Price Reduction!! Your Own Private Retreat, get away from the Rat Race and make this a gr...	2 beds \| 1 baths \| N/A	$600,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 0.74% Airbnb Rental Income: $2847 Traditional Rental Income: $1720 Airbnb ROI: 1.57% Traditional ROI: 0.74%
5211 AL JONES DRIVE Shady Side, MD Great New Price ... here is your chance to own and enjoy a coastal contemporary cottage wi...	2 beds \| 2 baths \| 1,244 sq.ft.	$554,500	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.29% Airbnb Rental Income: $2847 Traditional Rental Income: $2264 Airbnb ROI: 2.14% Traditional ROI: 2.29%
1711 COLUMBIA BEACH ROAD Shady Side, MD Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond ...	4 beds \| 3 baths \| 2,176 sq.ft.	$499,900	Airbnb cash on cash: 7.04% Traditional cash on cash: 4.32% Airbnb Rental Income: $5433 Traditional Rental Income: $3067 Airbnb ROI: 7.04% Traditional ROI: 4.32%
1601 SNUG HARBOR RD Shady Side, MD Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boa...	4 beds \| 3 baths \| N/A	$599,999	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.5% Airbnb Rental Income: $5433 Traditional Rental Income: $3125 Airbnb ROI: 5.67% Traditional ROI: 3.5%
4819 AVERY ROAD Shady Side, MD Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront ...	5 beds \| 5 baths \| 5,151 sq.ft.	$2,295,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 1.38% Airbnb Rental Income: $6725 Traditional Rental Income: $6269 Airbnb ROI: 0.98% Traditional ROI: 1.38%
1100 STEAMBOAT ROAD Shady Side, MD Spectacular West River waterfront! A serene lot with panoramic water views, a custom-built...	4 beds \| 3 baths \| 3,745 sq.ft.	$2,250,000	Airbnb cash on cash: 0.48% Traditional cash on cash: -0.06% Airbnb Rental Income: $5433 Traditional Rental Income: $3200 Airbnb ROI: 0.48% Traditional ROI: -0.06%
4725 IDLEWILDE ROAD Shady Side, MD Calling all investors, second-home seekers, and visionariesthis is the project youve been ...	2 beds \| 1 baths \| 1,000 sq.ft.	$275,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 5.26% Airbnb Rental Income: $2847 Traditional Rental Income: $1932 Airbnb ROI: 6.23% Traditional ROI: 5.26%
1731 COLUMBIA BEACH RD Shady Side, MD Just Reduced, seller says sell! Welcome to this delightful coastal cottage nestled in the ...	2 beds \| 1 baths \| N/A	$345,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 2.95% Airbnb Rental Income: $2847 Traditional Rental Income: $1682 Airbnb ROI: 4.5% Traditional ROI: 2.95%
1220 GROVE AVENUE Shady Side, MD This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Commun...	5 beds \| 2 baths \| 1,812 sq.ft.	$485,500	Airbnb cash on cash: 10% Traditional cash on cash: 4.51% Airbnb Rental Income: $6725 Traditional Rental Income: $2922 Airbnb ROI: 10% Traditional ROI: 4.51%
1195 CEDAR AVENUE Shady Side, MD This beautifully crafted home blends timeless coastal charm with modern luxury. Featuring ...	4 beds \| 3 baths \| 2,710 sq.ft.	$699,500	Airbnb cash on cash: 5.32% Traditional cash on cash: 3.75% Airbnb Rental Income: $5433 Traditional Rental Income: $3316 Airbnb ROI: 5.32% Traditional ROI: 3.75%
4738 WASHINGTON AVENUE Shady Side, MD Charming Rancher Just Steps from the Bay Front! Nestled on a peaceful corner lot and surr...	3 beds \| 1 baths \| 1,000 sq.ft.	$360,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.73% Airbnb Rental Income: $3981 Traditional Rental Income: $1988 Airbnb ROI: 7.11% Traditional ROI: 3.73%
1617 WINTERS AVENUE Shady Side, MD Welcome to 1617 Winters Ave Coastal Charm with Modern Updates in Idlewild on the Bay Beau...	2 beds \| 2 baths \| 1,000 sq.ft.	$378,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.9% Airbnb Rental Income: $2847 Traditional Rental Income: $2127 Airbnb ROI: 4.06% Traditional ROI: 3.9%
1330 JORDAN DRIVE Shady Side, MD Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highl...	3 beds \| 3 baths \| 1,440 sq.ft.	$435,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 4.71% Airbnb Rental Income: $3981 Traditional Rental Income: $2743 Airbnb ROI: 5.65% Traditional ROI: 4.71%
1700 BAYVIEW ROAD Shady Side, MD Don't miss this charming and well-maintained home! The main level features stylish LVP flo...	2 beds \| 2 baths \| 852 sq.ft.	$339,900	Airbnb cash on cash: 4.68% Traditional cash on cash: 4.5% Airbnb Rental Income: $2847 Traditional Rental Income: $2126 Airbnb ROI: 4.68% Traditional ROI: 4.5%
4727 OAK ROAD Shady Side, MD Rare Chesapeake Bay waterfront property with panoramic views and endless potential! This 3...	3 beds \| 2 baths \| 1,806 sq.ft.	$599,900	Airbnb cash on cash: 3.47% Traditional cash on cash: 3% Airbnb Rental Income: $3981 Traditional Rental Income: $2863 Airbnb ROI: 3.47% Traditional ROI: 3%
4949 IDLEWILDE ROAD Shady Side, MD This spacious and well-maintained home offers the ease of one-level living at it's best. T...	3 beds \| 2 baths \| 2,024 sq.ft.	$545,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 3.47% Airbnb Rental Income: $3981 Traditional Rental Income: $2798 Airbnb ROI: 4.11% Traditional ROI: 3.47%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shady Side, MD

1197 POPLAR AVENUE

Shady Side, MD

3 beds | 1 baths | 1,088 sq.ft.

$340,000

Airbnb cash on cash: 7.77%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $3981

Traditional Rental Income: $2146

Airbnb ROI: 7.77%

Traditional ROI: 4.7%

1462 SNUG HARBOR ROAD

Shady Side, MD

4 beds | 2 baths | 2,144 sq.ft.

$735,000

Airbnb cash on cash: 4.74%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $5433

Traditional Rental Income: $3065

Airbnb ROI: 4.74%

Traditional ROI: 2.88%

1337 W RIVER RD

Shady Side, MD

2 beds | 1 baths | N/A

$600,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $2847

Traditional Rental Income: $1720

Airbnb ROI: 1.57%

Traditional ROI: 0.74%

5211 AL JONES DRIVE

Shady Side, MD

2 beds | 2 baths | 1,244 sq.ft.

$554,500

Airbnb cash on cash: 2.14%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2847

Traditional Rental Income: $2264

Airbnb ROI: 2.14%

Traditional ROI: 2.29%

1711 COLUMBIA BEACH ROAD

Shady Side, MD

4 beds | 3 baths | 2,176 sq.ft.

$499,900

Airbnb cash on cash: 7.04%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $5433

Traditional Rental Income: $3067

Airbnb ROI: 7.04%

Traditional ROI: 4.32%

1601 SNUG HARBOR RD

Shady Side, MD

4 beds | 3 baths | N/A

$599,999

Airbnb cash on cash: 5.67%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $5433

Traditional Rental Income: $3125

Airbnb ROI: 5.67%

Traditional ROI: 3.5%

4819 AVERY ROAD

Shady Side, MD

5 beds | 5 baths | 5,151 sq.ft.

$2,295,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $6725

Traditional Rental Income: $6269

Airbnb ROI: 0.98%

Traditional ROI: 1.38%

1100 STEAMBOAT ROAD

Shady Side, MD

4 beds | 3 baths | 3,745 sq.ft.

$2,250,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $5433

Traditional Rental Income: $3200

Airbnb ROI: 0.48%