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.

Investment Property for Sale in Shady Side, MD

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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%

Real Estate investment in Shady-side, MD

There are 18 properties for sale in the city of Shady Side . The median list price in Shady Side is $499,900 and the average price per square foot is $257. In September 2025, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,771.

Shady-side, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 18 investment properties available for sale in Shady-side.

In 2025, the best neighborhood to buy investment property is Shady Side.

The ROI for Short-Term is higher than the Long-Term in Shady-side with average rental income of $3,981.

Your search for investment property begins and ends here

Investment Property 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%