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 20 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
1462 Snug Harbor Rd Shady Side, MD 4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunit...	4 beds \| 1 baths \| 2,144 sq.ft.	$750,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 2.76% Airbnb Rental Income: $2551 Traditional Rental Income: $3065 Airbnb ROI: 1.14% Traditional ROI: 2.76%
1199 Oak Ave Shady Side, MD Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhur...	4 beds \| 1 baths \| 1,399 sq.ft.	$400,000	Airbnb cash on cash: 3% Traditional cash on cash: 5.27% Airbnb Rental Income: $2551 Traditional Rental Income: $2786 Airbnb ROI: 3% Traditional ROI: 5.27%
5191 SPRING AVE Shady Side, MD Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on t...	4 beds \| 3 baths \| N/A	$460,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 5.59% Airbnb Rental Income: $2551 Traditional Rental Income: $3197 Airbnb ROI: 2.66% Traditional ROI: 5.59%
4908 Olive St Shady Side, MD 4/3/26 Foundation started. EXPECTED SUMMER 2026 DELIVERY. Must use builder contract - buye...	4 beds \| 2 baths \| 2,091 sq.ft.	$599,990	Airbnb cash on cash: 2.23% Traditional cash on cash: 4.21% Airbnb Rental Income: $2551 Traditional Rental Income: $3051 Airbnb ROI: 2.23% Traditional ROI: 4.21%
1419 Shady Rest Rd Shady Side, MD SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house present...	3 beds \| 1 baths \| 1,022 sq.ft.	$270,750	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.45% Airbnb Rental Income: $1416 Traditional Rental Income: $1497 Airbnb ROI: 1.47% Traditional ROI: 3.45%
4949 Idlewilde Rd 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.	$529,650	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.53% Airbnb Rental Income: $1416 Traditional Rental Income: $2798 Airbnb ROI: -0.12% Traditional ROI: 3.53%
1650 Cedar Ln Shady Side, MD Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home...	3 beds \| 2 baths \| 1,866 sq.ft.	$729,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.38% Airbnb Rental Income: $1416 Traditional Rental Income: $2795 Airbnb ROI: -0.27% Traditional ROI: 2.38%
1160 Oak Ave Shady Side, MD Experience the epitome of luxury living in this stunning Colonial home, beautifully renova...	3 beds \| 1 baths \| 1,320 sq.ft.	$439,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.35% Airbnb Rental Income: $1416 Traditional Rental Income: $2213 Airbnb ROI: 0.38% Traditional ROI: 3.35%
1161 Steamboat Rd Shady Side, MD Welcome to this inviting single-family home in the heart of Shady Side! This lovely reside...	3 beds \| 2 baths \| 2,235 sq.ft.	$469,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 5% Airbnb Rental Income: $1416 Traditional Rental Income: $3172 Airbnb ROI: 0.03% Traditional ROI: 5%
1209 Johnson Dr Shady Side, MD HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their l...	4 beds \| 2 baths \| 2,068 sq.ft.	$599,990	Airbnb cash on cash: 1.21% Traditional cash on cash: 3.2% Airbnb Rental Income: $2551 Traditional Rental Income: $3051 Airbnb ROI: 1.21% Traditional ROI: 3.2%
1225 Juniper St Shady Side, MD THIS IS A TO BE BUILT HOME	4 beds \| 2 baths \| 2,091 sq.ft.	$579,990	Airbnb cash on cash: 2.18% Traditional cash on cash: 4.16% Airbnb Rental Income: $2551 Traditional Rental Income: $3011 Airbnb ROI: 2.18% Traditional ROI: 4.16%
1379 MCDONALD RD Shady Side, MD *BRAND NEW & READY FOR IMMEDIATE OCCUPANCY* this stunning Arts & Crafts home by Laine ...	4 beds \| 3 baths \| N/A	$835,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 2.74% Airbnb Rental Income: $2551 Traditional Rental Income: $3106 Airbnb ROI: 1.24% Traditional ROI: 2.74%
1235 Spruce Ave Shady Side, MD THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home wit...	4 beds \| 2 baths \| 2,710 sq.ft.	$649,990	Airbnb cash on cash: 1.84% Traditional cash on cash: 4.1% Airbnb Rental Income: $2551 Traditional Rental Income: $3307 Airbnb ROI: 1.84% Traditional ROI: 4.1%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shady Side, MD

1462 Snug Harbor Rd

Shady Side, MD

4 beds | 1 baths | 2,144 sq.ft.

$750,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2551

Traditional Rental Income: $3065

Airbnb ROI: 1.14%

Traditional ROI: 2.76%

1199 Oak Ave

Shady Side, MD

4 beds | 1 baths | 1,399 sq.ft.

$400,000

Airbnb cash on cash: 3%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $2551

Traditional Rental Income: $2786

Airbnb ROI: 3%

Traditional ROI: 5.27%

5191 SPRING AVE

Shady Side, MD

4 beds | 3 baths | N/A

$460,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $2551

Traditional Rental Income: $3197

Airbnb ROI: 2.66%

Traditional ROI: 5.59%

4908 Olive St

Shady Side, MD

4 beds | 2 baths | 2,091 sq.ft.

$599,990

Airbnb cash on cash: 2.23%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $2551

Traditional Rental Income: $3051

Airbnb ROI: 2.23%

Traditional ROI: 4.21%

1419 Shady Rest Rd

Shady Side, MD

3 beds | 1 baths | 1,022 sq.ft.

$270,750

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $1416

Traditional Rental Income: $1497

Airbnb ROI: 1.47%

Traditional ROI: 3.45%

4949 Idlewilde Rd

Shady Side, MD

3 beds | 2 baths | 2,024 sq.ft.

$529,650

Airbnb cash on cash: -0.12%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1416

Traditional Rental Income: $2798

Airbnb ROI: -0.12%

Traditional ROI: 3.53%

1650 Cedar Ln

Shady Side, MD

3 beds | 2 baths | 1,866 sq.ft.

$729,900

Airbnb cash on cash: -0.27%

Traditional cash on cash: 2.38%

Airbnb Rental Income: $1416

Traditional Rental Income: $2795

Airbnb ROI: -0.27%

Traditional ROI: 2.38%

1160 Oak Ave

Shady Side, MD

3 beds | 1 baths | 1,320 sq.ft.

$439,900

Airbnb cash on cash: 0.38%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1416

Traditional Rental Income: $2213

Airbnb ROI: 0.38%