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
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%
1220 SHESLEY Road Shady Side, MD Charming Coastal Opportunity Near the Chesapeake Bay Discover the potential of this charmi...	2 beds \| 1 baths \| 880 sq.ft.	$323,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.13% Airbnb Rental Income: $1270 Traditional Rental Income: $1960 Airbnb ROI: 0.54% Traditional ROI: 4.13%
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%

Real Estate investment in Shady-side, MD

There are 30 properties for sale in the city of Shady Side . The median list price in Shady Side is $499,325 and the average price per square foot is $284. In April 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $2,770.

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

There are 30 investment properties available for sale in Shady-side.

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

The ROI for Long-Term is higher than the Short-Term in Shady-side with average rental income of $2,770.

Your search for investment property begins and ends here

Investment Property 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%