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
4715 GIRTON Avenue Shady Side, MD Welcome to 4715 Girton Avenue in the Idlewild community. This home features 2 bedrooms, 2 ...	2 beds \| 2 baths \| 1,028 sq.ft.	$239,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 6.43% Airbnb Rental Income: $1270 Traditional Rental Income: $2041 Airbnb ROI: 1.25% Traditional ROI: 6.43%
4912 MARINERS Drive Shady Side, MD Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, whe...	3 beds \| 2 baths \| 1,386 sq.ft.	$429,900	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.4% Airbnb Rental Income: $1421 Traditional Rental Income: $2638 Airbnb ROI: 0.32% Traditional ROI: 4.4%
1462 SNUG HARBOR Road Shady Side, MD 4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunit...	4 beds \| 2 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 \| 2 baths \| N/A	$399,900	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%
1510 CALLAWAY DR Shady Side, MD Beautiful Brick-Front Cape Cod with loads of Curb Appeal. You don't want to miss this met...	4 beds \| 2 baths \| N/A	$480,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.75% Airbnb Rental Income: $2551 Traditional Rental Income: $2622 Airbnb ROI: 2.22% Traditional ROI: 3.75%
4908 OLIVE Street Shady Side, MD 4/15/26 Under roof. EXPECTED SUMMER 2026 DELIVERY. 100% financing available with USDA loan...	4 beds \| 3 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%
5314 AL JONES Drive Shady Side, MD 4/6/26. Just broke ground. Late summer delivery. Coastal Living Just Steps from the Chesap...	4 beds \| 3 baths \| 2,710 sq.ft.	$659,990	Airbnb cash on cash: 0.91% Traditional cash on cash: -0.98% Airbnb Rental Income: $2551 Traditional Rental Income: $771 Airbnb ROI: 0.91% Traditional ROI: -0.98%
1650 CEDAR Lane 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: $1421 Traditional Rental Income: $2795 Airbnb ROI: -0.27% Traditional ROI: 2.38%
1512 LINCOLN Road Shady Side, MD Luxury Fully Rebuilt Home in Gated Water-Access Community - Turn-Key and Move-In Ready Thi...	3 beds \| 3 baths \| 1,512 sq.ft.	$499,900	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.61% Airbnb Rental Income: $1421 Traditional Rental Income: $2147 Airbnb ROI: 0.14% Traditional ROI: 2.61%
1161 STEAMBOAT Road Shady Side, MD Welcome to this inviting single-family home in the heart of Shady Side! This lovely reside...	3 beds \| 3 baths \| 2,235 sq.ft.	$469,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 5% Airbnb Rental Income: $1421 Traditional Rental Income: $3172 Airbnb ROI: 0.04% Traditional ROI: 5%
1209 JOHNSON Drive Shady Side, MD HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their l...	4 beds \| 3 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 Street Shady Side, MD THIS IS A TO BE BUILT HOME	4 beds \| 3 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%
1235 SPRUCE Avenue Shady Side, MD THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home wit...	4 beds \| 3 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%
1469 CEDARHURST RD Shady Side, MD OFFER DEADLINE Sunday, April 12th at 4pm. Enjoy privacy and space in this charming ranch-s...	3 beds \| 2 baths \| N/A	$389,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 4.27% Airbnb Rental Income: $1421 Traditional Rental Income: $2356 Airbnb ROI: 0.54% Traditional ROI: 4.27%
1222 JUNIPER Street Shady Side, MD Would you love to live in a water oriented community? Have you ever? Come take a look at t...	3 beds \| 3 baths \| 1,598 sq.ft.	$474,990	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.24% Airbnb Rental Income: $1421 Traditional Rental Income: $2738 Airbnb ROI: 0.32% Traditional ROI: 4.24%

Real Estate investment in Shady-side, MD

There are 15 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 $256. In May 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $2,688.

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

There are 15 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 $2,688.

Your search for investment property begins and ends here

Investment Property for Sale in Shady Side, MD

4715 GIRTON Avenue

Shady Side, MD

2 beds | 2 baths | 1,028 sq.ft.

$239,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 6.43%

Airbnb Rental Income: $1270

Traditional Rental Income: $2041

Airbnb ROI: 1.25%

Traditional ROI: 6.43%

4912 MARINERS Drive

Shady Side, MD

3 beds | 2 baths | 1,386 sq.ft.

$429,900

Airbnb cash on cash: 0.32%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $1421

Traditional Rental Income: $2638

Airbnb ROI: 0.32%

Traditional ROI: 4.4%

1462 SNUG HARBOR Road

Shady Side, MD

4 beds | 2 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 | 2 baths | N/A

$399,900

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%

1510 CALLAWAY DR

Shady Side, MD

4 beds | 2 baths | N/A

$480,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2551

Traditional Rental Income: $2622

Airbnb ROI: 2.22%

Traditional ROI: 3.75%

4908 OLIVE Street

Shady Side, MD

4 beds | 3 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%

5314 AL JONES Drive

Shady Side, MD

4 beds | 3 baths | 2,710 sq.ft.

$659,990

Airbnb cash on cash: 0.91%

Traditional cash on cash: -0.98%

Airbnb Rental Income: $2551

Traditional Rental Income: $771

Airbnb ROI: 0.91%

Traditional ROI: -0.98%

1650 CEDAR Lane

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: $1421

Traditional Rental Income: $2795

Airbnb ROI: -0.27%