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.

Golden Highlands Investment Property for Sale in Shady Side, MD

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

Showing 31 Golden Highlands Investment Property 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
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 Dr Shady Side, MD Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, whe...	3 beds \| 1 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 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.	$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 St Shady Side, MD 4/15/26 Under roof. EXPECTED SUMMER 2026 DELIVERY. 100% financing available with USDA loan...	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%
5314 Al Jones Dr Shady Side, MD 4/6/26. Just broke ground. Late summer delivery. Coastal Living Just Steps from the Chesap...	4 beds \| 2 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 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: $1421 Traditional Rental Income: $2795 Airbnb ROI: -0.27% Traditional ROI: 2.38%
1512 Lincoln Rd Shady Side, MD Best value luxury home in Shady Side- turn key in every way for long term low maintenance ...	3 beds \| 2 baths \| 1,512 sq.ft.	$474,900	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.79% Airbnb Rental Income: $1421 Traditional Rental Income: $2147 Airbnb ROI: 0.2% Traditional ROI: 2.79%
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: 0.04% Traditional cash on cash: 5% Airbnb Rental Income: $1421 Traditional Rental Income: $3172 Airbnb ROI: 0.04% 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%
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%
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 St Shady Side, MD Would you love to live in a water oriented community? Have you ever? Come take a look at t...	3 beds \| 2 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%

Your search for investment property begins and ends here

Golden Highlands 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 Dr

Shady Side, MD

3 beds | 1 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 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.

$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 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%

5314 Al Jones Dr

Shady Side, MD

4 beds | 2 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 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: $1421

Traditional Rental Income: $2795

Airbnb ROI: -0.27%