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 21 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
1217 Pine Ave Shady Side, MD Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner...	3 beds \| 2 baths \| 2,006 sq.ft.	$450,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.31% Airbnb Rental Income: $1421 Traditional Rental Income: $2729 Airbnb ROI: 0.2% Traditional ROI: 4.31%
1316 Azalia St Shady Side, MD Move in condition & 100% financing approved (USDA Loan). Very well maintained home in a wa...	3 beds \| N/A baths \| 1,500 sq.ft.	$465,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 2.07% Airbnb Rental Income: $1421 Traditional Rental Income: $1691 Airbnb ROI: 0.47% Traditional ROI: 2.07%
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: 1.18% Traditional cash on cash: 2.76% Airbnb Rental Income: $2584 Traditional Rental Income: $3065 Airbnb ROI: 1.18% Traditional ROI: 2.76%
1411 Haile Pkwy Shady Side, MD Rivendale Homes introduces the Cedarbury house type to Shady Side! This gorgeous custom bu...	4 beds \| 3 baths \| 1,905 sq.ft.	$550,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 4.1% Airbnb Rental Income: $2584 Traditional Rental Income: $2755 Airbnb ROI: 2.56% Traditional ROI: 4.1%
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: 3.08% Traditional cash on cash: 5.27% Airbnb Rental Income: $2584 Traditional Rental Income: $2786 Airbnb ROI: 3.08% 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: 2.28% Traditional cash on cash: 3.75% Airbnb Rental Income: $2584 Traditional Rental Income: $2622 Airbnb ROI: 2.28% Traditional ROI: 3.75%
1268 Hayes Rd Shady Side, MD Jaw-dropping sunrises! Fantastic neighborhood! Seller motivated! PRICE IMPROVED! Spectac...	3 beds \| 2 baths \| 1,964 sq.ft.	$1,149,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.5% Airbnb Rental Income: $1421 Traditional Rental Income: $2242 Airbnb ROI: -0.67% Traditional ROI: 0.5%
4908 Olive St Shady Side, MD 5/16/26 Under roof and ready for drywall. EXPECTED JULY 2026 DELIVERY. 100% financing avai...	4 beds \| 2 baths \| 2,091 sq.ft.	$599,990	Airbnb cash on cash: 2.27% Traditional cash on cash: 4.21% Airbnb Rental Income: $2584 Traditional Rental Income: $3051 Airbnb ROI: 2.27% Traditional ROI: 4.21%
5211 Al Jones Dr Shady Side, MD Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. ...	2 beds \| 1 baths \| 1,244 sq.ft.	$550,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.14% Airbnb Rental Income: $1744 Traditional Rental Income: $2264 Airbnb ROI: 0.2% Traditional ROI: 2.14%
5235-A Al Jones Dr Shady Side, MD 5235-A Al Jones Dr, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 3 baths \| 3,727 sq.ft.	$1,470,000	Airbnb cash on cash: -0.74% Traditional cash on cash: -0.18% Airbnb Rental Income: $2584 Traditional Rental Income: $2727 Airbnb ROI: -0.74% Traditional ROI: -0.18%
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: 0.96% Traditional cash on cash: -0.98% Airbnb Rental Income: $2584 Traditional Rental Income: $771 Airbnb ROI: 0.96% 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 This is a luxury home in Shady Side- turn key in every way for long term low maintenance l...	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%
4750 Frederick Ave Shady Side, MD This 5136 square foot single family home has 5 bedrooms and 6.0 bathrooms. This home is lo...	5 beds \| 5 baths \| 4,620 sq.ft.	$3,500,000	Airbnb cash on cash: -1.13% Traditional cash on cash: -0.05% Airbnb Rental Income: $4053 Traditional Rental Income: $6710 Airbnb ROI: -1.13% Traditional ROI: -0.05%
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: 2.23% Traditional cash on cash: 4.16% Airbnb Rental Income: $2584 Traditional Rental Income: $3011 Airbnb ROI: 2.23% 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: 1.88% Traditional cash on cash: 4.1% Airbnb Rental Income: $2584 Traditional Rental Income: $3307 Airbnb ROI: 1.88% Traditional ROI: 4.1%
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.	$464,990	Airbnb cash on cash: 0.35% Traditional cash on cash: 4.35% Airbnb Rental Income: $1421 Traditional Rental Income: $2738 Airbnb ROI: 0.35% Traditional ROI: 4.35%
1316 Juniper St Shady Side, MD This Stylish New home is move in ready and just in time to enjoy the summer breezes at the...	4 beds \| 2 baths \| 1,949 sq.ft.	$569,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 4.49% Airbnb Rental Income: $2584 Traditional Rental Income: $3137 Airbnb ROI: 2.28% Traditional ROI: 4.49%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shady Side, MD

1217 Pine Ave

Shady Side, MD

3 beds | 2 baths | 2,006 sq.ft.

$450,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1421

Traditional Rental Income: $2729

Airbnb ROI: 0.2%

Traditional ROI: 4.31%

1316 Azalia St

Shady Side, MD

3 beds | N/A baths | 1,500 sq.ft.

$465,000

Airbnb cash on cash: 0.47%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $1421

Traditional Rental Income: $1691

Airbnb ROI: 0.47%

Traditional ROI: 2.07%

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: 1.18%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2584

Traditional Rental Income: $3065

Airbnb ROI: 1.18%

Traditional ROI: 2.76%

1411 Haile Pkwy

Shady Side, MD

4 beds | 3 baths | 1,905 sq.ft.

$550,000

Airbnb cash on cash: 2.56%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $2584

Traditional Rental Income: $2755

Airbnb ROI: 2.56%

Traditional ROI: 4.1%

1199 Oak Ave

Shady Side, MD

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

$399,900

Airbnb cash on cash: 3.08%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $2584

Traditional Rental Income: $2786

Airbnb ROI: 3.08%

Traditional ROI: 5.27%

1510 CALLAWAY DR

Shady Side, MD

4 beds | 2 baths | N/A

$480,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2584

Traditional Rental Income: $2622

Airbnb ROI: 2.28%

Traditional ROI: 3.75%

1268 Hayes Rd

Shady Side, MD

3 beds | 2 baths | 1,964 sq.ft.

$1,149,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.5%

Airbnb Rental Income: $1421

Traditional Rental Income: $2242

Airbnb ROI: -0.67%