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 23 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
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%
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: 1.15% Traditional cash on cash: 2.76% Airbnb Rental Income: $2556 Traditional Rental Income: $3065 Airbnb ROI: 1.15% 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.	$565,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 3.96% Airbnb Rental Income: $2556 Traditional Rental Income: $2755 Airbnb ROI: 2.42% Traditional ROI: 3.96%
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: 3.02% Traditional cash on cash: 5.27% Airbnb Rental Income: $2556 Traditional Rental Income: $2786 Airbnb ROI: 3.02% 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: 2.67% Traditional cash on cash: 5.59% Airbnb Rental Income: $2556 Traditional Rental Income: $3197 Airbnb ROI: 2.67% Traditional ROI: 5.59%
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: 2.23% Traditional cash on cash: 3.75% Airbnb Rental Income: $2556 Traditional Rental Income: $2622 Airbnb ROI: 2.23% 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%
1205 Hawthorne St Shady Side, MD Amazing Deal! Brand new custom home in Avalon Shores with an easy commute to DC/Annapolis/...	4 beds \| 3 baths \| 1,967 sq.ft.	$600,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.49% Airbnb Rental Income: $2556 Traditional Rental Income: $3410 Airbnb ROI: 1.86% Traditional ROI: 4.49%
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: $2556 Traditional Rental Income: $3051 Airbnb ROI: 2.23% 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: -0.57% Traditional cash on cash: 2.14% Airbnb Rental Income: $1270 Traditional Rental Income: $2264 Airbnb ROI: -0.57% Traditional ROI: 2.14%
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: 1.49% Traditional cash on cash: 3.45% Airbnb Rental Income: $1421 Traditional Rental Income: $1497 Airbnb ROI: 1.49% Traditional ROI: 3.45%
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: -0.75% Traditional cash on cash: -0.18% Airbnb Rental Income: $2556 Traditional Rental Income: $2727 Airbnb ROI: -0.75% 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: 0.92% Traditional cash on cash: -0.98% Airbnb Rental Income: $2556 Traditional Rental Income: $771 Airbnb ROI: 0.92% 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 fully renovated 3-bedroom, 2.5-bath home offers a thoughtful blend of modern updates ...	3 beds \| 2 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 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: 1.22% Traditional cash on cash: 3.2% Airbnb Rental Income: $2556 Traditional Rental Income: $3051 Airbnb ROI: 1.22% Traditional ROI: 3.2%
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: -1.54% Traditional cash on cash: -0.05% Airbnb Rental Income: $2478 Traditional Rental Income: $6710 Airbnb ROI: -1.54% 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: 2.18% Traditional cash on cash: 4.16% Airbnb Rental Income: $2556 Traditional Rental Income: $3011 Airbnb ROI: 2.18% Traditional ROI: 4.16%
1502 Garst Rd Shady Side, MD 1502 Garst Rd, Shady Side, MD 20764 \| Single Family Residential	2 beds \| 1 baths \| 736 sq.ft.	$235,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 3.48% Airbnb Rental Income: $1270 Traditional Rental Income: $1328 Airbnb ROI: 1.42% Traditional ROI: 3.48%
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: 1.85% Traditional cash on cash: 4.1% Airbnb Rental Income: $2556 Traditional Rental Income: $3307 Airbnb ROI: 1.85% 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.	$499,990	Airbnb cash on cash: 0.25% Traditional cash on cash: 3.98% Airbnb Rental Income: $1421 Traditional Rental Income: $2738 Airbnb ROI: 0.25% Traditional ROI: 3.98%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shady Side, MD

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%

1462 Snug Harbor Rd

Shady Side, MD

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

$750,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $2556

Traditional Rental Income: $3065

Airbnb ROI: 1.15%

Traditional ROI: 2.76%

1411 Haile Pkwy

Shady Side, MD

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

$565,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $2556

Traditional Rental Income: $2755

Airbnb ROI: 2.42%

Traditional ROI: 3.96%

1199 Oak Ave

Shady Side, MD

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

$399,900

Airbnb cash on cash: 3.02%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $2556

Traditional Rental Income: $2786

Airbnb ROI: 3.02%

Traditional ROI: 5.27%

5191 SPRING AVE

Shady Side, MD

4 beds | 3 baths | N/A

$460,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $2556

Traditional Rental Income: $3197

Airbnb ROI: 2.67%

Traditional ROI: 5.59%

1510 CALLAWAY DR

Shady Side, MD

4 beds | 2 baths | N/A

$480,000

Airbnb cash on cash: 2.23%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2556

Traditional Rental Income: $2622

Airbnb ROI: 2.23%

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%

Traditional ROI: 0.5%

1205 Hawthorne St

Shady Side, MD

4 beds | 3 baths | 1,967 sq.ft.

$600,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $2556

Traditional Rental Income: $3410

Airbnb ROI: 1.86%