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
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%
4907 Quince St Shady Side, MD 4907 Quince St, GALESVILLE, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$50,000	Airbnb cash on cash: 9.03% Traditional cash on cash: 11.5% Airbnb Rental Income: $1015 Traditional Rental Income: $783 Airbnb ROI: 9.03% Traditional ROI: 11.5%
Mayo Rd Shady Side, MD Mayo Rd, Shady Side, MD 21106 \| Other	N/A beds \| N/A baths \| N/A	$149,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.26% Airbnb Rental Income: $1015 Traditional Rental Income: $1001 Airbnb ROI: 1.86% Traditional ROI: 4.26%
5250 Al Jones Dr Shady Side, MD 5250 Al Jones Dr, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$149,999	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.65% Airbnb Rental Income: $1015 Traditional Rental Income: $799 Airbnb ROI: 1.66% Traditional ROI: 2.65%
1436 Haile Pkwy Shady Side, MD 1436 Haile Pkwy, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.12% Airbnb Rental Income: $1015 Traditional Rental Income: $792 Airbnb ROI: 3.73% Traditional ROI: 5.12%
1445 & 1447 Haile Pkwy Shady Side, MD 1445 & 1447 Haile Pkwy, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.12% Airbnb Rental Income: $1015 Traditional Rental Income: $792 Airbnb ROI: 3.73% Traditional ROI: 5.12%
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%
1495 Shady Rest Rd Shady Side, MD 1495 Shady Rest Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.76% Airbnb Rental Income: $1015 Traditional Rental Income: $795 Airbnb ROI: 2.61% Traditional ROI: 3.76%

Real Estate investment in Shady-side, MD

There are 28 properties for sale in the city of Shady Side . The median list price in Shady Side is $465,000 and the average price per square foot is $224. In May 2026, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,253.

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

There are 28 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 $2,253.

Your search for investment property begins and ends here

Investment Property 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%