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 Avenue 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: 1.06% Traditional cash on cash: 4.31% Airbnb Rental Income: $1859 Traditional Rental Income: $2729 Airbnb ROI: 1.06% Traditional ROI: 4.31%
4721 Oak Rd Shady Side, MD Sweeping, panoramic views of Chesapeake Bay! Crab from your private pier or just enjoy th...	4 beds \| 3 baths \| 1,868 sq.ft.	$1,160,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 0.75% Airbnb Rental Income: $3207 Traditional Rental Income: $2526 Airbnb ROI: 0.71% Traditional ROI: 0.75%
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: 1.31% Traditional cash on cash: 2.07% Airbnb Rental Income: $1859 Traditional Rental Income: $1691 Airbnb ROI: 1.31% Traditional ROI: 2.07%
4725 FREDERICK Avenue Shady Side, MD Adorable and fully renovated rancher situated on a rare double lot in the water-oriented I...	3 beds \| 2 baths \| 912 sq.ft.	$465,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.16% Airbnb Rental Income: $1859 Traditional Rental Income: $2213 Airbnb ROI: 1.2% Traditional ROI: 3.16%
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: 1.93% Traditional cash on cash: 2.76% Airbnb Rental Income: $3207 Traditional Rental Income: $3065 Airbnb ROI: 1.93% 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: 3.57% Traditional cash on cash: 4.1% Airbnb Rental Income: $3207 Traditional Rental Income: $2755 Airbnb ROI: 3.57% 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 \| 2 baths \| N/A	$399,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 5.27% Airbnb Rental Income: $3207 Traditional Rental Income: $2786 Airbnb ROI: 4.46% Traditional ROI: 5.27%
1191 POPLAR Avenue Shady Side, MD Welcome to Cedarhurst on the Bay! Water Provilege Community Within Walking Distance to Com...	4 beds \| 3 baths \| 2,272 sq.ft.	$540,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 2.8% Airbnb Rental Income: $3207 Traditional Rental Income: $2543 Airbnb ROI: 2.69% Traditional ROI: 2.8%
4912 Beech St Shady Side, MD PLEASE NOTE THE TIME CHANGE FOR THE OPEN HOUSE TO SUNDAY 2 - 4pm Welcome to this cha...	2 beds \| 2 baths \| 864 sq.ft.	$365,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 4.09% Airbnb Rental Income: $2077 Traditional Rental Income: $2141 Airbnb ROI: 2.34% Traditional ROI: 4.09%
5211 AL JONES Drive Shady Side, MD Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. ...	2 beds \| 2 baths \| 1,244 sq.ft.	$550,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 2.14% Airbnb Rental Income: $2077 Traditional Rental Income: $2264 Airbnb ROI: 0.74% Traditional ROI: 2.14%
4738 Washington Ave Shady Side, MD Peaceful Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrifici...	3 beds \| 2 baths \| 1,223 sq.ft.	$399,900	Airbnb cash on cash: 1.59% Traditional cash on cash: 3.27% Airbnb Rental Income: $1859 Traditional Rental Income: $1988 Airbnb ROI: 1.59% Traditional ROI: 3.27%
1617 Winters Ave Shady Side, MD Welcome to 1617 Winters Ave - Coastal Charm with Modern Updates in Idlewild on the Bay Bea...	2 beds \| 2 baths \| 1,000 sq.ft.	$354,500	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.22% Airbnb Rental Income: $2077 Traditional Rental Income: $2127 Airbnb ROI: 2.46% Traditional ROI: 4.22%
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: 2.79% Traditional cash on cash: 4.26% Airbnb Rental Income: $1175 Traditional Rental Income: $1001 Airbnb ROI: 2.79% 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: 2.59% Traditional cash on cash: 2.65% Airbnb Rental Income: $1175 Traditional Rental Income: $799 Airbnb ROI: 2.59% 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: 5.1% Traditional cash on cash: 5.12% Airbnb Rental Income: $1175 Traditional Rental Income: $792 Airbnb ROI: 5.1% 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: 5.1% Traditional cash on cash: 5.12% Airbnb Rental Income: $1175 Traditional Rental Income: $792 Airbnb ROI: 5.1% Traditional ROI: 5.12%
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: 1.8% Traditional cash on cash: -0.98% Airbnb Rental Income: $3207 Traditional Rental Income: $771 Airbnb ROI: 1.8% 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: $1859 Traditional Rental Income: $2795 Airbnb ROI: 0.27% Traditional ROI: 2.38%
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.	$444,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 5.33% Airbnb Rental Income: $1859 Traditional Rental Income: $3172 Airbnb ROI: 0.97% Traditional ROI: 5.33%
5341 AL JONES Drive Shady Side, MD Fantastic opportunity to own your own land lighthouse-inspired round house with water view...	3 beds \| 2 baths \| 1,962 sq.ft.	$745,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.12% Airbnb Rental Income: $1859 Traditional Rental Income: $2175 Airbnb ROI: -0.06% Traditional ROI: 1.12%
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: -1.3% Traditional cash on cash: -0.05% Airbnb Rental Income: $3388 Traditional Rental Income: $6710 Airbnb ROI: -1.3% Traditional ROI: -0.05%
1225 JUNIPER Street Shady Side, MD THIS IS A TO BE BUILT HOME	4 beds \| 3 baths \| 2,091 sq.ft.	$595,990	Airbnb cash on cash: 3.08% Traditional cash on cash: 4.02% Airbnb Rental Income: $3207 Traditional Rental Income: $3011 Airbnb ROI: 3.08% Traditional ROI: 4.02%
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.	$674,990	Airbnb cash on cash: 2.6% Traditional cash on cash: 3.91% Airbnb Rental Income: $3207 Traditional Rental Income: $3307 Airbnb ROI: 2.6% Traditional ROI: 3.91%
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 \| 3 baths \| N/A	$569,900	Airbnb cash on cash: 3.26% Traditional cash on cash: 4.49% Airbnb Rental Income: $3207 Traditional Rental Income: $3137 Airbnb ROI: 3.26% 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: 3.72% Traditional cash on cash: 3.76% Airbnb Rental Income: $1175 Traditional Rental Income: $795 Airbnb ROI: 3.72% Traditional ROI: 3.76%
1430 Haile Pkwy Shady Side, MD 1430 Haile Pkwy, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 3 baths \| 3,100 sq.ft.	$650,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 2.43% Airbnb Rental Income: $3207 Traditional Rental Income: $2829 Airbnb ROI: 1.86% Traditional ROI: 2.43%
1186 & 1188 Poplar Ave Shady Side, MD 1186 & 1188 Poplar Ave, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 4.05% Airbnb Rental Income: $1175 Traditional Rental Income: $801 Airbnb ROI: 3.95% Traditional ROI: 4.05%

Real Estate investment in Shady-side, MD

There are 34 properties for sale in the city of Shady Side . The median list price in Shady Side is $449,768 and the average price per square foot is $241. In June 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $2,159.

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

There are 34 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 $2,159.

Your search for investment property begins and ends here

Investment Property for Sale in Shady Side, MD

1217 PINE Avenue

Shady Side, MD

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

$450,000

Airbnb cash on cash: 1.06%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1859

Traditional Rental Income: $2729

Airbnb ROI: 1.06%

Traditional ROI: 4.31%

4721 Oak Rd

Shady Side, MD

4 beds | 3 baths | 1,868 sq.ft.

$1,160,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $3207

Traditional Rental Income: $2526

Airbnb ROI: 0.71%

Traditional ROI: 0.75%

1316 Azalia St

Shady Side, MD

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

$465,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $1859

Traditional Rental Income: $1691

Airbnb ROI: 1.31%

Traditional ROI: 2.07%

4725 FREDERICK Avenue

Shady Side, MD

3 beds | 2 baths | 912 sq.ft.

$465,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $1859

Traditional Rental Income: $2213

Airbnb ROI: 1.2%

Traditional ROI: 3.16%

1462 SNUG HARBOR Road

Shady Side, MD

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

$750,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3207

Traditional Rental Income: $3065

Airbnb ROI: 1.93%

Traditional ROI: 2.76%

1411 Haile Pkwy

Shady Side, MD

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

$550,000

Airbnb cash on cash: 3.57%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $3207

Traditional Rental Income: $2755

Airbnb ROI: 3.57%

Traditional ROI: 4.1%

1199 OAK AVE

Shady Side, MD

4 beds | 2 baths | N/A

$399,900

Airbnb cash on cash: 4.46%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $3207

Traditional Rental Income: $2786

Airbnb ROI: 4.46%

Traditional ROI: 5.27%

1191 POPLAR Avenue

Shady Side, MD

4 beds | 3 baths | 2,272 sq.ft.

$540,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $3207

Traditional Rental Income: $2543

Airbnb ROI: 2.69%