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 34 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: 1.6% Traditional cash on cash: 4.31% Airbnb Rental Income: $2131 Traditional Rental Income: $2729 Airbnb ROI: 1.6% Traditional ROI: 4.31%
4721 Oak Rd Shady Side, MD Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking...	4 beds \| 3 baths \| 1,868 sq.ft.	$998,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 0.87% Airbnb Rental Income: $4030 Traditional Rental Income: $2526 Airbnb ROI: 1.56% Traditional ROI: 0.87%
1211 Linton Ln Shady Side, MD Welcome to 1211 Linton Lane, where space, comfort, and water-access living come together i...	3 beds \| 3 baths \| 3,192 sq.ft.	$799,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.68% Airbnb Rental Income: $2131 Traditional Rental Income: $2606 Airbnb ROI: 0.31% Traditional ROI: 1.68%
1241 Johnson Dr Shady Side, MD Welcome to the Honey Hole of the South Creek! New roof & gutters freshly installed! Welcom...	3 beds \| 2 baths \| 2,176 sq.ft.	$699,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 2.22% Airbnb Rental Income: $2131 Traditional Rental Income: $2851 Airbnb ROI: 0.34% Traditional ROI: 2.22%
1172 Cedar Ave Shady Side, MD Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Penins...	3 beds \| 1 baths \| 864 sq.ft.	$325,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.08% Airbnb Rental Income: $2131 Traditional Rental Income: $1929 Airbnb ROI: 2.96% Traditional ROI: 4.08%
4909 Olive St Shady Side, MD Water privileged community! Lots of land- Tear down or rebuild existing home AND property ...	3 beds \| 2 baths \| 1,848 sq.ft.	$480,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 3.28% Airbnb Rental Income: $2131 Traditional Rental Income: $2286 Airbnb ROI: 1.76% Traditional ROI: 3.28%
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: 1.83% Traditional cash on cash: 2.07% Airbnb Rental Income: $2131 Traditional Rental Income: $1691 Airbnb ROI: 1.83% 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.	$699,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 3.03% Airbnb Rental Income: $4030 Traditional Rental Income: $3065 Airbnb ROI: 3.19% Traditional ROI: 3.03%
4921 Olive St Shady Side, MD * SELLER OFFERS A $5,000 CLOSING CREDIT! * Coastal charm meets modern comfort in Avalo...	3 beds \| 1 baths \| 1,008 sq.ft.	$349,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.77% Airbnb Rental Income: $2131 Traditional Rental Income: $1942 Airbnb ROI: 2.69% Traditional ROI: 3.77%
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.	$525,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 4.34% Airbnb Rental Income: $4030 Traditional Rental Income: $2755 Airbnb ROI: 5.18% Traditional ROI: 4.34%
1500 Garst Rd Shady Side, MD Welcome to 1500 Garst Road in the water oriented Columbia Beach community of Shady Side. E...	2 beds \| 1 baths \| 1,144 sq.ft.	$364,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 3.71% Airbnb Rental Income: $2177 Traditional Rental Income: $2058 Airbnb ROI: 2.44% Traditional ROI: 3.71%
1527 Lincoln Rd Shady Side, MD Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the...	3 beds \| 2 baths \| 1,200 sq.ft.	$394,700	Airbnb cash on cash: 2.07% Traditional cash on cash: 3.71% Airbnb Rental Income: $2131 Traditional Rental Income: $2203 Airbnb ROI: 2.07% Traditional ROI: 3.71%
1175 Maple Ave Shady Side, MD Welcome home to this beautifully maintained split-foyer in Cedarhurst on the Bay, Shadysid...	3 beds \| 2 baths \| 1,838 sq.ft.	$540,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 4.03% Airbnb Rental Income: $2131 Traditional Rental Income: $3044 Airbnb ROI: 1.14% Traditional ROI: 4.03%
4734 Oak Rd Shady Side, MD Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint water...	4 beds \| 2 baths \| 2,511 sq.ft.	$625,000	Airbnb cash on cash: 3.53% Traditional cash on cash: 3.55% Airbnb Rental Income: $4030 Traditional Rental Income: $3181 Airbnb ROI: 3.53% Traditional ROI: 3.55%
1220 Grove Ave Shady Side, MD Welcome to the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shad...	5 beds \| 2 baths \| 1,812 sq.ft.	$465,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 4.63% Airbnb Rental Income: $3314 Traditional Rental Income: $2922 Airbnb ROI: 3.84% Traditional ROI: 4.63%
5314 Al Jones Dr Shady Side, MD Home is ready for immediate occupancy. Ask about 3.99% for FHA & VA loans. Coastal Living ...	4 beds \| 2 baths \| 2,710 sq.ft.	$649,990	Airbnb cash on cash: 2.88% Traditional cash on cash: -0.99% Airbnb Rental Income: $4030 Traditional Rental Income: $771 Airbnb ROI: 2.88% Traditional ROI: -0.99%
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.	$699,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.52% Airbnb Rental Income: $2131 Traditional Rental Income: $2795 Airbnb ROI: 0.67% Traditional ROI: 2.52%
4701 Girton Ave Shady Side, MD 4701 Girton Ave, Shady Side, MD 20764 \| Single Family Residential	8 beds \| 6 baths \| 6,873 sq.ft.	$1,600,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 1.37% Airbnb Rental Income: $3314 Traditional Rental Income: $5232 Airbnb ROI: -0.42% Traditional ROI: 1.37%
1161 Steamboat Rd Shady Side, MD Welcome to this charming home located in a sought-after water-privileged community, just a...	3 beds \| 2 baths \| 2,235 sq.ft.	$429,900	Airbnb cash on cash: 1.6% Traditional cash on cash: 5.54% Airbnb Rental Income: $2131 Traditional Rental Income: $3172 Airbnb ROI: 1.6% Traditional ROI: 5.54%
5341 Al Jones Dr 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.	$725,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 1.17% Airbnb Rental Income: $2131 Traditional Rental Income: $2175 Airbnb ROI: 0.3% Traditional ROI: 1.17%
1225 Juniper St Shady Side, MD Move-in Ready!!! Builder offering special financing with preferred Lender and Title Compan...	4 beds \| 2 baths \| 2,091 sq.ft.	$549,990	Airbnb cash on cash: 4.5% Traditional cash on cash: 4.2% Airbnb Rental Income: $4030 Traditional Rental Income: $3011 Airbnb ROI: 4.5% Traditional ROI: 4.2%
1235 Spruce Ave Shady Side, MD AUGUST Delivier!!!! Enjoy water views of the community harbor with 60 boat slips and direc...	4 beds \| 2 baths \| 2,710 sq.ft.	$650,990	Airbnb cash on cash: 3.86% Traditional cash on cash: 4.09% Airbnb Rental Income: $4030 Traditional Rental Income: $3307 Airbnb ROI: 3.86% Traditional ROI: 4.09%
4951 Bonniewood Dr Shady Side, MD Welcome to this beautiful home in the highly sought-after Avalon Shores community, offered...	3 beds \| 2 baths \| 1,456 sq.ft.	$470,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 2.83% Airbnb Rental Income: $2131 Traditional Rental Income: $2142 Airbnb ROI: 1.57% Traditional ROI: 2.83%
4950 Bonniewood Dr Shady Side, MD Waterfront living with a private dock-all for only $775,000! Nestled in the charming Avalo...	3 beds \| 2 baths \| 2,304 sq.ft.	$775,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 1.26% Airbnb Rental Income: $2131 Traditional Rental Income: $2310 Airbnb ROI: 0.26% Traditional ROI: 1.26%
1582 Snug Harbor Rd Shady Side, MD 1582 Snug Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 1,915 sq.ft.	$599,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 1.76% Airbnb Rental Income: $4030 Traditional Rental Income: $2280 Airbnb ROI: 3.32% Traditional ROI: 1.76%
6372 Shady Side Rd W Shady Side, MD Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady...	3 beds \| 3 baths \| 2,450 sq.ft.	$380,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 7.11% Airbnb Rental Income: $2131 Traditional Rental Income: $3449 Airbnb ROI: 1.88% Traditional ROI: 7.11%
1237 Spruce Ave Shady Side, MD Enjoy water views of the community harbor with 60 boat slips and direct access to the Ches...	4 beds \| 2 baths \| N/A	$619,990	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.51% Airbnb Rental Income: $4030 Traditional Rental Income: $3404 Airbnb ROI: 4.1% Traditional ROI: 4.51%
1737 Cedar Ave Shady Side, MD 1737 Cedar Ave, Shady Side, MD 20764 \| Single Family Residential	1 beds \| 1 baths \| 672 sq.ft.	$249,900	Airbnb cash on cash: -2.25% Traditional cash on cash: 2.02% Airbnb Rental Income: $287 Traditional Rental Income: $1117 Airbnb ROI: -2.25% Traditional ROI: 2.02%
6066 Shady Side Rd Shady Side, MD 6066 Shady Side Rd, Shady Side, MD 20764 \| Single Family Residential	5 beds \| 3 baths \| 3,100 sq.ft.	$699,000	Airbnb cash on cash: 1.35% Traditional cash on cash: N/A Airbnb Rental Income: $3314 Traditional Rental Income: $0 Airbnb ROI: 1.35% Traditional ROI: N/A
1193 Oak Ave Shady Side, MD Welcome to the Chesapeake Bay lifestyle in the waterfront community of Cedarhurst! Just on...	3 beds \| 2 baths \| 1,296 sq.ft.	$415,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 4.84% Airbnb Rental Income: $2131 Traditional Rental Income: $2777 Airbnb ROI: 1.85% Traditional ROI: 4.84%
1194 Oak Ave Shady Side, MD 1194 Oak Ave, Shady Side, MD 20764 \| Single Family Residential	5 beds \| 4 baths \| 2,680 sq.ft.	$499,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 3.97% Airbnb Rental Income: $3314 Traditional Rental Income: $3087 Airbnb ROI: 2.93% Traditional ROI: 3.97%
4911 Magnolia St Shady Side, MD Welcome to this charming 2-bedroom, 2-bath rambler in the desirable water community of Wes...	2 beds \| 2 baths \| 960 sq.ft.	$370,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 4.45% Airbnb Rental Income: $2177 Traditional Rental Income: $2288 Airbnb ROI: 2.54% Traditional ROI: 4.45%

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: 1.6%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2131

Traditional Rental Income: $2729

Airbnb ROI: 1.6%

Traditional ROI: 4.31%

4721 Oak Rd

Shady Side, MD

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

$998,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $4030

Traditional Rental Income: $2526

Airbnb ROI: 1.56%

Traditional ROI: 0.87%

1211 Linton Ln

Shady Side, MD

3 beds | 3 baths | 3,192 sq.ft.

$799,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $2131

Traditional Rental Income: $2606

Airbnb ROI: 0.31%

Traditional ROI: 1.68%

1241 Johnson Dr

Shady Side, MD

3 beds | 2 baths | 2,176 sq.ft.

$699,000

Airbnb cash on cash: 0.34%

Traditional cash on cash: 2.22%

Airbnb Rental Income: $2131

Traditional Rental Income: $2851

Airbnb ROI: 0.34%

Traditional ROI: 2.22%

1172 Cedar Ave

Shady Side, MD

3 beds | 1 baths | 864 sq.ft.

$325,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $2131

Traditional Rental Income: $1929

Airbnb ROI: 2.96%

Traditional ROI: 4.08%

4909 Olive St

Shady Side, MD

3 beds | 2 baths | 1,848 sq.ft.

$480,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $2131

Traditional Rental Income: $2286

Airbnb ROI: 1.76%

Traditional ROI: 3.28%

1316 Azalia St

Shady Side, MD

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

$465,000

Airbnb cash on cash: 1.83%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2131

Traditional Rental Income: $1691

Airbnb ROI: 1.83%

Traditional ROI: 2.07%

1462 Snug Harbor Rd

Shady Side, MD

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

$699,000

Airbnb cash on cash: 3.19%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $4030

Traditional Rental Income: $3065

Airbnb ROI: 3.19%