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 41 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: 2.07% Traditional cash on cash: 4.31% Airbnb Rental Income: $2366 Traditional Rental Income: $2729 Airbnb ROI: 2.07% 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: 1.27% Traditional cash on cash: 0.87% Airbnb Rental Income: $3702 Traditional Rental Income: $2526 Airbnb ROI: 1.27% 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: 0.57% Traditional cash on cash: 1.68% Airbnb Rental Income: $2366 Traditional Rental Income: $2606 Airbnb ROI: 0.57% 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: 0.68% Traditional cash on cash: 2.32% Airbnb Rental Income: $2366 Traditional Rental Income: $2851 Airbnb ROI: 0.68% Traditional ROI: 2.32%
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: 3.6% Traditional cash on cash: 4.08% Airbnb Rental Income: $2366 Traditional Rental Income: $1929 Airbnb ROI: 3.6% 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: 2.25% Traditional cash on cash: 3.37% Airbnb Rental Income: $2366 Traditional Rental Income: $2286 Airbnb ROI: 2.25% Traditional ROI: 3.37%
1704 Maryland Ave Shady Side, MD PRICE REDUCED! Chesapeake Waterview/access with Your Very Own Dock. Property Consists of S...	4 beds \| 2 baths \| 1,930 sq.ft.	$330,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 6.14% Airbnb Rental Income: $3702 Traditional Rental Income: $2656 Airbnb ROI: 6.88% Traditional ROI: 6.14%
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: 2.28% Traditional cash on cash: 2.07% Airbnb Rental Income: $2366 Traditional Rental Income: $1691 Airbnb ROI: 2.28% Traditional ROI: 2.07%
4924 Kellam Rd Shady Side, MD This 2 bedroom 1 bathroom home has been renovated from top to bottom AND it sits on 1.25 a...	2 beds \| 1 baths \| 808 sq.ft.	$399,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.66% Airbnb Rental Income: $2265 Traditional Rental Income: $2071 Airbnb ROI: 2.67% Traditional ROI: 3.66%
1240 Hawthorne St Shady Side, MD OPEN HOUSE 4/11/2020 CANCELLED! Contract Pending! Seller offering closing help with accept...	3 beds \| 2 baths \| 1,632 sq.ft.	$489,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 3.62% Airbnb Rental Income: $2366 Traditional Rental Income: $2576 Airbnb ROI: 1.92% Traditional ROI: 3.62%
1221 Bast Ln Shady Side, MD Almost 1 acre of land with water views! Wood burning fireplace! Large detached garage! Se...	4 beds \| 2 baths \| 2,089 sq.ft.	$625,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.45% Airbnb Rental Income: $3702 Traditional Rental Income: $2424 Airbnb ROI: 3.26% Traditional ROI: 2.45%
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.	$669,500	Airbnb cash on cash: 2.77% Traditional cash on cash: 3.03% Airbnb Rental Income: $3702 Traditional Rental Income: $3065 Airbnb ROI: 2.77% Traditional ROI: 3.03%
1437 Cedarhurst Rd Shady Side, MD A brand-new look. One-floor living 3 bedrooms and 2 full bathroom and with 1 car attache...	3 beds \| 2 baths \| 1,248 sq.ft.	$419,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 4.43% Airbnb Rental Income: $2366 Traditional Rental Income: $2516 Airbnb ROI: 2.56% Traditional ROI: 4.43%
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: 3.29% Traditional cash on cash: 3.77% Airbnb Rental Income: $2366 Traditional Rental Income: $1942 Airbnb ROI: 3.29% 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: 4.62% Traditional cash on cash: 4.34% Airbnb Rental Income: $3702 Traditional Rental Income: $2755 Airbnb ROI: 4.62% 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: 2.65% Traditional cash on cash: 3.71% Airbnb Rental Income: $2265 Traditional Rental Income: $2058 Airbnb ROI: 2.65% Traditional ROI: 3.71%
5060 Lerch Dr Shady Side, MD What's not to love? Wake to sunrise on the beautiful South Creek, just off of the West Ri...	3 beds \| 4 baths \| 2,642 sq.ft.	$1,100,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 1.45% Airbnb Rental Income: $2366 Traditional Rental Income: $3132 Airbnb ROI: 0.13% Traditional ROI: 1.45%
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.	$515,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 4.27% Airbnb Rental Income: $2366 Traditional Rental Income: $3044 Airbnb ROI: 1.65% Traditional ROI: 4.27%
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: 3.06% Traditional cash on cash: 3.55% Airbnb Rental Income: $3702 Traditional Rental Income: $3181 Airbnb ROI: 3.06% 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: 6.57% Traditional cash on cash: 4.75% Airbnb Rental Income: $4684 Traditional Rental Income: $2922 Airbnb ROI: 6.57% Traditional ROI: 4.75%
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.	$619,990	Airbnb cash on cash: 2.76% Traditional cash on cash: -0.91% Airbnb Rental Income: $3702 Traditional Rental Income: $771 Airbnb ROI: 2.76% Traditional ROI: -0.91%
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: 0.97% Traditional cash on cash: 2.52% Airbnb Rental Income: $2366 Traditional Rental Income: $2795 Airbnb ROI: 0.97% 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: 0.35% Traditional cash on cash: 1.37% Airbnb Rental Income: $4684 Traditional Rental Income: $5232 Airbnb ROI: 0.35% 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: 2.09% Traditional cash on cash: 5.54% Airbnb Rental Income: $2366 Traditional Rental Income: $3172 Airbnb ROI: 2.09% 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: 0.59% Traditional cash on cash: 1.17% Airbnb Rental Income: $2366 Traditional Rental Income: $2175 Airbnb ROI: 0.59% 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: 4.22% Traditional cash on cash: 4.44% Airbnb Rental Income: $3702 Traditional Rental Income: $3011 Airbnb ROI: 4.22% Traditional ROI: 4.44%
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.	$599,990	Airbnb cash on cash: 3.41% Traditional cash on cash: 4.09% Airbnb Rental Income: $3702 Traditional Rental Income: $3307 Airbnb ROI: 3.41% 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: 2.02% Traditional cash on cash: 2.83% Airbnb Rental Income: $2366 Traditional Rental Income: $2142 Airbnb ROI: 2.02% 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.	$765,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 1.26% Airbnb Rental Income: $2366 Traditional Rental Income: $2310 Airbnb ROI: 0.53% 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: 2.92% Traditional cash on cash: 1.82% Airbnb Rental Income: $3702 Traditional Rental Income: $2280 Airbnb ROI: 2.92% Traditional ROI: 1.82%
1183 Cedar Ave Shady Side, MD Professional pictures coming!! Rarely available and proudly offered for the first time, th...	4 beds \| 3 baths \| 1,964 sq.ft.	$499,900	Airbnb cash on cash: 3.85% Traditional cash on cash: 3.42% Airbnb Rental Income: $3702 Traditional Rental Income: $2686 Airbnb ROI: 3.85% Traditional ROI: 3.42%
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: 2.43% Traditional cash on cash: 7.11% Airbnb Rental Income: $2366 Traditional Rental Income: $3449 Airbnb ROI: 2.43% 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 \| 2,710 sq.ft.	$619,990	Airbnb cash on cash: 3.63% Traditional cash on cash: 4.51% Airbnb Rental Income: $3702 Traditional Rental Income: $3404 Airbnb ROI: 3.63% 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: -2.99% Traditional cash on cash: 2.26% Airbnb Rental Income: $79 Traditional Rental Income: $1117 Airbnb ROI: -2.99% Traditional ROI: 2.26%
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: 3.47% Traditional cash on cash: N/A Airbnb Rental Income: $4684 Traditional Rental Income: $0 Airbnb ROI: 3.47% 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: 2.42% Traditional cash on cash: 4.98% Airbnb Rental Income: $2366 Traditional Rental Income: $2777 Airbnb ROI: 2.42% Traditional ROI: 4.98%
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: 5.68% Traditional cash on cash: 4.33% Airbnb Rental Income: $4684 Traditional Rental Income: $3087 Airbnb ROI: 5.68% Traditional ROI: 4.33%
4922 Dogwood St Shady Side, MD 4922 Dogwood St, Shady Side, MD 20764 \| Single Family Residential	3 beds \| 2 baths \| 1,171 sq.ft.	$429,950	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.82% Airbnb Rental Income: $2366 Traditional Rental Income: $2066 Airbnb ROI: 2.11% Traditional ROI: 2.82%

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: 2.07%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $2366

Traditional Rental Income: $2729

Airbnb ROI: 2.07%

Traditional ROI: 4.31%

4721 Oak Rd

Shady Side, MD

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

$998,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $3702

Traditional Rental Income: $2526

Airbnb ROI: 1.27%

Traditional ROI: 0.87%

1211 Linton Ln

Shady Side, MD

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

$799,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $2366

Traditional Rental Income: $2606

Airbnb ROI: 0.57%

Traditional ROI: 1.68%

1241 Johnson Dr

Shady Side, MD

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

$699,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $2366

Traditional Rental Income: $2851

Airbnb ROI: 0.68%

Traditional ROI: 2.32%

1172 Cedar Ave

Shady Side, MD

3 beds | 1 baths | 864 sq.ft.

$325,000

Airbnb cash on cash: 3.6%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $2366

Traditional Rental Income: $1929

Airbnb ROI: 3.6%

Traditional ROI: 4.08%

4909 Olive St

Shady Side, MD

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

$480,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2366

Traditional Rental Income: $2286

Airbnb ROI: 2.25%

Traditional ROI: 3.37%

1704 Maryland Ave

Shady Side, MD

4 beds | 2 baths | 1,930 sq.ft.

$330,000

Airbnb cash on cash: 6.88%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $3702

Traditional Rental Income: $2656

Airbnb ROI: 6.88%

Traditional ROI: 6.14%

1316 Azalia St

Shady Side, MD

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

$465,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2366

Traditional Rental Income: $1691

Airbnb ROI: 2.28%