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: 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.	$344,900	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.	$499,900	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.	$699,000	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%
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: 5.56% Traditional cash on cash: 5.27% Airbnb Rental Income: $3702 Traditional Rental Income: $2786 Airbnb ROI: 5.56% Traditional ROI: 5.27%
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%
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.	$380,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 3.95% Airbnb Rental Income: $2366 Traditional Rental Income: $2203 Airbnb ROI: 2.78% Traditional ROI: 3.95%
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%
6152 Shady Side Rd Shady Side, MD 6152 Shady Side Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$54,900	Airbnb cash on cash: 8.84% Traditional cash on cash: 10.62% Airbnb Rental Income: $1064 Traditional Rental Income: $796 Airbnb ROI: 8.84% Traditional ROI: 10.62%
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: 9.83% Traditional cash on cash: 11.5% Airbnb Rental Income: $1064 Traditional Rental Income: $783 Airbnb ROI: 9.83% 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: 2.14% Traditional cash on cash: 4.26% Airbnb Rental Income: $1064 Traditional Rental Income: $1001 Airbnb ROI: 2.14% 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	$89,999	Airbnb cash on cash: 4.49% Traditional cash on cash: 5.64% Airbnb Rental Income: $1064 Traditional Rental Income: $799 Airbnb ROI: 4.49% Traditional ROI: 5.64%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$249,999	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.9% Airbnb Rental Income: $1064 Traditional Rental Income: $796 Airbnb ROI: 0.48% Traditional ROI: 0.9%
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: 4.15% Traditional cash on cash: 5.12% Airbnb Rental Income: $1064 Traditional Rental Income: $792 Airbnb ROI: 4.15% 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: 4.15% Traditional cash on cash: 5.12% Airbnb Rental Income: $1064 Traditional Rental Income: $792 Airbnb ROI: 4.15% Traditional ROI: 5.12%
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.	$650,990	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%
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	$539,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.79% Airbnb Rental Income: $3702 Traditional Rental Income: $3137 Airbnb ROI: 4.31% Traditional ROI: 4.79%
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: 2.95% Traditional cash on cash: 3.76% Airbnb Rental Income: $1064 Traditional Rental Income: $795 Airbnb ROI: 2.95% Traditional ROI: 3.76%

Real Estate investment in Shady-side, MD

There are 59 properties for sale in the city of Shady Side . The median list price in Shady Side is $468,719 and the average price per square foot is $233. In September 2026, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,297.

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

There are 59 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 $2,297.

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: 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.

$344,900

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%