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: 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: 0.7% Traditional cash on cash: 0.75% Airbnb Rental Income: $3200 Traditional Rental Income: $2526 Airbnb ROI: 0.7% Traditional ROI: 0.75%
5222 Spring Ave Shady Side, MD Set on a large double corner lot in the waterfront community of Cedarhurst, this four-bedr...	4 beds \| 3 baths \| 1,730 sq.ft.	$495,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.32% Airbnb Rental Income: $3200 Traditional Rental Income: $2569 Airbnb ROI: 3.12% Traditional ROI: 3.32%
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: 2.22% Traditional cash on cash: 4.08% Airbnb Rental Income: $1859 Traditional Rental Income: $1929 Airbnb ROI: 2.22% 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.	$499,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.2% Airbnb Rental Income: $1859 Traditional Rental Income: $2286 Airbnb ROI: 1.22% Traditional ROI: 3.2%
6213 SHADY SIDE Road Shady Side, MD Deadline- 6/28 (All offers must submitted by noon) Charming 4-bedroom, 2-bath cottage situ...	4 beds \| 2 baths \| 1,713 sq.ft.	$560,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 2.92% Airbnb Rental Income: $3200 Traditional Rental Income: $2662 Airbnb ROI: 2.56% Traditional ROI: 2.92%
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%
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: 1.92% Traditional cash on cash: 2.76% Airbnb Rental Income: $3200 Traditional Rental Income: $3065 Airbnb ROI: 1.92% Traditional ROI: 2.76%
4921 Olive St Shady Side, MD Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s c...	3 beds \| 1 baths \| 1,008 sq.ft.	$419,900	Airbnb cash on cash: 1.51% Traditional cash on cash: 2.99% Airbnb Rental Income: $1859 Traditional Rental Income: $1942 Airbnb ROI: 1.51% Traditional ROI: 2.99%
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: 3.56% Traditional cash on cash: 4.1% Airbnb Rental Income: $3200 Traditional Rental Income: $2755 Airbnb ROI: 3.56% 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: 4.45% Traditional cash on cash: 5.27% Airbnb Rental Income: $3200 Traditional Rental Income: $2786 Airbnb ROI: 4.45% Traditional ROI: 5.27%
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.	$424,700	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.44% Airbnb Rental Income: $1859 Traditional Rental Income: $2203 Airbnb ROI: 1.32% Traditional ROI: 3.44%
1191 Poplar Ave Shady Side, MD OPEN HOUSE! SUNDAY, JUNE 28, 2026 FROM 1 TO 3 P.M. Cedarhurst on the Bay only 4 Blocks fro...	4 beds \| 2 baths \| 2,272 sq.ft.	$535,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 2.84% Airbnb Rental Income: $3200 Traditional Rental Income: $2543 Airbnb ROI: 2.71% Traditional ROI: 2.84%
4912 Beech St Shady Side, MD Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon ...	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 Dr Shady Side, MD Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. ...	2 beds \| 1 baths \| 1,244 sq.ft.	$535,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 2.38% Airbnb Rental Income: $2077 Traditional Rental Income: $2264 Airbnb ROI: 0.94% Traditional ROI: 2.38%
5235 Al Jones Dr Shady Side, MD Unique Waterfront Dream Home Opportunity at Columbia Beach - Build Your Dream Home on the ...	N/A beds \| N/A baths \| N/A	$349,870	Airbnb cash on cash: 0.04% Traditional cash on cash: 8.69% Airbnb Rental Income: $1175 Traditional Rental Income: $3633 Airbnb ROI: 0.04% Traditional ROI: 8.69%
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.	$379,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.49% Airbnb Rental Income: $1859 Traditional Rental Income: $1988 Airbnb ROI: 1.73% Traditional ROI: 3.49%
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%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$249,999	Airbnb cash on cash: 0.88% Traditional cash on cash: 0.9% Airbnb Rental Income: $1175 Traditional Rental Income: $796 Airbnb ROI: 0.88% 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: 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 Dr Shady Side, MD 6/26/26. Home is under roof ready for drywall. August delivery. Coastal Living Just Steps ...	4 beds \| 2 baths \| 2,710 sq.ft.	$659,990	Airbnb cash on cash: 1.79% Traditional cash on cash: -0.98% Airbnb Rental Income: $3200 Traditional Rental Income: $771 Airbnb ROI: 1.79% 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: $1859 Traditional Rental Income: $2795 Airbnb ROI: 0.27% Traditional ROI: 2.38%
1209 Johnson Dr Shady Side, MD 6/15/26 HOME UNDER ROOF. EXPECTED JULY/AUGUST 2026 DELIVERY. Schaefer Homes brings to you ...	4 beds \| 2 baths \| 2,068 sq.ft.	$599,990	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.11% Airbnb Rental Income: $3200 Traditional Rental Income: $3051 Airbnb ROI: 2.11% Traditional ROI: 3.11%
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.	$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 St Shady Side, MD THIS IS A TO BE BUILT HOME	4 beds \| 2 baths \| 2,091 sq.ft.	$589,990	Airbnb cash on cash: 3.06% Traditional cash on cash: 4.02% Airbnb Rental Income: $3200 Traditional Rental Income: $3011 Airbnb ROI: 3.06% Traditional ROI: 4.02%
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: 2.72% Traditional cash on cash: 4.09% Airbnb Rental Income: $3200 Traditional Rental Income: $3307 Airbnb ROI: 2.72% 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 \| 2 baths \| 1,949 sq.ft.	$549,900	Airbnb cash on cash: 3.25% Traditional cash on cash: 4.49% Airbnb Rental Income: $3200 Traditional Rental Income: $3137 Airbnb ROI: 3.25% 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: 1.85% Traditional cash on cash: 2.43% Airbnb Rental Income: $3200 Traditional Rental Income: $2829 Airbnb ROI: 1.85% Traditional ROI: 2.43%
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.	$475,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 2.79% Airbnb Rental Income: $1859 Traditional Rental Income: $2142 Airbnb ROI: 1.03% Traditional ROI: 2.79%
4950 Bonniewood Dr Shady Side, MD Waterfront living with a private dock-all for under $800,000! Nestled in the charming Aval...	3 beds \| 2 baths \| 2,304 sq.ft.	$795,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.2% Airbnb Rental Income: $1859 Traditional Rental Income: $2310 Airbnb ROI: -0.08% Traditional ROI: 1.2%
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%
1582 Snug Rd Shady Side, MD 1582 Snug Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 1,915 sq.ft.	$619,900	Airbnb cash on cash: 2.04% Traditional cash on cash: 1.7% Airbnb Rental Income: $3200 Traditional Rental Income: $2280 Airbnb ROI: 2.04% Traditional ROI: 1.7%

Real Estate investment in Shady-side, MD

There are 43 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 $252. In July 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $2,239.

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

There are 43 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 $2,239.

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: 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: 0.7%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $3200

Traditional Rental Income: $2526

Airbnb ROI: 0.7%

Traditional ROI: 0.75%

5222 Spring Ave

Shady Side, MD

4 beds | 3 baths | 1,730 sq.ft.

$495,000

Airbnb cash on cash: 3.12%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $3200

Traditional Rental Income: $2569

Airbnb ROI: 3.12%

Traditional ROI: 3.32%

1172 Cedar Ave

Shady Side, MD

3 beds | 1 baths | 864 sq.ft.

$325,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $1859

Traditional Rental Income: $1929

Airbnb ROI: 2.22%

Traditional ROI: 4.08%

4909 Olive St

Shady Side, MD

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

$499,900

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $1859

Traditional Rental Income: $2286

Airbnb ROI: 1.22%

Traditional ROI: 3.2%

6213 SHADY SIDE Road

Shady Side, MD

4 beds | 2 baths | 1,713 sq.ft.

$560,000

Airbnb cash on cash: 2.56%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $3200

Traditional Rental Income: $2662

Airbnb ROI: 2.56%

Traditional ROI: 2.92%

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%

1462 Snug Harbor Rd

Shady Side, MD

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

$750,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3200

Traditional Rental Income: $3065

Airbnb ROI: 1.92%