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: 1.6% 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 Sweeping, panoramic views of Chesapeake Bay! Crab from your private pier or just enjoy th...	4 beds \| 3 baths \| 1,868 sq.ft.	$998,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 0.82% Airbnb Rental Income: $4030 Traditional Rental Income: $2526 Airbnb ROI: 1.45% Traditional ROI: 0.82%
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: 4.62% Traditional cash on cash: 3.32% Airbnb Rental Income: $4030 Traditional Rental Income: $2569 Airbnb ROI: 4.62% Traditional ROI: 3.32%
1211 Linton Ln Shady Side, MD Days Gone By ... Vintage 3 Story FarmHome Circa 1914 Down a Country Lane Brimming w/ Char...	3 beds \| 3 baths \| 3,192 sq.ft.	$799,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.1% Airbnb Rental Income: $2131 Traditional Rental Income: $2606 Airbnb ROI: 0.73% Traditional ROI: 2.1%
1241 Johnson Dr Shady Side, MD Beautiful serene waterfront home at the head of the creek with your own private pier. Perf...	3 beds \| 2 baths \| 2,176 sq.ft.	$750,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 2.26% Airbnb Rental Income: $2131 Traditional Rental Income: $2851 Airbnb ROI: 0.45% Traditional ROI: 2.26%
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.	$490,000	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%
4912 Mariners Dr Shady Side, MD Coastal Affordable Living with a Boat Slip Included Discover the charm of Snug Harbor, whe...	3 beds \| 1 baths \| 1,386 sq.ft.	$389,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 4.95% Airbnb Rental Income: $2131 Traditional Rental Income: $2638 Airbnb ROI: 2.07% Traditional ROI: 4.95%
6201 Shady Side Rd Shady Side, MD Spacious 2,807 sq. ft. home offering exceptional potential for investors, multi-generation...	4 beds \| 3 baths \| 2,807 sq.ft.	$399,900	Airbnb cash on cash: 6.09% Traditional cash on cash: 7.17% Airbnb Rental Income: $4030 Traditional Rental Income: $3576 Airbnb ROI: 6.09% Traditional ROI: 7.17%
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 Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s c...	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: 5.03% Traditional cash on cash: 4.21% Airbnb Rental Income: $4030 Traditional Rental Income: $2755 Airbnb ROI: 5.03% Traditional ROI: 4.21%
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: 6.29% Traditional cash on cash: 5.27% Airbnb Rental Income: $4030 Traditional Rental Income: $2786 Airbnb ROI: 6.29% 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.	$399,700	Airbnb cash on cash: 1.99% Traditional cash on cash: 3.6% Airbnb Rental Income: $2131 Traditional Rental Income: $2203 Airbnb ROI: 1.99% Traditional ROI: 3.6%
1191 Poplar Ave Shady Side, MD OPEN HOUSE!!! July 11, 2026 1 - 3 pm. PRICE REDUCED. Cedarhurst on the Bay only 4 Blocks f...	4 beds \| 2 baths \| 2,272 sq.ft.	$525,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 2.91% Airbnb Rental Income: $4030 Traditional Rental Income: $2543 Airbnb ROI: 4.19% Traditional ROI: 2.91%
1311 Avalon Blvd Shady Side, MD Wonderful home that offers bright and sunny kitchen, spacious living room with rear entran...	3 beds \| 1 baths \| 1,248 sq.ft.	$375,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 2.84% Airbnb Rental Income: $2131 Traditional Rental Income: $1708 Airbnb ROI: 2.49% Traditional ROI: 2.84%
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%
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: 1.1% Traditional cash on cash: 2.38% Airbnb Rental Income: $2177 Traditional Rental Income: $2264 Airbnb ROI: 1.1% 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: 0.43% Traditional cash on cash: 8.69% Airbnb Rental Income: $1327 Traditional Rental Income: $3633 Airbnb ROI: 0.43% 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.	$349,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 3.87% Airbnb Rental Income: $2131 Traditional Rental Income: $1988 Airbnb ROI: 2.65% Traditional ROI: 3.87%
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: 3.67% Traditional cash on cash: 4.26% Airbnb Rental Income: $1327 Traditional Rental Income: $1001 Airbnb ROI: 3.67% 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	$95,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 5.26% Airbnb Rental Income: $1327 Traditional Rental Income: $799 Airbnb ROI: 6.53% Traditional ROI: 5.26%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$249,999	Airbnb cash on cash: 1.41% Traditional cash on cash: 0.9% Airbnb Rental Income: $1327 Traditional Rental Income: $796 Airbnb ROI: 1.41% 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: 6.4% Traditional cash on cash: 5.12% Airbnb Rental Income: $1327 Traditional Rental Income: $792 Airbnb ROI: 6.4% 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: 6.4% Traditional cash on cash: 5.12% Airbnb Rental Income: $1327 Traditional Rental Income: $792 Airbnb ROI: 6.4% 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.	$649,990	Airbnb cash on cash: 2.99% Traditional cash on cash: -0.96% Airbnb Rental Income: $4030 Traditional Rental Income: $771 Airbnb ROI: 2.99% Traditional ROI: -0.96%
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: 0.6% Traditional cash on cash: 2.38% Airbnb Rental Income: $2131 Traditional Rental Income: $2795 Airbnb ROI: 0.6% Traditional ROI: 2.38%
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.	$439,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.39% Airbnb Rental Income: $2131 Traditional Rental Income: $3172 Airbnb ROI: 1.54% Traditional ROI: 5.39%
1209 Johnson Dr Shady Side, MD 6/29/26 DRYWALL INSTALLED. EXPECTED JULY/AUGUST 2026 DELIVERY. Schaefer Homes brings to yo...	4 beds \| 2 baths \| 2,068 sq.ft.	$599,990	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.2% Airbnb Rental Income: $4030 Traditional Rental Income: $3051 Airbnb ROI: 3.41% Traditional ROI: 3.2%
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: 0.27% Traditional cash on cash: 1.12% Airbnb Rental Income: $2131 Traditional Rental Income: $2175 Airbnb ROI: 0.27% 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: -1.32% Traditional cash on cash: -0.05% Airbnb Rental Income: $3314 Traditional Rental Income: $6710 Airbnb ROI: -1.32% Traditional ROI: -0.05%
1225 Juniper St Shady Side, MD AUGUST DELIVERY! Enjoy water views of the community harbor with 60 boat slips and direct a...	4 beds \| 2 baths \| 2,091 sq.ft.	$589,990	Airbnb cash on cash: 4.36% Traditional cash on cash: 4.07% Airbnb Rental Income: $4030 Traditional Rental Income: $3011 Airbnb ROI: 4.36% Traditional ROI: 4.07%
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%
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.	$539,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 4.68% Airbnb Rental Income: $4030 Traditional Rental Income: $3137 Airbnb ROI: 4.75% Traditional ROI: 4.68%

Real Estate investment in Shady-side, MD

There are 58 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 $234. In August 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $2,304.

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

There are 58 investment properties available for sale in Shady-side.

In 2026, the best neighborhood to buy investment property is Shady Side.

The ROI for Short-Term is higher than the Long-Term in Shady-side with average rental income of $2,131.

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: 1.6%

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: 1.45%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $4030

Traditional Rental Income: $2526

Airbnb ROI: 1.45%

Traditional ROI: 0.82%

5222 Spring Ave

Shady Side, MD

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

$495,000

Airbnb cash on cash: 4.62%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $4030

Traditional Rental Income: $2569

Airbnb ROI: 4.62%

Traditional ROI: 3.32%

1211 Linton Ln

Shady Side, MD

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

$799,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $2131

Traditional Rental Income: $2606

Airbnb ROI: 0.73%

Traditional ROI: 2.1%

1241 Johnson Dr

Shady Side, MD

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

$750,000

Airbnb cash on cash: 0.45%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $2131

Traditional Rental Income: $2851

Airbnb ROI: 0.45%

Traditional ROI: 2.26%

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.

$490,000

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%