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 44 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 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%
1500 Garst Rd Shady Side, MD Enjoy water views and the best of coastal living in this charming home, ideally located in...	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.	$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%
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%
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%
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: 2.99% Traditional cash on cash: 2.43% Airbnb Rental Income: $4030 Traditional Rental Income: $2829 Airbnb ROI: 2.99% 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: 1.54% Traditional cash on cash: 2.79% Airbnb Rental Income: $2131 Traditional Rental Income: $2142 Airbnb ROI: 1.54% 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.	$775,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 1.2% Airbnb Rental Income: $2131 Traditional Rental Income: $2310 Airbnb ROI: 0.23% Traditional ROI: 1.2%
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.	$609,900	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%
1183 Cedar Ave Shady Side, MD 1183 Cedar Ave, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 3 baths \| 1,964 sq.ft.	$525,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 3.1% Airbnb Rental Income: $4030 Traditional Rental Income: $2686 Airbnb ROI: 4.07% Traditional ROI: 3.1%
6372 Shady Side Rd W Shady Side, MD 6372 Shady Side Rd W, Shady Side, MD 20764 \| Single Family Residential	3 beds \| 3 baths \| 2,450 sq.ft.	$380,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 4.89% Airbnb Rental Income: $2131 Traditional Rental Income: $2576 Airbnb ROI: 2.11% Traditional ROI: 4.89%
1237 Spruce Ave Shady Side, MD 1237 Spruce Ave, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| N/A	$619,990	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.13% Airbnb Rental Income: $4030 Traditional Rental Income: $2530 Airbnb ROI: 3.23% Traditional ROI: 2.13%
4958 Lerch Dr Shady Side, MD 4958 Lerch Dr, Shady Side, MD 20764 \| Single Family Residential	3 beds \| 2 baths \| 1,887 sq.ft.	$995,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 0.6% Airbnb Rental Income: $2131 Traditional Rental Income: $2576 Airbnb ROI: -0.47% Traditional ROI: 0.6%

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: 1.45%

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%