Airbnb Properties for Sale in Shady Side, MD

Looking for a vacation rental investment in Shady Side, MD with high ROI ?

Explore a range of newly added short-term rental homes in Shady Side, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Shady Side, MD

Q: How many Airbnb properties are available for sale in Shady-side?

There are 27 Airbnb properties available for sale in Shady-side

Q: How to get Shady-side, MD Airbnb data?

Airbnb data on vacation rentals in Shady-side, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Shady-side, MD market insights, guest information and booking details, seasonality trends and historical Shady-side, MD Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4900 THOMAS DRIVE Shady Side, MD Just two doors from the water and steps from a childrens park and boat ramp, this 3-bedroo...	3 beds \| 2 baths \| 1,408 sq.ft.	$395,000	Airbnb cash on cash: 6.35% Traditional cash on cash: 4.03% Airbnb Rental Income: $3981 Traditional Rental Income: $2267 Airbnb ROI: 6.35% Traditional ROI: 4.03%
1462 SNUG HARBOR ROAD Shady Side, MD 4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes ...	4 beds \| 2 baths \| 2,144 sq.ft.	$735,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 2.88% Airbnb Rental Income: $5433 Traditional Rental Income: $3065 Airbnb ROI: 4.74% Traditional ROI: 2.88%
1337 W RIVER RD Shady Side, MD Price Reduction!! Your Own Private Retreat, get away from the Rat Race and make this a gr...	2 beds \| 1 baths \| N/A	$600,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 0.74% Airbnb Rental Income: $2847 Traditional Rental Income: $1720 Airbnb ROI: 1.57% Traditional ROI: 0.74%
1711 COLUMBIA BEACH ROAD Shady Side, MD Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond ...	4 beds \| 3 baths \| 2,176 sq.ft.	$499,900	Airbnb cash on cash: 7.04% Traditional cash on cash: 4.32% Airbnb Rental Income: $5433 Traditional Rental Income: $3067 Airbnb ROI: 7.04% Traditional ROI: 4.32%
1601 SNUG HARBOR RD Shady Side, MD Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boa...	4 beds \| 3 baths \| N/A	$599,999	Airbnb cash on cash: 5.67% Traditional cash on cash: 3.5% Airbnb Rental Income: $5433 Traditional Rental Income: $3125 Airbnb ROI: 5.67% Traditional ROI: 3.5%
4725 IDLEWILDE ROAD Shady Side, MD Calling all investors, second-home seekers, and visionariesthis is the project youve been ...	2 beds \| 1 baths \| 1,000 sq.ft.	$275,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 5.26% Airbnb Rental Income: $2847 Traditional Rental Income: $1932 Airbnb ROI: 6.23% Traditional ROI: 5.26%
1731 COLUMBIA BEACH RD Shady Side, MD Just Reduced, seller says sell! Welcome to this delightful coastal cottage nestled in the ...	2 beds \| 1 baths \| N/A	$345,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 2.95% Airbnb Rental Income: $2847 Traditional Rental Income: $1682 Airbnb ROI: 4.5% Traditional ROI: 2.95%
1220 GROVE AVENUE Shady Side, MD This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Commun...	5 beds \| 2 baths \| 1,812 sq.ft.	$485,500	Airbnb cash on cash: 10% Traditional cash on cash: 4.51% Airbnb Rental Income: $6725 Traditional Rental Income: $2922 Airbnb ROI: 10% Traditional ROI: 4.51%
1195 CEDAR AVENUE Shady Side, MD This beautifully crafted home blends timeless coastal charm with modern luxury. Featuring ...	4 beds \| 3 baths \| 2,710 sq.ft.	$699,500	Airbnb cash on cash: 5.32% Traditional cash on cash: 3.75% Airbnb Rental Income: $5433 Traditional Rental Income: $3316 Airbnb ROI: 5.32% Traditional ROI: 3.75%
4738 WASHINGTON AVENUE Shady Side, MD Charming Rancher Just Steps from the Bay Front! Nestled on a peaceful corner lot and surr...	3 beds \| 1 baths \| 1,000 sq.ft.	$360,000	Airbnb cash on cash: 7.11% Traditional cash on cash: 3.73% Airbnb Rental Income: $3981 Traditional Rental Income: $1988 Airbnb ROI: 7.11% Traditional ROI: 3.73%
1617 WINTERS AVENUE Shady Side, MD Welcome to 1617 Winters Ave Coastal Charm with Modern Updates in Idlewild on the Bay Beau...	2 beds \| 2 baths \| 1,000 sq.ft.	$378,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.9% Airbnb Rental Income: $2847 Traditional Rental Income: $2127 Airbnb ROI: 4.06% Traditional ROI: 3.9%
1330 JORDAN DRIVE Shady Side, MD Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highl...	3 beds \| 3 baths \| 1,440 sq.ft.	$435,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 4.71% Airbnb Rental Income: $3981 Traditional Rental Income: $2743 Airbnb ROI: 5.65% Traditional ROI: 4.71%
1700 BAYVIEW ROAD Shady Side, MD Don't miss this charming and well-maintained home! The main level features stylish LVP flo...	2 beds \| 2 baths \| 852 sq.ft.	$329,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.66% Airbnb Rental Income: $2847 Traditional Rental Income: $2126 Airbnb ROI: 4.85% Traditional ROI: 4.66%
4727 OAK ROAD Shady Side, MD Rare Chesapeake Bay waterfront property with panoramic views and endless potential! This 3...	3 beds \| 2 baths \| 1,806 sq.ft.	$565,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.24% Airbnb Rental Income: $3981 Traditional Rental Income: $2863 Airbnb ROI: 3.75% Traditional ROI: 3.24%
4949 IDLEWILDE ROAD Shady Side, MD This spacious and well-maintained home offers the ease of one-level living at it's best. T...	3 beds \| 2 baths \| 2,024 sq.ft.	$539,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 3.51% Airbnb Rental Income: $3981 Traditional Rental Income: $2798 Airbnb ROI: 4.16% Traditional ROI: 3.51%
1457 Nieman Rd Shady Side, MD 1457 Nieman Rd, Shady Side, MD 20764 \| Single Family Residential	5 beds \| 4 baths \| 3,064 sq.ft.	$1,500,000	Airbnb cash on cash: 1.74% Traditional cash on cash: -0.07% Airbnb Rental Income: $6725 Traditional Rental Income: $2898 Airbnb ROI: 1.74% Traditional ROI: -0.07%
1192 Oak Ave Shady Side, MD	3 beds \| 2 baths \| 1,224 sq.ft.	$449,950	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.58% Airbnb Rental Income: $3981 Traditional Rental Income: $2058 Airbnb ROI: 5.12% Traditional ROI: 2.58%
5235-A Al Jones Dr Shady Side, MD 5235-A Al Jones Dr, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 3 baths \| 3,727 sq.ft.	$1,525,000	Airbnb cash on cash: 0.89% Traditional cash on cash: -0.25% Airbnb Rental Income: $5433 Traditional Rental Income: $2727 Airbnb ROI: 0.89% Traditional ROI: -0.25%
4180 Shoreham Beach Rd Shady Side, MD 4180 Shoreham Beach Rd, Shady Side, MD 21037 \| Single Family Residential	N/A beds \| N/A baths \| 1,064 sq.ft.	$449,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 0.3% Airbnb Rental Income: $2085 Traditional Rental Income: $1096 Airbnb ROI: 1.38% Traditional ROI: 0.3%
5860 Shady Side Rd Shady Side, MD 5860 Shady Side Rd, Shady Side, MD 20733 \| Other	N/A beds \| N/A baths \| N/A	$625,000	Airbnb cash on cash: 0.41% Traditional cash on cash: -0.88% Airbnb Rental Income: $2085 Traditional Rental Income: $796 Airbnb ROI: 0.41% Traditional ROI: -0.88%
Shady Side Rd Shady Side, MD Shady Side Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$150,000	Airbnb cash on cash: 8.07% Traditional cash on cash: 2.83% Airbnb Rental Income: $2085 Traditional Rental Income: $796 Airbnb ROI: 8.07% Traditional ROI: 2.83%
Mayo Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 1.77% Airbnb Rental Income: $2085 Traditional Rental Income: $1001 Airbnb ROI: 4.09% Traditional ROI: 1.77%
5250 Al Jones Dr Shady Side, MD 5250 Al Jones Dr, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$175,000	Airbnb cash on cash: 6.49% Traditional cash on cash: 1.99% Airbnb Rental Income: $2085 Traditional Rental Income: $799 Airbnb ROI: 6.49% Traditional ROI: 1.99%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$259,999	Airbnb cash on cash: 3.85% Traditional cash on cash: 0.79% Airbnb Rental Income: $2085 Traditional Rental Income: $796 Airbnb ROI: 3.85% Traditional ROI: 0.79%
1520 Lincoln Rd Shady Side, MD 1520 Lincoln Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 1,248 sq.ft.	$441,000	Airbnb cash on cash: 8.2% Traditional cash on cash: 2.98% Airbnb Rental Income: $5433 Traditional Rental Income: $2185 Airbnb ROI: 8.2% Traditional ROI: 2.98%
1323 JORDAN DR Shady Side, MD OFFER DEADLINE SUNDAY SEPTEMBER 14th AT 6:00PMOPEN HOUSES THIS WEEKEND ONLY, SATURDAY ...	5 beds \| 3 baths \| N/A	$1,050,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 1.87% Airbnb Rental Income: $6725 Traditional Rental Income: $3675 Airbnb ROI: 3.65% Traditional ROI: 1.87%

Vacation Rentals in Shady Side

There are 27 vacation rental properties available for sale in the city of Shady Side . The median list price of Airbnb properties available for sale in Shady Side is $449,000 and the average price per square foot is $255. The cash on cash return on vacation rentals in Shady Side is 5.00%. The average monthly short term rental income in Shady Side is $3,981.

Shady Side, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 27 Airbnb properties available for sale in Shady Side.

In 2025, the best neighborhood to buy short term rental property is Shady Side.

In September 2025, the average Airbnb occupancy rate in Shady Side is 35%.

Airbnb data on vacation rentals in Shady Side, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Shady Side, MD market insights, guest information and booking details, seasonality trends and historical Shady Side, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Shady Side, MD

4900 THOMAS DRIVE

Shady Side, MD

3 beds | 2 baths | 1,408 sq.ft.

$395,000

Airbnb cash on cash: 6.35%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $3981

Traditional Rental Income: $2267

Airbnb ROI: 6.35%

Traditional ROI: 4.03%

1462 SNUG HARBOR ROAD

Shady Side, MD

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

$735,000

Airbnb cash on cash: 4.74%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $5433

Traditional Rental Income: $3065

Airbnb ROI: 4.74%

Traditional ROI: 2.88%

1337 W RIVER RD

Shady Side, MD

2 beds | 1 baths | N/A

$600,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $2847

Traditional Rental Income: $1720

Airbnb ROI: 1.57%

Traditional ROI: 0.74%

1711 COLUMBIA BEACH ROAD

Shady Side, MD

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

$499,900

Airbnb cash on cash: 7.04%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $5433

Traditional Rental Income: $3067

Airbnb ROI: 7.04%

Traditional ROI: 4.32%

1601 SNUG HARBOR RD

Shady Side, MD

4 beds | 3 baths | N/A

$599,999

Airbnb cash on cash: 5.67%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $5433

Traditional Rental Income: $3125

Airbnb ROI: 5.67%

Traditional ROI: 3.5%

4725 IDLEWILDE ROAD

Shady Side, MD

2 beds | 1 baths | 1,000 sq.ft.

$275,000

Airbnb cash on cash: 6.23%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $2847

Traditional Rental Income: $1932

Airbnb ROI: 6.23%

Traditional ROI: 5.26%

1731 COLUMBIA BEACH RD

Shady Side, MD

2 beds | 1 baths | N/A

$345,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $2847

Traditional Rental Income: $1682

Airbnb ROI: 4.5%

Traditional ROI: 2.95%

1220 GROVE AVENUE

Shady Side, MD

5 beds | 2 baths | 1,812 sq.ft.

$485,500

Airbnb cash on cash: 10%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $6725

Traditional Rental Income: $2922

Airbnb ROI: 10%