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 Single Family Residential 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 16 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
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%
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%
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%
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%
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%
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%
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%
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%
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%
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%
1102-A Collison Rd Shady Side, MD 1102-A Collison Rd, Shady Side, MD 21106 \| Single Family Residential	4 beds \| 2 baths \| 1,696 sq.ft.	$724,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 1.65% Airbnb Rental Income: $4030 Traditional Rental Income: $2612 Airbnb ROI: 2.47% Traditional ROI: 1.65%
5078 Lerch Dr Shady Side, MD 5078 Lerch Dr, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 2,060 sq.ft.	$699,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 1.43% Airbnb Rental Income: $4030 Traditional Rental Income: $2388 Airbnb ROI: 2.63% Traditional ROI: 1.43%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Shady Side, MD

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%

1462 Snug Harbor Rd

Shady Side, MD

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%

1411 Haile Pkwy

Shady Side, MD

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

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%

1191 Poplar Ave

Shady Side, MD

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%

5314 Al Jones Dr

Shady Side, MD

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%

1209 Johnson Dr

Shady Side, MD

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%