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 23 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
1223 Pine Ave Shady Side, MD Welcome to this charming 2-bedroom home tucked away on a quiet street in the peaceful wate...	2 beds \| 1 baths \| 960 sq.ft.	$330,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 3.77% Airbnb Rental Income: $2266 Traditional Rental Income: $1893 Airbnb ROI: 3.14% Traditional ROI: 3.77%
1213 OAK AVE Shady Side, MD A Charming Cedarhurst Cottage Near the Water - This charming 1944 cottage in Cedarhurst on...	2 beds \| 1 baths \| N/A	$295,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 2.97% Airbnb Rental Income: $2266 Traditional Rental Income: $1457 Airbnb ROI: 3.84% Traditional ROI: 2.97%
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: 2.06% Traditional cash on cash: 2.76% Airbnb Rental Income: $3319 Traditional Rental Income: $3065 Airbnb ROI: 2.06% Traditional ROI: 2.76%
4938 Rullman Rd Shady Side, MD HAPPY NEW YAR!! Westelee Welcome's You Home TO this 2.5 year old "Pottery Barn" Colonial h...	4 beds \| 2 baths \| 2,200 sq.ft.	$697,015	Airbnb cash on cash: 1.97% Traditional cash on cash: 2.49% Airbnb Rental Income: $3319 Traditional Rental Income: $2917 Airbnb ROI: 1.97% Traditional ROI: 2.49%
4912 Beech St Shady Side, MD PLEASE NOTE THE TIME CHANGE FOR THE OPEN HOUSE TO SUNDAY 2 - 4pm Welcome to this cha...	2 beds \| 2 baths \| 864 sq.ft.	$350,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.3% Airbnb Rental Income: $2266 Traditional Rental Income: $2141 Airbnb ROI: 2.96% Traditional ROI: 4.3%
1711 Columbia Beach Rd Shady Side, MD Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond ...	4 beds \| 2 baths \| 2,176 sq.ft.	$499,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 4.32% Airbnb Rental Income: $3319 Traditional Rental Income: $3067 Airbnb ROI: 3.27% Traditional ROI: 4.32%
1419 Shady Rest Rd Shady Side, MD SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house present...	3 beds \| 1 baths \| 1,022 sq.ft.	$270,750	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.45% Airbnb Rental Income: $2063 Traditional Rental Income: $1497 Airbnb ROI: 3.58% Traditional ROI: 3.45%
4738 Washington Ave Shady Side, MD Peaceful Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrifici...	3 beds \| 1 baths \| 1,000 sq.ft.	$355,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.8% Airbnb Rental Income: $2063 Traditional Rental Income: $1988 Airbnb ROI: 2.43% Traditional ROI: 3.8%
1330 Jordan Dr Shady Side, MD Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highl...	3 beds \| 2 baths \| 1,440 sq.ft.	$419,900	Airbnb cash on cash: 1.83% Traditional cash on cash: 4.91% Airbnb Rental Income: $2063 Traditional Rental Income: $2743 Airbnb ROI: 1.83% Traditional ROI: 4.91%
4949 Idlewilde Rd 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.	$529,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.53% Airbnb Rental Income: $2063 Traditional Rental Income: $2798 Airbnb ROI: 0.97% Traditional ROI: 3.53%
1302 Spruce St Shady Side, MD FEBRUARY 2026 DELIVERY. Introducing the Adams model - a beautifully designed home featurin...	4 beds \| 2 baths \| 2,424 sq.ft.	$589,990	Airbnb cash on cash: 3.51% Traditional cash on cash: 4.62% Airbnb Rental Income: $3319 Traditional Rental Income: $3191 Airbnb ROI: 3.51% Traditional ROI: 4.62%
4721 Girton Ave Shady Side, MD Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake B...	3 beds \| 2 baths \| 1,456 sq.ft.	$419,900	Airbnb cash on cash: 1.88% Traditional cash on cash: 4.77% Airbnb Rental Income: $2063 Traditional Rental Income: $2666 Airbnb ROI: 1.88% Traditional ROI: 4.77%
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: 0.52% Traditional cash on cash: 2.38% Airbnb Rental Income: $2063 Traditional Rental Income: $2795 Airbnb ROI: 0.52% Traditional ROI: 2.38%
1512 Lincoln Rd Shady Side, MD Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to th...	3 beds \| 2 baths \| 1,512 sq.ft.	$335,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 4.35% Airbnb Rental Income: $2063 Traditional Rental Income: $2147 Airbnb ROI: 2.39% Traditional ROI: 4.35%
4701 Girton Ave Shady Side, MD 4701 Girton Ave, Shady Side, MD 20764 \| Single Family Residential	9 beds \| 6 baths \| 9,325 sq.ft.	$2,550,000	Airbnb cash on cash: -1.4% Traditional cash on cash: 0.09% Airbnb Rental Income: $2270 Traditional Rental Income: $5232 Airbnb ROI: -1.4% Traditional ROI: 0.09%
1160 Oak Ave Shady Side, MD Offers cannot be submitted for seller review until 1/18/26. Set in a peaceful bayside comm...	3 beds \| 1 baths \| 1,320 sq.ft.	$269,950	Airbnb cash on cash: 3.16% Traditional cash on cash: 5.84% Airbnb Rental Income: $2063 Traditional Rental Income: $2213 Airbnb ROI: 3.16% Traditional ROI: 5.84%
1161 Steamboat Rd Shady Side, MD Welcome to this inviting single-family home in the heart of Shady Side! This lovely reside...	3 beds \| 2 baths \| 2,235 sq.ft.	$479,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.93% Airbnb Rental Income: $2063 Traditional Rental Income: $2300 Airbnb ROI: 1.21% Traditional ROI: 2.93%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shady Side, MD

1223 Pine Ave

Shady Side, MD

2 beds | 1 baths | 960 sq.ft.

$330,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2266

Traditional Rental Income: $1893

Airbnb ROI: 3.14%

Traditional ROI: 3.77%

1213 OAK AVE

Shady Side, MD

2 beds | 1 baths | N/A

$295,000

Airbnb cash on cash: 3.84%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $2266

Traditional Rental Income: $1457

Airbnb ROI: 3.84%

Traditional ROI: 2.97%

1462 Snug Harbor Rd

Shady Side, MD

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

$750,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3319

Traditional Rental Income: $3065

Airbnb ROI: 2.06%

Traditional ROI: 2.76%

4938 Rullman Rd

Shady Side, MD

4 beds | 2 baths | 2,200 sq.ft.

$697,015

Airbnb cash on cash: 1.97%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $3319

Traditional Rental Income: $2917

Airbnb ROI: 1.97%

Traditional ROI: 2.49%

4912 Beech St

Shady Side, MD

2 beds | 2 baths | 864 sq.ft.

$350,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $2266

Traditional Rental Income: $2141

Airbnb ROI: 2.96%

Traditional ROI: 4.3%

1711 Columbia Beach Rd

Shady Side, MD

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

$499,900

Airbnb cash on cash: 3.27%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $3319

Traditional Rental Income: $3067

Airbnb ROI: 3.27%

Traditional ROI: 4.32%

1419 Shady Rest Rd

Shady Side, MD

3 beds | 1 baths | 1,022 sq.ft.

$270,750

Airbnb cash on cash: 3.58%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2063

Traditional Rental Income: $1497

Airbnb ROI: 3.58%

Traditional ROI: 3.45%

4738 Washington Ave

Shady Side, MD

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

$355,000

Airbnb cash on cash: 2.43%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2063

Traditional Rental Income: $1988

Airbnb ROI: 2.43%