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
1223 PINE Avenue 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%
4938 RULLMAN Road Shady Side, MD HAPPY NEW YAR!! Westelee Welcome's You Home TO this 2.5 year old "Pottery Barn" Colonial h...	4 beds \| 3 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 Street 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%
4908 OLIVE Street Shady Side, MD HOME TO BE BUILT. EXISTING HOME TO BE TORN DOWN. EXPECTED SPRING/SUMMER 2026 DELIVERY. Mus...	4 beds \| 3 baths \| 2,091 sq.ft.	$599,990	Airbnb cash on cash: 3.37% Traditional cash on cash: 4.21% Airbnb Rental Income: $3319 Traditional Rental Income: $3051 Airbnb ROI: 3.37% Traditional ROI: 4.21%
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: 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 Road 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 Avenue 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 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.	$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 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.	$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%
Mayo Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.77% Airbnb Rental Income: $976 Traditional Rental Income: $1001 Airbnb ROI: 0.17% Traditional ROI: 1.77%
1302 SPRUCE Street Shady Side, MD FEBRUARY 2026 DELIVERY. Introducing the Adams model - a beautifully designed home featurin...	4 beds \| 3 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%
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: 3.4% Traditional cash on cash: 5.12% Airbnb Rental Income: $976 Traditional Rental Income: $792 Airbnb ROI: 3.4% Traditional ROI: 5.12%
1408 & 1410 Haile Pkwy Shady Side, MD 1408 & 1410 Haile Pkwy, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$65,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 8.77% Airbnb Rental Income: $976 Traditional Rental Income: $795 Airbnb ROI: 6.14% Traditional ROI: 8.77%
4721 GIRTON Avenue 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 Lane 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 Road Shady Side, MD Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to th...	3 beds \| 3 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%
4937 ASPEN Street Shady Side, MD OPEN HOUSE SATURDAY JANUARY 17TH- NOON to 2 PM After a busy Saturday, we're hosting anothe...	2 beds \| 2 baths \| 886 sq.ft.	$379,999	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.42% Airbnb Rental Income: $2266 Traditional Rental Income: $1607 Airbnb ROI: 2.68% Traditional ROI: 2.42%
1160 OAK Avenue Shady Side, MD Offers cannot be submitted for seller review until 1/18/26. Set in a peaceful bayside comm...	3 beds \| 2 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 Road Shady Side, MD Welcome to this inviting single-family home in the heart of Shady Side! This lovely reside...	3 beds \| 3 baths \| 2,235 sq.ft.	$479,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 3.08% Airbnb Rental Income: $2063 Traditional Rental Income: $2300 Airbnb ROI: 1.36% Traditional ROI: 3.08%

Real Estate investment in Shady-side, MD

There are 21 properties for sale in the city of Shady Side . The median list price in Shady Side is $335,000 and the average price per square foot is $221. In January 2026, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,141.

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

There are 21 investment properties available for sale in Shady-side.

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

The ROI for Long-Term is higher than the Short-Term in Shady-side with average rental income of $2,141.

Your search for investment property begins and ends here

Investment Property for Sale in Shady Side, MD

1223 PINE Avenue

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%

4938 RULLMAN Road

Shady Side, MD

4 beds | 3 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 Street

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%

4908 OLIVE Street

Shady Side, MD

4 beds | 3 baths | 2,091 sq.ft.

$599,990

Airbnb cash on cash: 3.37%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3319

Traditional Rental Income: $3051

Airbnb ROI: 3.37%

Traditional ROI: 4.21%

1711 COLUMBIA BEACH Road

Shady Side, MD

4 beds | 3 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 Road

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 Avenue

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%