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 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%
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: -0.38% Traditional cash on cash: 2.07% Airbnb Rental Income: $976 Traditional Rental Income: $1691 Airbnb ROI: -0.38% Traditional ROI: 2.07%
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%
1191 Poplar Ave Shady Side, MD Welcome to Cedarhurst on the Bay! Water Provilege Community Within Walking Distance to Com...	4 beds \| 2 baths \| 2,272 sq.ft.	$540,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.8% Airbnb Rental Income: $3319 Traditional Rental Income: $2543 Airbnb ROI: 2.87% Traditional ROI: 2.8%
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.	$405,067	Airbnb cash on cash: 1.93% Traditional cash on cash: 5.12% Airbnb Rental Income: $2063 Traditional Rental Income: $2743 Airbnb ROI: 1.93% Traditional ROI: 5.12%
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%
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.	$1,470,000	Airbnb cash on cash: -0.35% Traditional cash on cash: -0.24% Airbnb Rental Income: $3319 Traditional Rental Income: $2727 Airbnb ROI: -0.35% Traditional ROI: -0.24%
6152 Shady Side Rd Shady Side, MD 6152 Shady Side Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$54,900	Airbnb cash on cash: 7.52% Traditional cash on cash: 10.62% Airbnb Rental Income: $976 Traditional Rental Income: $796 Airbnb ROI: 7.52% Traditional ROI: 10.62%
4907 Quince St Shady Side, MD 4907 Quince St, GALESVILLE, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$50,000	Airbnb cash on cash: 8.39% Traditional cash on cash: 11.5% Airbnb Rental Income: $976 Traditional Rental Income: $783 Airbnb ROI: 8.39% Traditional ROI: 11.5%
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: 1.63% Traditional cash on cash: 2.83% Airbnb Rental Income: $976 Traditional Rental Income: $796 Airbnb ROI: 1.63% Traditional ROI: 2.83%
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%
5250 Al Jones Dr Shady Side, MD 5250 Al Jones Dr, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$169,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.11% Airbnb Rental Income: $976 Traditional Rental Income: $799 Airbnb ROI: 1.04% Traditional ROI: 2.11%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$249,999	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.79% Airbnb Rental Income: $976 Traditional Rental Income: $796 Airbnb ROI: 0.09% Traditional ROI: 0.79%
1133 Steamboat Rd Shady Side, MD 1133 Steamboat Rd, GALESVILLE, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$997,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -1.34% Airbnb Rental Income: $976 Traditional Rental Income: $783 Airbnb ROI: -1.51% Traditional ROI: -1.34%
1436 Haile Pkwy Shady Side, MD 1436 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%
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 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%
6512 Shady Side Rd Shady Side, MD 6512 Shady Side Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 2,485 sq.ft.	$815,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 0.9% Airbnb Rental Income: $3319 Traditional Rental Income: $2354 Airbnb ROI: 1.19% Traditional ROI: 0.9%
1461 Cedarhurst Rd Shady Side, MD 1461 Cedarhurst Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$54,000	Airbnb cash on cash: 7.67% Traditional cash on cash: 10.34% Airbnb Rental Income: $976 Traditional Rental Income: $770 Airbnb ROI: 7.67% Traditional ROI: 10.34%
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 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%
6508 Shady Side Rd Shady Side, MD 6508 Shady Side Rd, Shady Side, MD 20764 \| Single Family Residential	3 beds \| 2 baths \| 2,225 sq.ft.	$799,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 0.97% Airbnb Rental Income: $2063 Traditional Rental Income: $2370 Airbnb ROI: -0.16% Traditional ROI: 0.97%
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.	$469,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.87% Airbnb Rental Income: $2063 Traditional Rental Income: $3172 Airbnb ROI: 1.21% Traditional ROI: 4.87%
1241 Steamboat Rd Shady Side, MD Estate sale handled by an attorney. This well-loved home has been in the same family since...	2 beds \| 1 baths \| 1,728 sq.ft.	$325,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 5.37% Airbnb Rental Income: $2266 Traditional Rental Income: $2519 Airbnb ROI: 2.87% Traditional ROI: 5.37%
1209 Johnson Dr Shady Side, MD HOME TO BE BUILT. EXPECTED SUMMER 2026 DELIVERY. Schaefer Homes brings to you their latest...	4 beds \| 2 baths \| 2,068 sq.ft.	$579,990	Airbnb cash on cash: 2.5% Traditional cash on cash: 3.38% Airbnb Rental Income: $3319 Traditional Rental Income: $3051 Airbnb ROI: 2.5% Traditional ROI: 3.38%
306 Linden Ave Shady Side, MD 306 Linden Ave, Shady Side, MD 21106 \| Single Family Residential	2 beds \| 1 baths \| 804 sq.ft.	$400,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.81% Airbnb Rental Income: $2266 Traditional Rental Income: $1552 Airbnb ROI: 2.2% Traditional ROI: 1.81%
1205 Poplar Ave Shady Side, MD 1205 Poplar Ave, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$50,000	Airbnb cash on cash: 8.39% Traditional cash on cash: 9.09% Airbnb Rental Income: $976 Traditional Rental Income: $660 Airbnb ROI: 8.39% Traditional ROI: 9.09%
Pine Ave Shady Side, MD Pine Ave, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$55,000	Airbnb cash on cash: 8.39% Traditional cash on cash: 9.09% Airbnb Rental Income: $976 Traditional Rental Income: $660 Airbnb ROI: 8.39% Traditional ROI: 9.09%

Real Estate investment in Shady-side, MD

There are 36 properties for sale in the city of Shady Side . The median list price in Shady Side is $349,900 and the average price per square foot is $161. In February 2026, the average monthly cash on cash return in Shady Side is 3.00%. The average monthly rental income in Shady Side is $1,988.

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

There are 36 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 $1,988.

Your search for investment property begins and ends here

Investment Property 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%

1316 Azalia St

Shady Side, MD

3 beds | N/A baths | 1,500 sq.ft.

$465,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $976

Traditional Rental Income: $1691

Airbnb ROI: -0.38%

Traditional ROI: 2.07%

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%

1191 Poplar Ave

Shady Side, MD

4 beds | 2 baths | 2,272 sq.ft.

$540,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $3319

Traditional Rental Income: $2543

Airbnb ROI: 2.87%

Traditional ROI: 2.8%

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%