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
4900 THOMAS Drive Shady Side, MD Just two doors from the water and steps from a children's park and boat ramp, this 3-bedro...	3 beds \| 2 baths \| 1,408 sq.ft.	$375,000	Airbnb cash on cash: 6.74% Traditional cash on cash: 4.29% Airbnb Rental Income: $3981 Traditional Rental Income: $2267 Airbnb ROI: 6.74% Traditional ROI: 4.29%
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%
4922 LERCH Drive Shady Side, MD You can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stu...	3 beds \| 3 baths \| 1,920 sq.ft.	$699,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 2.87% Airbnb Rental Income: $3981 Traditional Rental Income: $3188 Airbnb ROI: 2.78% Traditional ROI: 2.87%
4738 IDLEWILDE Road Shady Side, MD Amazing opportunity to own a beautifully remodeled home in the waterfront community of Idl...	4 beds \| 2 baths \| 1,300 sq.ft.	$449,000	Airbnb cash on cash: 8.43% Traditional cash on cash: 3.68% Airbnb Rental Income: $5433 Traditional Rental Income: $2346 Airbnb ROI: 8.43% Traditional ROI: 3.68%
4908 ASPEN Street Shady Side, MD Welcome to this 2-story home nestled in the serene Avalon Shores community. This home feat...	3 beds \| 3 baths \| 1,500 sq.ft.	$304,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 7.1% Airbnb Rental Income: $3981 Traditional Rental Income: $2756 Airbnb ROI: 8.4% Traditional ROI: 7.1%
5211 AL JONES Drive Shady Side, MD Coastal Living in a Gated Waterfront Community a Short Distance from Annapolis and Washing...	2 beds \| 2 baths \| 1,244 sq.ft.	$554,500	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.29% Airbnb Rental Income: $2847 Traditional Rental Income: $2264 Airbnb ROI: 2.14% Traditional ROI: 2.29%
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%
4725 IDLEWILDE Road Shady Side, MD Calling all investors, second-home seekers, and visionaries-this is the project you've bee...	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	$336,900	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.04% Airbnb Rental Income: $2847 Traditional Rental Income: $1682 Airbnb ROI: 4.63% Traditional ROI: 3.04%
4738 WASHINGTON Avenue Shady Side, MD Easy Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrificing c...	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 Bea...	2 beds \| 2 baths \| 1,000 sq.ft.	$368,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 4.03% Airbnb Rental Income: $2847 Traditional Rental Income: $2127 Airbnb ROI: 4.19% Traditional ROI: 4.03%
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.	$429,000	Airbnb cash on cash: 5.75% Traditional cash on cash: 4.79% Airbnb Rental Income: $3981 Traditional Rental Income: $2743 Airbnb ROI: 5.75% Traditional ROI: 4.79%
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.	$535,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.55% Airbnb Rental Income: $3981 Traditional Rental Income: $2798 Airbnb ROI: 4.21% Traditional ROI: 3.55%
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.	$1,524,000	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%
1219 Rogers Rd Shady Side, MD 1219 Rogers Rd, Shady Side, MD 21037 \| Single Family Residential	N/A beds \| N/A baths \| 792 sq.ft.	$2,200,000	Airbnb cash on cash: -1.37% Traditional cash on cash: -1.74% Airbnb Rental Income: $2085 Traditional Rental Income: $796 Airbnb ROI: -1.37% Traditional ROI: -1.74%
6118 Shady Side Rd Shady Side, MD 6118 Shady Side Rd, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$239,500	Airbnb cash on cash: 4.35% Traditional cash on cash: 1.03% Airbnb Rental Income: $2085 Traditional Rental Income: $796 Airbnb ROI: 4.35% Traditional ROI: 1.03%
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 Road Shady Side, MD Great Cape Cod on 4 lots with nice upgrades in beautiful gated beach community. Photos com...	4 beds \| 2 baths \| 1,248 sq.ft.	$441,000	Airbnb cash on cash: 8.55% Traditional cash on cash: 3.33% Airbnb Rental Income: $5433 Traditional Rental Income: $2185 Airbnb ROI: 8.55% Traditional ROI: 3.33%
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%
1261 Mayo Ridge Rd Shady Side, MD 1261 Mayo Ridge Rd, Shady Side, MD 21037 \| Single Family Residential	6 beds \| 6 baths \| 4,371 sq.ft.	$949,800	Airbnb cash on cash: 3.94% Traditional cash on cash: 4.64% Airbnb Rental Income: $6725 Traditional Rental Income: $6041 Airbnb ROI: 3.94% Traditional ROI: 4.64%
1250 Juniper St Shady Side, MD 1250 Juniper St, Shady Side, MD 20764 \| Single Family Residential	3 beds \| 2 baths \| 1,332 sq.ft.	$449,950	Airbnb cash on cash: 5.12% Traditional cash on cash: 2.63% Airbnb Rental Income: $3981 Traditional Rental Income: $2076 Airbnb ROI: 5.12% Traditional ROI: 2.63%
6440 W Shady Side Rd Shady Side, MD 6440 W Shady Side Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 2,000 sq.ft.	$619,900	Airbnb cash on cash: 5.26% Traditional cash on cash: 1.89% Airbnb Rental Income: $5433 Traditional Rental Income: $2389 Airbnb ROI: 5.26% Traditional ROI: 1.89%
1302 SPRUCE Street Shady Side, MD 10/10/25 Update: Home is under roof. Estimated completion is projected for January/Februar...	4 beds \| 3 baths \| 2,424 sq.ft.	$609,990	Airbnb cash on cash: 6.45% Traditional cash on cash: 4.44% Airbnb Rental Income: $5433 Traditional Rental Income: $3191 Airbnb ROI: 6.45% Traditional ROI: 4.44%
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.	$435,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 4.57% Airbnb Rental Income: $3981 Traditional Rental Income: $2666 Airbnb ROI: 5.7% Traditional ROI: 4.57%
5314 Al Jones Dr Shady Side, MD 5314 Al Jones Dr, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$145,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 2.81% Airbnb Rental Income: $2085 Traditional Rental Income: $771 Airbnb ROI: 8.4% Traditional ROI: 2.81%
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: 3.51% Traditional cash on cash: 0.9% Airbnb Rental Income: $5433 Traditional Rental Income: $2354 Airbnb ROI: 3.51% Traditional ROI: 0.9%
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: 2.87% Traditional cash on cash: 2.38% Airbnb Rental Income: $3981 Traditional Rental Income: $2795 Airbnb ROI: 2.87% Traditional ROI: 2.38%

Real Estate investment in Shady-side, MD

There are 32 properties for sale in the city of Shady Side . The median list price in Shady Side is $375,000 and the average price per square foot is $218. In October 2025, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,156.

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

There are 32 investment properties available for sale in Shady-side.

In 2025, the best neighborhood to buy investment property is Shady Side.

The ROI for Short-Term is higher than the Long-Term in Shady-side with average rental income of $3,981.

Your search for investment property begins and ends here

Investment Property for Sale in Shady Side, MD

4900 THOMAS Drive

Shady Side, MD

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

$375,000

Airbnb cash on cash: 6.74%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $3981

Traditional Rental Income: $2267

Airbnb ROI: 6.74%

Traditional ROI: 4.29%

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%

4922 LERCH Drive

Shady Side, MD

3 beds | 3 baths | 1,920 sq.ft.

$699,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $3981

Traditional Rental Income: $3188

Airbnb ROI: 2.78%

Traditional ROI: 2.87%

4738 IDLEWILDE Road

Shady Side, MD

4 beds | 2 baths | 1,300 sq.ft.

$449,000

Airbnb cash on cash: 8.43%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $5433

Traditional Rental Income: $2346

Airbnb ROI: 8.43%

Traditional ROI: 3.68%

4908 ASPEN Street

Shady Side, MD

3 beds | 3 baths | 1,500 sq.ft.

$304,000

Airbnb cash on cash: 8.4%

Traditional cash on cash: 7.1%

Airbnb Rental Income: $3981

Traditional Rental Income: $2756

Airbnb ROI: 8.4%

Traditional ROI: 7.1%

5211 AL JONES Drive

Shady Side, MD

2 beds | 2 baths | 1,244 sq.ft.

$554,500

Airbnb cash on cash: 2.14%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2847

Traditional Rental Income: $2264

Airbnb ROI: 2.14%

Traditional ROI: 2.29%

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%

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%