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
1208 OAK Avenue Shady Side, MD This beautiful home is steps from the Chesapeake Bay and the community marina, beach, play...	3 beds \| 2 baths \| 1,062 sq.ft.	$385,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 3.83% Airbnb Rental Income: $2063 Traditional Rental Income: $2168 Airbnb ROI: 2.06% Traditional ROI: 3.83%
4950 W END Avenue Shady Side, MD Welcome to 4950 W End Ave - a charming coastal bungalow just steps from the Chesapeake Bay...	2 beds \| 2 baths \| 984 sq.ft.	$319,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 4.97% Airbnb Rental Income: $2266 Traditional Rental Income: $2163 Airbnb ROI: 3.43% Traditional ROI: 4.97%
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: 2.2% Traditional cash on cash: 4.29% Airbnb Rental Income: $2063 Traditional Rental Income: $2267 Airbnb ROI: 2.2% Traditional ROI: 4.29%
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%
4992 LERCH Drive Shady Side, MD WATERFRONT LUXURY LIVING with panoramic West River views & unbelievable sunsets! This "3-y...	4 beds \| 5 baths \| 3,432 sq.ft.	$1,050,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 3.57% Airbnb Rental Income: $3319 Traditional Rental Income: $5324 Airbnb ROI: 0.75% Traditional ROI: 3.57%
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: 0.33% Traditional cash on cash: 2.87% Airbnb Rental Income: $2063 Traditional Rental Income: $3188 Airbnb ROI: 0.33% Traditional ROI: 2.87%
4938 RULLMAN Road Shady Side, MD Westelee Welcome's You Home! This 2.5 year old "Pottery Barn" Colonial home is set perfect...	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%
6070 Shady Side Rd Shady Side, MD Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	4 beds \| 2 baths \| 1,344 sq.ft.	$300,000	Airbnb cash on cash: 6.75% Traditional cash on cash: 5.51% Airbnb Rental Income: $3319 Traditional Rental Income: $2228 Airbnb ROI: 6.75% Traditional ROI: 5.51%
4912 BEECH Street Shady Side, MD Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon ...	2 beds \| 2 baths \| 864 sq.ft.	$365,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 4.09% Airbnb Rental Income: $2266 Traditional Rental Income: $2141 Airbnb ROI: 2.8% Traditional ROI: 4.09%
4738 IDLEWILDE Road Shady Side, MD NEW PRICE!! Amazing opportunity to own an affordable beautifully remodeled home in the wat...	4 beds \| 2 baths \| 1,300 sq.ft.	$444,900	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.73% Airbnb Rental Income: $3319 Traditional Rental Income: $2346 Airbnb ROI: 4.28% Traditional ROI: 3.73%
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: 1.2% Traditional cash on cash: 2.29% Airbnb Rental Income: $2266 Traditional Rental Income: $2264 Airbnb ROI: 1.2% 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: 3.27% Traditional cash on cash: 4.32% Airbnb Rental Income: $3319 Traditional Rental Income: $3067 Airbnb ROI: 3.27% 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: 4.36% Traditional cash on cash: 5.26% Airbnb Rental Income: $2266 Traditional Rental Income: $1932 Airbnb ROI: 4.36% Traditional ROI: 5.26%
1220 GROVE Avenue Shady Side, MD This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Commun...	5 beds \| 2 baths \| 1,812 sq.ft.	$480,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 4.57% Airbnb Rental Income: $2270 Traditional Rental Income: $2922 Airbnb ROI: 1.86% Traditional ROI: 4.57%
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%
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: 2.79% Traditional cash on cash: 4.03% Airbnb Rental Income: $2266 Traditional Rental Income: $2127 Airbnb ROI: 2.79% Traditional ROI: 4.03%
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.	$534,969	Airbnb cash on cash: 1.01% Traditional cash on cash: 3.55% Airbnb Rental Income: $2063 Traditional Rental Income: $2798 Airbnb ROI: 1.01% 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: -0.35% Traditional cash on cash: -0.25% Airbnb Rental Income: $3319 Traditional Rental Income: $2727 Airbnb ROI: -0.35% 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: -0.82% Traditional cash on cash: 0.3% Airbnb Rental Income: $976 Traditional Rental Income: $1096 Airbnb ROI: -0.82% Traditional ROI: 0.3%
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%
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: 0.27% Traditional cash on cash: 1.03% Airbnb Rental Income: $976 Traditional Rental Income: $796 Airbnb ROI: 0.27% 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: 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%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$259,999	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%
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: 3.36% Traditional cash on cash: 4.44% Airbnb Rental Income: $3319 Traditional Rental Income: $3191 Airbnb ROI: 3.36% Traditional ROI: 4.44%
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 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%
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 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.	$375,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.79% Airbnb Rental Income: $2063 Traditional Rental Income: $2147 Airbnb ROI: 2.04% Traditional ROI: 3.79%
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%
1503 CALLAWAY Drive Shady Side, MD Great opportunity to live by the water! Welcome to Columbia Beach!!! This gated community ...	3 beds \| 2 baths \| 1,356 sq.ft.	$265,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 6.39% Airbnb Rental Income: $2063 Traditional Rental Income: $2398 Airbnb ROI: 2.92% Traditional ROI: 6.39%

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 $375,000 and the average price per square foot is $187. In December 2025, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,228.

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

There are 36 investment properties available for sale in Shady-side.

In 2025, 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 $2,228.

Your search for investment property begins and ends here

Investment Property for Sale in Shady Side, MD

1208 OAK Avenue

Shady Side, MD

3 beds | 2 baths | 1,062 sq.ft.

$385,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $2063

Traditional Rental Income: $2168

Airbnb ROI: 2.06%

Traditional ROI: 3.83%

4950 W END Avenue

Shady Side, MD

2 beds | 2 baths | 984 sq.ft.

$319,900

Airbnb cash on cash: 3.43%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $2266

Traditional Rental Income: $2163

Airbnb ROI: 3.43%

Traditional ROI: 4.97%

4900 THOMAS Drive

Shady Side, MD

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

$375,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2063

Traditional Rental Income: $2267

Airbnb ROI: 2.2%

Traditional ROI: 4.29%

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%

4992 LERCH Drive

Shady Side, MD

4 beds | 5 baths | 3,432 sq.ft.

$1,050,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3319

Traditional Rental Income: $5324

Airbnb ROI: 0.75%

Traditional ROI: 3.57%

4922 LERCH Drive

Shady Side, MD

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

$699,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $2063

Traditional Rental Income: $3188

Airbnb ROI: 0.33%

Traditional ROI: 2.87%

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%

6070 Shady Side Rd

Shady Side, MD

4 beds | 2 baths | 1,344 sq.ft.

$300,000

Airbnb cash on cash: 6.75%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $3319

Traditional Rental Income: $2228

Airbnb ROI: 6.75%