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.

W Wheatfield Twp Investment Property for Sale in Shady Side, MD

Search for W Wheatfield Twp Investment Property for Sale in Shady Side, Maryland. Browse all of Mashvisor’s W Wheatfield Twp Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 34 W Wheatfield Twp Investment Property 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
1168 MAPLE Avenue Shady Side, MD Built in 2019 and set in Cedarhurst on the Bay, this newer Cape Cod offers a South County ...	3 beds \| 2 baths \| 1,500 sq.ft.	$460,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 2.92% Airbnb Rental Income: $2063 Traditional Rental Income: $2194 Airbnb ROI: 1.38% Traditional ROI: 2.92%
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: 1.7% Traditional cash on cash: 2.07% Airbnb Rental Income: $2063 Traditional Rental Income: $1691 Airbnb ROI: 1.7% Traditional ROI: 2.07%
1191 Spruce Ave Shady Side, MD Welcome to Cedarhurst on the Bay! This lovely well kept two story colonial is ready for it...	N/A beds \| N/A baths \| 1,296 sq.ft.	$412,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.86% Airbnb Rental Income: $976 Traditional Rental Income: $1737 Airbnb ROI: -0.3% Traditional ROI: 2.86%
1462 SNUG HARBOR Road Shady Side, MD 4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunit...	4 beds \| 2 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%
1411 Haile Pkwy Shady Side, MD Rivendale Homes introduces the Cedarbury house type to Shady Side! This gorgeous custom bu...	4 beds \| 3 baths \| 1,905 sq.ft.	$575,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.89% Airbnb Rental Income: $3319 Traditional Rental Income: $2760 Airbnb ROI: 3.55% Traditional ROI: 3.89%
1199 OAK AVE Shady Side, MD Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhur...	4 beds \| 2 baths \| N/A	$400,000	Airbnb cash on cash: 4.71% Traditional cash on cash: 5.2% Airbnb Rental Income: $3319 Traditional Rental Income: $2760 Airbnb ROI: 4.71% Traditional ROI: 5.2%
5191 SPRING AVE Shady Side, MD Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on t...	4 beds \| 3 baths \| N/A	$460,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 5.59% Airbnb Rental Income: $3319 Traditional Rental Income: $3197 Airbnb ROI: 4.15% Traditional ROI: 5.59%
4908 OLIVE Street Shady Side, MD EXPECTED SUMMER 2026 DELIVERY. Must use builder contract - buyer responsible for 100% tran...	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%
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%
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.	$529,650	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: -0.29% Traditional cash on cash: -0.18% Airbnb Rental Income: $3319 Traditional Rental Income: $2727 Airbnb ROI: -0.29% Traditional ROI: -0.18%
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 Mayo Rd, Shady Side, MD 21106 \| Other	N/A beds \| N/A baths \| N/A	$149,900	Airbnb cash on cash: 1.63% Traditional cash on cash: 4.26% Airbnb Rental Income: $976 Traditional Rental Income: $1001 Airbnb ROI: 1.63% Traditional ROI: 4.26%
5250 Al Jones Dr Shady Side, MD 5250 Al Jones Dr, Shady Side, MD 20764 \| Other	N/A beds \| N/A baths \| N/A	$149,999	Airbnb cash on cash: 1.44% Traditional cash on cash: 2.65% Airbnb Rental Income: $976 Traditional Rental Income: $799 Airbnb ROI: 1.44% Traditional ROI: 2.65%
4846 Woods Wharf Rd Shady Side, MD	N/A beds \| N/A baths \| N/A	$249,999	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.9% Airbnb Rental Income: $976 Traditional Rental Income: $796 Airbnb ROI: 0.17% 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%
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.	$469,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 5% Airbnb Rental Income: $2063 Traditional Rental Income: $3172 Airbnb ROI: 1.26% Traditional ROI: 5%
1209 JOHNSON Drive Shady Side, MD HOME TO BE BUILT. EXPECTED LATE SUMMER 2026 DELIVERY. Schaefer Homes brings to you their l...	4 beds \| 3 baths \| 2,068 sq.ft.	$595,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.24% Airbnb Rental Income: $3319 Traditional Rental Income: $3051 Airbnb ROI: 2.39% Traditional ROI: 3.24%
306 Linden Ave Shady Side, MD 306 Linden Ave, Shady Side, MD 21106 \| Single Family Residential	2 beds \| 1 baths \| 804 sq.ft.	$375,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 2.06% Airbnb Rental Income: $2266 Traditional Rental Income: $1552 Airbnb ROI: 2.48% Traditional ROI: 2.06%
1225 JUNIPER Street Shady Side, MD THIS IS A TO BE BUILT HOME	4 beds \| 3 baths \| 2,091 sq.ft.	$579,990	Airbnb cash on cash: 3.36% Traditional cash on cash: 4.16% Airbnb Rental Income: $3319 Traditional Rental Income: $3011 Airbnb ROI: 3.36% Traditional ROI: 4.16%
1379 MCDONALD RD Shady Side, MD *BRAND NEW & READY FOR IMMEDIATE OCCUPANCY* this stunning Arts & Crafts home by Laine ...	4 beds \| 3 baths \| N/A	$835,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 2.74% Airbnb Rental Income: $3319 Traditional Rental Income: $3106 Airbnb ROI: 2.06% Traditional ROI: 2.74%
1340 E WEST SHADY SIDE RD Shady Side, MD *BRAND NEW CONSTRUCTION READY FOR IMMEDIATE OCCUPANCY* this Modern Farmhouse by local ...	3 beds \| 3 baths \| N/A	$799,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 1.63% Airbnb Rental Income: $2063 Traditional Rental Income: $2194 Airbnb ROI: 0.74% Traditional ROI: 1.63%
1160 OAK Shady Side, MD Experience the epitome of luxury living in this stunning Colonial home, beautifully renova...	3 beds \| 2 baths \| 1,320 sq.ft.	$439,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 1.71% Airbnb Rental Income: $2063 Traditional Rental Income: $1655 Airbnb ROI: 1.41% Traditional ROI: 1.71%
1502 Garst Rd Shady Side, MD 1502 Garst Rd, Shady Side, MD 20764 \| Single Family Residential	2 beds \| 1 baths \| 736 sq.ft.	$235,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 3.48% Airbnb Rental Income: $2266 Traditional Rental Income: $1328 Airbnb ROI: 5.15% Traditional ROI: 3.48%
1235 SPRUCE Avenue Shady Side, MD THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home wit...	4 beds \| 3 baths \| 2,710 sq.ft.	$649,990	Airbnb cash on cash: 2.89% Traditional cash on cash: 4.1% Airbnb Rental Income: $3319 Traditional Rental Income: $3307 Airbnb ROI: 2.89% Traditional ROI: 4.1%

Your search for investment property begins and ends here

W Wheatfield Twp Investment Property for Sale in Shady Side, MD

1168 MAPLE Avenue

Shady Side, MD

3 beds | 2 baths | 1,500 sq.ft.

$460,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $2063

Traditional Rental Income: $2194

Airbnb ROI: 1.38%

Traditional ROI: 2.92%

1316 Azalia St

Shady Side, MD

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

$465,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2063

Traditional Rental Income: $1691

Airbnb ROI: 1.7%

Traditional ROI: 2.07%

1191 Spruce Ave

Shady Side, MD

N/A beds | N/A baths | 1,296 sq.ft.

$412,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $976

Traditional Rental Income: $1737

Airbnb ROI: -0.3%

Traditional ROI: 2.86%

1462 SNUG HARBOR Road

Shady Side, MD

4 beds | 2 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%

1411 Haile Pkwy

Shady Side, MD

4 beds | 3 baths | 1,905 sq.ft.

$575,000

Airbnb cash on cash: 3.55%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $3319

Traditional Rental Income: $2760

Airbnb ROI: 3.55%

Traditional ROI: 3.89%

1199 OAK AVE

Shady Side, MD

4 beds | 2 baths | N/A

$400,000

Airbnb cash on cash: 4.71%

Traditional cash on cash: 5.2%

Airbnb Rental Income: $3319

Traditional Rental Income: $2760

Airbnb ROI: 4.71%

Traditional ROI: 5.2%

5191 SPRING AVE

Shady Side, MD

4 beds | 3 baths | N/A

$460,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $3319

Traditional Rental Income: $3197

Airbnb ROI: 4.15%

Traditional ROI: 5.59%

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%