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.

Amasa Investment Property for Sale in Shady Side, MD

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

Showing 35 Amasa Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

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%
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%
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.	$345,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.94% Airbnb Rental Income: $2063 Traditional Rental Income: $1988 Airbnb ROI: 2.52% Traditional ROI: 3.94%
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%
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

Amasa 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%

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%

Traditional ROI: 4.21%

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%