Real Estate Investment Properties for Sale in Woodsboro, MD

Looking for investment property in Woodsboro, MD with high ROI ?

Explore a variety of short-term homes & houses in Woodsboro, MD. Invest wisely with VRBO & Woodsboro, 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 Woodsboro, MD

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
11715 CLYDE YOUNG ROAD WOODSBORO, MD Own a piece of paradise! If you are have been looking for the perfect farmette or the perf...	2 beds \| 2 baths \| 1,334 sq.ft.	$575,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 2.66% Airbnb Rental Income: $2838 Traditional Rental Income: $2422 Airbnb ROI: 2.21% Traditional ROI: 2.66%
206 S 2ND STREET WOODSBORO, MD Welcome Home to 206 2nd St, Woodsboro, Maryland!! This charming 3-bedroom, 1-bath rambler ...	3 beds \| 1 baths \| 1,190 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2035 Airbnb ROI: N/A Traditional ROI: 4.35%
11 ROSEWOOD COURT #101 WOODSBORO, MD Major Price Modification... THIS UNIT COMES WITH A 1 CAR GARAGE... Seller will consider "S...	2 beds \| 2 baths \| 1,285 sq.ft.	$265,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 6.27% Airbnb Rental Income: $2838 Traditional Rental Income: $2174 Airbnb ROI: 6.27% Traditional ROI: 6.27%
Investment Properties for Sale in Other Cities of Maryland
3029 HUDSON STREET Baltimore , MD Welcome to this beautifully reimagined Canton residence, where historic charm meets modern...	4 beds \| 3 baths \| 1,748 sq.ft.	$520,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 3.34% Airbnb Rental Income: $4486 Traditional Rental Income: $2649 Airbnb ROI: 5.19% Traditional ROI: 3.34%
675 PRESIDENT STREET #2904 Baltimore , MD Elevated high above Harbor East, this impeccable two-story penthouse at The Vue offers an ...	4 beds \| 4 baths \| 5,071 sq.ft.	$2,695,000	Airbnb cash on cash: -1.57% Traditional cash on cash: -0.5% Airbnb Rental Income: $1948 Traditional Rental Income: $4106 Airbnb ROI: -1.57% Traditional ROI: -0.5%
1200 STEUART STREET #426 Baltimore , MD Welcome to the largest one-bedroom, one-and-a-half-bath residence at Silo Point. This spac...	1 beds \| 2 baths \| 1,590 sq.ft.	$389,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.21% Airbnb Rental Income: $2320 Traditional Rental Income: $2585 Airbnb ROI: 0.91% Traditional ROI: 3.21%
3916 CLOVERHILL ROAD Baltimore , MD **OPEN HOUSE SUNDAY, SEPTEMBER 14TH, 11:30-1:30 Discover your charming retreat in the hear...	5 beds \| 2 baths \| 2,016 sq.ft.	$575,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.28% Airbnb Rental Income: $2247 Traditional Rental Income: $2612 Airbnb ROI: 0.56% Traditional ROI: 2.28%
221 RIDGEMEDE ROAD #106 Baltimore , MD Rarely available end unit condo with private entrance in coveted Tuscany-Canterbury. The c...	1 beds \| 1 baths \| 743 sq.ft.	$139,500	Airbnb cash on cash: 9.13% Traditional cash on cash: 8.35% Airbnb Rental Income: $2183 Traditional Rental Income: $1526 Airbnb ROI: 9.13% Traditional ROI: 8.35%
16 138TH STREET #106 Ocean City , MD Expansive 4-Bedroom Condo with Ocean Views in Island Breeze Rarely Available! Welcome to o...	4 beds \| 3 baths \| 2,570 sq.ft.	$975,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.46% Airbnb Rental Income: $4007 Traditional Rental Income: $3157 Airbnb ROI: 1.46% Traditional ROI: 1.46%
738 ARNCLIFFE ROAD Baltimore , MD Welcome to this beautifully updated 2-bedroom, 1-bath row home that perfectly blends comfo...	2 beds \| 1 baths \| 1,016 sq.ft.	$189,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 5.84% Airbnb Rental Income: $2013 Traditional Rental Income: $1465 Airbnb ROI: 5.98% Traditional ROI: 5.84%
2812 KILDAIRE DRIVE Baltimore , MD Seller is willing to negotiate closing cost assistance !!! Nestled in a prime location wit...	3 beds \| 2 baths \| 1,388 sq.ft.	$313,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 4.59% Airbnb Rental Income: $2587 Traditional Rental Income: $2134 Airbnb ROI: 4.02% Traditional ROI: 4.59%
2933 FAIT AVENUE Baltimore , MD Enjoy City life in this fully remolded home in Canton. The open floor plan of the main lev...	3 beds \| 3 baths \| 1,152 sq.ft.	$449,999	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.09% Airbnb Rental Income: $3308 Traditional Rental Income: $2089 Airbnb ROI: 3.23% Traditional ROI: 2.09%
19804 LARENTIA DRIVE Germantown , MD Modern Comfort in Waterbury Downs Renovated 3BR Townhome! Welcome to 19804 Larentia Drive...	3 beds \| 3 baths \| 1,604 sq.ft.	$384,900	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.76% Airbnb Rental Income: $2638 Traditional Rental Income: $2632 Airbnb ROI: 3.04% Traditional ROI: 4.76%
2331 GUILFORD AVENUE Baltimore , MD Charles Village, Beautiful interior and spacious rooms. Great location with rear yard. Ha...	3 beds \| 2 baths \| N/A	$298,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 4.42% Airbnb Rental Income: $2685 Traditional Rental Income: $1978 Airbnb ROI: 4.68% Traditional ROI: 4.42%
5511 WESLEY AVENUE Baltimore , MD Step into this beautifully renovated home, where classic character meets modern living. Fr...	4 beds \| 3 baths \| 1,566 sq.ft.	$350,000	Airbnb cash on cash: 4.49% Traditional cash on cash: 4.81% Airbnb Rental Income: $2980 Traditional Rental Income: $2400 Airbnb ROI: 4.49% Traditional ROI: 4.81%
110 ZEPPELIN AVE LINTHICUM , MD **Hard to find colonial in Pumphrey at this price point with a nice-sized, flat yard with ...	3 beds \| 4 baths \| N/A	$380,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 6.8% Airbnb Rental Income: $4107 Traditional Rental Income: $3141 Airbnb ROI: 7.07% Traditional ROI: 6.8%
414 WATER STREET #2805 Baltimore , MD Discover the best of urban living in this high-rise condominium, ideally located in the he...	2 beds \| 1 baths \| 789 sq.ft.	$179,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 7.77% Airbnb Rental Income: $1389 Traditional Rental Income: $1963 Airbnb ROI: 1.96% Traditional ROI: 7.77%
5359 GIST AVENUE Baltimore , MD Contact the listing agent to schedule a showing of this property. By appointment only.	3 beds \| 2 baths \| 1,620 sq.ft.	$199,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 7.71% Airbnb Rental Income: $1729 Traditional Rental Income: $2101 Airbnb ROI: 3.21% Traditional ROI: 7.71%

Real Estate investment in Woodsboro, MD

There are 3 properties for sale in the city of Woodsboro . The median list price in Woodsboro is $325,000 and the average price per square foot is $256. In September 2025, the average monthly cash on cash return in Woodsboro is 4.00%. The average monthly rental income in Woodsboro is $2,174.

Woodsboro, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Woodsboro.

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

The ROI for Short-Term is higher than the Long-Term in Woodsboro with average rental income of $2,838.

Your search for investment property begins and ends here

Investment Property for Sale in Woodsboro, MD

11715 CLYDE YOUNG ROAD

WOODSBORO, MD

2 beds | 2 baths | 1,334 sq.ft.

$575,000

Airbnb cash on cash: 2.21%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $2838

Traditional Rental Income: $2422

Airbnb ROI: 2.21%

Traditional ROI: 2.66%

206 S 2ND STREET

WOODSBORO, MD

3 beds | 1 baths | 1,190 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.35%

Airbnb Rental Income: $null

Traditional Rental Income: $2035

Airbnb ROI: N/A

Traditional ROI: 4.35%

11 ROSEWOOD COURT #101

WOODSBORO, MD

2 beds | 2 baths | 1,285 sq.ft.

$265,000

Airbnb cash on cash: 6.27%

Traditional cash on cash: 6.27%

Airbnb Rental Income: $2838

Traditional Rental Income: $2174

Airbnb ROI: 6.27%

Traditional ROI: 6.27%

Investment Properties for Sale in Other Cities of Maryland

Baltimore , MD

4 beds | 3 baths | 1,748 sq.ft.

$520,000

Airbnb cash on cash: 5.19%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $4486

Traditional Rental Income: $2649

Airbnb ROI: 5.19%

Traditional ROI: 3.34%

Baltimore , MD

4 beds | 4 baths | 5,071 sq.ft.

$2,695,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $1948

Traditional Rental Income: $4106

Airbnb ROI: -1.57%

Traditional ROI: -0.5%

Baltimore , MD

1 beds | 2 baths | 1,590 sq.ft.

$389,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $2320

Traditional Rental Income: $2585

Airbnb ROI: 0.91%

Traditional ROI: 3.21%

Baltimore , MD

5 beds | 2 baths | 2,016 sq.ft.

$575,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2247

Traditional Rental Income: $2612

Airbnb ROI: 0.56%

Traditional ROI: 2.28%

Baltimore , MD

1 beds | 1 baths | 743 sq.ft.

$139,500

Airbnb cash on cash: 9.13%

Traditional cash on cash: 8.35%

Airbnb Rental Income: $2183

Traditional Rental Income: $1526

Airbnb ROI: 9.13%

Traditional ROI: 8.35%

Ocean City , MD

4 beds | 3 baths | 2,570 sq.ft.

$975,000