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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
231 CORNELL Drive WOODSBORO, MD Impressive 4-bedroom, 2.5-bath colonial ideally situated at the end of a quiet cul-de-sac ...	4 beds \| 3 baths \| 2,720 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $2806 Airbnb ROI: N/A Traditional ROI: 3.13%
102 WOODSBORO CREAGERSTOWN Road WOODSBORO, MD Welcome to this charming and updated farmhouse-style home in the heart of Woodsboro. Origi...	3 beds \| 2 baths \| 1,400 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $2189 Airbnb ROI: N/A Traditional ROI: 4.4%
2 N 2ND Street WOODSBORO, MD * Motivated Seller- Ask about available Closing Cost Assistance with Acceptable Offer* Wel...	3 beds \| 3 baths \| 2,412 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.41% Airbnb Rental Income: $null Traditional Rental Income: $3095 Airbnb ROI: N/A Traditional ROI: 6.41%
12235 LEGORE BRIDGE Road WOODSBORO, MD Mountain views and country privacy! Welcome to this beautifully FULLY renovated home offer...	4 beds \| 3 baths \| 2,176 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.04% Airbnb Rental Income: $null Traditional Rental Income: $3229 Airbnb ROI: N/A Traditional ROI: 5.04%

Real Estate investment in Woodsboro, MD

There are 5 properties for sale in the city of Woodsboro . The median list price in Woodsboro is $424,281 and the average price per square foot is $178. In June 2026, the average monthly cash on cash return in Woodsboro is 4.00%. The average monthly rental income in Woodsboro is $3,095.

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

There are 5 investment properties available for sale in Woodsboro.

In 2026, 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Woodsboro, MD

231 CORNELL Drive

WOODSBORO, MD

4 beds | 3 baths | 2,720 sq.ft.

$575,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.13%

Airbnb Rental Income: $null

Traditional Rental Income: $2806

Airbnb ROI: N/A

Traditional ROI: 3.13%

102 WOODSBORO CREAGERSTOWN Road

WOODSBORO, MD

3 beds | 2 baths | 1,400 sq.ft.

$374,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2189

Airbnb ROI: N/A

Traditional ROI: 4.4%

2 N 2ND Street

WOODSBORO, MD

3 beds | 3 baths | 2,412 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.41%

Airbnb Rental Income: $null

Traditional Rental Income: $3095

Airbnb ROI: N/A

Traditional ROI: 6.41%

12235 LEGORE BRIDGE Road

WOODSBORO, MD

4 beds | 3 baths | 2,176 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.04%

Airbnb Rental Income: $null

Traditional Rental Income: $3229

Airbnb ROI: N/A

Traditional ROI: 5.04%

Real Estate investment in Woodsboro, MD

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

How many investment properties are available for sale in Woodsboro?

Which neighborhoods in Woodsboro to invest in 2026?

Long-Term vs. Short-Term Rentals in Woodsboro, Maryland: Which will earn the best returns?

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