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
102 Woodsboro Creagerstown Rd WOODSBORO, MD NEW PHOTOS COMING MONDAY 12/8!! Welcome to this charming and updated farmhouse-style home ...	3 beds \| 2 baths \| 1,400 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $2189 Airbnb ROI: N/A Traditional ROI: 4.26%
101 ARNOLD ALLEY WOODSBORO, MD Perched high on a hilltop overlooking all of Woodsboro, this meticulously maintained and m...	3 beds \| 3 baths \| N/A	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2613 Airbnb ROI: N/A Traditional ROI: 4.42%
10543 Woodsboro Rd WOODSBORO, MD	4 beds \| 3 baths \| 3,286 sq.ft.	$1,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.66% Airbnb Rental Income: $null Traditional Rental Income: $2932 Airbnb ROI: N/A Traditional ROI: -0.66%
10 Rosewood Ct #311 WOODSBORO, MD 10 Rosewood Ct #311, WOODSBORO, MD 21798 \| Condo/Coop	2 beds \| 2 baths \| 1,298 sq.ft.	$254,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 2.72% Airbnb Rental Income: $1735 Traditional Rental Income: $1666 Airbnb ROI: 1.02% Traditional ROI: 2.72%

Real Estate investment in Woodsboro, MD

There are 9 properties for sale in the city of Woodsboro . The median list price in Woodsboro is $404,950 and the average price per square foot is $221. In March 2026, the average monthly cash on cash return in Woodsboro is 4.00%. The average monthly rental income in Woodsboro is $2,241.

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

There are 9 investment properties available for sale in Woodsboro.

In 2026, the best neighborhood to buy investment property is WOODSBORO.

The ROI for Long-Term is higher than the Short-Term in Woodsboro with average rental income of $2,241.

Your search for investment property begins and ends here

Investment Property for Sale in Woodsboro, MD

102 Woodsboro Creagerstown Rd

WOODSBORO, MD

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

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.26%

Airbnb Rental Income: $null

Traditional Rental Income: $2189

Airbnb ROI: N/A

Traditional ROI: 4.26%

101 ARNOLD ALLEY

WOODSBORO, MD

3 beds | 3 baths | N/A

$424,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.42%

Airbnb Rental Income: $null

Traditional Rental Income: $2613

Airbnb ROI: N/A

Traditional ROI: 4.42%

10543 Woodsboro Rd

WOODSBORO, MD

4 beds | 3 baths | 3,286 sq.ft.

$1,950,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.66%

Airbnb Rental Income: $null

Traditional Rental Income: $2932

Airbnb ROI: N/A

Traditional ROI: -0.66%

10 Rosewood Ct #311

WOODSBORO, MD

2 beds | 2 baths | 1,298 sq.ft.

$254,000

Airbnb cash on cash: 1.02%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $1735

Traditional Rental Income: $1666

Airbnb ROI: 1.02%

Traditional ROI: 2.72%

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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