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
106 Main St N WOODSBORO, MD Welcome to this charming three-bedroom, two full-bath single-family home in the heart of W...	3 beds \| 2 baths \| 1,144 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.64% Airbnb Rental Income: $null Traditional Rental Income: $2292 Airbnb ROI: N/A Traditional ROI: 6.64%
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.	$385,000	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%
4 James St WOODSBORO, MD 4 James St, WOODSBORO, MD 21798 \| Single Family Residential	3 beds \| 2 baths \| 1,872 sq.ft.	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $1973 Airbnb ROI: N/A Traditional ROI: 2.64%
10543 Woodsboro Rd WOODSBORO, MD	4 beds \| 3 baths \| 3,286 sq.ft.	$2,150,000	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%
Muth Rd WOODSBORO, MD Muth Rd, WOODSBORO, MD 21798 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $660 Airbnb ROI: N/A Traditional ROI: 3.76%
11646 Creagerstown Rd WOODSBORO, MD Welcome to this exceptional Colonial home offering a rare blend of comfort, versatility, a...	3 beds \| 3 baths \| 2,000 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.68% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 4.68%

Real Estate investment in Woodsboro, MD

There are 8 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 February 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 8 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

106 Main St N

WOODSBORO, MD

3 beds | 2 baths | 1,144 sq.ft.

$265,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.64%

Airbnb Rental Income: $null

Traditional Rental Income: $2292

Airbnb ROI: N/A

Traditional ROI: 6.64%

102 Woodsboro Creagerstown Rd

WOODSBORO, MD

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

$385,000

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%

4 James St

WOODSBORO, MD

3 beds | 2 baths | 1,872 sq.ft.

$424,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.64%

Airbnb Rental Income: $null

Traditional Rental Income: $1973

Airbnb ROI: N/A

Traditional ROI: 2.64%

10543 Woodsboro Rd

WOODSBORO, MD

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

$2,150,000

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%

Muth Rd

WOODSBORO, MD

N/A beds | N/A baths | N/A

$100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.76%

Airbnb Rental Income: $null

Traditional Rental Income: $660

Airbnb ROI: N/A

Traditional ROI: 3.76%

11646 Creagerstown Rd

WOODSBORO, MD

3 beds | 3 baths | 2,000 sq.ft.

$550,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.68%

Airbnb Rental Income: $null

Traditional Rental Income: $3308

Airbnb ROI: N/A