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
106 MAIN Street 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.	$272,000	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%
11 ROSEWOOD Court unit: 101 #101 WOODSBORO, MD * BIG PRICE ADJUSTMENT * NEW PRICE $250,000*** Major Price Modification... THIS UNIT C...	2 beds \| 2 baths \| 1,285 sq.ft.	$250,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 6.69% Airbnb Rental Income: $1735 Traditional Rental Income: $2174 Airbnb ROI: 2.81% Traditional ROI: 6.69%
102 WOODSBORO CREAGERSTOWN Road 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%
1 BARRICK Lane WOODSBORO, MD Welcome to 1 Barricks Lane, Woodsboro, Maryland! This beautifully updated rancher offers e...	4 beds \| 3 baths \| 2,464 sq.ft.	$482,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.72% Airbnb Rental Income: $null Traditional Rental Income: $3478 Airbnb ROI: N/A Traditional ROI: 5.72%

Real Estate investment in Woodsboro, MD

There are 5 properties for sale in the city of Woodsboro . The median list price in Woodsboro is $385,000 and the average price per square foot is $245. In December 2025, the average monthly cash on cash return in Woodsboro is 6.00%. The average monthly rental income in Woodsboro is $2,292.

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

There are 5 investment properties available for sale in Woodsboro.

In 2025, 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 $2,292.

Your search for investment property begins and ends here

Investment Property for Sale in Woodsboro, MD

106 MAIN Street N

WOODSBORO, MD

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

$272,000

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%

11 ROSEWOOD Court unit: 101 #101

WOODSBORO, MD

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

$250,000

Airbnb cash on cash: 2.81%

Traditional cash on cash: 6.69%

Airbnb Rental Income: $1735

Traditional Rental Income: $2174

Airbnb ROI: 2.81%

Traditional ROI: 6.69%

102 WOODSBORO CREAGERSTOWN Road

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%

1 BARRICK Lane

WOODSBORO, MD

4 beds | 3 baths | 2,464 sq.ft.

$482,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3478

Airbnb ROI: N/A

Traditional ROI: 5.72%

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 2025?

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

Use analytics to find lucrative traditional or Airbnb properties in a matter of minutes.

No more spreadsheets, no more searching.