Real Estate Investment Properties for Sale in Callaway, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
44905 Widgeon Pl CALLAWAY, MD This home has something for every family member!! Kitchen w/ island ,breakfast bar& break...	5 beds \| 3 baths \| 3,257 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $2884 Airbnb ROI: N/A Traditional ROI: 4.23%
20811 Harlequin Ln CALLAWAY, MD Two large bedrooms each with it's own bath! Stainless appliances, carpet, tile, new light...	2 beds \| 2 baths \| 1,588 sq.ft.	$249,900	Airbnb cash on cash: 4.24% Traditional cash on cash: 5.14% Airbnb Rental Income: $2060 Traditional Rental Income: $1740 Airbnb ROI: 4.24% Traditional ROI: 5.14%
Piney Point Rd CALLAWAY, MD Piney Point Rd, CALLAWAY, MD 20620 \| Other	N/A beds \| N/A baths \| N/A	$85,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 5.03% Airbnb Rental Income: $853 Traditional Rental Income: $684 Airbnb ROI: 3.08% Traditional ROI: 5.03%
20098 Piney Point Rd CALLAWAY, MD Welcome to Ms. Piney Point! This beautiful and classic 3 bedroom, 2 and half bathroom ranc...	3 beds \| 2 baths \| 5,939 sq.ft.	$1,100,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.19% Airbnb Rental Income: $2488 Traditional Rental Income: $2782 Airbnb ROI: 0.31% Traditional ROI: 1.19%
20275 Jackson Rd CALLAWAY, MD Opportunity awaits on this beautiful 3.05-acre parcel tucked away on a quiet paved road in...	2 beds \| 2 baths \| 924 sq.ft.	$250,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 5.06% Airbnb Rental Income: $2060 Traditional Rental Income: $1677 Airbnb ROI: 4.43% Traditional ROI: 5.06%
44911 Buck Redman Rd CALLAWAY, MD 44911 Buck Redman Rd, CALLAWAY, MD 20620 \| Single Family Residential	3 beds \| 1 baths \| 1,040 sq.ft.	$325,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.34% Airbnb Rental Income: $2488 Traditional Rental Income: $1748 Airbnb ROI: 3.78% Traditional ROI: 3.34%

Real Estate investment in Callaway, MD

There are 6 properties for sale in the city of Callaway . The median list price in Callaway is $365,231 and the average price per square foot is $212. In August 2026, the average monthly cash on cash return in Callaway is 5.00%. The average monthly rental income in Callaway is $1,744.

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

There are 6 investment properties available for sale in Callaway.

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

The ROI for Long-Term is higher than the Short-Term in Callaway with average rental income of $1,744.

Your search for investment property begins and ends here

Investment Property for Sale in Callaway, MD

44905 Widgeon Pl

CALLAWAY, MD

5 beds | 3 baths | 3,257 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.23%

Airbnb Rental Income: $null

Traditional Rental Income: $2884

Airbnb ROI: N/A

Traditional ROI: 4.23%

20811 Harlequin Ln

CALLAWAY, MD

2 beds | 2 baths | 1,588 sq.ft.

$249,900

Airbnb cash on cash: 4.24%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $2060

Traditional Rental Income: $1740

Airbnb ROI: 4.24%

Traditional ROI: 5.14%

Piney Point Rd

CALLAWAY, MD

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

$85,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $853

Traditional Rental Income: $684

Airbnb ROI: 3.08%

Traditional ROI: 5.03%

20098 Piney Point Rd

CALLAWAY, MD

3 beds | 2 baths | 5,939 sq.ft.

$1,100,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $2488

Traditional Rental Income: $2782

Airbnb ROI: 0.31%

Traditional ROI: 1.19%

20275 Jackson Rd

CALLAWAY, MD

2 beds | 2 baths | 924 sq.ft.

$250,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2060

Traditional Rental Income: $1677

Airbnb ROI: 4.43%

Traditional ROI: 5.06%

44911 Buck Redman Rd

CALLAWAY, MD

3 beds | 1 baths | 1,040 sq.ft.

$325,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 3.34%

Airbnb Rental Income: $2488

Traditional Rental Income: $1748

Airbnb ROI: 3.78%

Traditional ROI: 3.34%

Real Estate investment in Callaway, MD

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

How many investment properties are available for sale in Callaway?

Which neighborhoods in Callaway to invest in 2026?

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

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