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
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: 4.13% Traditional cash on cash: 5.14% Airbnb Rental Income: $2031 Traditional Rental Income: $1740 Airbnb ROI: 4.13% 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: 3.53% Traditional cash on cash: 5.03% Airbnb Rental Income: $898 Traditional Rental Income: $684 Airbnb ROI: 3.53% Traditional ROI: 5.03%
20098 Piney Point Rd CALLAWAY, MD Want to live near your business?! This beautiful and classic 3 bedroom, 2 and half bathroo...	3 beds \| 2 baths \| 5,939 sq.ft.	$1,100,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.19% Airbnb Rental Income: $2207 Traditional Rental Income: $2782 Airbnb ROI: 0.08% 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: 4.32% Traditional cash on cash: 5.06% Airbnb Rental Income: $2031 Traditional Rental Income: $1677 Airbnb ROI: 4.32% 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: 3.02% Traditional cash on cash: 2.46% Airbnb Rental Income: $2207 Traditional Rental Income: $1479 Airbnb ROI: 3.02% Traditional ROI: 2.46%
20999 Black Duck Ct CALLAWAY, MD 20999 Black Duck Ct, CALLAWAY, MD 20620 \| Single Family Residential	3 beds \| 2 baths \| 1,588 sq.ft.	$389,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 2.83% Airbnb Rental Income: $2207 Traditional Rental Income: $1909 Airbnb ROI: 2.12% Traditional ROI: 2.83%

Real Estate investment in Callaway, MD

There are 7 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 $222. In September 2026, the average monthly cash on cash return in Callaway is 3.00%. The average monthly rental income in Callaway is $1,740.

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

There are 7 investment properties available for sale in Callaway.

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

The ROI for Short-Term is higher than the Long-Term in Callaway with average rental income of $2,207.

Your search for investment property begins and ends here

Investment Property for Sale in Callaway, MD

20811 Harlequin Ln

CALLAWAY, MD

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

$249,900

Airbnb cash on cash: 4.13%

Traditional cash on cash: 5.14%

Airbnb Rental Income: $2031

Traditional Rental Income: $1740

Airbnb ROI: 4.13%

Traditional ROI: 5.14%

Piney Point Rd

CALLAWAY, MD

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

$85,000

Airbnb cash on cash: 3.53%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $898

Traditional Rental Income: $684

Airbnb ROI: 3.53%

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: 0.08%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $2207

Traditional Rental Income: $2782

Airbnb ROI: 0.08%

Traditional ROI: 1.19%

20275 Jackson Rd

CALLAWAY, MD

2 beds | 2 baths | 924 sq.ft.

$250,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2031

Traditional Rental Income: $1677

Airbnb ROI: 4.32%

Traditional ROI: 5.06%

44911 Buck Redman Rd

CALLAWAY, MD

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

$325,000

Airbnb cash on cash: 3.02%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $2207

Traditional Rental Income: $1479

Airbnb ROI: 3.02%

Traditional ROI: 2.46%

20999 Black Duck Ct

CALLAWAY, MD

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

$389,900

Airbnb cash on cash: 2.12%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $2207

Traditional Rental Income: $1909

Airbnb ROI: 2.12%

Traditional ROI: 2.83%

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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