Real Estate Investment Properties for Sale in Oakland, PA

Looking for investment property in Oakland, PA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
144 North Dithridge St #404 Oakland, PA Beautiful Condo in the heart of Oakland - Prime location near Universities & Hospitals. We...	1 beds \| 1 baths \| N/A	$185,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.3% Airbnb Rental Income: $942 Traditional Rental Income: $957 Airbnb ROI: 0.24% Traditional ROI: 2.3%
307 S Dithridge St #207 Oakland, PA Beautifully updated 2-story condo in one of Oaklandâs most sought-after buildingsâjust...	2 beds \| 3 baths \| N/A	$399,000	Airbnb cash on cash: -3.43% Traditional cash on cash: 0.29% Airbnb Rental Income: $1258 Traditional Rental Income: $2250 Airbnb ROI: -3.43% Traditional ROI: 0.29%
21 Mackey St Oakland, PA Spacious 3-bedroom, 2-bath home in a prime location near Pitt, Point Park University, Carl...	3 beds \| 2 baths \| N/A	$150,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 9.96% Airbnb Rental Income: $1388 Traditional Rental Income: $1814 Airbnb ROI: 4.06% Traditional ROI: 9.96%
220 N Bellefield #1003 Oakland, PA Welcome to effortless city living in the heart of Oakland! This spacious and light-filled ...	3 beds \| 2 baths \| N/A	$799,000	Airbnb cash on cash: -3.54% Traditional cash on cash: -1.98% Airbnb Rental Income: $1388 Traditional Rental Income: $2127 Airbnb ROI: -3.54% Traditional ROI: -1.98%
128 N Craig St #911 Oakland, PA Park Plaza Prime location Top floor Beautiful view Freshly painted Gleaming Parquet floors...	2 beds \| 2 baths \| N/A	$250,000	Airbnb cash on cash: -2.9% Traditional cash on cash: 1.18% Airbnb Rental Income: $1258 Traditional Rental Income: $1823 Airbnb ROI: -2.9% Traditional ROI: 1.18%
245-247 Semple St Oakland, PA 245-247 Semple St, Oakland, PA 15213 \| Multi Family	6 beds \| 2 baths \| N/A	$850,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -0.28% Airbnb Rental Income: $1258 Traditional Rental Income: $1903 Airbnb ROI: -1.6% Traditional ROI: -0.28%
19 Mackey St Oakland, PA Great investment opportunity - 3-bedroom, 1.5-bath property located just minutes from Pitt...	3 beds \| 2 baths \| N/A	$150,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 6.12% Airbnb Rental Income: $1388 Traditional Rental Income: $1163 Airbnb ROI: 4.76% Traditional ROI: 6.12%

Real Estate investment in Oakland, PA

There are 7 properties for sale in the city of Oakland . The median list price in Oakland is $250,000 and the average price per square foot is $NaN. In October 2025, the average monthly cash on cash return in Oakland is 1.00%. The average monthly rental income in Oakland is $1,823.

Oakland, PA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 7 investment properties available for sale in Oakland.

In 2025, the best neighborhood to buy investment property is Oakland.

The ROI for Long-Term is higher than the Short-Term in Oakland with average rental income of $1,823.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, PA

144 North Dithridge St #404

Oakland, PA

1 beds | 1 baths | N/A

$185,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 2.3%

Airbnb Rental Income: $942

Traditional Rental Income: $957

Airbnb ROI: 0.24%

Traditional ROI: 2.3%

307 S Dithridge St #207

Oakland, PA

2 beds | 3 baths | N/A

$399,000

Airbnb cash on cash: -3.43%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $1258

Traditional Rental Income: $2250

Airbnb ROI: -3.43%

Traditional ROI: 0.29%

21 Mackey St

Oakland, PA

3 beds | 2 baths | N/A

$150,000

Airbnb cash on cash: 4.06%

Traditional cash on cash: 9.96%

Airbnb Rental Income: $1388

Traditional Rental Income: $1814

Airbnb ROI: 4.06%

Traditional ROI: 9.96%

220 N Bellefield #1003

Oakland, PA

3 beds | 2 baths | N/A

$799,000

Airbnb cash on cash: -3.54%

Traditional cash on cash: -1.98%

Airbnb Rental Income: $1388

Traditional Rental Income: $2127

Airbnb ROI: -3.54%

Traditional ROI: -1.98%

128 N Craig St #911

Oakland, PA

2 beds | 2 baths | N/A

$250,000

Airbnb cash on cash: -2.9%

Traditional cash on cash: 1.18%

Airbnb Rental Income: $1258

Traditional Rental Income: $1823

Airbnb ROI: -2.9%

Traditional ROI: 1.18%

245-247 Semple St

Oakland, PA

6 beds | 2 baths | N/A

$850,000

Airbnb cash on cash: -1.6%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $1258

Traditional Rental Income: $1903

Airbnb ROI: -1.6%

Traditional ROI: -0.28%

19 Mackey St

Oakland, PA

3 beds | 2 baths | N/A

$150,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 6.12%

Airbnb Rental Income: $1388

Traditional Rental Income: $1163

Airbnb ROI: 4.76%

Traditional ROI: 6.12%

Real Estate investment in Oakland, PA

Oakland, PA Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Oakland?

Which neighborhoods in Oakland to invest in 2025?

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

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