Real Estate Investment Properties for Sale in Oldsmar, FL

Looking for investment property in Oldsmar, FL with high ROI ?

Explore a variety of short-term homes & houses in Oldsmar, FL. Invest wisely with VRBO & Oldsmar, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Oldsmar, FL

Search for Condo for Sale in Oldsmar, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
304 WOODLAKE WYNDE #304 Oldsmar, FL Price cut!!! If youâre looking for a waterfront location and an exceptional condominium,...	1 beds \| 1 baths \| 674 sq.ft.	$159,900	Airbnb cash on cash: 9.6% Traditional cash on cash: 4.34% Airbnb Rental Income: $3108 Traditional Rental Income: $1598 Airbnb ROI: 9.6% Traditional ROI: 4.34%
Other Investment Properties for Sale in Oldsmar
3858 SHORE BOULEVARD Oldsmar , FL Experience the laid back lifestyle of Oldsmar, a sought-after community nestled between th...	3 beds \| 2 baths \| 1,594 sq.ft.	$1,150,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 0.6% Airbnb Rental Income: $6169 Traditional Rental Income: $2617 Airbnb ROI: 2.78% Traditional ROI: 0.6%
436 LAFAYETTE BOULEVARD Oldsmar , FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mu...	4 beds \| 3 baths \| 2,695 sq.ft.	$700,000	Airbnb cash on cash: 8.14% Traditional cash on cash: 3.77% Airbnb Rental Income: $8687 Traditional Rental Income: $4193 Airbnb ROI: 8.14% Traditional ROI: 3.77%
1007 STATE STREET E Oldsmar , FL Under contract-accepting backup offers. Tucked away beneath majestic oak trees on over an ...	4 beds \| 3 baths \| 2,379 sq.ft.	$695,000	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.5% Airbnb Rental Income: $8687 Traditional Rental Income: $3559 Airbnb ROI: 8.89% Traditional ROI: 3.5%
360 S WOODLANDS DRIVE Oldsmar , FL Welcome to 360 S Woodlands Drive, a beautifully renovated 2-bedroom, 2-bath patio home nes...	2 beds \| 2 baths \| 1,590 sq.ft.	$414,900	Airbnb cash on cash: 5.79% Traditional cash on cash: 2.45% Airbnb Rental Income: $4556 Traditional Rental Income: $2310 Airbnb ROI: 5.79% Traditional ROI: 2.45%
1471 BRIARGROVE WAY Oldsmar , FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Li...	5 beds \| 4 baths \| 3,140 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $6000 Airbnb ROI: N/A Traditional ROI: 4.65%
112 BRENT CIRCLE Oldsmar , FL Under contract-accepting backup offers. PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. ...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 2.47% Airbnb Rental Income: $6169 Traditional Rental Income: $2697 Airbnb ROI: 7.3% Traditional ROI: 2.47%
9009 PALM KEY AVENUE Oldsmar , FL Searching for a low-maintenance waterfront escape in Tampa Bay? Whether youâre looking f...	4 beds \| 3 baths \| 2,587 sq.ft.	$649,900	Airbnb cash on cash: 8.38% Traditional cash on cash: 2.85% Airbnb Rental Income: $8687 Traditional Rental Income: $3694 Airbnb ROI: 8.38% Traditional ROI: 2.85%
137 BRENT CIRCLE Oldsmar , FL Set within a gated, waterfront community in Oldsmar, this expansive townhouse at 137 Brent...	3 beds \| 2 baths \| 2,309 sq.ft.	$749,900	Airbnb cash on cash: 4.51% Traditional cash on cash: 1.39% Airbnb Rental Income: $6169 Traditional Rental Income: $2776 Airbnb ROI: 4.51% Traditional ROI: 1.39%
2013 SUNSET WIND LOOP Oldsmar , FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the heart of Oldsma...	3 beds \| 3 baths \| 1,667 sq.ft.	$400,000	Airbnb cash on cash: 9% Traditional cash on cash: 3.19% Airbnb Rental Income: $6169 Traditional Rental Income: $2773 Airbnb ROI: 9% Traditional ROI: 3.19%
108 BRENT CIRCLE Oldsmar , FL Welcome to coastal lifestyle living in one of Oldsmarâs most desirable gated waterfront ...	3 beds \| 3 baths \| 1,834 sq.ft.	$384,000	Airbnb cash on cash: 9.69% Traditional cash on cash: 3.64% Airbnb Rental Income: $6169 Traditional Rental Income: $2773 Airbnb ROI: 9.69% Traditional ROI: 3.64%
10 ARBOR LANE Oldsmar , FL Beautiful 4-bedroom, 2-bathroom pool home on a corner lot with views of the 5th hole in Ea...	4 beds \| 2 baths \| 2,318 sq.ft.	$669,000	Airbnb cash on cash: 8.54% Traditional cash on cash: 2.34% Airbnb Rental Income: $8687 Traditional Rental Income: $3177 Airbnb ROI: 8.54% Traditional ROI: 2.34%
5163 PINNACLE DRIVE Oldsmar , FL Under contract-accepting backup offers. Offering over $23,000 in upgrades! Located in X Fl...	3 beds \| 2 baths \| 1,886 sq.ft.	$635,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 1.14% Airbnb Rental Income: $6169 Traditional Rental Income: $2622 Airbnb ROI: 5.07% Traditional ROI: 1.14%
3133 HURON AVENUE Oldsmar , FL Amazing opportunity to purchase a duplex with potential assumable financing at an attracti...	6 beds \| N/A baths \| 1,978 sq.ft.	$499,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 2.62% Airbnb Rental Income: $4556 Traditional Rental Income: $2317 Airbnb ROI: 5.38% Traditional ROI: 2.62%
20 EVELYN COURT Oldsmar , FL PRICE IMPROVEMENT! - Tucked within the gated community of East Lake Woodlands, this beaut...	2 beds \| 2 baths \| 1,380 sq.ft.	$249,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 3.56% Airbnb Rental Income: $4556 Traditional Rental Income: $2147 Airbnb ROI: 9.77% Traditional ROI: 3.56%
403 PARK BOULEVARD Oldsmar , FL One or more photo(s) has been virtually staged. Welcome to 403 Park Blvd, a brand-new 2025...	4 beds \| 4 baths \| 2,900 sq.ft.	$899,000	Airbnb cash on cash: 7.09% Traditional cash on cash: 4.01% Airbnb Rental Income: $8687 Traditional Rental Income: $4479 Airbnb ROI: 7.09% Traditional ROI: 4.01%

Your search for investment property begins and ends here

Condos for Sale in Oldsmar, FL

304 WOODLAKE WYNDE #304

Oldsmar, FL

1 beds | 1 baths | 674 sq.ft.

$159,900

Airbnb cash on cash: 9.6%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $3108

Traditional Rental Income: $1598

Airbnb ROI: 9.6%

Traditional ROI: 4.34%

Other Investment Properties for Sale in Oldsmar

Oldsmar , FL

3 beds | 2 baths | 1,594 sq.ft.

$1,150,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $6169

Traditional Rental Income: $2617

Airbnb ROI: 2.78%

Traditional ROI: 0.6%

Oldsmar , FL

4 beds | 3 baths | 2,695 sq.ft.

$700,000

Airbnb cash on cash: 8.14%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $8687

Traditional Rental Income: $4193

Airbnb ROI: 8.14%

Traditional ROI: 3.77%

Oldsmar , FL

4 beds | 3 baths | 2,379 sq.ft.

$695,000

Airbnb cash on cash: 8.89%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $8687

Traditional Rental Income: $3559

Airbnb ROI: 8.89%

Traditional ROI: 3.5%

Oldsmar , FL

2 beds | 2 baths | 1,590 sq.ft.

$414,900

Airbnb cash on cash: 5.79%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $4556

Traditional Rental Income: $2310

Airbnb ROI: 5.79%

Traditional ROI: 2.45%

Oldsmar , FL

5 beds | 4 baths | 3,140 sq.ft.

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $6000

Airbnb ROI: N/A

Traditional ROI: 4.65%

Oldsmar , FL

3 beds | 3 baths | 1,834 sq.ft.

$499,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6169

Traditional Rental Income: $2697

Airbnb ROI: 7.3%

Traditional ROI: 2.47%

Oldsmar , FL

4 beds | 3 baths | 2,587 sq.ft.

$649,900

Airbnb cash on cash: 8.38%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $8687

Traditional Rental Income: $3694

Airbnb ROI: 8.38%

Traditional ROI: 2.85%

Oldsmar , FL

3 beds | 2 baths | 2,309 sq.ft.

$749,900

Airbnb cash on cash: 4.51%

Traditional cash on cash: 1.39%