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.

Townhouses for Sale in Oldsmar, FL

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

Showing 24 Townhouse 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
388 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL 2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-b...	2 beds \| 2 baths \| 1,105 sq.ft.	$246,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $1396 Traditional Rental Income: $2347 Airbnb ROI: N/A Traditional ROI: 5.91%
120 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Are you dreaming of your own stylish urban OASIS s...	3 beds \| 3 baths \| 1,834 sq.ft.	$520,000	Airbnb cash on cash: -2% Traditional cash on cash: 1.53% Airbnb Rental Income: $1381 Traditional Rental Income: $2675 Airbnb ROI: -2% Traditional ROI: 1.53%
152 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Welcome to Seaside Estates, a gated waterfront com...	3 beds \| 3 baths \| 1,791 sq.ft.	$550,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $1381 Traditional Rental Income: $2901 Airbnb ROI: -1.27% Traditional ROI: 2.5%
209 HEMINGWAY DRIVE Oldsmar, FL Stunning Sun Ketch Townhome \| Bright, Airy & Move-In Ready! Welcome to your slice of par...	2 beds \| 2 baths \| 1,086 sq.ft.	$294,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 6.01% Airbnb Rental Income: $1396 Traditional Rental Income: $2371 Airbnb ROI: 0.98% Traditional ROI: 6.01%
112 BRENT CIRCLE Oldsmar, FL PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the ...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2697 Airbnb ROI: -1.25% Traditional ROI: 2.47%
9009 PALM KEY AVENUE Oldsmar, FL Seller is offering a $5,000 CREDIT towards closing costs or an interest rate buy down! â...	4 beds \| 3 baths \| 2,587 sq.ft.	$674,900	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.7% Airbnb Rental Income: $1908 Traditional Rental Income: $3694 Airbnb ROI: -0.94% Traditional ROI: 2.7%
291 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Welcome to the highly sought-after gated community of Countryside Key, ideally located in ...	2 beds \| 3 baths \| 1,110 sq.ft.	$258,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 4.97% Airbnb Rental Income: $1396 Traditional Rental Income: $2258 Airbnb ROI: -0.3% Traditional ROI: 4.97%
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.	$399,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 3.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2773 Airbnb ROI: -1.37% Traditional ROI: 3.47%
129 BRENT CIRCLE Oldsmar, FL HUGE PRICE IMPROVEMENT of $60k- WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath town...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.15% Airbnb Rental Income: $1381 Traditional Rental Income: $2794 Airbnb ROI: -0.78% Traditional ROI: 3.15%
1008 MANGO COURT Oldsmar, FL SUPERIOR LOCATION nestled deep in the community with WATER VIEW from the side of the FRONT...	3 beds \| 3 baths \| 1,667 sq.ft.	$359,000	Airbnb cash on cash: -1.76% Traditional cash on cash: 3.61% Airbnb Rental Income: $1381 Traditional Rental Income: $2774 Airbnb ROI: -1.76% Traditional ROI: 3.61%
2313 SUNSET WIND LOOP Oldsmar, FL Experience coastal luxury and step into a lifestyle of refinement in this stunning 3-bedro...	3 beds \| 3 baths \| 2,230 sq.ft.	$440,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 4.1% Airbnb Rental Income: $1381 Traditional Rental Income: $3526 Airbnb ROI: -2.13% Traditional ROI: 4.1%
62 EMERALD BAY DRIVE Oldsmar, FL Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 B...	2 beds \| 3 baths \| 1,264 sq.ft.	$220,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 6.89% Airbnb Rental Income: $1396 Traditional Rental Income: $2333 Airbnb ROI: 0.37% Traditional ROI: 6.89%
244 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. Brand new fresh carpets. The mo...	2 beds \| 3 baths \| 1,110 sq.ft.	$220,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 4.65% Airbnb Rental Income: $1396 Traditional Rental Income: $2113 Airbnb ROI: -0.82% Traditional ROI: 4.65%
403 E TUSCAN LANE E Oldsmar, FL Under contract-accepting backup offers. Welcome home in Oldsmar, FL! This two-story 1,525 ...	3 beds \| 3 baths \| 1,525 sq.ft.	$330,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 3.13% Airbnb Rental Income: $1381 Traditional Rental Income: $2217 Airbnb ROI: -0.91% Traditional ROI: 3.13%
140 BRENT CIRCLE Oldsmar, FL Seller Motivated! Asking price is under last appraisal value. Come take a look at this be...	3 beds \| 3 baths \| 1,791 sq.ft.	$565,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.5% Airbnb Rental Income: $1381 Traditional Rental Income: $2794 Airbnb ROI: -0.97% Traditional ROI: 2.5%
1505 SUNSET WIND LOOP Oldsmar, FL This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gat...	3 beds \| 3 baths \| 1,667 sq.ft.	$390,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 3.58% Airbnb Rental Income: $1381 Traditional Rental Income: $2894 Airbnb ROI: -1.7% Traditional ROI: 3.58%
271 HEMINGWAY DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to this inviting 3-bedroom, 2.5-ba...	3 beds \| 3 baths \| 1,452 sq.ft.	$385,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.79% Airbnb Rental Income: $1381 Traditional Rental Income: $2586 Airbnb ROI: 0.29% Traditional ROI: 4.79%
4007 PALM KEY AVENUE Oldsmar, FL Walk in the front door and look straight out to the water. Head out to the screened-in bac...	4 beds \| 3 baths \| 2,587 sq.ft.	$639,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 2.81% Airbnb Rental Income: $1908 Traditional Rental Income: $3695 Airbnb ROI: -1.04% Traditional ROI: 2.81%
2208 SUNSET WIND LOOP Oldsmar, FL Under contract-accepting backup offers. This beautiful 3 bedroom, 2.5 bathroom townhome lo...	3 beds \| 3 baths \| 1,667 sq.ft.	$365,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 4.76% Airbnb Rental Income: $1381 Traditional Rental Income: $2812 Airbnb ROI: -0.64% Traditional ROI: 4.76%
116 BRENT CIRCLE Oldsmar, FL Elevated Gated Community. WATERFRONT 3 bedrooms, 3 full baths plus a tandem 2-3 car garage...	3 beds \| 3 baths \| 1,834 sq.ft.	$485,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 2.52% Airbnb Rental Income: $1381 Traditional Rental Income: $2858 Airbnb ROI: -1.66% Traditional ROI: 2.52%
904 VINEYARD LANE Oldsmar, FL Under contract-accepting backup offers. Private Preserve Views \| Move-In Ready \| Optional ...	3 beds \| 3 baths \| 1,525 sq.ft.	$340,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 4.77% Airbnb Rental Income: $1381 Traditional Rental Income: $2692 Airbnb ROI: -0.65% Traditional ROI: 4.77%
908 VINEYARD LANE Oldsmar, FL $16,000 PRICE REDUCTION! SPACIOUS END-UNIT; RARE OPPORTUNITY IN OLDSMAR; A-RATED SCHOOL DI...	3 beds \| 3 baths \| 1,773 sq.ft.	$369,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.06% Airbnb Rental Income: $1381 Traditional Rental Income: $3036 Airbnb ROI: -0.93% Traditional ROI: 5.06%
1004 MANGO COURT Oldsmar, FL Welcome to refined coastal living in a highly desirable waterfront community in Oldsmar. T...	3 beds \| 3 baths \| 2,230 sq.ft.	$525,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2865 Airbnb ROI: -1.41% Traditional ROI: 2.47%
138 BRENT CIRCLE Oldsmar, FL Welcome to 138 Brent Circle in desirable gated Seaside Estatesâan exceptional opportunit...	4 beds \| 3 baths \| 2,258 sq.ft.	$725,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.32% Airbnb Rental Income: $1908 Traditional Rental Income: $3114 Airbnb ROI: -1.21% Traditional ROI: 1.32%

Your search for investment property begins and ends here

Townhouses for Sale in Oldsmar, FL

388 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

2 beds | 2 baths | 1,105 sq.ft.

$246,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.91%

Airbnb Rental Income: $1396

Traditional Rental Income: $2347

Airbnb ROI: N/A

Traditional ROI: 5.91%

120 BRENT CIRCLE

Oldsmar, FL

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

$520,000

Airbnb cash on cash: -2%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $1381

Traditional Rental Income: $2675

Airbnb ROI: -2%

Traditional ROI: 1.53%

152 BRENT CIRCLE

Oldsmar, FL

3 beds | 3 baths | 1,791 sq.ft.

$550,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $1381

Traditional Rental Income: $2901

Airbnb ROI: -1.27%

Traditional ROI: 2.5%

209 HEMINGWAY DRIVE

Oldsmar, FL

2 beds | 2 baths | 1,086 sq.ft.

$294,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 6.01%

Airbnb Rental Income: $1396

Traditional Rental Income: $2371

Airbnb ROI: 0.98%

Traditional ROI: 6.01%

112 BRENT CIRCLE

Oldsmar, FL

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

$499,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1381

Traditional Rental Income: $2697

Airbnb ROI: -1.25%

Traditional ROI: 2.47%

9009 PALM KEY AVENUE

Oldsmar, FL

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

$674,900

Airbnb cash on cash: -0.94%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $1908

Traditional Rental Income: $3694

Airbnb ROI: -0.94%

Traditional ROI: 2.7%

291 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

2 beds | 3 baths | 1,110 sq.ft.

$258,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $1396

Traditional Rental Income: $2258

Airbnb ROI: -0.3%

Traditional ROI: 4.97%

108 BRENT CIRCLE

Oldsmar, FL

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

$399,000

Airbnb cash on cash: -1.37%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1381

Traditional Rental Income: $2773

Airbnb ROI: -1.37%