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.

Single Family Homes for Sale in Oldsmar, FL

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

Showing 61 Single Family Residential 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
5250 PINEHURST Court Oldsmar, FL RARELY AVAILABLE VILLA OPPORTUNITY IN PRIVATE PINNACLE COMMUNITY OF EAST LAKE WOODLANDS. "...	3 beds \| 2 baths \| 2,074 sq.ft.	$640,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 1.88% Airbnb Rental Income: $2524 Traditional Rental Income: $2785 Airbnb ROI: 0.43% Traditional ROI: 1.88%
601 SHORE Drive E Oldsmar, FL Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the heart of Oldsmar, of...	3 beds \| 2 baths \| 1,856 sq.ft.	$525,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 3.35% Airbnb Rental Income: $2524 Traditional Rental Income: $2661 Airbnb ROI: 1.82% Traditional ROI: 3.35%
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.	$1,100,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 0.67% Airbnb Rental Income: $2524 Traditional Rental Income: $2617 Airbnb ROI: -0.02% Traditional ROI: 0.67%
1705 IRONWOOD Court E Oldsmar, FL Welcome to this beautifully renovated 2-bedroom, 2-bathroom home-perfect for first-time bu...	2 beds \| 2 baths \| 1,206 sq.ft.	$320,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 6.04% Airbnb Rental Income: $2376 Traditional Rental Income: $2361 Airbnb ROI: 4.15% Traditional ROI: 6.04%
743 WELLINGTON Court Oldsmar, FL Welcome to luxury living in the highly sought-after Wellington Estates community of Oldsma...	4 beds \| 4 baths \| 3,058 sq.ft.	$800,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.98% Airbnb Rental Income: $3040 Traditional Rental Income: $3826 Airbnb ROI: 0.99% Traditional ROI: 2.98%
416 MAPLEWOOD Drive Oldsmar, FL PRICE IMPROVEMENT Your opportunity just got better.! This beautiful home is now offere...	3 beds \| 2 baths \| 1,395 sq.ft.	$449,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 4.51% Airbnb Rental Income: $2524 Traditional Rental Income: $2540 Airbnb ROI: 3.02% Traditional ROI: 4.51%
100 LISA Lane Oldsmar, FL Previous contract fell through due to financing. Owner is motivated. The property has a cl...	2 beds \| 2 baths \| 1,320 sq.ft.	$299,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.19% Airbnb Rental Income: $2376 Traditional Rental Income: $2042 Airbnb ROI: 3.3% Traditional ROI: 4.19%
1745 OAK POND Court Oldsmar, FL Welcome to 1745 Oak Pond Court! Welcome to 1745 Oak Pond Court, a beautiful home located i...	4 beds \| 3 baths \| 2,324 sq.ft.	$599,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.38% Airbnb Rental Income: $3040 Traditional Rental Income: $3364 Airbnb ROI: 1.55% Traditional ROI: 3.38%
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: 1% Traditional cash on cash: 2.34% Airbnb Rental Income: $3040 Traditional Rental Income: $3177 Airbnb ROI: 1% Traditional ROI: 2.34%
550 PALMDALE Drive Oldsmar, FL A True Find for exceptional living in the highly desirable Gated Golf Community of East La...	4 beds \| 2 baths \| 2,211 sq.ft.	$599,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 3.04% Airbnb Rental Income: $3040 Traditional Rental Income: $3140 Airbnb ROI: 1.62% Traditional ROI: 3.04%
1723 CAPTIVA Drive Oldsmar, FL Virtually Staged. Welcome to an exceptional 2,736-square-foot luxury home nestled within C...	4 beds \| 3 baths \| 2,736 sq.ft.	$830,700	Airbnb cash on cash: 1.58% Traditional cash on cash: 3.26% Airbnb Rental Income: $3040 Traditional Rental Income: $3645 Airbnb ROI: 1.58% Traditional ROI: 3.26%
206 BEDFORD Street Oldsmar, FL Virtually Staged. Short Sale. BANKRUPTCY PROPERTY - AND THE PRICE IS PRE-APPROVED! This be...	3 beds \| 2 baths \| 1,274 sq.ft.	$355,700	Airbnb cash on cash: 3.4% Traditional cash on cash: 4.23% Airbnb Rental Income: $2524 Traditional Rental Income: $2189 Airbnb ROI: 3.4% Traditional ROI: 4.23%
415 MAPLEWOOD Circle Oldsmar, FL A beautifully maintained home in the desirable Sheffield Village area of Oldsmar, this pro...	3 beds \| 1 baths \| 1,583 sq.ft.	$349,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.76% Airbnb Rental Income: $2524 Traditional Rental Income: $2434 Airbnb ROI: 3.17% Traditional ROI: 4.76%
347 COUNTRY CLUB Drive Oldsmar, FL "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Po...	3 beds \| 2 baths \| 1,280 sq.ft.	$419,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 6.24% Airbnb Rental Income: $2524 Traditional Rental Income: $3077 Airbnb ROI: 3.28% Traditional ROI: 6.24%
432 COUNTRY CLUB Drive Oldsmar, FL Tucked inside a quiet neighborhood, but only one street away from the magnificent Tampa ba...	3 beds \| 3 baths \| 1,936 sq.ft.	$465,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 8.59% Airbnb Rental Income: $2524 Traditional Rental Income: $4597 Airbnb ROI: 2.43% Traditional ROI: 8.59%
204 SHORE Drive W Oldsmar, FL Investor special with exceptional upside! This 3-bedroom, 2-bath, 1-car garage home sits o...	3 beds \| 2 baths \| 1,374 sq.ft.	$299,900	Airbnb cash on cash: 3.43% Traditional cash on cash: 5.18% Airbnb Rental Income: $2524 Traditional Rental Income: $2409 Airbnb ROI: 3.43% Traditional ROI: 5.18%
704 LEMONWOOD Drive Oldsmar, FL Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car gar...	2 beds \| 2 baths \| 1,064 sq.ft.	$259,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 5.17% Airbnb Rental Income: $2376 Traditional Rental Income: $1962 Airbnb ROI: 4.48% Traditional ROI: 5.17%
3087 DUANE Avenue Oldsmar, FL Set on nearly one-third of an acre with NO HOA restrictions, the property offers ample spa...	3 beds \| 2 baths \| 1,296 sq.ft.	$365,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.9% Airbnb Rental Income: $2524 Traditional Rental Income: $2498 Airbnb ROI: 3.2% Traditional ROI: 4.9%
343 SHORE Drive E Oldsmar, FL Some photos have be virtually staged. Beautifully renovated 3 bedroom 2 bath in desirable ...	3 beds \| 2 baths \| 1,169 sq.ft.	$399,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 3.79% Airbnb Rental Income: $2524 Traditional Rental Income: $2133 Airbnb ROI: 3.21% Traditional ROI: 3.79%
475 HOLLY HILL Road Oldsmar, FL Welcome to this exceptional 4-bedroom, 4-bathroom pool home located on a corner lot within...	4 beds \| 4 baths \| 3,441 sq.ft.	$849,500	Airbnb cash on cash: 0.87% Traditional cash on cash: 4.33% Airbnb Rental Income: $3040 Traditional Rental Income: $5082 Airbnb ROI: 0.87% Traditional ROI: 4.33%
102 SHORE Drive E Oldsmar, FL Welcome to the TAMPA BAY LIFESTYLE WITHOUT THE WATERFRONT PRICE TAG. This beautifully full...	3 beds \| 2 baths \| 1,416 sq.ft.	$439,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 3.05% Airbnb Rental Income: $2524 Traditional Rental Income: $2264 Airbnb ROI: 2.2% Traditional ROI: 3.05%
317 SHORE Drive E Oldsmar, FL STUNNING TAMPA BAY VIEWS! UPDATED OLDSMAR SPLIT-LEVEL WITH RV/BOAT PAD! Breathtaking Tampa...	3 beds \| 2 baths \| 1,660 sq.ft.	$484,700	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.07% Airbnb Rental Income: $2524 Traditional Rental Income: $3036 Airbnb ROI: 1.6% Traditional ROI: 4.07%
413 COUNTRY CLUB Drive Oldsmar, FL Wake up to water views and end your day watching the sun set over the canal. This renovate...	3 beds \| 2 baths \| 1,323 sq.ft.	$324,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 8.18% Airbnb Rental Income: $2524 Traditional Rental Income: $3252 Airbnb ROI: 3.8% Traditional ROI: 8.18%
2328 WARWICK Drive Oldsmar, FL PRICE ADJUSTMENT! Buy now to get settled in over the summer! Welcome to Warwick Hills with...	4 beds \| 4 baths \| 3,294 sq.ft.	$829,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 7.32% Airbnb Rental Income: $3040 Traditional Rental Income: $7188 Airbnb ROI: 1.04% Traditional ROI: 7.32%
190 Water Oak Way Oldsmar, FL Experience the perfect blend of elegance, comfort, and breathtaking views in this exceptio...	3 beds \| 3 baths \| 2,061 sq.ft.	$619,990	Airbnb cash on cash: 0.57% Traditional cash on cash: 5.26% Airbnb Rental Income: $2524 Traditional Rental Income: $4624 Airbnb ROI: 0.57% Traditional ROI: 5.26%
380 ROSALIND Lane Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to your private retreat in the gat...	3 beds \| 3 baths \| 2,423 sq.ft.	$599,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.33% Airbnb Rental Income: $2524 Traditional Rental Income: $3634 Airbnb ROI: 1.26% Traditional ROI: 4.33%
416 COUNTRY CLUB Drive Oldsmar, FL Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. Y...	3 beds \| 2 baths \| 1,293 sq.ft.	$385,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 6.21% Airbnb Rental Income: $2524 Traditional Rental Income: $2758 Airbnb ROI: 3.87% Traditional ROI: 6.21%
35 GREENHAVEN Trail Oldsmar, FL Homes like this rarely become available in the highly sought-after gated community of East...	4 beds \| 3 baths \| 3,098 sq.ft.	$1,099,900	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.73% Airbnb Rental Income: $3040 Traditional Rental Income: $5752 Airbnb ROI: 0.4% Traditional ROI: 3.73%
1795 BAYHILL Drive Oldsmar, FL This unique home exudes character and is located on a peaceful conservation lot with no re...	3 beds \| 2 baths \| 1,844 sq.ft.	$524,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.72% Airbnb Rental Income: $2524 Traditional Rental Income: $2427 Airbnb ROI: 0.67% Traditional ROI: 1.72%
208 CUTLASS Way Oldsmar, FL NEW PRICE! Location, location, location is the key to finding the perfect home - and this ...	3 beds \| 3 baths \| 1,392 sq.ft.	$340,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 4.37% Airbnb Rental Income: $2524 Traditional Rental Income: $2442 Airbnb ROI: 2.71% Traditional ROI: 4.37%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oldsmar, FL

5250 PINEHURST Court

Oldsmar, FL

3 beds | 2 baths | 2,074 sq.ft.

$640,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2524

Traditional Rental Income: $2785

Airbnb ROI: 0.43%

Traditional ROI: 1.88%

601 SHORE Drive E

Oldsmar, FL

3 beds | 2 baths | 1,856 sq.ft.

$525,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $2524

Traditional Rental Income: $2661

Airbnb ROI: 1.82%

Traditional ROI: 3.35%

3858 SHORE Boulevard

Oldsmar, FL

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

$1,100,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $2524

Traditional Rental Income: $2617

Airbnb ROI: -0.02%

Traditional ROI: 0.67%

1705 IRONWOOD Court E

Oldsmar, FL

2 beds | 2 baths | 1,206 sq.ft.

$320,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $2376

Traditional Rental Income: $2361

Airbnb ROI: 4.15%

Traditional ROI: 6.04%

743 WELLINGTON Court

Oldsmar, FL

4 beds | 4 baths | 3,058 sq.ft.

$800,000

Airbnb cash on cash: 0.99%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $3040

Traditional Rental Income: $3826

Airbnb ROI: 0.99%

Traditional ROI: 2.98%

416 MAPLEWOOD Drive

Oldsmar, FL

3 beds | 2 baths | 1,395 sq.ft.

$449,000

Airbnb cash on cash: 3.02%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $2524

Traditional Rental Income: $2540

Airbnb ROI: 3.02%

Traditional ROI: 4.51%

100 LISA Lane

Oldsmar, FL

2 beds | 2 baths | 1,320 sq.ft.

$299,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $2376

Traditional Rental Income: $2042

Airbnb ROI: 3.3%

Traditional ROI: 4.19%

1745 OAK POND Court

Oldsmar, FL

4 beds | 3 baths | 2,324 sq.ft.

$599,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $3040

Traditional Rental Income: $3364

Airbnb ROI: 1.55%