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 93 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
505 OAKWOOD BOULEVARD Oldsmar, FL Welcome to this CHARMING HOME tucked away on a quiet, divided street in BEAUTIFUL DOWNTOWN...	4 beds \| 2 baths \| 1,993 sq.ft.	$449,000	Airbnb cash on cash: 6.48% Traditional cash on cash: 4.89% Airbnb Rental Income: $4558 Traditional Rental Income: $2944 Airbnb ROI: 6.48% Traditional ROI: 4.89%
436 LAFAYETTE BOULEVARD Oldsmar, FL One or more photo(s) has been virtually staged. Must see this 4 bedroom/2.5 bath home with...	4 beds \| 3 baths \| 2,695 sq.ft.	$700,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 2.65% Airbnb Rental Income: $4558 Traditional Rental Income: $3466 Airbnb ROI: 2.87% Traditional ROI: 2.65%
2044 SHEFFIELD COURT Oldsmar, FL Under contract-accepting backup offers. Short Sale. High and dry with NEW ROOF and NEW HVA...	2 beds \| 2 baths \| 1,296 sq.ft.	$190,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 8.56% Airbnb Rental Income: $2403 Traditional Rental Income: $2092 Airbnb ROI: 7.01% Traditional ROI: 8.56%
204 BAY ARBOR BOULEVARD Oldsmar, FL Under contract-accepting backup offers. Welcome to your beautifully upgraded 3 bed / 2 bat...	3 beds \| 2 baths \| 2,026 sq.ft.	$639,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.37% Airbnb Rental Income: $3329 Traditional Rental Income: $2966 Airbnb ROI: 1.73% Traditional ROI: 2.37%
382 ROSALIND LANE Oldsmar, FL Welcome to 382 Rosalind Ln., an extraordinary home in the exclusive gated community of Bay...	4 beds \| 3 baths \| 3,273 sq.ft.	$849,990	Airbnb cash on cash: 2.37% Traditional cash on cash: 1.2% Airbnb Rental Income: $4558 Traditional Rental Income: $2684 Airbnb ROI: 2.37% Traditional ROI: 1.2%
1909 CASTLE BAY COURT Oldsmar, FL --WONT LAST LONG---Discover this immaculate 3-bedroom, 2-bath home with garage located on ...	3 beds \| 2 baths \| 1,410 sq.ft.	$394,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.3% Airbnb Rental Income: $3329 Traditional Rental Income: $2304 Airbnb ROI: 5.06% Traditional ROI: 4.3%
1471 BRIARGROVE WAY Oldsmar, FL One or more photo(s) has been virtually staged. Live the Florida lifestyle in the gated Ab...	5 beds \| 4 baths \| 3,140 sq.ft.	$945,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $4795 Airbnb ROI: N/A Traditional ROI: 3.07%
1516 E LAKE WOODLANDS PARKWAY Oldsmar, FL WELCOME TO GREENHAVEN IN AN EXCLUSIVE GATED GOLF COURSE COMMUNITY OF EAST LAKE WOODLANDS. ...	4 beds \| 3 baths \| 2,642 sq.ft.	$749,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 2.31% Airbnb Rental Income: $4558 Traditional Rental Income: $3805 Airbnb ROI: 2.03% Traditional ROI: 2.31%
646 TIMBER BAY CIRCLE W Oldsmar, FL PRICE IMPROVEMENT - LOCATION - LOCATION - LOCATION - LOVE WHERE YOU LIVE - ONE STORY POOL ...	3 beds \| 2 baths \| 1,554 sq.ft.	$409,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 4.36% Airbnb Rental Income: $3329 Traditional Rental Income: $2570 Airbnb ROI: 4.4% Traditional ROI: 4.36%
421 SHORE DRIVE E Oldsmar, FL Under contract-accepting backup offers. Prime investment opportunity in one of Oldsmarâs...	3 beds \| 2 baths \| 1,416 sq.ft.	$285,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.41% Airbnb Rental Income: $3329 Traditional Rental Income: $2438 Airbnb ROI: 6.96% Traditional ROI: 6.41%
648 TIMBER BAY CIRCLE E Oldsmar, FL Discover your own slice of paradise with this beautifully updated 4-bedroom, 2-bath home, ...	4 beds \| 2 baths \| 1,253 sq.ft.	$379,000	Airbnb cash on cash: 7.64% Traditional cash on cash: 7.29% Airbnb Rental Income: $4558 Traditional Rental Income: $3487 Airbnb ROI: 7.64% Traditional ROI: 7.29%
4954 TURTLE CREEK TRAIL Oldsmar, FL Welcome to this exceptional Costanza custom-built home, perfectly situated on over one acr...	5 beds \| 4 baths \| 4,144 sq.ft.	$1,425,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.44% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A Traditional ROI: 0.44%
350 HOLLY HILL ROAD Oldsmar, FL Under contract-accepting backup offers. UNDER CONTRACT ACCEPTING BACK UP OFFERSWelcome t...	4 beds \| 2 baths \| 2,510 sq.ft.	$669,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.48% Airbnb Rental Income: $4558 Traditional Rental Income: $2931 Airbnb ROI: 3.56% Traditional ROI: 2.48%
40 GRETCHEN COURT Oldsmar, FL SELLER FINANCING WITH ACCEPTABLE OFFER! Step through the front door of this charming vill...	2 beds \| 2 baths \| 1,502 sq.ft.	$338,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.5% Airbnb Rental Income: $2403 Traditional Rental Income: $2203 Airbnb ROI: 2.28% Traditional ROI: 3.5%
316 LAFAYETTE BOULEVARD Oldsmar, FL Under contract-accepting backup offers. Live the ultimate Florida lifestyle in this specta...	4 beds \| 4 baths \| 2,848 sq.ft.	$640,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.77% Airbnb Rental Income: $4558 Traditional Rental Income: $3604 Airbnb ROI: 3.78% Traditional ROI: 3.77%
5163 PINNACLE DRIVE Oldsmar, FL Welcome to 5163 Pinnacle Drive, a beautifully maintained home in the highly sought-after g...	3 beds \| 2 baths \| 1,886 sq.ft.	$619,700	Airbnb cash on cash: 1.09% Traditional cash on cash: 1.15% Airbnb Rental Income: $3329 Traditional Rental Income: $2622 Airbnb ROI: 1.09% Traditional ROI: 1.15%
504 FEDERAL STREET Oldsmar, FL Under Construction. Experience the perfect blend of modern luxury, thoughtful design, and ...	4 beds \| 4 baths \| 2,961 sq.ft.	$1,200,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.58% Airbnb Rental Income: $4558 Traditional Rental Income: $4207 Airbnb ROI: 2.04% Traditional ROI: 2.58%
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: 2.97% Traditional cash on cash: 3.62% Airbnb Rental Income: $4558 Traditional Rental Income: $4153 Airbnb ROI: 2.97% Traditional ROI: 3.62%
347 COUNTRY CLUB DRIVE Oldsmar, FL "Move-In Ready"... Beautifully and Completely Refurbished Single Family Pool Home, (3) Bed...	3 beds \| 2 baths \| 1,280 sq.ft.	$449,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.23% Airbnb Rental Income: $3329 Traditional Rental Income: $2431 Airbnb ROI: 4.59% Traditional ROI: 4.23%
316 SHORE DRIVE E Oldsmar, FL Wake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfr...	4 beds \| 3 baths \| 2,496 sq.ft.	$1,500,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.35% Airbnb Rental Income: $4558 Traditional Rental Income: $3597 Airbnb ROI: 0.36% Traditional ROI: 0.35%
375 WELLINGTON AVENUE Oldsmar, FL COMPLETE LUXURY MAKEOVER! (Back on market after buyer couldn't get financing) Welcome to y...	4 beds \| 3 baths \| 3,270 sq.ft.	$1,325,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.77% Airbnb Rental Income: $4558 Traditional Rental Income: $4002 Airbnb ROI: 1.46% Traditional ROI: 1.77%
1358 FORESTEDGE BOULEVARD Oldsmar, FL Under contract-accepting backup offers. BACK ON THE MARKET! Exceptional move-in ready home...	4 beds \| 3 baths \| 2,808 sq.ft.	$925,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 2.56% Airbnb Rental Income: $4558 Traditional Rental Income: $4583 Airbnb ROI: 1.43% Traditional ROI: 2.56%
380 WELLINGTON AVENUE Oldsmar, FL PRICE REDUCTION! Now priced below value, this is your chance to own this incredible Key We...	4 beds \| 4 baths \| 3,420 sq.ft.	$1,155,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 3.02% Airbnb Rental Income: $4558 Traditional Rental Income: $4974 Airbnb ROI: 1.75% Traditional ROI: 3.02%
205 BENGAL CIRCLE Oldsmar, FL HIGH AND DRY! Elevation certificate available. Backing up to a nature preserve, this 4 bed...	4 beds \| 3 baths \| 2,733 sq.ft.	$799,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 1.79% Airbnb Rental Income: $4558 Traditional Rental Income: $2950 Airbnb ROI: 2.68% Traditional ROI: 1.79%
603 SHORE DRIVE E Oldsmar, FL This exceptional 3-bedroom, 2-bathroom pool home, nestled in the heart of Oldsmar and Tamp...	3 beds \| 2 baths \| 1,722 sq.ft.	$485,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 3.96% Airbnb Rental Income: $3329 Traditional Rental Income: $2987 Airbnb ROI: 3.07% Traditional ROI: 3.96%
210 LEE STREET Oldsmar, FL One or more photo(s) has been virtually staged. Experience the perfect blend of modern com...	3 beds \| 3 baths \| 2,094 sq.ft.	$450,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 6.22% Airbnb Rental Income: $3329 Traditional Rental Income: $3290 Airbnb ROI: 4.55% Traditional ROI: 6.22%
311 SHORE DRIVE E Oldsmar, FL Under APPRAISED VALUE! Waterfront Luxury Meets Complete Modern Renovation in this Gem in E...	3 beds \| 2 baths \| 1,632 sq.ft.	$424,500	Airbnb cash on cash: 4.12% Traditional cash on cash: 4.56% Airbnb Rental Income: $3329 Traditional Rental Income: $2761 Airbnb ROI: 4.12% Traditional ROI: 4.56%
1701 HIBISCUS CIRCLE S Oldsmar, FL Discover this charming single-story 3-bedroom, 3-bath home featuring a spacious open floor...	3 beds \| 3 baths \| 1,452 sq.ft.	$369,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 6.16% Airbnb Rental Income: $3329 Traditional Rental Income: $3073 Airbnb ROI: 4.75% Traditional ROI: 6.16%
102 SHOREVIEW LANE Oldsmar, FL No water damage! High & Dry!!!Charming 3-Bedroom Home with Pool on Corner Lot! Welcome to ...	3 beds \| 2 baths \| 1,250 sq.ft.	$399,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 3.16% Airbnb Rental Income: $3329 Traditional Rental Income: $2057 Airbnb ROI: 4.57% Traditional ROI: 3.16%
602 DARTMOUTH AVENUE E Oldsmar, FL PRICE IMPROVEMENT! Welcome to this spacious 5 bedroom, 3.5 bathroom home offering nearly 3...	5 beds \| 4 baths \| 2,930 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $3903 Airbnb ROI: N/A Traditional ROI: 4.12%
429 EVERGREEN DRIVE Oldsmar, FL Under contract-accepting backup offers. High & Dry from the storms! Welcome to your dream ...	4 beds \| 2 baths \| 1,523 sq.ft.	$360,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.92% Airbnb Rental Income: $4558 Traditional Rental Income: $2849 Airbnb ROI: 8.17% Traditional ROI: 5.92%
20 SYLVIA PLACE Oldsmar, FL One or more photo(s) has been virtually staged. # Price Drop. Perfect Timing. **The morni...	4 beds \| 2 baths \| 1,550 sq.ft.	$337,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 5.29% Airbnb Rental Income: $4558 Traditional Rental Income: $2790 Airbnb ROI: 7.88% Traditional ROI: 5.29%
303 SHORE DRIVE W Oldsmar, FL IMPROVED PRICE! BRING ALL OFFERS. WATER VIEWS! On over 1/3 of an Acre of Land! Property to...	2 beds \| 2 baths \| 1,106 sq.ft.	$365,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.12% Airbnb Rental Income: $2403 Traditional Rental Income: $2037 Airbnb ROI: 2.46% Traditional ROI: 3.12%
2159 WARWICK DRIVE Oldsmar, FL BACK ON MARKET- BUYER CANCELLED BEFORE INSPECTIONS. Settle in to your dream home in the c...	4 beds \| 3 baths \| 2,673 sq.ft.	$835,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 2.58% Airbnb Rental Income: $4558 Traditional Rental Income: $3592 Airbnb ROI: 2.6% Traditional ROI: 2.58%
335 PALMDALE DRIVE Oldsmar, FL Under contract-accepting backup offers. Step into timeless elegance and modern comfort in ...	5 beds \| 3 baths \| 3,035 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $3619 Airbnb ROI: N/A Traditional ROI: 2.08%
4915 AUGUSTA AVENUE Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	5 beds \| 3 baths \| 3,294 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.72% Airbnb Rental Income: $null Traditional Rental Income: $3680 Airbnb ROI: N/A Traditional ROI: 2.72%
211 ARLINGTON AVENUE E Oldsmar, FL One or more photo(s) has been virtually staged. Located in one of Oldsmar's most sought af...	4 beds \| 3 baths \| 1,954 sq.ft.	$535,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 4.05% Airbnb Rental Income: $4558 Traditional Rental Income: $2868 Airbnb ROI: 5.54% Traditional ROI: 4.05%
316 COUNTRY CLUB DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Step into this mid-century modern 3-bedroo...	3 beds \| 2 baths \| 1,344 sq.ft.	$369,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 5.34% Airbnb Rental Income: $3329 Traditional Rental Income: $2344 Airbnb ROI: 6.04% Traditional ROI: 5.34%
4886 WESTCHESTER COURT Oldsmar, FL Looking for PRIVACY and STUNNING WATER VIEWS with NO FRONT OR REAR NEIGHBORS? Discover the...	3 beds \| 2 baths \| 1,920 sq.ft.	$585,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 2.91% Airbnb Rental Income: $3329 Traditional Rental Income: $2885 Airbnb ROI: 2.36% Traditional ROI: 2.91%
288 MOBBLY BAY DRIVE Oldsmar, FL Luxury living with an abundance of privacy, amazing views, an open floor plan, and ample c...	4 beds \| 6 baths \| 5,260 sq.ft.	$1,650,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.34% Airbnb Rental Income: $4558 Traditional Rental Income: $7971 Airbnb ROI: 0.49% Traditional ROI: 3.34%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oldsmar, FL

505 OAKWOOD BOULEVARD

Oldsmar, FL

4 beds | 2 baths | 1,993 sq.ft.

$449,000

Airbnb cash on cash: 6.48%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $4558

Traditional Rental Income: $2944

Airbnb ROI: 6.48%

Traditional ROI: 4.89%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

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

$700,000

Airbnb cash on cash: 2.87%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $4558

Traditional Rental Income: $3466

Airbnb ROI: 2.87%

Traditional ROI: 2.65%

2044 SHEFFIELD COURT

Oldsmar, FL

2 beds | 2 baths | 1,296 sq.ft.

$190,000

Airbnb cash on cash: 7.01%

Traditional cash on cash: 8.56%

Airbnb Rental Income: $2403

Traditional Rental Income: $2092

Airbnb ROI: 7.01%

Traditional ROI: 8.56%

204 BAY ARBOR BOULEVARD

Oldsmar, FL

3 beds | 2 baths | 2,026 sq.ft.

$639,900

Airbnb cash on cash: 1.73%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $3329

Traditional Rental Income: $2966

Airbnb ROI: 1.73%

Traditional ROI: 2.37%

382 ROSALIND LANE

Oldsmar, FL

4 beds | 3 baths | 3,273 sq.ft.

$849,990

Airbnb cash on cash: 2.37%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $4558

Traditional Rental Income: $2684

Airbnb ROI: 2.37%

Traditional ROI: 1.2%

1909 CASTLE BAY COURT

Oldsmar, FL

3 beds | 2 baths | 1,410 sq.ft.

$394,000

Airbnb cash on cash: 5.06%

Traditional cash on cash: 4.3%

Airbnb Rental Income: $3329

Traditional Rental Income: $2304

Airbnb ROI: 5.06%

Traditional ROI: 4.3%

1471 BRIARGROVE WAY

Oldsmar, FL

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

$945,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.07%

Airbnb Rental Income: $null

Traditional Rental Income: $4795

Airbnb ROI: N/A

Traditional ROI: 3.07%

1516 E LAKE WOODLANDS PARKWAY

Oldsmar, FL

4 beds | 3 baths | 2,642 sq.ft.

$749,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $4558

Traditional Rental Income: $3805

Airbnb ROI: 2.03%