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 107 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.	$465,000	Airbnb cash on cash: 6.22% Traditional cash on cash: 4.69% Airbnb Rental Income: $4558 Traditional Rental Income: $2944 Airbnb ROI: 6.22% Traditional ROI: 4.69%
502 TIMBER BAY CIRCLE E Oldsmar, FL Welcome to this stunningly spacious and well-maintained pool home nestled in one of the mo...	4 beds \| 2 baths \| 1,658 sq.ft.	$425,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 3.9% Airbnb Rental Income: $4558 Traditional Rental Income: $2555 Airbnb ROI: 6.55% Traditional ROI: 3.9%
2002 SHEFFIELD COURT Oldsmar, FL Under contract-accepting backup offers. This spacious and well-maintained 2 bedroom 2 bath...	2 beds \| 2 baths \| 1,296 sq.ft.	$219,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 6% Airbnb Rental Income: $2403 Traditional Rental Income: $1995 Airbnb ROI: 5.13% Traditional ROI: 6%
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 Short Sale. High and dry with NEW ROOF and NEW HVAC!! Welcome to this charming 2-bedroom,...	2 beds \| 2 baths \| 1,296 sq.ft.	$215,000	Airbnb cash on cash: 6.1% Traditional cash on cash: 7.47% Airbnb Rental Income: $2403 Traditional Rental Income: $2092 Airbnb ROI: 6.1% Traditional ROI: 7.47%
200 GRETCHEN COURT Oldsmar, FL WELCOME HOME! Enjoy maintenance free Living in this Gated Community of Quail Forest which ...	3 beds \| 2 baths \| 1,445 sq.ft.	$374,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.1% Airbnb Rental Income: $3329 Traditional Rental Income: $2258 Airbnb ROI: 4.03% Traditional ROI: 3.1%
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%
150 TADS TRAIL Oldsmar, FL VILLA with TRANQUIL GOLF COURSE VIEWS IN EAST LAKE WOODLANDS. This well Maintained VILLA...	3 beds \| 2 baths \| 1,695 sq.ft.	$379,500	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.04% Airbnb Rental Income: $3329 Traditional Rental Income: $2485 Airbnb ROI: 3.32% Traditional ROI: 3.04%
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 LOVE WHERE YOU LIVE - ONE STORY POOL HOME! Welcome to this MOVE IN READY 3 bedroom, 2 remo...	3 beds \| 2 baths \| 1,554 sq.ft.	$429,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 4.12% Airbnb Rental Income: $3329 Traditional Rental Income: $2570 Airbnb ROI: 4.15% Traditional ROI: 4.12%
2000 SHEFFIELD COURT Oldsmar, FL Beautifully UPDATED 1296 sq ft, 2-bedroom, 2-bath villa with VAULTED CEILINGS and Stunning...	2 beds \| 2 baths \| 1,296 sq.ft.	$250,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 6.14% Airbnb Rental Income: $2403 Traditional Rental Income: $2076 Airbnb ROI: 5.03% Traditional ROI: 6.14%
826 CHRISTINA CIRCLE Oldsmar, FL Significant Price Adjustment â Waterfront Beauty in Coveted East Lake Corridor â The B...	3 beds \| 2 baths \| 2,164 sq.ft.	$1,225,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.41% Airbnb Rental Income: $3329 Traditional Rental Income: $2645 Airbnb ROI: 0.36% Traditional ROI: 0.41%
341 BAY ARBOR BOULEVARD Oldsmar, FL NEW PRICE IMPROVEMENT Spectacularly remodeled home nestled on a conservation/pond lot in...	3 beds \| 2 baths \| 2,034 sq.ft.	$614,900	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.97% Airbnb Rental Income: $3329 Traditional Rental Income: $2982 Airbnb ROI: 2.28% Traditional ROI: 2.97%
350 HOLLY HILL ROAD Oldsmar, FL Welcome to this inviting 4-bedroom, 2-bathroom home located in the highly sought-after Eas...	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.	$342,500	Airbnb cash on cash: 2.24% Traditional cash on cash: 3.45% Airbnb Rental Income: $2403 Traditional Rental Income: $2203 Airbnb ROI: 2.24% Traditional ROI: 3.45%
30 TADS TRAIL Oldsmar, FL Move in ready corner unit villa in desirable Eastlake woodlands gated community. All the w...	3 beds \| 2 baths \| 1,450 sq.ft.	$410,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.69% Airbnb Rental Income: $3329 Traditional Rental Income: $2434 Airbnb ROI: 3.08% Traditional ROI: 2.69%
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%
10 ARBOR LANE Oldsmar, FL BRAND NEW AC / NEW ROOF 2022 / POOL RE-SURFACED 2018 / RARE TO MARKET GOLF COURSE FRONTAGE...	4 beds \| 2 baths \| 2,318 sq.ft.	$669,000	Airbnb cash on cash: 3.11% Traditional cash on cash: 2.41% Airbnb Rental Income: $4558 Traditional Rental Income: $3177 Airbnb ROI: 3.11% Traditional ROI: 2.41%
303 NATIONAL ORANGE AVENUE Oldsmar, FL Under contract-accepting backup offers. PRICE ADJUSTMENT ON THIS WONDERFUL HOME! Updated ...	3 beds \| 2 baths \| 1,744 sq.ft.	$450,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.63% Airbnb Rental Income: $3329 Traditional Rental Income: $3017 Airbnb ROI: 3.61% Traditional ROI: 4.63%
5163 PINNACLE DRIVE Oldsmar, FL Welcome to 5163 Pinnacle Drive, a beautifully maintained residence nestled in the highly s...	3 beds \| 2 baths \| 1,886 sq.ft.	$659,900	Airbnb cash on cash: 0.96% Traditional cash on cash: 1.02% Airbnb Rental Income: $3329 Traditional Rental Income: $2622 Airbnb ROI: 0.96% Traditional ROI: 1.02%
1631 SHADY OAKS DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to your Florida dream home in Eastlake Oak...	3 beds \| 2 baths \| 1,938 sq.ft.	$599,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 2.82% Airbnb Rental Income: $3329 Traditional Rental Income: $2850 Airbnb ROI: 2.35% Traditional ROI: 2.82%
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.	$1,050,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.96% Airbnb Rental Income: $4558 Traditional Rental Income: $4153 Airbnb ROI: 2.41% Traditional ROI: 2.96%
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.	$1,575,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.29% Airbnb Rental Income: $4558 Traditional Rental Income: $3597 Airbnb ROI: 0.29% Traditional ROI: 0.29%
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 BACK ON THE MARKET! Exceptional move-in ready home behind the private gates of the highly-...	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%
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.	$499,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 3.82% Airbnb Rental Income: $3329 Traditional Rental Income: $2987 Airbnb ROI: 2.96% Traditional ROI: 3.82%
210 LEE STREET Oldsmar, FL PERFECT FOR ENTERTAINING!!! Beautiful 2000+ sq/ft, 3 bedroom, 3 bathroom, pool home in th...	3 beds \| 3 baths \| 2,094 sq.ft.	$445,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 6.3% Airbnb Rental Income: $3329 Traditional Rental Income: $3290 Airbnb ROI: 4.61% Traditional ROI: 6.3%
311 SHORE DRIVE E Oldsmar, FL FINANCING SPECIAL WITH OUR APPROVED LENDER, SELLER AND LENDER WILL COVER BUYER CLOSI...	3 beds \| 2 baths \| 1,632 sq.ft.	$445,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 4.31% Airbnb Rental Income: $3329 Traditional Rental Income: $2761 Airbnb ROI: 3.88% Traditional ROI: 4.31%
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%
613 CHESTNUT STREET Oldsmar, FL NEW PRICE!Great Location! HUGE LOT! Fixer-upper with Lots of Potential! 3 Living Space...	5 beds \| 4 baths \| 2,572 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.21% Airbnb Rental Income: $null Traditional Rental Income: $4284 Airbnb ROI: N/A Traditional ROI: 9.21%
204 SHORE DRIVE W Oldsmar, FL Prime Oldsmar Location! This 3-bedroom, 2-bath, 1-car garage home sits on a spacious quart...	3 beds \| 2 baths \| 1,374 sq.ft.	$380,000	Airbnb cash on cash: 4.57% Traditional cash on cash: 4.08% Airbnb Rental Income: $3329 Traditional Rental Income: $2409 Airbnb ROI: 4.57% Traditional ROI: 4.08%
704 LEMONWOOD DRIVE Oldsmar, FL PRICED TO SELL!Beautiful Lake Front View. No Rear Neighbors. Great Location! Short Walk...	2 beds \| 2 baths \| 1,064 sq.ft.	$220,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 6.27% Airbnb Rental Income: $2403 Traditional Rental Income: $1962 Airbnb ROI: 5.56% Traditional ROI: 6.27%
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 Welcome to this spacious 5 bedroom, 3.5 bathroom home offering nearly 3,000 square feet of...	5 beds \| 4 baths \| 2,930 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.05% Airbnb Rental Income: $null Traditional Rental Income: $3903 Airbnb ROI: N/A Traditional ROI: 4.05%
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%
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 Settle in to your dream home in the coveted subdivision of Warwick Hills within Eastlake W...	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%

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.

$465,000

Airbnb cash on cash: 6.22%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $4558

Traditional Rental Income: $2944

Airbnb ROI: 6.22%

Traditional ROI: 4.69%

502 TIMBER BAY CIRCLE E

Oldsmar, FL

4 beds | 2 baths | 1,658 sq.ft.

$425,000

Airbnb cash on cash: 6.55%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $4558

Traditional Rental Income: $2555

Airbnb ROI: 6.55%

Traditional ROI: 3.9%

2002 SHEFFIELD COURT

Oldsmar, FL

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

$219,000

Airbnb cash on cash: 5.13%

Traditional cash on cash: 6%

Airbnb Rental Income: $2403

Traditional Rental Income: $1995

Airbnb ROI: 5.13%

Traditional ROI: 6%

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.

$215,000

Airbnb cash on cash: 6.1%

Traditional cash on cash: 7.47%

Airbnb Rental Income: $2403

Traditional Rental Income: $2092

Airbnb ROI: 6.1%

Traditional ROI: 7.47%

200 GRETCHEN COURT

Oldsmar, FL

3 beds | 2 baths | 1,445 sq.ft.

$374,900

Airbnb cash on cash: 4.03%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $3329

Traditional Rental Income: $2258

Airbnb ROI: 4.03%

Traditional ROI: 3.1%

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%