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 104 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
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.	$448,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 3.65% Airbnb Rental Income: $4558 Traditional Rental Income: $2555 Airbnb ROI: 6.17% Traditional ROI: 3.65%
1640 GRAY BARK DRIVE Oldsmar, FL Welcome to the home that truly has everything! No detail has been overlooked in this fully...	3 beds \| 2 baths \| 1,927 sq.ft.	$585,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.23% Airbnb Rental Income: $3329 Traditional Rental Income: $2859 Airbnb ROI: 2.73% Traditional ROI: 3.23%
2002 SHEFFIELD COURT Oldsmar, FL This spacious and well-maintained 2 bedroom 2 bath end-unit Villa offers an exceptional 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%
632 LAKE CYPRESS CIRCLE Oldsmar, FL Under contract-accepting backup offers. Reduced. Florida Pool Home! Welcome to your brigh...	4 beds \| 2 baths \| 1,906 sq.ft.	$563,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.33% Airbnb Rental Income: $4558 Traditional Rental Income: $2911 Airbnb ROI: 4.66% Traditional ROI: 3.33%
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.	$800,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 2.2% Airbnb Rental Income: $4558 Traditional Rental Income: $3466 Airbnb ROI: 2.39% Traditional ROI: 2.2%
2044 SHEFFIELD COURT Oldsmar, FL High and dry with NEW ROOF and NEW HVAC!! Welcome to this charming 2-bedroom, 2-bathroom ...	2 beds \| 2 baths \| 1,296 sq.ft.	$237,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 6.7% Airbnb Rental Income: $2403 Traditional Rental Income: $2092 Airbnb ROI: 5.46% Traditional ROI: 6.7%
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.	$852,990	Airbnb cash on cash: 2.35% Traditional cash on cash: 1.19% Airbnb Rental Income: $4558 Traditional Rental Income: $2684 Airbnb ROI: 2.35% Traditional ROI: 1.19%
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%
1232 HOLLY CIRCLE Oldsmar, FL Welcome to a piece of paradise in Forest Lakes, Oldsmar, where peaceful living meets capti...	3 beds \| 2 baths \| 1,186 sq.ft.	$390,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 4.87% Airbnb Rental Income: $3329 Traditional Rental Income: $2347 Airbnb ROI: 5.52% Traditional ROI: 4.87%
2000 SHEFFIELD COURT Oldsmar, FL Welcome to this Beautifully UPDATED 1296 sq ft, 2-bedroom, 2-bath villa with VAULTED CEILI...	2 beds \| 2 baths \| 1,296 sq.ft.	$269,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 5.65% Airbnb Rental Income: $2403 Traditional Rental Income: $2076 Airbnb ROI: 4.61% Traditional ROI: 5.65%
321 SHORE DRIVE E Oldsmar, FL Welcome to this beautiful Home, fully remodeled ,4-bedroom, 2 bath. And step outside to yo...	4 beds \| 2 baths \| 1,523 sq.ft.	$465,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 4.72% Airbnb Rental Income: $4558 Traditional Rental Income: $2913 Airbnb ROI: 6.32% Traditional ROI: 4.72%
826 CHRISTINA CIRCLE Oldsmar, FL Just Reintroduced at a New Price â The Best Lot in this highly desired Community! Motiva...	3 beds \| 2 baths \| 2,164 sq.ft.	$1,275,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 0.36% Airbnb Rental Income: $3329 Traditional Rental Income: $2645 Airbnb ROI: 0.31% Traditional ROI: 0.36%
341 BAY ARBOR BOULEVARD Oldsmar, FL Spectacularly remodeled home nestled on a conservation/pond lot in a gated community of Ba...	3 beds \| 2 baths \| 2,034 sq.ft.	$624,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 2.91% Airbnb Rental Income: $3329 Traditional Rental Income: $2982 Airbnb ROI: 2.23% Traditional ROI: 2.91%
4797 STONEBRIAR DRIVE Oldsmar, FL Under contract-accepting backup offers. Donât miss this beautifully upgraded and meticul...	4 beds \| 3 baths \| 2,486 sq.ft.	$749,999	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.84% Airbnb Rental Income: $4558 Traditional Rental Income: $3692 Airbnb ROI: 2.72% Traditional ROI: 2.84%
40 GRETCHEN COURT Oldsmar, FL Step through the front door of this charming villa, and you feel at home. The welcoming o...	2 beds \| 2 baths \| 1,502 sq.ft.	$345,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 3.41% Airbnb Rental Income: $2403 Traditional Rental Income: $2203 Airbnb ROI: 2.21% Traditional ROI: 3.41%
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 Live the ultimate Florida lifestyle in this spectacular Craftsman-style home in the heart ...	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%
1630 GRAY BARK DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome home to 1630 Gray Bark Drive! This beautif...	3 beds \| 2 baths \| 1,358 sq.ft.	$465,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.13% Airbnb Rental Income: $3329 Traditional Rental Income: $2500 Airbnb ROI: 3.33% Traditional ROI: 3.13%
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.	$679,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.36% Airbnb Rental Income: $4558 Traditional Rental Income: $3177 Airbnb ROI: 3.05% Traditional ROI: 2.36%
303 NATIONAL ORANGE AVENUE Oldsmar, FL PRICE ADJUSTMENT ON THIS WONDERFUL HOME! Updated and charming 3-bedroom homes in Oldsmar....	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%
1631 SHADY OAKS DRIVE Oldsmar, FL JUST REDUCED â DONâT MISS OUT ON THIS ONE! Come see this exceptional 3 bedroom, 2 bath...	3 beds \| 2 baths \| 1,938 sq.ft.	$614,500	Airbnb cash on cash: 2.26% Traditional cash on cash: 2.73% Airbnb Rental Income: $3329 Traditional Rental Income: $2850 Airbnb ROI: 2.26% Traditional ROI: 2.73%
2031 DOVER COURT Oldsmar, FL Welcome to your peaceful retreat! This beautifully maintained 2-bedroom, 2-bathroom, 1-car...	2 beds \| 2 baths \| 1,215 sq.ft.	$279,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 4.37% Airbnb Rental Income: $2403 Traditional Rental Income: $2025 Airbnb ROI: 3.57% Traditional ROI: 4.37%
206 BEDFORD STREET Oldsmar, FL *PRICE IMPROVEMENT-MOTIVATED SELLER* This meticulously maintained 3 bedroom, 2 bath, 2...	3 beds \| 2 baths \| 1,274 sq.ft.	$399,900	Airbnb cash on cash: 4.73% Traditional cash on cash: 3.67% Airbnb Rental Income: $3329 Traditional Rental Income: $2189 Airbnb ROI: 4.73% Traditional ROI: 3.67%
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%
140 DALE PLACE Oldsmar, FL TURN KEY VILLA perfect for Snow Birds, nestled in the GATED COMMUNITY of East Lake Woodlan...	3 beds \| 2 baths \| 1,445 sq.ft.	$368,500	Airbnb cash on cash: 3.93% Traditional cash on cash: 3.56% Airbnb Rental Income: $3329 Traditional Rental Income: $2457 Airbnb ROI: 3.93% Traditional ROI: 3.56%
347 COUNTRY CLUB DRIVE Oldsmar, FL Beautifully and Completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths wi...	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 Under contract-accepting backup offers. COMPLETE LUXURY MAKEOVER! Welcome to your modern d...	4 beds \| 3 baths \| 3,270 sq.ft.	$1,350,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 1.72% Airbnb Rental Income: $4558 Traditional Rental Income: $4002 Airbnb ROI: 1.41% Traditional ROI: 1.72%
1358 FORESTEDGE BOULEVARD Oldsmar, FL PICK YOUR COLOR - MAKE THIS BEAUTIFUL HOME YOUR OWN!! Sellers are offering a $6500 paintin...	4 beds \| 3 baths \| 2,808 sq.ft.	$909,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.62% Airbnb Rental Income: $4558 Traditional Rental Income: $4583 Airbnb ROI: 1.47% Traditional ROI: 2.62%
309 CONGRESS STREET Oldsmar, FL HIGH & DRY, NEVER FLOODED! Donât miss your chance to own this beautifully renovated like...	3 beds \| 2 baths \| 2,792 sq.ft.	$675,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 1.99% Airbnb Rental Income: $3329 Traditional Rental Income: $2240 Airbnb ROI: 2.53% Traditional ROI: 1.99%
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.	$1,150,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 3.04% Airbnb Rental Income: $4558 Traditional Rental Income: $4974 Airbnb ROI: 1.76% Traditional ROI: 3.04%
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.	$449,900	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 Waterfront Luxury Meets Complete Modern Renovation in this Gem in East Lake High Zone! ...	3 beds \| 2 baths \| 1,632 sq.ft.	$489,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.83% Airbnb Rental Income: $3329 Traditional Rental Income: $2761 Airbnb ROI: 3.45% Traditional ROI: 3.83%
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.	$379,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 5.97% Airbnb Rental Income: $3329 Traditional Rental Income: $3073 Airbnb ROI: 4.6% Traditional ROI: 5.97%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oldsmar, FL

502 TIMBER BAY CIRCLE E

Oldsmar, FL

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

$448,000

Airbnb cash on cash: 6.17%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $4558

Traditional Rental Income: $2555

Airbnb ROI: 6.17%

Traditional ROI: 3.65%

1640 GRAY BARK DRIVE

Oldsmar, FL

3 beds | 2 baths | 1,927 sq.ft.

$585,000

Airbnb cash on cash: 2.73%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $3329

Traditional Rental Income: $2859

Airbnb ROI: 2.73%

Traditional ROI: 3.23%

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%

632 LAKE CYPRESS CIRCLE

Oldsmar, FL

4 beds | 2 baths | 1,906 sq.ft.

$563,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $4558

Traditional Rental Income: $2911

Airbnb ROI: 4.66%

Traditional ROI: 3.33%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

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

$800,000

Airbnb cash on cash: 2.39%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $4558

Traditional Rental Income: $3466

Airbnb ROI: 2.39%

Traditional ROI: 2.2%

2044 SHEFFIELD COURT

Oldsmar, FL

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

$237,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 6.7%

Airbnb Rental Income: $2403

Traditional Rental Income: $2092

Airbnb ROI: 5.46%

Traditional ROI: 6.7%

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.

$852,990

Airbnb cash on cash: 2.35%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $4558

Traditional Rental Income: $2684

Airbnb ROI: 2.35%