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.

Ernest Investment Property for Sale in Oldsmar, FL

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

Showing 147 Ernest Investment Property 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%
110 CYPRESS COURT #3-82 Oldsmar, FL Welcome to a condo that instantly feels like home the moment you walk in, beautifully upda...	2 beds \| 2 baths \| 1,054 sq.ft.	$175,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 7.84% Airbnb Rental Income: $2403 Traditional Rental Income: $1833 Airbnb ROI: 7.72% Traditional ROI: 7.84%
1203 CLAYS TRAIL #406 Oldsmar, FL OUTSTANDING BLACK FRIDAY/CYBER MONDAY PRICING!! 1203 Clays Trail #406 nestled in the highl...	2 beds \| 2 baths \| 1,910 sq.ft.	$299,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 7.23% Airbnb Rental Income: $2403 Traditional Rental Income: $2600 Airbnb ROI: 4.44% Traditional ROI: 7.23%
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.	$843,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 1.22% Airbnb Rental Income: $4558 Traditional Rental Income: $2684 Airbnb ROI: 2.39% Traditional ROI: 1.22%
1909 CASTLE BAY COURT Oldsmar, FL --GREAT CURB APPEAL--Discover this IMMACULATE 3-bedroom, 2-bath home with garage located o...	3 beds \| 2 baths \| 1,410 sq.ft.	$390,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 4.36% Airbnb Rental Income: $3329 Traditional Rental Income: $2304 Airbnb ROI: 5.13% Traditional ROI: 4.36%
134 SYCAMORE LANE #H Oldsmar, FL This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, ...	2 beds \| 2 baths \| 915 sq.ft.	$169,000	Airbnb cash on cash: 7.88% Traditional cash on cash: 7.5% Airbnb Rental Income: $2403 Traditional Rental Income: $1752 Airbnb ROI: 7.88% Traditional ROI: 7.5%
396 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Offers 1% lender credit at closing. Welcome to this beautifully updated 2-bedroom, 2.5-bat...	2 beds \| 3 baths \| 1,110 sq.ft.	$280,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 5.16% Airbnb Rental Income: $2403 Traditional Rental Income: $1909 Airbnb ROI: 4.8% Traditional ROI: 5.16%
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%
128 CAMPHOR CIRCLE #C Oldsmar, FL Under contract-accepting backup offers. Welcome home to this beautifully updated 2-bedroom...	2 beds \| 2 baths \| 915 sq.ft.	$154,900	Airbnb cash on cash: 9.16% Traditional cash on cash: 8.82% Airbnb Rental Income: $2403 Traditional Rental Income: $1763 Airbnb ROI: 9.16% Traditional ROI: 8.82%
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%
315 WOODS LANDING TRAIL Oldsmar, FL Completely updated, water view townhome within the 24hr guard gated, golf cart friendly, c...	2 beds \| 3 baths \| 1,200 sq.ft.	$319,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.71% Airbnb Rental Income: $2403 Traditional Rental Income: $1956 Airbnb ROI: 1.23% Traditional ROI: 1.71%
210 MARTHA LANE #210 Oldsmar, FL Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 2-bathroom con...	2 beds \| 2 baths \| 1,094 sq.ft.	$169,900	Airbnb cash on cash: 6.18% Traditional cash on cash: 6.2% Airbnb Rental Income: $2403 Traditional Rental Income: $1818 Airbnb ROI: 6.18% Traditional ROI: 6.2%
124 NINA WAY #24 Oldsmar, FL Welcome Home! This renovated condo is simply beautiful! Located in the premier golf comm...	2 beds \| 2 baths \| 1,094 sq.ft.	$209,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.72% Airbnb Rental Income: $2403 Traditional Rental Income: $1817 Airbnb ROI: 3.7% Traditional ROI: 3.72%
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%
163 BRENT CIRCLE Oldsmar, FL Deeded Boat Slip with Lift Nestled in a serene, small gated community, this exquisite...	3 beds \| 3 baths \| 1,834 sq.ft.	$565,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.01% Airbnb Rental Income: $3329 Traditional Rental Income: $2620 Airbnb ROI: 1.94% Traditional ROI: 2.01%
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: 4.31% Airbnb Rental Income: $4558 Traditional Rental Income: $2426 Airbnb ROI: 7.64% Traditional ROI: 4.31%
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%
100 INGRID PLACE Oldsmar, FL Great opportunity to own this Lovely Updated 3 Bed, 2.5 Bath East Lake Woodlands Townhouse...	3 beds \| 3 baths \| 1,755 sq.ft.	$299,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 4.51% Airbnb Rental Income: $3329 Traditional Rental Income: $2484 Airbnb ROI: 4.87% Traditional ROI: 4.51%
5163 PINNACLE DRIVE Oldsmar, FL Located in X Flood zone with no flood insurance required! Welcome to 5163 Pinnacle Drive...	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%
106 CUTLASS WAY Oldsmar, FL Fully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Par...	3 beds \| 3 baths \| 1,365 sq.ft.	$365,000	Airbnb cash on cash: 4.31% Traditional cash on cash: 3.06% Airbnb Rental Income: $3329 Traditional Rental Income: $2156 Airbnb ROI: 4.31% Traditional ROI: 3.06%
1608 SUNSET WIND LOOP Oldsmar, FL Under contract-accepting backup offers. **This home has over $90,000 in upgrades and has e...	3 beds \| 3 baths \| 1,928 sq.ft.	$500,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 2.01% Airbnb Rental Income: $3329 Traditional Rental Income: $2666 Airbnb ROI: 1.84% Traditional ROI: 2.01%
129 BRENT CIRCLE Oldsmar, FL MOTIVATED SELLER - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situa...	3 beds \| 3 baths \| 1,834 sq.ft.	$569,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 2.48% Airbnb Rental Income: $3329 Traditional Rental Income: $2705 Airbnb ROI: 2.25% Traditional ROI: 2.48%
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 OWNER MOTIVATED!! HIGH AND DRY! Elevation certificate available. Backing up to a nature pr...	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.	$435,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 6.46% Airbnb Rental Income: $3329 Traditional Rental Income: $3290 Airbnb ROI: 4.73% Traditional ROI: 6.46%
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%
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

Ernest Investment Property 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%

110 CYPRESS COURT #3-82

Oldsmar, FL

2 beds | 2 baths | 1,054 sq.ft.

$175,000

Airbnb cash on cash: 7.72%

Traditional cash on cash: 7.84%

Airbnb Rental Income: $2403

Traditional Rental Income: $1833

Airbnb ROI: 7.72%

Traditional ROI: 7.84%

1203 CLAYS TRAIL #406

Oldsmar, FL

2 beds | 2 baths | 1,910 sq.ft.

$299,000

Airbnb cash on cash: 4.44%

Traditional cash on cash: 7.23%

Airbnb Rental Income: $2403

Traditional Rental Income: $2600

Airbnb ROI: 4.44%

Traditional ROI: 7.23%

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.

$843,000

Airbnb cash on cash: 2.39%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $4558

Traditional Rental Income: $2684

Airbnb ROI: 2.39%

Traditional ROI: 1.22%

1909 CASTLE BAY COURT

Oldsmar, FL

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

$390,000

Airbnb cash on cash: 5.13%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $3329

Traditional Rental Income: $2304

Airbnb ROI: 5.13%