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.

Investment Property for Sale in Oldsmar, FL

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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%
102 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Huge Price Reduction immediate equity! Ready to m...	3 beds \| 3 baths \| 1,834 sq.ft.	$360,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 5.45% Airbnb Rental Income: $3329 Traditional Rental Income: $2518 Airbnb ROI: 5.65% Traditional ROI: 5.45%
1203 CLAYS TRAIL #406 Oldsmar, FL Welcome to 1203 Clays Trail #406 nestled in the highly sought after community of Eastlake ...	2 beds \| 2 baths \| 1,910 sq.ft.	$329,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 6.49% Airbnb Rental Income: $2403 Traditional Rental Income: $2600 Airbnb ROI: 3.95% Traditional ROI: 6.49%
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%
130 SABAL COURT #C Oldsmar, FL Welcome to your charming retreat at 130 Sabal Ct. Unit C, is nestled in the heart of Oldsm...	2 beds \| 2 baths \| 915 sq.ft.	$155,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 9.37% Airbnb Rental Income: $2403 Traditional Rental Income: $1860 Airbnb ROI: 9.06% Traditional ROI: 9.37%
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%
2052 SHEFFIELD COURT Oldsmar, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	2 beds \| 2 baths \| 1,296 sq.ft.	$234,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 5.71% Airbnb Rental Income: $2403 Traditional Rental Income: $1994 Airbnb ROI: 4.89% Traditional ROI: 5.71%
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%
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%
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%
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 Welcome to this charming 2-bedroom, 2-bathroom condo in the highly sought-after gated comm...	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 HUGE PRICE REDUCTION! Stunning 2 Bedroom, 2 Bathroom Remodeled Condo in East Lake Woodland...	2 beds \| 2 baths \| 1,094 sq.ft.	$197,900	Airbnb cash on cash: 6.5% Traditional cash on cash: 6.52% Airbnb Rental Income: $2403 Traditional Rental Income: $1817 Airbnb ROI: 6.5% Traditional ROI: 6.52%
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%
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%
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.	$259,900	Airbnb cash on cash: 4.81% Traditional cash on cash: 5.88% Airbnb Rental Income: $2403 Traditional Rental Income: $2076 Airbnb ROI: 4.81% Traditional ROI: 5.88%
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%
103 LINDSAY LANE #13 Oldsmar, FL Under contract-accepting backup offers. Welcome to this inviting FIRST FLOOR condo in the ...	2 beds \| 2 baths \| 1,334 sq.ft.	$289,900	Airbnb cash on cash: 4.75% Traditional cash on cash: 5.95% Airbnb Rental Income: $2403 Traditional Rental Income: $2143 Airbnb ROI: 4.75% Traditional ROI: 5.95%
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%
150 POOLE PLACE Oldsmar, FL Welcome to this stunning, fully renovated 4 bedroom, 2 bathroom East Lake Woodlands villa!...	4 beds \| 2 baths \| 1,550 sq.ft.	$347,500	Airbnb cash on cash: 7.87% Traditional cash on cash: 3.98% Airbnb Rental Income: $4558 Traditional Rental Income: $2340 Airbnb ROI: 7.87% Traditional ROI: 3.98%
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%
367 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Move-in ready townhome in Oldsmar. Inside the gates of pet-friendly Countryside Key, this ...	2 beds \| 2 baths \| 1,105 sq.ft.	$245,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.22% Airbnb Rental Income: $2403 Traditional Rental Income: $1913 Airbnb ROI: 3.79% Traditional ROI: 4.22%
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 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%
906 VINEYARD LANE Oldsmar, FL One or more photo(s) has been virtually staged. Elegant 3-Bed, 2.5-Bath Townhome with 2.5%...	3 beds \| 3 baths \| 1,525 sq.ft.	$380,000	Airbnb cash on cash: 3.31% Traditional cash on cash: 2.41% Airbnb Rental Income: $3329 Traditional Rental Income: $2263 Airbnb ROI: 3.31% Traditional ROI: 2.41%
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%
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%
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%
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%
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%

Real Estate investment in Oldsmar, FL

There are 161 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $399,900 and the average price per square foot is $216. In October 2025, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,423.

Oldsmar, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 161 investment properties available for sale in Oldsmar.

In 2025, the best neighborhood to buy investment property is Oldsmar.

The ROI for Short-Term is higher than the Long-Term in Oldsmar with average rental income of $3,329.

Your search for investment property begins and ends here

Investment Property 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%

102 BRENT CIRCLE

Oldsmar, FL

3 beds | 3 baths | 1,834 sq.ft.

$360,000

Airbnb cash on cash: 5.65%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $3329

Traditional Rental Income: $2518

Airbnb ROI: 5.65%

Traditional ROI: 5.45%

1203 CLAYS TRAIL #406

Oldsmar, FL

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

$329,000

Airbnb cash on cash: 3.95%

Traditional cash on cash: 6.49%

Airbnb Rental Income: $2403

Traditional Rental Income: $2600

Airbnb ROI: 3.95%

Traditional ROI: 6.49%

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%

130 SABAL COURT #C

Oldsmar, FL

2 beds | 2 baths | 915 sq.ft.

$155,000

Airbnb cash on cash: 9.06%

Traditional cash on cash: 9.37%

Airbnb Rental Income: $2403

Traditional Rental Income: $1860

Airbnb ROI: 9.06%