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
502 TIMBER BAY CIRCLE E Oldsmar, FL Under contract-accepting backup offers. This beautifully cared-for pool home is tucked awa...	4 beds \| 2 baths \| 1,658 sq.ft.	$419,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 6.51% Airbnb Rental Income: $1908 Traditional Rental Income: $3557 Airbnb ROI: 1.03% Traditional ROI: 6.51%
438 LAFAYETTE BOULEVARD Oldsmar, FL This exceptional home is situated on almost Â½ acre fenced-in lot! Featuring 4 Bedrooms pl...	4 beds \| 2 baths \| 2,138 sq.ft.	$599,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 4.37% Airbnb Rental Income: $1908 Traditional Rental Income: $3867 Airbnb ROI: -0.03% Traditional ROI: 4.37%
1203 CLAYS TRAIL #406 Oldsmar, FL UNBELIEVVABLE VALUE in East Lake Woodlands!! 1203 Clays Trail #406 nestled in the highly s...	2 beds \| 2 baths \| 1,910 sq.ft.	$285,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 8.4% Airbnb Rental Income: $1396 Traditional Rental Income: $2807 Airbnb ROI: 1.58% Traditional ROI: 8.4%
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: -0.51% Traditional cash on cash: 3.77% Airbnb Rental Income: $1908 Traditional Rental Income: $4193 Airbnb ROI: -0.51% Traditional ROI: 3.77%
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: 2.37% Traditional cash on cash: 8.56% Airbnb Rental Income: $1396 Traditional Rental Income: $2092 Airbnb ROI: 2.37% Traditional ROI: 8.56%
382 ROSALIND LANE Oldsmar, FL NEW YEAR; NEW PRICE! Welcome to 382 Rosalind Ln., an extraordinary home in the exclusive g...	4 beds \| 3 baths \| 3,273 sq.ft.	$822,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4% Airbnb Rental Income: $1908 Traditional Rental Income: $4776 Airbnb ROI: -0.4% Traditional ROI: 4%
1705 IRONWOOD COURT E Oldsmar, FL Welcome to this beautifully renovated 2-bedroom, 2-bathroom homeâperfect for first-time ...	2 beds \| 2 baths \| 1,206 sq.ft.	$330,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 5.83% Airbnb Rental Income: $1396 Traditional Rental Income: $2361 Airbnb ROI: 1.36% Traditional ROI: 5.83%
201 DUNKIRK ROAD Oldsmar, FL Under contract-accepting backup offers. Welcome to this beautifully updated Oldsmar proper...	3 beds \| 2 baths \| 1,760 sq.ft.	$390,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 5.99% Airbnb Rental Income: $1381 Traditional Rental Income: $2964 Airbnb ROI: 0.52% Traditional ROI: 5.99%
240 TADS TRAIL Oldsmar, FL Under contract-accepting backup offers. One or more of the photos are virtually staged. En...	2 beds \| 2 baths \| 1,380 sq.ft.	$249,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 5.43% Airbnb Rental Income: $1396 Traditional Rental Income: $2448 Airbnb ROI: -0.84% Traditional ROI: 5.43%
1598 LOCKMEADE PLACE Oldsmar, FL Under contract-accepting backup offers. Exquisite Estate Home in the Prestigious Aberdeen ...	4 beds \| 4 baths \| 3,300 sq.ft.	$999,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 5.47% Airbnb Rental Income: $1908 Traditional Rental Income: $7188 Airbnb ROI: -0.75% Traditional ROI: 5.47%
1909 CASTLE BAY COURT Oldsmar, FL --GORGEOUS HOME--Discover this IMMACULATE 3-bedroom, 2-bath BLOCK home with garage located...	3 beds \| 2 baths \| 1,410 sq.ft.	$382,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 5.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2662 Airbnb ROI: 0.72% Traditional ROI: 5.47%
107 MARY DRIVE #107 Oldsmar, FL One or more photo(s) has been virtually staged. Move-In Ready Ground Floor Condo in Gated ...	2 beds \| 2 baths \| 1,094 sq.ft.	$189,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 8.22% Airbnb Rental Income: $1396 Traditional Rental Income: $2106 Airbnb ROI: 1.92% Traditional ROI: 8.22%
388 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL 2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-b...	2 beds \| 2 baths \| 1,105 sq.ft.	$246,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $1396 Traditional Rental Income: $2347 Airbnb ROI: N/A Traditional ROI: 5.91%
120 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Are you dreaming of your own stylish urban OASIS s...	3 beds \| 3 baths \| 1,834 sq.ft.	$520,000	Airbnb cash on cash: -2% Traditional cash on cash: 1.53% Airbnb Rental Income: $1381 Traditional Rental Income: $2675 Airbnb ROI: -2% Traditional ROI: 1.53%
20 FERNBROOK ROAD Oldsmar, FL Under contract-accepting backup offers. Tucked inside the 24-hour gated community of East ...	4 beds \| 2 baths \| 2,147 sq.ft.	$649,999	Airbnb cash on cash: -0.03% Traditional cash on cash: 2.72% Airbnb Rental Income: $1908 Traditional Rental Income: $3068 Airbnb ROI: -0.03% Traditional ROI: 2.72%
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.	$160,000	Airbnb cash on cash: 2.87% Traditional cash on cash: 9.9% Airbnb Rental Income: $1396 Traditional Rental Income: $2047 Airbnb ROI: 2.87% Traditional ROI: 9.9%
1732 SPLIT FORK DRIVE Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 3 baths \| 2,163 sq.ft.	$585,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 4.43% Airbnb Rental Income: $1381 Traditional Rental Income: $3921 Airbnb ROI: -0.99% Traditional ROI: 4.43%
100 KILSYTHE STREET Oldsmar, FL Tucked along picturesque Shore Drive E near the bay, this beautifully remodeled 3-bedroom,...	3 beds \| 3 baths \| 1,100 sq.ft.	$450,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.05% Airbnb Rental Income: $1381 Traditional Rental Income: $2326 Airbnb ROI: -0.19% Traditional ROI: 3.05%
1471 BRIARGROVE WAY Oldsmar, FL One or more photo(s) has been virtually staged. Live the Florida Lifestyle in Aberdeen at ...	5 beds \| 4 baths \| 3,140 sq.ft.	$899,999	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.65% Airbnb Rental Income: $2554 Traditional Rental Income: $6000 Airbnb ROI: -0.2% Traditional ROI: 4.65%
152 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Welcome to Seaside Estates, a gated waterfront com...	3 beds \| 3 baths \| 1,791 sq.ft.	$550,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.5% Airbnb Rental Income: $1381 Traditional Rental Income: $2901 Airbnb ROI: -1.27% Traditional ROI: 2.5%
209 HEMINGWAY DRIVE Oldsmar, FL Stunning Sun Ketch Townhome \| Bright, Airy & Move-In Ready! Welcome to your slice of par...	2 beds \| 2 baths \| 1,086 sq.ft.	$294,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 6.01% Airbnb Rental Income: $1396 Traditional Rental Income: $2371 Airbnb ROI: 0.98% Traditional ROI: 6.01%
2270 CHRISTY LANE Oldsmar, FL Under contract-accepting backup offers. Welcome to luxury living in the desirable Gated, G...	4 beds \| 5 baths \| 3,993 sq.ft.	$1,250,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 5.71% Airbnb Rental Income: $1908 Traditional Rental Income: $9180 Airbnb ROI: -0.99% Traditional ROI: 5.71%
850 CHRISTINA CIRCLE Oldsmar, FL Under contract-accepting backup offers. Tucked inside Bayâs End, a quiet coastal communi...	4 beds \| 2 baths \| 1,486 sq.ft.	$499,999	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.61% Airbnb Rental Income: $1908 Traditional Rental Income: $3117 Airbnb ROI: 0.94% Traditional ROI: 4.61%
112 BRENT CIRCLE Oldsmar, FL PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. Skip the rehab and move right in to the ...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2697 Airbnb ROI: -1.25% Traditional ROI: 2.47%
129 CAMPHOR CIRCLE #C Oldsmar, FL Welcome to The Gardens of Forest Lakes, one of Oldsmarâs well-kept secret communities. T...	2 beds \| 2 baths \| 915 sq.ft.	$180,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 9.7% Airbnb Rental Income: $1396 Traditional Rental Income: $1959 Airbnb ROI: 3.95% Traditional ROI: 9.7%
948 LUCAS LANE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to a truly impressive home set in ...	3 beds \| 2 baths \| 1,685 sq.ft.	$500,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 3.72% Airbnb Rental Income: $1381 Traditional Rental Income: $3320 Airbnb ROI: -1.32% Traditional ROI: 3.72%
124 NINA WAY #24 Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Wo...	2 beds \| 2 baths \| 1,094 sq.ft.	$199,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 5.12% Airbnb Rental Income: $1396 Traditional Rental Income: $2050 Airbnb ROI: -0.55% Traditional ROI: 5.12%
9009 PALM KEY AVENUE Oldsmar, FL Seller is offering a $5,000 CREDIT towards closing costs or an interest rate buy down! â...	4 beds \| 3 baths \| 2,587 sq.ft.	$674,900	Airbnb cash on cash: -0.94% Traditional cash on cash: 2.7% Airbnb Rental Income: $1908 Traditional Rental Income: $3694 Airbnb ROI: -0.94% Traditional ROI: 2.7%
826 CHRISTINA CIRCLE Oldsmar, FL Waterfront Beauty in Coveted East Lake Corridor â The Best Lot in this highly desired Co...	3 beds \| 2 baths \| 2,164 sq.ft.	$1,075,000	Airbnb cash on cash: -1.08% Traditional cash on cash: 2.32% Airbnb Rental Income: $1381 Traditional Rental Income: $4356 Airbnb ROI: -1.08% Traditional ROI: 2.32%
124 LOBLOLLY COURT #H Oldsmar, FL Investor-friendly opportunity: This turn-key property currently has a cash flowing year-lo...	2 beds \| 2 baths \| 915 sq.ft.	$160,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 5.34% Airbnb Rental Income: $1396 Traditional Rental Income: $2038 Airbnb ROI: -1.62% Traditional ROI: 5.34%
1499 E LAKE WOODLANDS PARKWAY Oldsmar, FL Under contract-accepting backup offers. Welcome to this beautifully remodeled brick estate...	3 beds \| 2 baths \| 2,356 sq.ft.	$825,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.74% Airbnb Rental Income: $1381 Traditional Rental Income: $3805 Airbnb ROI: -0.96% Traditional ROI: 2.74%
4954 TURTLE CREEK TRAIL Oldsmar, FL Under contract-accepting backup offers. Welcome to this exceptional Costanza custom-built ...	5 beds \| 4 baths \| 4,144 sq.ft.	$1,375,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 3.05% Airbnb Rental Income: $2554 Traditional Rental Income: $6803 Airbnb ROI: -0.76% Traditional ROI: 3.05%
634 TIMBER BAY CIRCLE W Oldsmar, FL Move-In Ready Oldsmar Home! Welcome to this 3-bedroom, 2-bath home home located in the hea...	3 beds \| 2 baths \| 1,056 sq.ft.	$324,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 5.58% Airbnb Rental Income: $1381 Traditional Rental Income: $2503 Airbnb ROI: 0.54% Traditional ROI: 5.58%
291 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Welcome to the highly sought-after gated community of Countryside Key, ideally located in ...	2 beds \| 3 baths \| 1,110 sq.ft.	$258,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 4.97% Airbnb Rental Income: $1396 Traditional Rental Income: $2258 Airbnb ROI: -0.3% Traditional ROI: 4.97%
108 BRENT CIRCLE Oldsmar, FL Welcome to coastal lifestyle living in one of Oldsmarâs most desirable gated waterfront ...	3 beds \| 3 baths \| 1,834 sq.ft.	$399,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 3.47% Airbnb Rental Income: $1381 Traditional Rental Income: $2773 Airbnb ROI: -1.37% Traditional ROI: 3.47%
130 WOODLAKE WYNDE #130 Oldsmar, FL One or more photo(s) has been virtually staged. Must See!! Beautifully renovated 2-bedroom...	2 beds \| 2 baths \| 924 sq.ft.	$204,500	Airbnb cash on cash: -1.38% Traditional cash on cash: 2.34% Airbnb Rental Income: $1396 Traditional Rental Income: $1695 Airbnb ROI: -1.38% Traditional ROI: 2.34%
207 CYPRESS LANE Oldsmar, FL First-floor 2-bedroom, 2-bathroom condo located in the East Lake Woodlands community in Ol...	2 beds \| 2 baths \| 1,054 sq.ft.	$180,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 7.47% Airbnb Rental Income: $1396 Traditional Rental Income: $1788 Airbnb ROI: 2.72% Traditional ROI: 7.47%
110 WOODGLEN COURT Oldsmar, FL Under contract-accepting backup offers. Fabulous East Lake Woodlands! Magnificent custom-b...	4 beds \| 4 baths \| 3,712 sq.ft.	$999,900	Airbnb cash on cash: -1.29% Traditional cash on cash: 2.66% Airbnb Rental Income: $1908 Traditional Rental Income: $5073 Airbnb ROI: -1.29% Traditional ROI: 2.66%
129 BRENT CIRCLE Oldsmar, FL HUGE PRICE IMPROVEMENT of $60k- WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath town...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 3.15% Airbnb Rental Income: $1381 Traditional Rental Income: $2794 Airbnb ROI: -0.78% Traditional ROI: 3.15%
206 BEDFORD STREET Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Sh...	3 beds \| 2 baths \| 1,274 sq.ft.	$359,700	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.17% Airbnb Rental Income: $1381 Traditional Rental Income: $2189 Airbnb ROI: 0.53% Traditional ROI: 4.17%

Real Estate investment in Oldsmar, FL

There are 161 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $399,450 and the average price per square foot is $217. In April 2026, the average monthly cash on cash return in Oldsmar is 5.00%. The average monthly rental income in Oldsmar is $2,675.

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

There are 161 investment properties available for sale in Oldsmar.

In 2026, 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 $1,396.

Your search for investment property begins and ends here

Investment Property for Sale in Oldsmar, FL

502 TIMBER BAY CIRCLE E

Oldsmar, FL

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

$419,900

Airbnb cash on cash: 1.03%

Traditional cash on cash: 6.51%

Airbnb Rental Income: $1908

Traditional Rental Income: $3557

Airbnb ROI: 1.03%

Traditional ROI: 6.51%

438 LAFAYETTE BOULEVARD

Oldsmar, FL

4 beds | 2 baths | 2,138 sq.ft.

$599,900

Airbnb cash on cash: -0.03%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $1908

Traditional Rental Income: $3867

Airbnb ROI: -0.03%

Traditional ROI: 4.37%

1203 CLAYS TRAIL #406

Oldsmar, FL

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

$285,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 8.4%

Airbnb Rental Income: $1396

Traditional Rental Income: $2807

Airbnb ROI: 1.58%

Traditional ROI: 8.4%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

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

$700,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $1908

Traditional Rental Income: $4193

Airbnb ROI: -0.51%

Traditional ROI: 3.77%

2044 SHEFFIELD COURT

Oldsmar, FL

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

$190,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 8.56%

Airbnb Rental Income: $1396

Traditional Rental Income: $2092

Airbnb ROI: 2.37%

Traditional ROI: 8.56%

382 ROSALIND LANE

Oldsmar, FL

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

$822,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 4%

Airbnb Rental Income: $1908

Traditional Rental Income: $4776

Airbnb ROI: -0.4%

Traditional ROI: 4%

1705 IRONWOOD COURT E

Oldsmar, FL

2 beds | 2 baths | 1,206 sq.ft.

$330,000

Airbnb cash on cash: 1.36%

Traditional cash on cash: 5.83%

Airbnb Rental Income: $1396

Traditional Rental Income: $2361

Airbnb ROI: 1.36%

Traditional ROI: 5.83%

201 DUNKIRK ROAD

Oldsmar, FL

3 beds | 2 baths | 1,760 sq.ft.

$390,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 5.99%

Airbnb Rental Income: $1381

Traditional Rental Income: $2964

Airbnb ROI: 0.52%