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
90 CAMELIA COURT Oldsmar, FL **Beautiful single story split floor plan at the end of a cul-de-sac on the green of hole ...	4 beds \| 2 baths \| 2,288 sq.ft.	$715,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 2.14% Airbnb Rental Income: $3866 Traditional Rental Income: $3176 Airbnb ROI: 1.92% Traditional ROI: 2.14%
1807 SPLIT FORK DRIVE Oldsmar, FL Welcome to your own private paradise in Oldsmar! 3-bd, 2.5-ba POOL HOME (PLUS OFFICE or Bo...	3 beds \| 3 baths \| 2,173 sq.ft.	$575,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 5.42% Airbnb Rental Income: $4254 Traditional Rental Income: $3630 Airbnb ROI: 4.91% Traditional ROI: 5.42%
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.	$284,900	Airbnb cash on cash: 4.31% Traditional cash on cash: 5.07% Airbnb Rental Income: $2376 Traditional Rental Income: $1995 Airbnb ROI: 4.31% Traditional ROI: 5.07%
167 LAKEVIEW WAY #167 Oldsmar, FL Under contract-accepting backup offers. Live your best life in the highly sought-after, ga...	2 beds \| 2 baths \| 1,094 sq.ft.	$256,000	Airbnb cash on cash: 5.47% Traditional cash on cash: 5.93% Airbnb Rental Income: $2376 Traditional Rental Income: $1904 Airbnb ROI: 5.47% Traditional ROI: 5.93%
632 LAKE CYPRESS CIRCLE Oldsmar, FL WELCOME HOME to The Preserve at Cypress Lakes! This stunning, single-story 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,906 sq.ft.	$576,900	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.22% Airbnb Rental Income: $3866 Traditional Rental Income: $2911 Airbnb ROI: 3.45% Traditional ROI: 3.22%
10 AUSTIN PLACE #10 Oldsmar, FL One or more photo(s) has been virtually staged. If you're looking for peaceful, tranquil, ...	2 beds \| 2 baths \| 1,525 sq.ft.	$279,727	Airbnb cash on cash: 4.12% Traditional cash on cash: 5.94% Airbnb Rental Income: $2376 Traditional Rental Income: $2272 Airbnb ROI: 4.12% Traditional ROI: 5.94%
60 BALSAM DRIVE Oldsmar, FL I welcome to your next home in the exclusive, gated East Lake Woodlands golf community! Fr...	2 beds \| 2 baths \| 1,250 sq.ft.	$350,000	Airbnb cash on cash: 2.13% Traditional cash on cash: 2.63% Airbnb Rental Income: $2376 Traditional Rental Income: $1958 Airbnb ROI: 2.13% Traditional ROI: 2.63%
2014 MONTEGO COURT Oldsmar, FL Honey, stop the car! This 2 bedroom, 2 bathroom highly desirable end unit villa in Oldsmar...	2 beds \| 2 baths \| 1,143 sq.ft.	$299,900	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.77% Airbnb Rental Income: $2376 Traditional Rental Income: $1926 Airbnb ROI: 4.3% Traditional ROI: 4.77%
100 KILSYTHE STREET Oldsmar, FL Your Florida home awaits!!! This Gorgeous, totally remodeled 3/3/1 is a perfect home is hi...	3 beds \| 3 baths \| 1,431 sq.ft.	$469,900	Airbnb cash on cash: 5.76% Traditional cash on cash: 3.42% Airbnb Rental Income: $4254 Traditional Rental Income: $2326 Airbnb ROI: 5.76% Traditional ROI: 3.42%
1408 SYRAH DRIVE Oldsmar, FL Discover the charm of this beautiful townhome nestled in the exclusive, gated community of...	3 beds \| 3 baths \| 1,773 sq.ft.	$400,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 2.77% Airbnb Rental Income: $4254 Traditional Rental Income: $2412 Airbnb ROI: 5.29% Traditional ROI: 2.77%
520 PALMDALE DRIVE Oldsmar, FL Under contract-accepting backup offers. Storm-tested! No damage, Zone X! A rare opportunit...	4 beds \| 3 baths \| 2,646 sq.ft.	$799,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 2.13% Airbnb Rental Income: $3866 Traditional Rental Income: $3183 Airbnb ROI: 1.93% Traditional ROI: 2.13%
1434 WOODSTREAM DRIVE Oldsmar, FL Conservation Lot with Water View in Gated Community. Discover the beauty of maintenance-fr...	3 beds \| 2 baths \| 1,596 sq.ft.	$500,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.35% Airbnb Rental Income: $4254 Traditional Rental Income: $2696 Airbnb ROI: 3.76% Traditional ROI: 2.35%
110 WOODS LANDING TRAIL Oldsmar, FL Discover this beautifully updated townhome in the secluded Woods Landing community of East...	2 beds \| 3 baths \| 1,200 sq.ft.	$329,900	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.62% Airbnb Rental Income: $2376 Traditional Rental Income: $2245 Airbnb ROI: 2.15% Traditional ROI: 3.62%
163 BRENT CIRCLE Oldsmar, FL Nestled in a serene, small gated community, this exquisite waterfront townhouse offers the...	3 beds \| 3 baths \| 1,834 sq.ft.	$615,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 1.89% Airbnb Rental Income: $4254 Traditional Rental Income: $2620 Airbnb ROI: 3.17% Traditional ROI: 1.89%
321 SHORE DRIVE E Oldsmar, FL Under contract-accepting backup offers. OUTSTANDING INVESTMENT OPPORTUNITY. This FOUR be...	4 beds \| 2 baths \| 1,627 sq.ft.	$300,000	Airbnb cash on cash: 8.25% Traditional cash on cash: 7.82% Airbnb Rental Income: $3866 Traditional Rental Income: $2913 Airbnb ROI: 8.25% Traditional ROI: 7.82%
9009 PALM KEY AVENUE Oldsmar, FL HIGH AND DRY!! NO STORM SURGE /WATER DAMAGE TO HOME FROM HURRICANE HELENE!! Peace of mind ...	4 beds \| 3 baths \| 2,587 sq.ft.	$775,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 1.57% Airbnb Rental Income: $3866 Traditional Rental Income: $3073 Airbnb ROI: 1.51% Traditional ROI: 1.57%
516 ARLINGTON AVENUE E Oldsmar, FL * * DO NOT MISS OUT ON THIS SPECTACULAR POOL HOME * * MASSIVE CORNER LOT with plenty of ro...	3 beds \| 2 baths \| 1,657 sq.ft.	$534,900	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.84% Airbnb Rental Income: $4254 Traditional Rental Income: $2667 Airbnb ROI: 4.22% Traditional ROI: 2.84%
1862 E LAKE WOODLANDS PARKWAY Oldsmar, FL Spectacular Private Setting. Gorgeous Newer Built Home in EastLake Woodlands. Set amid...	4 beds \| 3 baths \| 3,426 sq.ft.	$1,400,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 0.36% Airbnb Rental Income: $3866 Traditional Rental Income: $3354 Airbnb ROI: 0.12% Traditional ROI: 0.36%
130 LISA LANE Oldsmar, FL Enjoy gorgeous golf course views plus the privacy of a single family home without all of t...	2 beds \| 2 baths \| 1,590 sq.ft.	$399,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.59% Airbnb Rental Income: $2376 Traditional Rental Income: $2354 Airbnb ROI: 2.09% Traditional ROI: 3.59%
503 TANGERINE DRIVE Oldsmar, FL THIS HOUSE STOOD STRONG! WAS NOT DAMAGED DURING HURRICANE! NO WATER INTRUSION! Discover th...	3 beds \| 2 baths \| 1,539 sq.ft.	$424,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 3.98% Airbnb Rental Income: $4254 Traditional Rental Income: $2329 Airbnb ROI: 6.57% Traditional ROI: 3.98%
1719 MAPLELEAF BOULEVARD Oldsmar, FL Welcome to this beautifully maintained 2,040 sqft single-family home, offering the perfect...	3 beds \| 2 baths \| 2,040 sq.ft.	$525,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 3% Airbnb Rental Income: $4254 Traditional Rental Income: $2623 Airbnb ROI: 4.5% Traditional ROI: 3%
306 CONGRESS STREET Oldsmar, FL This impressive Oldsmar bungalow has distinctive curb appeal and charm with an oversized p...	3 beds \| 2 baths \| 1,037 sq.ft.	$382,500	Airbnb cash on cash: 7.44% Traditional cash on cash: 4.01% Airbnb Rental Income: $4254 Traditional Rental Income: $2125 Airbnb ROI: 7.44% Traditional ROI: 4.01%
320 VISTA CRUISER LANE Oldsmar, FL This Meticulously Kept 3 bedroom, 2.5 bath Detached Townhouse offers a Unique Blend of Mod...	3 beds \| 3 baths \| 1,445 sq.ft.	$450,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 2.76% Airbnb Rental Income: $4254 Traditional Rental Income: $2268 Airbnb ROI: 5.34% Traditional ROI: 2.76%
525 WOODS LANDING TRAIL Oldsmar, FL GATED East Lake Woodlands - Welcome Home! Beautiful 2 bedroom, 2 Â½ bathroom townhome with...	2 beds \| 3 baths \| 1,200 sq.ft.	$274,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 2.01% Airbnb Rental Income: $2376 Traditional Rental Income: $1947 Airbnb ROI: 1.41% Traditional ROI: 2.01%
637 JETSTAR LANE Oldsmar, FL One or more photo(s) has been virtually staged. Priced to SELL...Tastefully updated 3 bedr...	3 beds \| 3 baths \| 1,264 sq.ft.	$359,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 4.1% Airbnb Rental Income: $4254 Traditional Rental Income: $2279 Airbnb ROI: 7.3% Traditional ROI: 4.1%
325 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL If you're looking for a cozy, untouched haven post-hurricane, you've found it at 325 Count...	2 beds \| 2 baths \| 1,105 sq.ft.	$283,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 3.26% Airbnb Rental Income: $2376 Traditional Rental Income: $1884 Airbnb ROI: 2.91% Traditional ROI: 3.26%
201 ARLINGTON AVENUE E Oldsmar, FL Welcome to your dream home nestled in the heart of one of the most charming neighborhoods ...	3 beds \| 2 baths \| 1,636 sq.ft.	$410,000	Airbnb cash on cash: 5.99% Traditional cash on cash: 4.63% Airbnb Rental Income: $4254 Traditional Rental Income: $2832 Airbnb ROI: 5.99% Traditional ROI: 4.63%
4929 POINTE CIRCLE Oldsmar, FL * * * WHAT A GREAT OPPORTUNITY TO OWN THE ONLY 4,000 Sqft Plus HOME IN EAST LAKE WOODLAND ...	5 beds \| 5 baths \| 4,181 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $5721 Airbnb ROI: N/A Traditional ROI: 4.34%
284 HEMINGWAY DRIVE Oldsmar, FL No storm issues from Hurricane Helene or Milton. Many updates throughout this townhome hav...	3 beds \| 3 baths \| 1,604 sq.ft.	$389,900	Airbnb cash on cash: 5.89% Traditional cash on cash: 3.01% Airbnb Rental Income: $4254 Traditional Rental Income: $2305 Airbnb ROI: 5.89% Traditional ROI: 3.01%
152 CYPRESS LANE #152 Oldsmar, FL One or more photo(s) has been virtually staged. Welcome Home! Enjoy this 2 Bedroom, 2 Bath...	2 beds \| 2 baths \| 1,053 sq.ft.	$199,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 4.33% Airbnb Rental Income: $2376 Traditional Rental Income: $1784 Airbnb ROI: 4.36% Traditional ROI: 4.33%
310 JEFFERSON AVENUE S Oldsmar, FL Under contract-accepting backup offers. NEW CONSTRUCTION HOME THAT IS HIGH & DRY! Perfectl...	4 beds \| 3 baths \| 2,655 sq.ft.	$796,500	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.43% Airbnb Rental Income: $3866 Traditional Rental Income: $2833 Airbnb ROI: 2.7% Traditional ROI: 2.43%
1010 STATE STREET E Oldsmar, FL Welcome to 1010 State St E in Oldsmar, FL, a stunning home that was built in 1982. This th...	3 beds \| 4 baths \| 2,506 sq.ft.	$759,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 3.33% Airbnb Rental Income: $4254 Traditional Rental Income: $4083 Airbnb ROI: 2.31% Traditional ROI: 3.33%
208 CLAYS TRAIL #208 Oldsmar, FL Under contract-accepting backup offers. Beautifully updated condo in East Lake Woodlands w...	3 beds \| 2 baths \| 1,835 sq.ft.	$439,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 3.81% Airbnb Rental Income: $4254 Traditional Rental Income: $2410 Airbnb ROI: 6.11% Traditional ROI: 3.81%
320 MICHAELS CIRCLE Oldsmar, FL Welcome to East Lake Woodlands! Discover this exquisite corner unit villa, boasting a semi...	2 beds \| 2 baths \| 1,200 sq.ft.	$285,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.98% Airbnb Rental Income: $2376 Traditional Rental Income: $1944 Airbnb ROI: 2.41% Traditional ROI: 2.98%
1203 SAWGRASS COURT Oldsmar, FL One or more photo(s) has been virtually staged. * Property was not affected at all from th...	3 beds \| 2 baths \| 1,307 sq.ft.	$419,900	Airbnb cash on cash: 5.9% Traditional cash on cash: 2.78% Airbnb Rental Income: $4254 Traditional Rental Income: $2129 Airbnb ROI: 5.9% Traditional ROI: 2.78%
270 PINEWINDS BOULEVARD Oldsmar, FL LIVE LIFE WITHOUT WORRY! Welcome home to the immensely sought after East Lake Woodlands co...	2 beds \| 2 baths \| 1,320 sq.ft.	$343,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 1.4% Airbnb Rental Income: $2376 Traditional Rental Income: $2037 Airbnb ROI: 0.64% Traditional ROI: 1.4%
108 WOODLANDS COURT #108 Oldsmar, FL This adorable 2nd floor, 2 bedroom, 2 bathroom condo in the guarded/gated community of Eas...	2 beds \| 2 baths \| 1,151 sq.ft.	$205,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 6.95% Airbnb Rental Income: $2376 Traditional Rental Income: $1861 Airbnb ROI: 6.59% Traditional ROI: 6.95%
205 BENGAL CIRCLE Oldsmar, FL HIGH AND DRY! This home has never flooded. Elevation certificate available. Oldsmar is cer...	4 beds \| 3 baths \| 2,733 sq.ft.	$885,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 1.77% Airbnb Rental Income: $3866 Traditional Rental Income: $2950 Airbnb ROI: 1.87% Traditional ROI: 1.77%
199 BENGAL CIRCLE Oldsmar, FL High and Dry - No Flooding Has Affected This Property. Welcome to your new sanctuary! This...	3 beds \| 2 baths \| 2,235 sq.ft.	$685,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 3.68% Airbnb Rental Income: $4254 Traditional Rental Income: $3678 Airbnb ROI: 3.17% Traditional ROI: 3.68%
602 LEMONWOOD DRIVE Oldsmar, FL Adorable home in great neighborhood. NO HURRICANE or FLOOD DAMAGE. Home features SPLIT B...	3 beds \| 2 baths \| 1,572 sq.ft.	$350,000	Airbnb cash on cash: 7.75% Traditional cash on cash: 4.67% Airbnb Rental Income: $4254 Traditional Rental Income: $2342 Airbnb ROI: 7.75% Traditional ROI: 4.67%

Real Estate investment in Oldsmar, FL

There are 134 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $349,450 and the average price per square foot is $214. In November 2024, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,232.

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

There are 134 investment properties available for sale in Oldsmar.

In 2024, 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 $3,866.

Your search for investment property begins and ends here

Investment Property for Sale in Oldsmar, FL

90 CAMELIA COURT

Oldsmar, FL

4 beds | 2 baths | 2,288 sq.ft.

$715,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 2.14%

Airbnb Rental Income: $3866

Traditional Rental Income: $3176

Airbnb ROI: 1.92%

Traditional ROI: 2.14%

1807 SPLIT FORK DRIVE

Oldsmar, FL

3 beds | 3 baths | 2,173 sq.ft.

$575,000

Airbnb cash on cash: 4.91%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $4254

Traditional Rental Income: $3630

Airbnb ROI: 4.91%

Traditional ROI: 5.42%

2002 SHEFFIELD COURT

Oldsmar, FL

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

$284,900

Airbnb cash on cash: 4.31%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $2376

Traditional Rental Income: $1995

Airbnb ROI: 4.31%

Traditional ROI: 5.07%

167 LAKEVIEW WAY #167

Oldsmar, FL

2 beds | 2 baths | 1,094 sq.ft.

$256,000

Airbnb cash on cash: 5.47%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $2376

Traditional Rental Income: $1904

Airbnb ROI: 5.47%

Traditional ROI: 5.93%

632 LAKE CYPRESS CIRCLE

Oldsmar, FL

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

$576,900

Airbnb cash on cash: 3.45%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $3866

Traditional Rental Income: $2911

Airbnb ROI: 3.45%

Traditional ROI: 3.22%

10 AUSTIN PLACE #10

Oldsmar, FL

2 beds | 2 baths | 1,525 sq.ft.

$279,727

Airbnb cash on cash: 4.12%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $2376

Traditional Rental Income: $2272

Airbnb ROI: 4.12%

Traditional ROI: 5.94%

60 BALSAM DRIVE

Oldsmar, FL

2 beds | 2 baths | 1,250 sq.ft.

$350,000

Airbnb cash on cash: 2.13%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2376

Traditional Rental Income: $1958

Airbnb ROI: 2.13%

Traditional ROI: 2.63%

2014 MONTEGO COURT

Oldsmar, FL

2 beds | 2 baths | 1,143 sq.ft.

$299,900

Airbnb cash on cash: 4.3%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $2376

Traditional Rental Income: $1926

Airbnb ROI: 4.3%