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 Welcome to this stunningly spacious and well-maintained pool home nestled in one of the mo...	3 beds \| 2 baths \| 1,658 sq.ft.	$475,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 3.39% Airbnb Rental Income: $3329 Traditional Rental Income: $2555 Airbnb ROI: 3.46% Traditional ROI: 3.39%
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.	$560,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 5.59% Airbnb Rental Income: $3329 Traditional Rental Income: $3630 Airbnb ROI: 3.59% Traditional ROI: 5.59%
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: 4.39% Traditional cash on cash: 5.07% Airbnb Rental Income: $2403 Traditional Rental Income: $1995 Airbnb ROI: 4.39% Traditional ROI: 5.07%
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: 4.2% Traditional cash on cash: 5.94% Airbnb Rental Income: $2403 Traditional Rental Income: $2272 Airbnb ROI: 4.2% Traditional ROI: 5.94%
1251 CLAYS TRAIL Oldsmar, FL Under contract-accepting backup offers. RARE OPPORTUNITY to own in Laurel Oaks at East Lak...	3 beds \| 3 baths \| 2,500 sq.ft.	$420,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 4.09% Airbnb Rental Income: $3329 Traditional Rental Income: $3227 Airbnb ROI: 2.46% Traditional ROI: 4.09%
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.	$295,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 5.21% Airbnb Rental Income: $2403 Traditional Rental Income: $2092 Airbnb ROI: 4.21% Traditional ROI: 5.21%
60 BALSAM DRIVE Oldsmar, FL Under contract-accepting backup offers. I welcome to your next home in the exclusive, gate...	2 beds \| 2 baths \| 1,250 sq.ft.	$350,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 2.63% Airbnb Rental Income: $2403 Traditional Rental Income: $1958 Airbnb ROI: 2.19% Traditional ROI: 2.63%
4953 EDGEWATER LANE Oldsmar, FL Situated within East Lake Woodlands' desirable Worthington subdivision, this beautiful 3-b...	3 beds \| 2 baths \| 1,965 sq.ft.	$599,999	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.5% Airbnb Rental Income: $3329 Traditional Rental Income: $2709 Airbnb ROI: 2.28% Traditional ROI: 2.5%
390 CYPRESS CREEK CIRCLE Oldsmar, FL MUST SEE EAST LAKE WOODLANDS TREASURE! A LOVELY WATERFRONT, 4 BEDROOM, 2 1/2 BATH, 2 CAR G...	4 beds \| 3 baths \| 2,677 sq.ft.	$669,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 3.55% Airbnb Rental Income: $4558 Traditional Rental Income: $3839 Airbnb ROI: 3.18% Traditional ROI: 3.55%
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: 4.37% Traditional cash on cash: 4.77% Airbnb Rental Income: $2403 Traditional Rental Income: $1926 Airbnb ROI: 4.37% Traditional ROI: 4.77%
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.	$390,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.87% Airbnb Rental Income: $3329 Traditional Rental Income: $2412 Airbnb ROI: 3.34% Traditional ROI: 2.87%
155 NINA WAY Oldsmar, FL Relaxation Awaits in Your Private Patio Home with Serene Pond Views! This FEE SIMPLE Vill...	2 beds \| 2 baths \| 1,262 sq.ft.	$380,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.34% Airbnb Rental Income: $2403 Traditional Rental Income: $2024 Airbnb ROI: 1.75% Traditional ROI: 2.34%
1434 WOODSTREAM DRIVE Oldsmar, FL Under contract-accepting backup offers. Conservation Lot with Water View in Gated Communit...	3 beds \| 2 baths \| 1,596 sq.ft.	$500,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.35% Airbnb Rental Income: $3329 Traditional Rental Income: $2696 Airbnb ROI: 2.11% 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: 2.22% Traditional cash on cash: 3.62% Airbnb Rental Income: $2403 Traditional Rental Income: $2245 Airbnb ROI: 2.22% Traditional ROI: 3.62%
163 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. Nestled in a serene, small gated community, this e...	3 beds \| 3 baths \| 1,834 sq.ft.	$615,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 1.89% Airbnb Rental Income: $3329 Traditional Rental Income: $2620 Airbnb ROI: 1.83% Traditional ROI: 1.89%
140 HUNTER LAKE DRIVE #H Oldsmar, FL Welcome to this renovated and meticulously maintained second floor 2-bedroom condo. Enjoy ...	2 beds \| 2 baths \| 915 sq.ft.	$220,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.25% Airbnb Rental Income: $2403 Traditional Rental Income: $1802 Airbnb ROI: 4.3% Traditional ROI: 4.25%
9009 PALM KEY AVENUE Oldsmar, FL Owner decided to lease! 25K PRICE IMPROVEMENT! HIGH AND DRY!! NO STORM SURGE /WATER DAMAGE...	4 beds \| 3 baths \| 2,587 sq.ft.	$750,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 1.65% Airbnb Rental Income: $4558 Traditional Rental Income: $3073 Airbnb ROI: 2.42% Traditional ROI: 1.65%
516 ARLINGTON AVENUE E Oldsmar, FL Under contract-accepting backup offers. * * DO NOT MISS OUT ON THIS SPECTACULAR POOL HOME ...	3 beds \| 2 baths \| 1,657 sq.ft.	$534,900	Airbnb cash on cash: 2.68% Traditional cash on cash: 2.84% Airbnb Rental Income: $3329 Traditional Rental Income: $2667 Airbnb ROI: 2.68% 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: 0.56% Traditional cash on cash: 0.36% Airbnb Rental Income: $4558 Traditional Rental Income: $3354 Airbnb ROI: 0.56% 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.	$379,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 3.83% Airbnb Rental Income: $2403 Traditional Rental Income: $2354 Airbnb ROI: 2.31% Traditional ROI: 3.83%
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.	$419,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 4.04% Airbnb Rental Income: $3329 Traditional Rental Income: $2329 Airbnb ROI: 4.69% Traditional ROI: 4.04%
115 BRENT CIRCLE Oldsmar, FL Welcome to Your Dream Home: The Ultimate Waterfront Oasis in Oldsmar! Discover thi...	3 beds \| 3 baths \| 1,834 sq.ft.	$529,500	Airbnb cash on cash: 1.95% Traditional cash on cash: 1.99% Airbnb Rental Income: $3329 Traditional Rental Income: $2604 Airbnb ROI: 1.95% Traditional ROI: 1.99%
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.	$500,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.2% Airbnb Rental Income: $3329 Traditional Rental Income: $2623 Airbnb ROI: 3.12% Traditional ROI: 3.2%
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: 5.29% Traditional cash on cash: 4.01% Airbnb Rental Income: $3329 Traditional Rental Income: $2125 Airbnb ROI: 5.29% Traditional ROI: 4.01%
320 VISTA CRUISER LANE Oldsmar, FL THE SELLER REQUESTED AN $11,600.00 PRICE REDUCTION, On this Meticulously Kept 3 bedroom, 2...	3 beds \| 3 baths \| 1,445 sq.ft.	$438,400	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.85% Airbnb Rental Income: $3329 Traditional Rental Income: $2268 Airbnb ROI: 3.63% Traditional ROI: 2.85%
220 WOODLAKE WYNDE #220 Oldsmar, FL One or more photo(s) has been virtually staged. Stunning 2-bedroom 2-bath and yes 2-balcon...	2 beds \| 2 baths \| 924 sq.ft.	$229,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 6.32% Airbnb Rental Income: $2403 Traditional Rental Income: $2012 Airbnb ROI: 5.4% Traditional ROI: 6.32%
325 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Under contract-accepting backup offers. If you're looking for a cozy, untouched haven post...	2 beds \| 2 baths \| 1,105 sq.ft.	$279,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 3.32% Airbnb Rental Income: $2403 Traditional Rental Income: $1884 Airbnb ROI: 3.05% Traditional ROI: 3.32%
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.	$869,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $5721 Airbnb ROI: N/A Traditional ROI: 4.53%
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: 3.78% Traditional cash on cash: 3.01% Airbnb Rental Income: $3329 Traditional Rental Income: $2305 Airbnb ROI: 3.78% 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: 4.48% Traditional cash on cash: 4.33% Airbnb Rental Income: $2403 Traditional Rental Income: $1784 Airbnb ROI: 4.48% Traditional ROI: 4.33%
1906 CASTLE BAY COURT Oldsmar, FL NO FLOODING OR FLOOD DAMAGE. NO HOA. NO HOA FEES. Roof is only 2 years old! just replace...	4 beds \| 2 baths \| 1,410 sq.ft.	$444,999	Airbnb cash on cash: 6.26% Traditional cash on cash: 4.23% Airbnb Rental Income: $4558 Traditional Rental Income: $2765 Airbnb ROI: 6.26% Traditional ROI: 4.23%
129 CAMPHOR CIRCLE #F Oldsmar, FL Welcome to Your Cozy Oldsmar Retreat! This 2-bedroom, 2-bath condo in the desirable Garden...	2 beds \| 2 baths \| 915 sq.ft.	$189,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 6.83% Airbnb Rental Income: $2403 Traditional Rental Income: $1781 Airbnb ROI: 7.01% Traditional ROI: 6.83%
1203 SAWGRASS COURT Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. * ...	3 beds \| 2 baths \| 1,307 sq.ft.	$419,900	Airbnb cash on cash: 3.94% Traditional cash on cash: 2.78% Airbnb Rental Income: $3329 Traditional Rental Income: $2129 Airbnb ROI: 3.94% Traditional ROI: 2.78%
270 PINEWINDS BOULEVARD Oldsmar, FL Year round Sunshine, on the Golf Course, and Maintenance Free Living..:Sign me up! Find ...	2 beds \| 2 baths \| 1,320 sq.ft.	$329,900	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.37% Airbnb Rental Income: $2403 Traditional Rental Income: $2037 Airbnb ROI: 0.65% Traditional ROI: 1.37%
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: 6.7% Traditional cash on cash: 6.95% Airbnb Rental Income: $2403 Traditional Rental Income: $1861 Airbnb ROI: 6.7% Traditional ROI: 6.95%
208 WASHINGTON AVENUE Oldsmar, FL Welcome to this stunning NEW CONSTRUCTION, two-story, 2446 square foot single-family home ...	4 beds \| 4 baths \| 2,446 sq.ft.	$849,900	Airbnb cash on cash: 3.23% Traditional cash on cash: 1.35% Airbnb Rental Income: $4558 Traditional Rental Income: $2125 Airbnb ROI: 3.23% Traditional ROI: 1.35%
205 BENGAL CIRCLE Oldsmar, FL HIGH AND DRY! This home has never flooded. Elevation certificate available. Owners are rel...	4 beds \| 3 baths \| 2,733 sq.ft.	$885,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.77% Airbnb Rental Income: $4558 Traditional Rental Income: $2950 Airbnb ROI: 2.57% Traditional ROI: 1.77%
199 BENGAL CIRCLE Oldsmar, FL Under contract-accepting backup offers. High and Dry - No Flooding Has Affected This Prope...	3 beds \| 2 baths \| 2,235 sq.ft.	$685,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.68% Airbnb Rental Income: $3329 Traditional Rental Income: $3678 Airbnb ROI: 1.96% 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: 5.41% Traditional cash on cash: 4.67% Airbnb Rental Income: $3329 Traditional Rental Income: $2342 Airbnb ROI: 5.41% Traditional ROI: 4.67%
210 LEE STREET Oldsmar, FL Exceptional Value for Investors or Snowbirds! Discover this remarkable pool home in the he...	3 beds \| 3 baths \| 2,095 sq.ft.	$469,900	Airbnb cash on cash: 4.33% Traditional cash on cash: 5.94% Airbnb Rental Income: $3329 Traditional Rental Income: $3290 Airbnb ROI: 4.33% Traditional ROI: 5.94%

Real Estate investment in Oldsmar, FL

There are 143 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $379,000 and the average price per square foot is $228. In December 2024, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,245.

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

There are 143 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 $3,329.

Your search for investment property begins and ends here

Investment Property for Sale in Oldsmar, FL

502 TIMBER BAY CIRCLE E

Oldsmar, FL

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

$475,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $3329

Traditional Rental Income: $2555

Airbnb ROI: 3.46%

Traditional ROI: 3.39%

1807 SPLIT FORK DRIVE

Oldsmar, FL

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

$560,000

Airbnb cash on cash: 3.59%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $3329

Traditional Rental Income: $3630

Airbnb ROI: 3.59%

Traditional ROI: 5.59%

2002 SHEFFIELD COURT

Oldsmar, FL

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

$284,900

Airbnb cash on cash: 4.39%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $2403

Traditional Rental Income: $1995

Airbnb ROI: 4.39%

Traditional ROI: 5.07%

10 AUSTIN PLACE #10

Oldsmar, FL

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

$279,727

Airbnb cash on cash: 4.2%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $2403

Traditional Rental Income: $2272

Airbnb ROI: 4.2%

Traditional ROI: 5.94%

1251 CLAYS TRAIL

Oldsmar, FL

3 beds | 3 baths | 2,500 sq.ft.

$420,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $3329

Traditional Rental Income: $3227

Airbnb ROI: 2.46%

Traditional ROI: 4.09%

2044 SHEFFIELD COURT

Oldsmar, FL

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

$295,000

Airbnb cash on cash: 4.21%

Traditional cash on cash: 5.21%

Airbnb Rental Income: $2403

Traditional Rental Income: $2092

Airbnb ROI: 4.21%

Traditional ROI: 5.21%

60 BALSAM DRIVE

Oldsmar, FL

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

$350,000

Airbnb cash on cash: 2.19%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2403

Traditional Rental Income: $1958

Airbnb ROI: 2.19%

Traditional ROI: 2.63%

4953 EDGEWATER LANE

Oldsmar, FL

3 beds | 2 baths | 1,965 sq.ft.

$599,999

Airbnb cash on cash: 2.28%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $3329

Traditional Rental Income: $2709

Airbnb ROI: 2.28%