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
3858 SHORE BOULEVARD Oldsmar, FL Experience the laid back lifestyle of Oldsmar, a sought-after community nestled between th...	3 beds \| 2 baths \| 1,594 sq.ft.	$1,150,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 0.6% Airbnb Rental Income: $6169 Traditional Rental Income: $2617 Airbnb ROI: 2.78% Traditional ROI: 0.6%
436 LAFAYETTE BOULEVARD Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mu...	4 beds \| 3 baths \| 2,695 sq.ft.	$700,000	Airbnb cash on cash: 8.14% Traditional cash on cash: 3.77% Airbnb Rental Income: $8687 Traditional Rental Income: $4193 Airbnb ROI: 8.14% Traditional ROI: 3.77%
1007 STATE STREET E Oldsmar, FL Under contract-accepting backup offers. Tucked away beneath majestic oak trees on over an ...	4 beds \| 3 baths \| 2,379 sq.ft.	$695,000	Airbnb cash on cash: 8.89% Traditional cash on cash: 3.5% Airbnb Rental Income: $8687 Traditional Rental Income: $3559 Airbnb ROI: 8.89% Traditional ROI: 3.5%
360 S WOODLANDS DRIVE Oldsmar, FL Welcome to 360 S Woodlands Drive, a beautifully renovated 2-bedroom, 2-bath patio home nes...	2 beds \| 2 baths \| 1,590 sq.ft.	$414,900	Airbnb cash on cash: 5.79% Traditional cash on cash: 2.45% Airbnb Rental Income: $4556 Traditional Rental Income: $2310 Airbnb ROI: 5.79% Traditional ROI: 2.45%
1471 BRIARGROVE WAY Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Li...	5 beds \| 4 baths \| 3,140 sq.ft.	$899,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $6000 Airbnb ROI: N/A Traditional ROI: 4.65%
112 BRENT CIRCLE Oldsmar, FL Under contract-accepting backup offers. PRICE IMPROVEMENT! LUXURY MEETS UNBEATABLE VALUE. ...	3 beds \| 3 baths \| 1,834 sq.ft.	$499,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 2.47% Airbnb Rental Income: $6169 Traditional Rental Income: $2697 Airbnb ROI: 7.3% Traditional ROI: 2.47%
9009 PALM KEY AVENUE Oldsmar, FL Searching for a low-maintenance waterfront escape in Tampa Bay? Whether youâre looking f...	4 beds \| 3 baths \| 2,587 sq.ft.	$649,900	Airbnb cash on cash: 8.38% Traditional cash on cash: 2.85% Airbnb Rental Income: $8687 Traditional Rental Income: $3694 Airbnb ROI: 8.38% Traditional ROI: 2.85%
137 BRENT CIRCLE Oldsmar, FL Set within a gated, waterfront community in Oldsmar, this expansive townhouse at 137 Brent...	3 beds \| 2 baths \| 2,309 sq.ft.	$749,900	Airbnb cash on cash: 4.51% Traditional cash on cash: 1.39% Airbnb Rental Income: $6169 Traditional Rental Income: $2776 Airbnb ROI: 4.51% Traditional ROI: 1.39%
2013 SUNSET WIND LOOP Oldsmar, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the heart of Oldsma...	3 beds \| 3 baths \| 1,667 sq.ft.	$400,000	Airbnb cash on cash: 9% Traditional cash on cash: 3.19% Airbnb Rental Income: $6169 Traditional Rental Income: $2773 Airbnb ROI: 9% Traditional ROI: 3.19%
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.	$384,000	Airbnb cash on cash: 9.69% Traditional cash on cash: 3.64% Airbnb Rental Income: $6169 Traditional Rental Income: $2773 Airbnb ROI: 9.69% Traditional ROI: 3.64%
10 ARBOR LANE Oldsmar, FL Beautiful 4-bedroom, 2-bathroom pool home on a corner lot with views of the 5th hole in Ea...	4 beds \| 2 baths \| 2,318 sq.ft.	$669,000	Airbnb cash on cash: 8.54% Traditional cash on cash: 2.34% Airbnb Rental Income: $8687 Traditional Rental Income: $3177 Airbnb ROI: 8.54% Traditional ROI: 2.34%
5163 PINNACLE DRIVE Oldsmar, FL Under contract-accepting backup offers. Offering over $23,000 in upgrades! Located in X Fl...	3 beds \| 2 baths \| 1,886 sq.ft.	$635,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 1.14% Airbnb Rental Income: $6169 Traditional Rental Income: $2622 Airbnb ROI: 5.07% Traditional ROI: 1.14%
3133 HURON AVENUE Oldsmar, FL Amazing opportunity to purchase a duplex with potential assumable financing at an attracti...	6 beds \| N/A baths \| 1,978 sq.ft.	$499,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 2.62% Airbnb Rental Income: $4556 Traditional Rental Income: $2317 Airbnb ROI: 5.38% Traditional ROI: 2.62%
20 EVELYN COURT Oldsmar, FL PRICE IMPROVEMENT! - Tucked within the gated community of East Lake Woodlands, this beaut...	2 beds \| 2 baths \| 1,380 sq.ft.	$249,000	Airbnb cash on cash: 9.77% Traditional cash on cash: 3.56% Airbnb Rental Income: $4556 Traditional Rental Income: $2147 Airbnb ROI: 9.77% Traditional ROI: 3.56%
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: 7.09% Traditional cash on cash: 4.01% Airbnb Rental Income: $8687 Traditional Rental Income: $4479 Airbnb ROI: 7.09% Traditional ROI: 4.01%
10 LESLEY LANE Oldsmar, FL Virtually Staged. Welcome to 10 Lesley Lane, located in the gated community of Quail Fores...	2 beds \| 2 baths \| 1,250 sq.ft.	$295,000	Airbnb cash on cash: 8.55% Traditional cash on cash: 2.57% Airbnb Rental Income: $4556 Traditional Rental Income: $1946 Airbnb ROI: 8.55% Traditional ROI: 2.57%
375 WELLINGTON AVENUE Oldsmar, FL Welcome to your modern dream homeâcompletely reimagined with a full 2024 designer remode...	4 beds \| 3 baths \| 2,624 sq.ft.	$1,280,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 1.99% Airbnb Rental Income: $8687 Traditional Rental Income: $5038 Airbnb ROI: 3.69% Traditional ROI: 1.99%
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: 4.95% Traditional cash on cash: 5.43% Airbnb Rental Income: $8687 Traditional Rental Income: $7562 Airbnb ROI: 4.95% Traditional ROI: 5.43%
110 DEERPATH DRIVE Oldsmar, FL Simply sensational in prestigious Deerpath of East Lake Woodlands!! Enter through double l...	5 beds \| 4 baths \| 4,246 sq.ft.	$1,199,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $7193 Airbnb ROI: N/A Traditional ROI: 4.24%
370 S WOODLANDS DRIVE Oldsmar, FL Virtually Staged some photos. Price Reduction!! Attention all Golfers and Tennis players ...	2 beds \| 2 baths \| 1,500 sq.ft.	$369,999	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.38% Airbnb Rental Income: $4556 Traditional Rental Income: $2485 Airbnb ROI: 6.61% Traditional ROI: 3.38%
140 BRENT CIRCLE Oldsmar, FL Seller Motivated! Asking price is under last appraisal value. Come take a look at this be...	3 beds \| 3 baths \| 1,791 sq.ft.	$565,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 2.5% Airbnb Rental Income: $6169 Traditional Rental Income: $2794 Airbnb ROI: 6.59% Traditional ROI: 2.5%
165 MOBBLY BAY DRIVE Oldsmar, FL Wow!! Picture perfect model home located in the exclusive gated community of âEstuary of...	5 beds \| 4 baths \| 3,945 sq.ft.	$1,124,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.21% Airbnb Rental Income: $null Traditional Rental Income: $6574 Airbnb ROI: N/A Traditional ROI: 4.21%
317 SHORE DRIVE E Oldsmar, FL STUNNING TAMPA BAY VIEWS! UPDATED OLDSMAR SPLIT-LEVEL WITH RV/BOAT PAD! Breathtaking Ta...	3 beds \| 2 baths \| 1,660 sq.ft.	$484,700	Airbnb cash on cash: 8.3% Traditional cash on cash: 4.07% Airbnb Rental Income: $6169 Traditional Rental Income: $3036 Airbnb ROI: 8.3% Traditional ROI: 4.07%
1505 SUNSET WIND LOOP Oldsmar, FL This beautiful townhouse (NEVER FLOODED) is located in the highly desirable waterfront gat...	3 beds \| 3 baths \| 1,667 sq.ft.	$380,000	Airbnb cash on cash: 9.47% Traditional cash on cash: 3.7% Airbnb Rental Income: $6169 Traditional Rental Income: $2894 Airbnb ROI: 9.47% Traditional ROI: 3.7%
2328 WARWICK DRIVE Oldsmar, FL PRICE ADJUSTMENT! Make an offer now, so you can get settled in over the summer! Welcome to...	4 beds \| 4 baths \| 3,294 sq.ft.	$829,000	Airbnb cash on cash: 7.14% Traditional cash on cash: 7.32% Airbnb Rental Income: $8687 Traditional Rental Income: $7188 Airbnb ROI: 7.14% Traditional ROI: 7.32%
1534 E LAKE WOODLANDS PARKWAY Oldsmar, FL Under contract-accepting backup offers. Welcome to this fully remodeled 4 bedroom (4th bed...	4 beds \| 4 baths \| 3,402 sq.ft.	$1,249,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 2.09% Airbnb Rental Income: $8687 Traditional Rental Income: $4566 Airbnb ROI: 4.23% Traditional ROI: 2.09%
1384 FORESTEDGE BOULEVARD Oldsmar, FL Under contract-accepting backup offers. Welcome to refined Florida living in the highly so...	4 beds \| 3 baths \| 2,814 sq.ft.	$699,000	Airbnb cash on cash: 7.36% Traditional cash on cash: 4.09% Airbnb Rental Income: $8687 Traditional Rental Income: $4921 Airbnb ROI: 7.36% Traditional ROI: 4.09%
190 Water Oak Way Oldsmar, FL Experience the perfect blend of elegance, comfort, and breathtaking views in this exceptio...	3 beds \| 3 baths \| 2,061 sq.ft.	$660,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 4.88% Airbnb Rental Income: $6169 Traditional Rental Income: $4624 Airbnb ROI: 5.41% Traditional ROI: 4.88%
4007 PALM KEY AVENUE Oldsmar, FL Walk in the front door and look straight out to the water. Head out to the screened-in bac...	4 beds \| 3 baths \| 2,587 sq.ft.	$629,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 2.87% Airbnb Rental Income: $8687 Traditional Rental Income: $3695 Airbnb ROI: 8.58% Traditional ROI: 2.87%
380 ROSALIND LANE Oldsmar, FL Virtually Staged. Welcome to your private retreat in the gated community of Bay Arbor! Nes...	3 beds \| 3 baths \| 2,423 sq.ft.	$619,999	Airbnb cash on cash: 6.43% Traditional cash on cash: 4.16% Airbnb Rental Income: $6169 Traditional Rental Income: $3634 Airbnb ROI: 6.43% Traditional ROI: 4.16%
2151 DIAMOND COURT Oldsmar, FL Welcome to 2151 Diamond Court ~ Where luxury meets everyday comfort and style. This beauti...	4 beds \| 3 baths \| 3,850 sq.ft.	$1,350,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.45% Airbnb Rental Income: $8687 Traditional Rental Income: $5440 Airbnb ROI: 3.73% Traditional ROI: 2.45%
116 BRENT CIRCLE Oldsmar, FL Elevated Gated Community. WATERFRONT 3 bedrooms, 3 full baths plus a tandem 2-3 car garage...	3 beds \| 3 baths \| 1,834 sq.ft.	$450,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 2.79% Airbnb Rental Income: $6169 Traditional Rental Income: $2858 Airbnb ROI: 7.76% Traditional ROI: 2.79%
50 WILLOWOOD LANE Oldsmar, FL **4 Bedrooms + Office + Flex Room (Potential 6th Bedroom) \| Private Entrance to Flex Space...	5 beds \| 5 baths \| 4,172 sq.ft.	$1,499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $7707 Airbnb ROI: N/A Traditional ROI: 3.7%
408 LAKEVIEW DRIVE Oldsmar, FL Price Reduced - This lakefront, pool home overlooks stunning sunsets and a wooded conserva...	3 beds \| 2 baths \| 1,598 sq.ft.	$480,000	Airbnb cash on cash: 8.96% Traditional cash on cash: 6.55% Airbnb Rental Income: $6169 Traditional Rental Income: $3866 Airbnb ROI: 8.96% Traditional ROI: 6.55%
387 TAVERNIER CIRCLE Oldsmar, FL Under contract-accepting backup offers. You've found your Florida dream home in the heart ...	3 beds \| 2 baths \| 1,808 sq.ft.	$459,900	Airbnb cash on cash: 9.58% Traditional cash on cash: 5.35% Airbnb Rental Income: $6169 Traditional Rental Income: $3134 Airbnb ROI: 9.58% Traditional ROI: 5.35%
600 S WOODLANDS DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. This beautifully updated 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,952 sq.ft.	$399,000	Airbnb cash on cash: 9.34% Traditional cash on cash: 3.58% Airbnb Rental Income: $6169 Traditional Rental Income: $2799 Airbnb ROI: 9.34% Traditional ROI: 3.58%
435 LAKEVIEW DRIVE Oldsmar, FL Welcome to Forest Lakes and this beautifully appointed, immaculately maintained 3-bedroom,...	3 beds \| 2 baths \| 1,570 sq.ft.	$475,000	Airbnb cash on cash: 8.45% Traditional cash on cash: 4.92% Airbnb Rental Income: $6169 Traditional Rental Income: $3380 Airbnb ROI: 8.45% Traditional ROI: 4.92%
1004 MANGO COURT Oldsmar, FL Under contract-accepting backup offers. PRICED TO SELL Welcome to refined coastal livi...	3 beds \| 3 baths \| 2,230 sq.ft.	$499,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 2.65% Airbnb Rental Income: $6169 Traditional Rental Income: $2865 Airbnb ROI: 7.12% Traditional ROI: 2.65%
1795 BAYHILL DRIVE Oldsmar, FL This unique home exudes character and is located on a peaceful conservation lot with no re...	2 beds \| 2 baths \| 1,844 sq.ft.	$539,900	Airbnb cash on cash: 3.98% Traditional cash on cash: 1.64% Airbnb Rental Income: $4556 Traditional Rental Income: $2427 Airbnb ROI: 3.98% Traditional ROI: 1.64%
138 BRENT CIRCLE Oldsmar, FL Welcome to 138 Brent Circle in desirable gated Seaside Estatesâan exceptional opportunit...	4 beds \| 3 baths \| 2,258 sq.ft.	$725,000	Airbnb cash on cash: 7.14% Traditional cash on cash: 1.32% Airbnb Rental Income: $8687 Traditional Rental Income: $3114 Airbnb ROI: 7.14% Traditional ROI: 1.32%

Real Estate investment in Oldsmar, FL

There are 56 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $419,649 and the average price per square foot is $248. In July 2026, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,283.

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

There are 56 investment properties available for sale in Oldsmar.

In 2026, the best neighborhood to buy investment property is Oldsmar.

The ROI for Long-Term is higher than the Short-Term in Oldsmar with average rental income of $2,283.

Your search for investment property begins and ends here

Investment Property for Sale in Oldsmar, FL

3858 SHORE BOULEVARD

Oldsmar, FL

3 beds | 2 baths | 1,594 sq.ft.

$1,150,000

Airbnb cash on cash: 2.78%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $6169

Traditional Rental Income: $2617

Airbnb ROI: 2.78%

Traditional ROI: 0.6%

436 LAFAYETTE BOULEVARD

Oldsmar, FL

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

$700,000

Airbnb cash on cash: 8.14%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $8687

Traditional Rental Income: $4193

Airbnb ROI: 8.14%

Traditional ROI: 3.77%

1007 STATE STREET E

Oldsmar, FL

4 beds | 3 baths | 2,379 sq.ft.

$695,000

Airbnb cash on cash: 8.89%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $8687

Traditional Rental Income: $3559

Airbnb ROI: 8.89%

Traditional ROI: 3.5%

360 S WOODLANDS DRIVE

Oldsmar, FL

2 beds | 2 baths | 1,590 sq.ft.

$414,900

Airbnb cash on cash: 5.79%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $4556

Traditional Rental Income: $2310

Airbnb ROI: 5.79%

Traditional ROI: 2.45%

1471 BRIARGROVE WAY

Oldsmar, FL

5 beds | 4 baths | 3,140 sq.ft.

$899,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $6000

Airbnb ROI: N/A

Traditional ROI: 4.65%

112 BRENT CIRCLE

Oldsmar, FL

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

$499,000

Airbnb cash on cash: 7.3%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6169

Traditional Rental Income: $2697

Airbnb ROI: 7.3%

Traditional ROI: 2.47%

9009 PALM KEY AVENUE

Oldsmar, FL

4 beds | 3 baths | 2,587 sq.ft.

$649,900

Airbnb cash on cash: 8.38%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $8687

Traditional Rental Income: $3694

Airbnb ROI: 8.38%

Traditional ROI: 2.85%

137 BRENT CIRCLE

Oldsmar, FL

3 beds | 2 baths | 2,309 sq.ft.

$749,900

Airbnb cash on cash: 4.51%

Traditional cash on cash: 1.39%

Airbnb Rental Income: $6169

Traditional Rental Income: $2776

Airbnb ROI: 4.51%