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.

Single Family Homes for Sale in Oldsmar, FL

Search for Single Family Residential for Sale in Oldsmar, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 42 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
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%
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%
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%
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%
2272 WARWICK DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to 2272 Warwick Driveâwhere timeless ele...	4 beds \| 3 baths \| 2,512 sq.ft.	$699,900	Airbnb cash on cash: 8.99% Traditional cash on cash: 3.86% Airbnb Rental Income: $8687 Traditional Rental Income: $3697 Airbnb ROI: 8.99% Traditional ROI: 3.86%
551 SALMON COURT Oldsmar, FL Under contract-accepting backup offers. Virtually Staged. Welcome to this well maintained ...	2 beds \| 2 baths \| 1,344 sq.ft.	$349,900	Airbnb cash on cash: 9.4% Traditional cash on cash: 5.07% Airbnb Rental Income: $4556 Traditional Rental Income: $2184 Airbnb ROI: 9.4% Traditional ROI: 5.07%
2034 MONTEGO COURT Oldsmar, FL Charming and low-maintenance 1-bedroom, 1-bath home tucked away on a quiet cul-de-sac in t...	1 beds \| 1 baths \| 1,024 sq.ft.	$220,000	Airbnb cash on cash: 8.96% Traditional cash on cash: 5% Airbnb Rental Income: $3108 Traditional Rental Income: $1576 Airbnb ROI: 8.96% Traditional ROI: 5%
3071 HURON AVENUE Oldsmar, FL Must see this amazing home in one of Oldsmar's best kept secret neighborhoods on the spark...	3 beds \| 3 baths \| 1,680 sq.ft.	$469,900	Airbnb cash on cash: 8.8% Traditional cash on cash: 2.87% Airbnb Rental Income: $6169 Traditional Rental Income: $2342 Airbnb ROI: 8.8% Traditional ROI: 2.87%
506 SHORE DRIVE E Oldsmar, FL Exceptional waterfront opportunity on one of Oldsmarâs most desirable streets. Situated ...	2 beds \| 2 baths \| 1,313 sq.ft.	$900,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 0.85% Airbnb Rental Income: $4556 Traditional Rental Income: $2563 Airbnb ROI: 2.1% Traditional ROI: 0.85%
355 VENTURA DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained and...	4 beds \| 2 baths \| 1,938 sq.ft.	$615,000	Airbnb cash on cash: 9.97% Traditional cash on cash: 2.61% Airbnb Rental Income: $8687 Traditional Rental Income: $2823 Airbnb ROI: 9.97% Traditional ROI: 2.61%
105 MOBBLY BAY DRIVE Oldsmar, FL Under contract-accepting backup offers. Discover an extraordinary tropical sanctuary withi...	5 beds \| 4 baths \| 3,941 sq.ft.	$1,224,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $4618 Airbnb ROI: N/A Traditional ROI: 2.06%
1623 GRAY BARK DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to 1623 Gray Bark Drive in the heart of Ol...	3 beds \| 2 baths \| 1,419 sq.ft.	$419,900	Airbnb cash on cash: 9.82% Traditional cash on cash: 3.05% Airbnb Rental Income: $6169 Traditional Rental Income: $2287 Airbnb ROI: 9.82% Traditional ROI: 3.05%
100 ARBOR LANE Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Mo...	3 beds \| 2 baths \| 1,852 sq.ft.	$570,000	Airbnb cash on cash: 7.31% Traditional cash on cash: 3.35% Airbnb Rental Income: $6169 Traditional Rental Income: $2842 Airbnb ROI: 7.31% Traditional ROI: 3.35%
412 SHORE DRIVE E Oldsmar, FL Unique opportunity to own a one-of-a-kind, beautiful property on Safety Harbour Bay with D...	5 beds \| 4 baths \| 4,454 sq.ft.	$2,700,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $6054 Airbnb ROI: N/A Traditional ROI: 0.82%
4856 WESTCHESTER COURT Oldsmar, FL Welcome to Kingsmill in the highly sought-after East Lake Woodlands community! This beauti...	3 beds \| 2 baths \| 2,184 sq.ft.	$589,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 3.09% Airbnb Rental Income: $6169 Traditional Rental Income: $3065 Airbnb ROI: 6.52% Traditional ROI: 3.09%
4878 SHERBROOK DRIVE Oldsmar, FL Come check out this 4 bed 3 bath 3 car garage pool home in the highly sought after East La...	4 beds \| 3 baths \| 2,730 sq.ft.	$650,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 4.1% Airbnb Rental Income: $8687 Traditional Rental Income: $3802 Airbnb ROI: 9.46% Traditional ROI: 4.1%

Your search for investment property begins and ends here

Single Family Homes 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%

10 ARBOR LANE

Oldsmar, FL

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

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%

20 EVELYN COURT

Oldsmar, FL

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%