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 96 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
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%
219 BAY ARBOR BOULEVARD Oldsmar, FL Mrs. Clean lived here!! This beautiful home is ready for its new owners! Vaulted ceilings ...	4 beds \| 3 baths \| 1,873 sq.ft.	$560,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 2.47% Airbnb Rental Income: $1908 Traditional Rental Income: $2757 Airbnb ROI: -0.12% Traditional ROI: 2.47%
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%
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%
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%
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%
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%
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%
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%
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%
504 FEDERAL STREET Oldsmar, FL This stunning new three-story residence by Danva Construction perfectly blends modern luxu...	4 beds \| 4 baths \| 2,961 sq.ft.	$1,270,000	Airbnb cash on cash: 0% Traditional cash on cash: 2.94% Airbnb Rental Income: $1908 Traditional Rental Income: $4873 Airbnb ROI: 0% Traditional ROI: 2.94%
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: 0.34% Traditional cash on cash: 4.01% Airbnb Rental Income: $1908 Traditional Rental Income: $4479 Airbnb ROI: 0.34% Traditional ROI: 4.01%
1730 OAK POND COURT Oldsmar, FL Under contract-accepting backup offers. Price Improvement.! Tucked inside the desirable Ea...	3 beds \| 3 baths \| 1,918 sq.ft.	$584,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.95% Airbnb Rental Income: $1381 Traditional Rental Income: $2966 Airbnb ROI: -0.72% Traditional ROI: 2.95%
501 LAKEVIEW DRIVE Oldsmar, FL Fabulous...Location! Location! Location! This stunning pool home in the sought after commu...	3 beds \| 2 baths \| 1,667 sq.ft.	$499,900	Airbnb cash on cash: -0.08% Traditional cash on cash: 5.2% Airbnb Rental Income: $1381 Traditional Rental Income: $3431 Airbnb ROI: -0.08% Traditional ROI: 5.2%
347 COUNTRY CLUB DRIVE Oldsmar, FL "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Po...	3 beds \| 2 baths \| 1,280 sq.ft.	$429,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 6.07% Airbnb Rental Income: $1381 Traditional Rental Income: $3077 Airbnb ROI: 0.81% Traditional ROI: 6.07%
316 SHORE DRIVE E Oldsmar, FL Wake up to million-dollar views, and unwind with spectacular sunsets - this is the waterfr...	4 beds \| 3 baths \| 2,496 sq.ft.	$1,469,999	Airbnb cash on cash: -1.23% Traditional cash on cash: 1.66% Airbnb Rental Income: $1908 Traditional Rental Income: $5349 Airbnb ROI: -1.23% Traditional ROI: 1.66%
432 COUNTRY CLUB DRIVE Oldsmar, FL Tucked inside a quiet neighborhood, but only one street away from the magnificent Tampa ba...	3 beds \| 3 baths \| 1,936 sq.ft.	$475,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 8.39% Airbnb Rental Income: $1381 Traditional Rental Income: $4597 Airbnb ROI: 0.21% Traditional ROI: 8.39%
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.	$1,299,000	Airbnb cash on cash: -1.06% Traditional cash on cash: 1.95% Airbnb Rental Income: $1908 Traditional Rental Income: $5038 Airbnb ROI: -1.06% Traditional ROI: 1.95%
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: -0.31% Traditional cash on cash: 5.43% Airbnb Rental Income: $1908 Traditional Rental Income: $7562 Airbnb ROI: -0.31% Traditional ROI: 5.43%
30 TURTLE CREEK CIRCLE Oldsmar, FL A Rare Find for the discriminating buyer! Stunning is the word to describe the updating th...	4 beds \| 3 baths \| 2,850 sq.ft.	$1,075,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 1.97% Airbnb Rental Income: $1908 Traditional Rental Income: $4639 Airbnb ROI: -1.27% Traditional ROI: 1.97%
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: -0.47% Traditional cash on cash: 4.24% Airbnb Rental Income: $2554 Traditional Rental Income: $7193 Airbnb ROI: -0.47% Traditional ROI: 4.24%
311 SHORE DRIVE E Oldsmar, FL Under contract-accepting backup offers. BACK ON THE MARKET â Buyerâs Financing Fell Th...	3 beds \| 2 baths \| 1,632 sq.ft.	$399,900	Airbnb cash on cash: 0.1% Traditional cash on cash: 6.08% Airbnb Rental Income: $1381 Traditional Rental Income: $3205 Airbnb ROI: 0.1% Traditional ROI: 6.08%
405 SHORE DRIVE E Oldsmar, FL Welcome to this beautifully updated 3-bedroom, 2-bath pool home with water views, located ...	3 beds \| 2 baths \| 1,864 sq.ft.	$484,900	Airbnb cash on cash: 0.09% Traditional cash on cash: 6.53% Airbnb Rental Income: $1381 Traditional Rental Income: $3887 Airbnb ROI: 0.09% Traditional ROI: 6.53%
2159 WARWICK DRIVE Oldsmar, FL It's time to buy in Eastlake Woodlands! Settle in to your dream home in the coveted subdi...	4 beds \| 3 baths \| 2,673 sq.ft.	$800,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.3% Airbnb Rental Income: $1908 Traditional Rental Income: $4807 Airbnb ROI: -0.27% Traditional ROI: 4.3%
40 SYLVIA PLACE Oldsmar, FL Welcome to this exceptional 3-bedroom villa located in the fabulous East Lake Woodlands co...	3 beds \| 2 baths \| 1,385 sq.ft.	$299,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 4.31% Airbnb Rental Income: $1381 Traditional Rental Income: $2592 Airbnb ROI: -1.48% Traditional ROI: 4.31%
335 PALMDALE DRIVE Oldsmar, FL Under contract-accepting backup offers. Step into timeless elegance and modern comfort in ...	5 beds \| 3 baths \| 3,035 sq.ft.	$799,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.08% Airbnb Rental Income: $2554 Traditional Rental Income: $3619 Airbnb ROI: -0.17% Traditional ROI: 2.08%
1811 FOREST DRIVE Oldsmar, FL Recently updated pool home located in Oldsmar with an open living room and dining room tha...	3 beds \| 2 baths \| 2,142 sq.ft.	$475,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 5.86% Airbnb Rental Income: $1381 Traditional Rental Income: $3768 Airbnb ROI: -0.46% Traditional ROI: 5.86%

Your search for investment property begins and ends here

Single Family Homes 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%

219 BAY ARBOR BOULEVARD

Oldsmar, FL

4 beds | 3 baths | 1,873 sq.ft.

$560,000

Airbnb cash on cash: -0.12%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1908

Traditional Rental Income: $2757

Airbnb ROI: -0.12%

Traditional ROI: 2.47%

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%