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 91 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
438 LAFAYETTE BOULEVARD Oldsmar, FL Seller is offering $10,000 toward Buyers Closing Cost! Custom built home is situated on Â½...	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%
3858 SHORE BOULEVARD Oldsmar, FL Welcome to Oldsmar, the highly desirable Tampa Bay suburb offering a perfect blend of smal...	3 beds \| 2 baths \| 1,594 sq.ft.	$1,200,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.53% Airbnb Rental Income: $1381 Traditional Rental Income: $2617 Airbnb ROI: -0.95% Traditional ROI: 0.53%
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.	$550,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.53% Airbnb Rental Income: $1908 Traditional Rental Income: $2757 Airbnb ROI: -0.11% Traditional ROI: 2.53%
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 Under contract-accepting backup offers. NEW YEAR; NEW PRICE! Welcome to 382 Rosalind Ln., ...	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%
420 CYPRESS VIEW DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to your private slice of paradise in Oldsm...	3 beds \| 2 baths \| 1,870 sq.ft.	$485,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.1% Airbnb Rental Income: $1381 Traditional Rental Income: $2972 Airbnb ROI: -0.33% Traditional ROI: 4.1%
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.	$320,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 6.04% Airbnb Rental Income: $1396 Traditional Rental Income: $2361 Airbnb ROI: 1.43% Traditional ROI: 6.04%
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%
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 --SERIOUS SELLER-WILLING TO NEGOTIATE--SUBMIT YOUR OFFER ASAP-- Check out this BEAUTIFUL 3...	3 beds \| 2 baths \| 1,410 sq.ft.	$370,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 5.67% Airbnb Rental Income: $1381 Traditional Rental Income: $2662 Airbnb ROI: 0.78% Traditional ROI: 5.67%
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%
604 LIMETREE DRIVE Oldsmar, FL If you love the beauty of Floridaâs outdoors, this home is a must-see. Just a short walk...	3 beds \| 3 baths \| 1,430 sq.ft.	$375,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.24% Airbnb Rental Income: $1381 Traditional Rental Income: $2225 Airbnb ROI: 0.65% Traditional ROI: 4.24%
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.	$440,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.14% Airbnb Rental Income: $1381 Traditional Rental Income: $2326 Airbnb ROI: -0.17% Traditional ROI: 3.14%
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: -0.2% Traditional cash on cash: 4.65% Airbnb Rental Income: $2554 Traditional Rental Income: $6000 Airbnb ROI: -0.2% Traditional ROI: 4.65%
1912 CUTTY BAY COURT Oldsmar, FL Must see this beautiful 3 bedroom, 2 bathroom, 1 car garage pool home ideally situated in ...	3 beds \| 2 baths \| 1,080 sq.ft.	$325,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 5.16% Airbnb Rental Income: $1381 Traditional Rental Income: $2192 Airbnb ROI: 1.14% Traditional ROI: 5.16%
948 LUCAS LANE Oldsmar, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ar...	3 beds \| 2 baths \| 1,685 sq.ft.	$475,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 3.97% Airbnb Rental Income: $1381 Traditional Rental Income: $3320 Airbnb ROI: -1.34% Traditional ROI: 3.97%
160 JAMES COURT Oldsmar, FL One or more photo(s) has been virtually staged. Fantastic Price - Welcome to this beautifu...	3 beds \| 2 baths \| 1,445 sq.ft.	$350,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 2.37% Airbnb Rental Income: $1381 Traditional Rental Income: $2253 Airbnb ROI: -1.56% Traditional ROI: 2.37%
1204 FORESTWOOD DRIVE Oldsmar, FL Picture yourself at 1204 Forestwood Dr, a residence recently refreshed with fresh interior...	3 beds \| 2 baths \| 1,186 sq.ft.	$315,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 4.83% Airbnb Rental Income: $1381 Traditional Rental Income: $2105 Airbnb ROI: 0.97% Traditional ROI: 4.83%
382 FOUNTAINVIEW CIRCLE Oldsmar, FL Under contract-accepting backup offers. Price Adjustment! Welcome home to this stunning, ...	4 beds \| 2 baths \| 1,875 sq.ft.	$509,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.13% Airbnb Rental Income: $1908 Traditional Rental Income: $2650 Airbnb ROI: 0.51% Traditional ROI: 3.13%
634 TIMBER BAY CIRCLE W Oldsmar, FL Under contract-accepting backup offers. Motivated Seller! Move-In Ready Oldsmar Home! Welc...	3 beds \| 2 baths \| 1,056 sq.ft.	$321,500	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.65% Airbnb Rental Income: $1381 Traditional Rental Income: $2503 Airbnb ROI: 0.56% Traditional ROI: 5.65%
368 TAVERNIER CIRCLE Oldsmar, FL BRAND NEW AIR CONDITIONER! GRADE A SCHOOL DISTRICT! COMPLETELY REMODELLED. WELL APPOINTED....	4 beds \| 2 baths \| 1,880 sq.ft.	$585,000	Airbnb cash on cash: 0% Traditional cash on cash: 2.91% Airbnb Rental Income: $1908 Traditional Rental Income: $2993 Airbnb ROI: 0% Traditional ROI: 2.91%
5163 PINNACLE DRIVE Oldsmar, FL Offering over $23,000 in upgrades! Located in X Flood Zone with no flood insurance require...	3 beds \| 2 baths \| 1,886 sq.ft.	$635,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 1.14% Airbnb Rental Income: $1381 Traditional Rental Income: $2622 Airbnb ROI: -1.66% Traditional ROI: 1.14%
2031 DOVER COURT Oldsmar, FL Short Sale. Welcome to your peaceful retreat! This beautifully updated 2-bedroom, 2-bathro...	2 beds \| 2 baths \| 1,215 sq.ft.	$265,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.45% Airbnb Rental Income: $1396 Traditional Rental Income: $2025 Airbnb ROI: 0.25% Traditional ROI: 4.45%
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.	$1,180,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.24% Airbnb Rental Income: $1908 Traditional Rental Income: $4873 Airbnb ROI: 0.08% Traditional ROI: 3.24%
20 EVELYN COURT Oldsmar, FL Tucked within the gated community of East Lake Woodlands, this beautifully refreshed 2-bed...	2 beds \| 2 baths \| 1,380 sq.ft.	$259,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 3.38% Airbnb Rental Income: $1396 Traditional Rental Income: $2147 Airbnb ROI: -1.41% Traditional ROI: 3.38%
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%
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%
10 LESLEY LANE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to 10 Lesley Lane, located in the ...	2 beds \| 2 baths \| 1,250 sq.ft.	$299,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.52% Airbnb Rental Income: $1396 Traditional Rental Income: $1946 Airbnb ROI: -0.93% Traditional ROI: 2.52%
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%
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%
2159 WARWICK DRIVE Oldsmar, FL Under contract-accepting backup offers. It's time to buy in Eastlake Woodlands! Settle in...	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 Under contract-accepting backup offers. NEW PRICE!! Welcome to this exceptional 3-bedroom...	3 beds \| 2 baths \| 1,385 sq.ft.	$289,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 4.49% Airbnb Rental Income: $1381 Traditional Rental Income: $2592 Airbnb ROI: -1.5% Traditional ROI: 4.49%
307 COUNTRY CLUB DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. HONEY STOP THE CAR! THIS IS THE ONE! LOCAT...	3 beds \| 2 baths \| 1,670 sq.ft.	$349,950	Airbnb cash on cash: 0.63% Traditional cash on cash: 6.54% Airbnb Rental Income: $1381 Traditional Rental Income: $2904 Airbnb ROI: 0.63% Traditional ROI: 6.54%
343 SHORE DRIVE E Oldsmar, FL Some photos have be virtually staged. Beautifully renovated 3 bedroom 2 bath in desirable...	3 beds \| 2 baths \| 1,169 sq.ft.	$399,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.79% Airbnb Rental Income: $1381 Traditional Rental Income: $2133 Airbnb ROI: 0.66% Traditional ROI: 3.79%
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: -0.98% Traditional cash on cash: 3.38% Airbnb Rental Income: $1396 Traditional Rental Income: $2485 Airbnb ROI: -0.98% Traditional ROI: 3.38%
311 VISTA CRUISER LANE Oldsmar, FL What else could you want ... This charming 3-bedroom, 2.5-bath home offers the perfect ble...	3 beds \| 3 baths \| 1,547 sq.ft.	$350,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 5.29% Airbnb Rental Income: $1381 Traditional Rental Income: $2768 Airbnb ROI: -0.2% Traditional ROI: 5.29%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oldsmar, FL

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%

3858 SHORE BOULEVARD

Oldsmar, FL

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

$1,200,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 0.53%

Airbnb Rental Income: $1381

Traditional Rental Income: $2617

Airbnb ROI: -0.95%

Traditional ROI: 0.53%

219 BAY ARBOR BOULEVARD

Oldsmar, FL

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

$550,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $1908

Traditional Rental Income: $2757

Airbnb ROI: -0.11%

Traditional ROI: 2.53%

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%

420 CYPRESS VIEW DRIVE

Oldsmar, FL

3 beds | 2 baths | 1,870 sq.ft.

$485,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $1381

Traditional Rental Income: $2972

Airbnb ROI: -0.33%

Traditional ROI: 4.1%

1705 IRONWOOD COURT E

Oldsmar, FL

2 beds | 2 baths | 1,206 sq.ft.

$320,000

Airbnb cash on cash: 1.43%

Traditional cash on cash: 6.04%

Airbnb Rental Income: $1396

Traditional Rental Income: $2361

Airbnb ROI: 1.43%