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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
505 OAKWOOD BOULEVARD Oldsmar, FL Welcome to this CHARMING HOME tucked away on a quiet, divided street in BEAUTIFUL DOWNTOWN...	4 beds \| 2 baths \| 1,993 sq.ft.	$449,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.89% Airbnb Rental Income: $1908 Traditional Rental Income: $2944 Airbnb ROI: 1.22% Traditional ROI: 4.89%
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: 2.65% Airbnb Rental Income: $1908 Traditional Rental Income: $3466 Airbnb ROI: -0.51% Traditional ROI: 2.65%
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: 1.27% Airbnb Rental Income: $1908 Traditional Rental Income: $2684 Airbnb ROI: -0.4% Traditional ROI: 1.27%
1909 CASTLE BAY COURT Oldsmar, FL --GREAT CURB APPEAL--Discover this IMMACULATE 3-bedroom, 2-bath home with garage located o...	3 beds \| 2 baths \| 1,410 sq.ft.	$387,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.4% Airbnb Rental Income: $1381 Traditional Rental Income: $2304 Airbnb ROI: 0.7% Traditional ROI: 4.4%
646 TIMBER BAY CIRCLE W Oldsmar, FL NEW PRICE - EXCELLENT VALUE - LOCATION - LOCATION - LOCATION - LOVE WHERE YOU LIVE - ONE S...	3 beds \| 2 baths \| 1,554 sq.ft.	$389,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 4.57% Airbnb Rental Income: $1381 Traditional Rental Income: $2570 Airbnb ROI: 0.16% Traditional ROI: 4.57%
648 TIMBER BAY CIRCLE E Oldsmar, FL END OF YEAR PRICE REDUCTION-Discover your own slice of paradise with this beautifully upda...	4 beds \| 2 baths \| 1,253 sq.ft.	$369,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.45% Airbnb Rental Income: $1908 Traditional Rental Income: $2426 Airbnb ROI: 1.49% Traditional ROI: 4.45%
220 BAY ARBOR BOULEVARD Oldsmar, FL Welcome to 220 Bay Arbor Blvd! Located in the gated Bay Arbor community, this renovated 3 ...	3 beds \| 2 baths \| 2,026 sq.ft.	$595,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 2.42% Airbnb Rental Income: $1381 Traditional Rental Income: $2623 Airbnb ROI: -0.57% Traditional ROI: 2.42%
4954 TURTLE CREEK TRAIL Oldsmar, FL Welcome to this exceptional Costanza custom-built home, perfectly situated on over one acr...	5 beds \| 4 baths \| 4,144 sq.ft.	$1,389,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.47% Airbnb Rental Income: $2554 Traditional Rental Income: $3535 Airbnb ROI: -0.76% Traditional ROI: 0.47%
40 GRETCHEN COURT Oldsmar, FL SELLER FINANCING WITH ACCEPTABLE OFFER! Step through the front door of this charming vill...	2 beds \| 2 baths \| 1,502 sq.ft.	$338,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.5% Airbnb Rental Income: $1396 Traditional Rental Income: $2203 Airbnb ROI: -0.36% Traditional ROI: 3.5%
35 PINEWINDS BOULEVARD Oldsmar, FL VERY DESIRABLE GATED COMMUNITY OF EAST LAKE WOODLANDS, CORNER VILLA has VIEWS OF POND. Vil...	2 beds \| 2 baths \| 1,053 sq.ft.	$388,000	Airbnb cash on cash: -1.42% Traditional cash on cash: 1.06% Airbnb Rental Income: $1396 Traditional Rental Income: $1876 Airbnb ROI: -1.42% Traditional ROI: 1.06%
1558 E LAKE WOODLANDS PARKWAY Oldsmar, FL Set on an exceptional oversized wooded corner lot, nearly half an acre, this elegant Ruten...	3 beds \| 2 baths \| 2,366 sq.ft.	$743,900	Airbnb cash on cash: -1.34% Traditional cash on cash: 1.27% Airbnb Rental Income: $1381 Traditional Rental Income: $2771 Airbnb ROI: -1.34% Traditional ROI: 1.27%
4729 PEBBLE BROOK DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Discover a rare opportunity to own a home ...	2 beds \| 2 baths \| 1,959 sq.ft.	$559,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 1.67% Airbnb Rental Income: $1396 Traditional Rental Income: $2425 Airbnb ROI: -1.1% Traditional ROI: 1.67%
206 BEDFORD STREET Oldsmar, FL Short Sale. This beautifully updated, single-level home offers a smart, open layout with 3...	3 beds \| 2 baths \| 1,274 sq.ft.	$369,700	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.03% Airbnb Rental Income: $1381 Traditional Rental Income: $2189 Airbnb ROI: 0.49% Traditional ROI: 4.03%
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: 3.62% Airbnb Rental Income: $1908 Traditional Rental Income: $4153 Airbnb ROI: 0.34% Traditional ROI: 3.62%
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.	$1,475,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.37% Airbnb Rental Income: $1908 Traditional Rental Income: $3597 Airbnb ROI: -1.23% Traditional ROI: 0.37%
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: 3.02% Airbnb Rental Income: $1908 Traditional Rental Income: $4974 Airbnb ROI: -0.31% Traditional ROI: 3.02%
603 SHORE DRIVE E Oldsmar, FL One or more photo(s) has been virtually staged. This exceptional 3-bedroom, 2-bathroom poo...	3 beds \| 2 baths \| 1,722 sq.ft.	$485,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.96% Airbnb Rental Income: $1381 Traditional Rental Income: $2987 Airbnb ROI: -0.51% Traditional ROI: 3.96%
110 DEERPATH DRIVE Oldsmar, FL Simply sensational in prestigious Deerpath of East Lake Woodlands!! Waltz through double l...	5 beds \| 4 baths \| 4,246 sq.ft.	$1,199,900	Airbnb cash on cash: -0.47% Traditional cash on cash: 2.23% Airbnb Rental Income: $2554 Traditional Rental Income: $4958 Airbnb ROI: -0.47% Traditional ROI: 2.23%
210 LEE STREET Oldsmar, FL One or more photo(s) has been virtually staged. Experience the perfect blend of modern com...	3 beds \| 3 baths \| 2,094 sq.ft.	$435,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 6.46% Airbnb Rental Income: $1381 Traditional Rental Income: $3290 Airbnb ROI: 0.75% Traditional ROI: 6.46%
311 SHORE DRIVE E Oldsmar, FL Under APPRAISED VALUE! Waterfront Luxury Meets Complete Modern Renovation in this Gem in E...	3 beds \| 2 baths \| 1,632 sq.ft.	$424,500	Airbnb cash on cash: 0.04% Traditional cash on cash: 4.56% Airbnb Rental Income: $1381 Traditional Rental Income: $2761 Airbnb ROI: 0.04% Traditional ROI: 4.56%
602 DARTMOUTH AVENUE E Oldsmar, FL MOTIVATED SELLER. Immediate occupancy available! Exceptional opportunity in the heart of O...	5 beds \| 4 baths \| 2,930 sq.ft.	$700,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.23% Airbnb Rental Income: $2554 Traditional Rental Income: $3903 Airbnb ROI: 1.22% Traditional ROI: 4.23%
20 SYLVIA PLACE Oldsmar, FL One or more photo(s) has been virtually staged. This is a 4-bedroom, 2-bath villa in a gat...	4 beds \| 2 baths \| 1,550 sq.ft.	$319,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 5.6% Airbnb Rental Income: $1908 Traditional Rental Income: $2790 Airbnb ROI: 0.97% Traditional ROI: 5.6%
303 SHORE DRIVE W Oldsmar, FL IMPROVED PRICE! BRING ALL OFFERS. WATER VIEWS! On over 1/3 of an Acre of Land! Property to...	2 beds \| 2 baths \| 1,106 sq.ft.	$365,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.12% Airbnb Rental Income: $1396 Traditional Rental Income: $2037 Airbnb ROI: 0.01% Traditional ROI: 3.12%
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%
394 FOUNTAINVIEW CIRCLE Oldsmar, FL LOCATION LOCATION LOCATION! - NO FLOOD ZONE HIGH AND DRY - Check out and view this THREE B...	3 beds \| 2 baths \| 1,714 sq.ft.	$599,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 2.93% Airbnb Rental Income: $1381 Traditional Rental Income: $2772 Airbnb ROI: -0.3% Traditional ROI: 2.93%
316 COUNTRY CLUB DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. Welcome home to this beautifully preserved...	3 beds \| 2 baths \| 1,344 sq.ft.	$355,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 5.59% Airbnb Rental Income: $1381 Traditional Rental Income: $2344 Airbnb ROI: 1.44% Traditional ROI: 5.59%
4886 WESTCHESTER COURT Oldsmar, FL Looking for PRIVACY and STUNNING WATER VIEWS with NO FRONT OR REAR NEIGHBORS? Discover the...	3 beds \| 2 baths \| 1,920 sq.ft.	$569,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.02% Airbnb Rental Income: $1381 Traditional Rental Income: $2885 Airbnb ROI: -0.6% Traditional ROI: 3.02%
531 CANAL WAY Oldsmar, FL CHARMING WATERFRONT HOME WITH NATURE VIEWS This home has remained untouched by recent hurr...	2 beds \| 2 baths \| 1,226 sq.ft.	$374,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 3.32% Airbnb Rental Income: $1396 Traditional Rental Income: $2035 Airbnb ROI: 0.31% Traditional ROI: 3.32%
288 MOBBLY BAY DRIVE Oldsmar, FL Luxury living with an abundance of privacy, amazing views, an open floor plan, and ample c...	4 beds \| 6 baths \| 5,260 sq.ft.	$1,650,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.34% Airbnb Rental Income: $1908 Traditional Rental Income: $7971 Airbnb ROI: -0.95% Traditional ROI: 3.34%
3087 DUANE AVENUE Oldsmar, FL HIGH AND DRY! THIS HOME NEVER FLOODED! Welcome to this charming, move-in-ready home offeri...	3 beds \| 2 baths \| 1,296 sq.ft.	$389,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.46% Airbnb Rental Income: $1381 Traditional Rental Income: $2103 Airbnb ROI: 0.33% Traditional ROI: 3.46%
412 PINEWOOD DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to this exquisite Florida home where tranq...	4 beds \| 2 baths \| 2,430 sq.ft.	$499,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.21% Airbnb Rental Income: $1908 Traditional Rental Income: $2911 Airbnb ROI: 0.98% Traditional ROI: 4.21%
116 SHORE DRIVE PLACE Oldsmar, FL Auction Property. AUCTION! Sold free and clear of all liens. Listing price is the opening ...	3 beds \| 2 baths \| 2,148 sq.ft.	$650,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 3.62% Airbnb Rental Income: $1381 Traditional Rental Income: $3201 Airbnb ROI: -0.07% Traditional ROI: 3.62%
4859 AUGUSTA AVENUE Oldsmar, FL This fully updated home features 4-bedrooms + bonus room (possible 5th bedroom), 2.5-bathr...	4 beds \| 3 baths \| 3,085 sq.ft.	$799,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.16% Airbnb Rental Income: $1908 Traditional Rental Income: $3846 Airbnb ROI: -0.12% Traditional ROI: 3.16%
1522 RIVERDALE DRIVE Oldsmar, FL Under contract-accepting backup offers. NEW PRICE ALERT - Owners Just Reduced $30,000 to S...	2 beds \| 2 baths \| 2,355 sq.ft.	$565,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 2.58% Airbnb Rental Income: $1396 Traditional Rental Income: $2927 Airbnb ROI: -1.12% Traditional ROI: 2.58%
235 WOODRIDGE CIRCLE Oldsmar, FL This warm and inviting one-story villa is ready for its' next owner - could that be you? ...	3 beds \| 2 baths \| 1,666 sq.ft.	$389,900	Airbnb cash on cash: -2.26% Traditional cash on cash: 1.79% Airbnb Rental Income: $1381 Traditional Rental Income: $2440 Airbnb ROI: -2.26% Traditional ROI: 1.79%
1751 SPLIT FORK DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. New Photos! Freshly painted on the interio...	5 beds \| 3 baths \| 2,952 sq.ft.	$624,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.88% Airbnb Rental Income: $2554 Traditional Rental Income: $3914 Airbnb ROI: 0.5% Traditional ROI: 3.88%
311 VISTA CRUISER LANE Oldsmar, FL This stunning 3-bedroom, 2.5-bath home offers the perfect blend of style, comfort, and pea...	3 beds \| 3 baths \| 1,547 sq.ft.	$375,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 3.5% Airbnb Rental Income: $1381 Traditional Rental Income: $2284 Airbnb ROI: -0.25% Traditional ROI: 3.5%
1801 FOREST DRIVE Oldsmar, FL Under contract-accepting backup offers. Welcome to 1801 Forest Drive â Your Florida Retr...	3 beds \| 2 baths \| 1,673 sq.ft.	$394,900	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.13% Airbnb Rental Income: $1381 Traditional Rental Income: $2653 Airbnb ROI: 0.56% Traditional ROI: 5.13%
302 COCO PLUM COURT Oldsmar, FL Welcome to 302 Coco Plum Court, a beautifully designed home in the sought-after Estuary of...	5 beds \| 5 baths \| 4,664 sq.ft.	$1,450,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 2.28% Airbnb Rental Income: $2554 Traditional Rental Income: $5914 Airbnb ROI: -0.67% Traditional ROI: 2.28%

Your search for investment property begins and ends here

Single Family Homes for Sale in Oldsmar, FL

505 OAKWOOD BOULEVARD

Oldsmar, FL

4 beds | 2 baths | 1,993 sq.ft.

$449,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $1908

Traditional Rental Income: $2944

Airbnb ROI: 1.22%

Traditional ROI: 4.89%

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: 2.65%

Airbnb Rental Income: $1908

Traditional Rental Income: $3466

Airbnb ROI: -0.51%

Traditional ROI: 2.65%

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: 1.27%

Airbnb Rental Income: $1908

Traditional Rental Income: $2684

Airbnb ROI: -0.4%

Traditional ROI: 1.27%

1909 CASTLE BAY COURT

Oldsmar, FL

3 beds | 2 baths | 1,410 sq.ft.

$387,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $1381

Traditional Rental Income: $2304

Airbnb ROI: 0.7%

Traditional ROI: 4.4%

646 TIMBER BAY CIRCLE W

Oldsmar, FL

3 beds | 2 baths | 1,554 sq.ft.

$389,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 4.57%

Airbnb Rental Income: $1381

Traditional Rental Income: $2570

Airbnb ROI: 0.16%

Traditional ROI: 4.57%

648 TIMBER BAY CIRCLE E

Oldsmar, FL

4 beds | 2 baths | 1,253 sq.ft.

$369,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 4.45%

Airbnb Rental Income: $1908

Traditional Rental Income: $2426

Airbnb ROI: 1.49%

Traditional ROI: 4.45%

220 BAY ARBOR BOULEVARD

Oldsmar, FL

3 beds | 2 baths | 2,026 sq.ft.

$595,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $1381

Traditional Rental Income: $2623

Airbnb ROI: -0.57%