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
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%
1203 CLAYS TRAIL #406 Oldsmar, FL OUTSTANDING BLACK FRIDAY/CYBER MONDAY PRICING!! 1203 Clays Trail #406 nestled in the highl...	2 beds \| 2 baths \| 1,910 sq.ft.	$299,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 7.23% Airbnb Rental Income: $1396 Traditional Rental Income: $2600 Airbnb ROI: 1.46% Traditional ROI: 7.23%
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%
107 MARY DRIVE #107 Oldsmar, FL One or more photo(s) has been virtually staged. Move-In Ready Ground Floor Condo in Gated ...	2 beds \| 2 baths \| 1,094 sq.ft.	$199,500	Airbnb cash on cash: 1.77% Traditional cash on cash: 6.15% Airbnb Rental Income: $1396 Traditional Rental Income: $1804 Airbnb ROI: 1.77% Traditional ROI: 6.15%
152 BRENT CIRCLE Oldsmar, FL Welcome to Seaside Estates, a gated waterfront community tucked along the peninsula of Old...	3 beds \| 3 baths \| 1,791 sq.ft.	$550,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.04% Airbnb Rental Income: $1381 Traditional Rental Income: $2664 Airbnb ROI: -1.27% Traditional ROI: 2.04%
112 BRENT CIRCLE Oldsmar, FL Welcome to this beautifully updated, move-in ready townhome offering private, upscale wate...	3 beds \| 3 baths \| 1,834 sq.ft.	$525,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.97% Airbnb Rental Income: $1381 Traditional Rental Income: $2535 Airbnb ROI: -1.24% Traditional ROI: 1.97%
315 WOODS LANDING TRAIL Oldsmar, FL Completely updated, water view townhome within the 24hr guard gated, golf cart friendly, c...	2 beds \| 3 baths \| 1,200 sq.ft.	$319,900	Airbnb cash on cash: -1.55% Traditional cash on cash: 1.71% Airbnb Rental Income: $1396 Traditional Rental Income: $1956 Airbnb ROI: -1.55% Traditional ROI: 1.71%
124 NINA WAY #24 Oldsmar, FL Welcome Home! This renovated condo is simply beautiful! Located in the premier golf comm...	2 beds \| 2 baths \| 1,094 sq.ft.	$204,900	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.83% Airbnb Rental Income: $1396 Traditional Rental Income: $1817 Airbnb ROI: -0.51% Traditional ROI: 3.83%
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%
163 BRENT CIRCLE Oldsmar, FL Deeded Boat Slip with Lift Nestled in a serene, small gated community, this exquisite...	3 beds \| 3 baths \| 1,834 sq.ft.	$545,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 2.12% Airbnb Rental Income: $1381 Traditional Rental Income: $2620 Airbnb ROI: -1.14% Traditional ROI: 2.12%
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%
9009 PALM KEY AVENUE Oldsmar, FL Experience elevated WATERFRONT LIVING in this beautifully upgraded townhome located within...	4 beds \| 3 baths \| 2,587 sq.ft.	$695,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 1.64% Airbnb Rental Income: $1908 Traditional Rental Income: $3073 Airbnb ROI: -0.94% Traditional ROI: 1.64%
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%
291 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Welcome to the highly sought-after gated community of Countryside Key, ideally located in ...	2 beds \| 3 baths \| 1,110 sq.ft.	$265,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 2.67% Airbnb Rental Income: $1396 Traditional Rental Income: $1834 Airbnb ROI: -0.76% Traditional ROI: 2.67%
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%
100 INGRID PLACE Oldsmar, FL Under contract-accepting backup offers. Motivated Sellers!! You won't find another 3 BED a...	3 beds \| 3 baths \| 1,755 sq.ft.	$285,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 4.78% Airbnb Rental Income: $1381 Traditional Rental Income: $2484 Airbnb ROI: -0.89% Traditional ROI: 4.78%
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%
106 CUTLASS WAY Oldsmar, FL Fully updated and move-in ready 3-bedroom, 2.5-bath townhome in highly desirable Hayes Par...	3 beds \| 3 baths \| 1,365 sq.ft.	$365,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.06% Airbnb Rental Income: $1381 Traditional Rental Income: $2156 Airbnb ROI: -0.43% Traditional ROI: 3.06%
129 BRENT CIRCLE Oldsmar, FL MOTIVATED SELLER - WATERVIEWS from All 3 Floors, This UPDATED 3Bed 3Bath townhome is situa...	3 beds \| 3 baths \| 1,834 sq.ft.	$569,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 2.48% Airbnb Rental Income: $1381 Traditional Rental Income: $2705 Airbnb ROI: -0.8% Traditional ROI: 2.48%
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%
238 PELICAN DRIVE N Oldsmar, FL This home is in highly desirable 55+ Gull-Aire Village! This beautifully updated Palm Harb...	2 beds \| 2 baths \| 1,286 sq.ft.	$225,900	Airbnb cash on cash: 1.81% Traditional cash on cash: 7.02% Airbnb Rental Income: $1396 Traditional Rental Income: $2088 Airbnb ROI: 1.81% Traditional ROI: 7.02%
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%
278 PELICAN DRIVE N Oldsmar, FL Don't miss this desirable and very active community of Gull-Aire Village! This is one of t...	2 beds \| 2 baths \| 1,128 sq.ft.	$195,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 7.52% Airbnb Rental Income: $1396 Traditional Rental Income: $1948 Airbnb ROI: 2.26% Traditional ROI: 7.52%
2313 SUNSET WIND LOOP Oldsmar, FL Experience coastal luxury and step into a lifestyle of refinement in this stunning 3-bedro...	3 beds \| 3 baths \| 2,230 sq.ft.	$445,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 3.72% Airbnb Rental Income: $1381 Traditional Rental Income: $3063 Airbnb ROI: -1.32% Traditional ROI: 3.72%
62 EMERALD BAY DRIVE Oldsmar, FL Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 B...	2 beds \| 3 baths \| 1,264 sq.ft.	$245,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.64% Airbnb Rental Income: $1396 Traditional Rental Income: $1996 Airbnb ROI: 0.23% Traditional ROI: 4.64%

Real Estate investment in Oldsmar, FL

There are 134 properties for sale in the city of Oldsmar . The median list price in Oldsmar is $386,000 and the average price per square foot is $210. In January 2026, the average monthly cash on cash return in Oldsmar is 4.00%. The average monthly rental income in Oldsmar is $2,254.

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

There are 134 investment properties available for sale in Oldsmar.

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

The ROI for Short-Term is higher than the Long-Term in Oldsmar with average rental income of $1,396.

Your search for investment property begins and ends here

Investment Property 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%

1203 CLAYS TRAIL #406

Oldsmar, FL

2 beds | 2 baths | 1,910 sq.ft.

$299,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 7.23%

Airbnb Rental Income: $1396

Traditional Rental Income: $2600

Airbnb ROI: 1.46%

Traditional ROI: 7.23%

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%

107 MARY DRIVE #107

Oldsmar, FL

2 beds | 2 baths | 1,094 sq.ft.

$199,500

Airbnb cash on cash: 1.77%

Traditional cash on cash: 6.15%

Airbnb Rental Income: $1396

Traditional Rental Income: $1804

Airbnb ROI: 1.77%

Traditional ROI: 6.15%

152 BRENT CIRCLE

Oldsmar, FL

3 beds | 3 baths | 1,791 sq.ft.

$550,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $1381

Traditional Rental Income: $2664

Airbnb ROI: -1.27%