Real Estate Investments for Sale in Oldsmar, FL With High ROI

Are you looking for a vacation rental in Oldsmar, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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.

Townhouses for Sale in Oldsmar, FL

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

Showing 22 Townhouse 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
110 WOODS LANDING TRAIL Oldsmar, FL Discover this beautifully updated townhome in the secluded Woods Landing community of East...	2 beds \| 3 baths \| 1,200 sq.ft.	$329,900	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.1% Airbnb Rental Income: $2376 Traditional Rental Income: $2085 Airbnb ROI: 2.15% Traditional ROI: 3.1%
163 BRENT CIRCLE Oldsmar, FL Nestled in a serene, small gated community, this exquisite waterfront townhouse offers the...	3 beds \| 3 baths \| 1,834 sq.ft.	$615,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 1.71% Airbnb Rental Income: $4254 Traditional Rental Income: $2517 Airbnb ROI: 3.17% Traditional ROI: 1.71%
9009 PALM KEY AVENUE Oldsmar, FL HIGH AND DRY!! NO STORM SURGE /WATER DAMAGE TO HOME FROM HURRICANE HELENE!! Peace of mind ...	4 beds \| 3 baths \| 2,587 sq.ft.	$775,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 1.31% Airbnb Rental Income: $3866 Traditional Rental Income: $2883 Airbnb ROI: 1.51% Traditional ROI: 1.31%
525 WOODS LANDING TRAIL Oldsmar, FL GATED East Lake Woodlands - Welcome Home! Beautiful 2 bedroom, 2 Â½ bathroom townhome with...	2 beds \| 3 baths \| 1,200 sq.ft.	$279,900	Airbnb cash on cash: 1.37% Traditional cash on cash: 2.17% Airbnb Rental Income: $2376 Traditional Rental Income: $2003 Airbnb ROI: 1.37% Traditional ROI: 2.17%
325 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL If you're looking for a cozy, untouched haven post-hurricane, you've found it at 325 Count...	2 beds \| 2 baths \| 1,105 sq.ft.	$283,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 3.49% Airbnb Rental Income: $2376 Traditional Rental Income: $1944 Airbnb ROI: 2.91% Traditional ROI: 3.49%
284 HEMINGWAY DRIVE Oldsmar, FL This end unit townhome has a private fenced back yard area. Enjoy pond views from your scr...	3 beds \| 3 baths \| 1,604 sq.ft.	$389,900	Airbnb cash on cash: 5.89% Traditional cash on cash: 2.77% Airbnb Rental Income: $4254 Traditional Rental Income: $2216 Airbnb ROI: 5.89% Traditional ROI: 2.77%
252 HEMINGWAY DRIVE Oldsmar, FL Under contract-accepting backup offers. This townhome is sure to check all the must have b...	3 beds \| 3 baths \| 1,604 sq.ft.	$399,800	Airbnb cash on cash: 6.2% Traditional cash on cash: 3.59% Airbnb Rental Income: $4254 Traditional Rental Income: $2380 Airbnb ROI: 6.2% Traditional ROI: 3.59%
1706 AZALEA COURT #A Oldsmar, FL One or more photo(s) has been virtually staged. Welcome to this beautiful home that combin...	2 beds \| 3 baths \| 1,360 sq.ft.	$275,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 5.25% Airbnb Rental Income: $2376 Traditional Rental Income: $1802 Airbnb ROI: 5.21% Traditional ROI: 5.25%
360 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Under contract-accepting backup offers. Welcome to this well-maintained home with a mainte...	2 beds \| 3 baths \| 1,110 sq.ft.	$278,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 2.02% Airbnb Rental Income: $2376 Traditional Rental Income: $1730 Airbnb ROI: 2.25% Traditional ROI: 2.02%
1171 CLAYS TRAIL Oldsmar, FL This 2,700 sq ft East Lake Woodlands beauty held up to Helene and Milton with absolutely n...	3 beds \| 3 baths \| 2,700 sq.ft.	$425,000	Airbnb cash on cash: 5.53% Traditional cash on cash: 5.08% Airbnb Rental Income: $4254 Traditional Rental Income: $3177 Airbnb ROI: 5.53% Traditional ROI: 5.08%
2313 SUNSET WIND LOOP Oldsmar, FL Welcome to this exquisite 3-bedroom, 2.5-bath deluxe townhome located in the exclusive gat...	3 beds \| 3 baths \| 2,230 sq.ft.	$495,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.84% Airbnb Rental Income: $4254 Traditional Rental Income: $2800 Airbnb ROI: 4.04% Traditional ROI: 2.84%
2503 ARCH AVENUE #139W Oldsmar, FL Under contract-accepting backup offers. Owner Financing is Available on this (Ormond Model...	3 beds \| 3 baths \| 1,888 sq.ft.	$424,900	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.56% Airbnb Rental Income: $4254 Traditional Rental Income: $2613 Airbnb ROI: 4.43% Traditional ROI: 2.56%
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.	$255,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 4.88% Airbnb Rental Income: $2376 Traditional Rental Income: $2011 Airbnb ROI: 3.96% Traditional ROI: 4.88%
2505 ARCH AVENUE Oldsmar, FL Owner Financing is Available on this (Ormond Model) with all amenities in the Bayside Terr...	3 beds \| 3 baths \| 1,888 sq.ft.	$424,900	Airbnb cash on cash: 4.37% Traditional cash on cash: 2.24% Airbnb Rental Income: $4254 Traditional Rental Income: $2508 Airbnb ROI: 4.37% Traditional ROI: 2.24%
847 AURORA WAY Oldsmar, FL No Flooding from Hurricane Helene or Milton NO damage or issues. Discover the perfect ...	3 beds \| 3 baths \| 1,365 sq.ft.	$349,000	Airbnb cash on cash: 7.3% Traditional cash on cash: 3.38% Airbnb Rental Income: $4254 Traditional Rental Income: $2071 Airbnb ROI: 7.3% Traditional ROI: 3.38%
2604 ARCH AVENUE Oldsmar, FL One or more photo(s) has been virtually staged. Beautiful Key West style, Waterfront Gated...	2 beds \| 3 baths \| 1,888 sq.ft.	$417,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.84% Airbnb Rental Income: $2376 Traditional Rental Income: $3224 Airbnb ROI: 1.18% Traditional ROI: 4.84%
305 WOODS LANDING TRAIL Oldsmar, FL Priced to selll! Come see this fully updated town home, with a water view and gorgeous out...	3 beds \| 3 baths \| 1,450 sq.ft.	$379,900	Airbnb cash on cash: 5.9% Traditional cash on cash: 3.05% Airbnb Rental Income: $4254 Traditional Rental Income: $2339 Airbnb ROI: 5.9% Traditional ROI: 3.05%
30 WOODS LANDING TRAIL Oldsmar, FL Welcome to your dream home in the prestigious, gated golf community of East Lake Woodlands...	3 beds \| 3 baths \| 1,450 sq.ft.	$350,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 2.83% Airbnb Rental Income: $4254 Traditional Rental Income: $2122 Airbnb ROI: 6.58% Traditional ROI: 2.83%
233 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL Welcome to Countryside Key, a sought-after gated community that blends comfort with conven...	2 beds \| 3 baths \| 1,110 sq.ft.	$269,900	Airbnb cash on cash: 2.79% Traditional cash on cash: 3.45% Airbnb Rental Income: $2376 Traditional Rental Income: $1958 Airbnb ROI: 2.79% Traditional ROI: 3.45%
201 HEMINGWAY DRIVE Oldsmar, FL One or more photo(s) has been virtually staged. This beautifully refreshed three-bedroom, ...	3 beds \| 3 baths \| 1,604 sq.ft.	$379,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 3.62% Airbnb Rental Income: $4254 Traditional Rental Income: $2210 Airbnb ROI: 6.85% Traditional ROI: 3.62%
1107 MANGO COURT Oldsmar, FL Under contract-accepting backup offers. MOVE-IN READY!!! Bayside Terrace Townhome built in...	3 beds \| 3 baths \| 1,928 sq.ft.	$499,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.55% Airbnb Rental Income: $4254 Traditional Rental Income: $2667 Airbnb ROI: 4.03% Traditional ROI: 2.55%
2001 PALM KEY AVENUE Oldsmar, FL Step into this Former Builder Model Home with Stunning Water Views of the bay and indulge ...	3 beds \| 3 baths \| 1,928 sq.ft.	$599,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 1.67% Airbnb Rental Income: $4254 Traditional Rental Income: $2492 Airbnb ROI: 3.22% Traditional ROI: 1.67%

Your search for investment property begins and ends here

Townhouses for Sale in Oldsmar, FL

110 WOODS LANDING TRAIL

Oldsmar, FL

2 beds | 3 baths | 1,200 sq.ft.

$329,900

Airbnb cash on cash: 2.15%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $2376

Traditional Rental Income: $2085

Airbnb ROI: 2.15%

Traditional ROI: 3.1%

163 BRENT CIRCLE

Oldsmar, FL

3 beds | 3 baths | 1,834 sq.ft.

$615,000

Airbnb cash on cash: 3.17%

Traditional cash on cash: 1.71%

Airbnb Rental Income: $4254

Traditional Rental Income: $2517

Airbnb ROI: 3.17%

Traditional ROI: 1.71%

9009 PALM KEY AVENUE

Oldsmar, FL

4 beds | 3 baths | 2,587 sq.ft.

$775,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $3866

Traditional Rental Income: $2883

Airbnb ROI: 1.51%

Traditional ROI: 1.31%

525 WOODS LANDING TRAIL

Oldsmar, FL

2 beds | 3 baths | 1,200 sq.ft.

$279,900

Airbnb cash on cash: 1.37%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2376

Traditional Rental Income: $2003

Airbnb ROI: 1.37%

Traditional ROI: 2.17%

325 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

2 beds | 2 baths | 1,105 sq.ft.

$283,000

Airbnb cash on cash: 2.91%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $2376

Traditional Rental Income: $1944

Airbnb ROI: 2.91%

Traditional ROI: 3.49%

284 HEMINGWAY DRIVE

Oldsmar, FL

3 beds | 3 baths | 1,604 sq.ft.

$389,900

Airbnb cash on cash: 5.89%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $4254

Traditional Rental Income: $2216

Airbnb ROI: 5.89%

Traditional ROI: 2.77%

252 HEMINGWAY DRIVE

Oldsmar, FL

3 beds | 3 baths | 1,604 sq.ft.

$399,800

Airbnb cash on cash: 6.2%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $4254

Traditional Rental Income: $2380

Airbnb ROI: 6.2%

Traditional ROI: 3.59%

1706 AZALEA COURT #A

Oldsmar, FL

2 beds | 3 baths | 1,360 sq.ft.

$275,000

Airbnb cash on cash: 5.21%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $2376

Traditional Rental Income: $1802

Airbnb ROI: 5.21%