Real Estate Investment Properties for Sale in Osteen, FL

Looking for investment property in Osteen, FL with high ROI ?

Explore a variety of short-term homes & houses in Osteen, FL. Invest wisely with VRBO & Osteen, 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 Osteen, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
723 RIVER RUN ROAD Osteen, FL Away from it all, but in the middle of it all" Well thought out floor plan with PLENTY ...	3 beds \| 2 baths \| 1,728 sq.ft.	$735,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 1.51% Airbnb Rental Income: $3563 Traditional Rental Income: $2204 Airbnb ROI: 2.35% Traditional ROI: 1.51%
820 CHICKEN FARM ROAD Osteen, FL Under contract-accepting backup offers. Looking for country living? Here it is! This 5 bea...	1 beds \| 1 baths \| 184 sq.ft.	$349,900	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.45% Airbnb Rental Income: $708 Traditional Rental Income: $1254 Airbnb ROI: -1.15% Traditional ROI: 1.45%
57 KOVE BOULEVARD Osteen, FL LAKEFRONT LIVING! RETIRE WITH CONFIDENCE!! Welcome to Kove Estate, a 55+ Co-Op community, ...	1 beds \| 1 baths \| 391 sq.ft.	$105,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 10.66% Airbnb Rental Income: $708 Traditional Rental Income: $1562 Airbnb ROI: -0.74% Traditional ROI: 10.66%
804 SWALLOW LANE Osteen, FL Under contract-accepting backup offers. RETIRE WITH CONFIDENCE!! Welcome to Kove Estate, a...	2 beds \| 2 baths \| 1,220 sq.ft.	$137,500	Airbnb cash on cash: 2.25% Traditional cash on cash: 8.41% Airbnb Rental Income: $1288 Traditional Rental Income: $1698 Airbnb ROI: 2.25% Traditional ROI: 8.41%
919 BLUE HERON BOULEVARD Osteen, FL The Kove Estates is a CO-OP, 55+ community offering a charming 2-bedroom, 2-bathroom home ...	2 beds \| 2 baths \| 1,104 sq.ft.	$137,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 7.19% Airbnb Rental Income: $1288 Traditional Rental Income: $1648 Airbnb ROI: 1.38% Traditional ROI: 7.19%
712 Whippoorwill Ln Osteen, FL Welcome to Resort Style Living! KOVE ESTATE is a 55+ CO-OP Community offering Free 9 Hole ...	2 beds \| 2 baths \| 1,056 sq.ft.	$119,900	Airbnb cash on cash: 3.1% Traditional cash on cash: 9.1% Airbnb Rental Income: $1288 Traditional Rental Income: $1578 Airbnb ROI: 3.1% Traditional ROI: 9.1%
1000 Peach Creek Dr Osteen, FL Why wait to build when you can own this like-new former model home in the quiet community ...	4 beds \| 3 baths \| 2,211 sq.ft.	$374,900	Airbnb cash on cash: 2.82% Traditional cash on cash: 4.47% Airbnb Rental Income: $2852 Traditional Rental Income: $2766 Airbnb ROI: 2.82% Traditional ROI: 4.47%
205 MEADOW LARK DRIVE Osteen, FL STOP THE CAR, THIS IS THE ONE! Fully Updated Top to Bottom, Inside and Out. Welcome to 205...	2 beds \| 2 baths \| 1,080 sq.ft.	$150,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 6.35% Airbnb Rental Income: $1288 Traditional Rental Income: $1640 Airbnb ROI: 1.09% Traditional ROI: 6.35%
904 BLUE HERON BOULEVARD Osteen, FL Under contract-accepting backup offers. GREAT HOME! Welcome to KOVE ESTATES, a community t...	2 beds \| 2 baths \| 1,260 sq.ft.	$110,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 11.11% Airbnb Rental Income: $1288 Traditional Rental Income: $1772 Airbnb ROI: 2.77% Traditional ROI: 11.11%
600 TABATHA DRIVE Osteen, FL Under contract-accepting backup offers. Your home search just came to a screeching halt! 1...	3 beds \| 2 baths \| 1,857 sq.ft.	$715,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 2.03% Airbnb Rental Income: $3563 Traditional Rental Income: $2366 Airbnb ROI: 2.66% Traditional ROI: 2.03%
314 LAKEVIEW DRIVE Osteen, FL Dreaming of Living on the Lake? Well, let's make your DREAMS come true. This adorable home...	2 beds \| 2 baths \| 1,526 sq.ft.	$172,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 7.66% Airbnb Rental Income: $1288 Traditional Rental Income: $1959 Airbnb ROI: 1.11% Traditional ROI: 7.66%
175 Bull Run Ave Osteen, FL âWhether youâre ready to move in or prefer to take advantage of this propertyâs stro...	2 beds \| 2 baths \| 1,360 sq.ft.	$399,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 3.57% Airbnb Rental Income: $1288 Traditional Rental Income: $2006 Airbnb ROI: 0.76% Traditional ROI: 3.57%
254 4TH STREET Osteen, FL Super cute and move in ready! This 3-bedroom 1-bath home features a brand-new roof. Situat...	3 beds \| 1 baths \| 1,185 sq.ft.	$290,000	Airbnb cash on cash: 8.22% Traditional cash on cash: 4.26% Airbnb Rental Income: $3563 Traditional Rental Income: $1700 Airbnb ROI: 8.22% Traditional ROI: 4.26%

Real Estate investment in Osteen, FL

There are 22 properties for sale in the city of Osteen . The median list price in Osteen is $165,950 and the average price per square foot is $133. In February 2026, the average monthly cash on cash return in Osteen is 7.00%. The average monthly rental income in Osteen is $1,776.

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

There are 22 investment properties available for sale in Osteen.

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

The ROI for Long-Term is higher than the Short-Term in Osteen with average rental income of $1,776.

Your search for investment property begins and ends here

Investment Property for Sale in Osteen, FL

723 RIVER RUN ROAD

Osteen, FL

3 beds | 2 baths | 1,728 sq.ft.

$735,000

Airbnb cash on cash: 2.35%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $3563

Traditional Rental Income: $2204

Airbnb ROI: 2.35%

Traditional ROI: 1.51%

820 CHICKEN FARM ROAD

Osteen, FL

1 beds | 1 baths | 184 sq.ft.

$349,900

Airbnb cash on cash: -1.15%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $708

Traditional Rental Income: $1254

Airbnb ROI: -1.15%

Traditional ROI: 1.45%

57 KOVE BOULEVARD

Osteen, FL

1 beds | 1 baths | 391 sq.ft.

$105,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 10.66%

Airbnb Rental Income: $708

Traditional Rental Income: $1562

Airbnb ROI: -0.74%

Traditional ROI: 10.66%

804 SWALLOW LANE

Osteen, FL

2 beds | 2 baths | 1,220 sq.ft.

$137,500

Airbnb cash on cash: 2.25%

Traditional cash on cash: 8.41%

Airbnb Rental Income: $1288

Traditional Rental Income: $1698

Airbnb ROI: 2.25%

Traditional ROI: 8.41%

919 BLUE HERON BOULEVARD

Osteen, FL

2 beds | 2 baths | 1,104 sq.ft.

$137,000

Airbnb cash on cash: 1.38%

Traditional cash on cash: 7.19%

Airbnb Rental Income: $1288

Traditional Rental Income: $1648

Airbnb ROI: 1.38%

Traditional ROI: 7.19%

712 Whippoorwill Ln

Osteen, FL

2 beds | 2 baths | 1,056 sq.ft.

$119,900

Airbnb cash on cash: 3.1%

Traditional cash on cash: 9.1%

Airbnb Rental Income: $1288

Traditional Rental Income: $1578

Airbnb ROI: 3.1%

Traditional ROI: 9.1%

1000 Peach Creek Dr

Osteen, FL

4 beds | 3 baths | 2,211 sq.ft.

$374,900

Airbnb cash on cash: 2.82%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $2852

Traditional Rental Income: $2766

Airbnb ROI: 2.82%

Traditional ROI: 4.47%

205 MEADOW LARK DRIVE

Osteen, FL

2 beds | 2 baths | 1,080 sq.ft.

$150,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 6.35%

Airbnb Rental Income: $1288

Traditional Rental Income: $1640

Airbnb ROI: 1.09%