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
538 MURRAY STREET Osteen, FL Over 8 Acres of Pure Osteen Paradise! Come enjoy this massive 4 bedroom 2 bath custom buil...	4 beds \| 2 baths \| 2,236 sq.ft.	$699,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 1.56% Airbnb Rental Income: $2852 Traditional Rental Income: $2475 Airbnb ROI: 1.12% Traditional ROI: 1.56%
723 RIVER RUN ROAD Osteen, FL Built in 2018, this custom-designed 3-bedroom, 2-bathroom home set on a sprawling 10-acres...	3 beds \| 2 baths \| 1,728 sq.ft.	$799,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 1.31% Airbnb Rental Income: $3563 Traditional Rental Income: $2204 Airbnb ROI: 2.08% Traditional ROI: 1.31%
601 PELICAN LANE Osteen, FL GREAT HOME! Welcome to KOVE ESTATES, a community that offers resort-style living, comfort,...	2 beds \| 2 baths \| 1,152 sq.ft.	$115,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 9.13% Airbnb Rental Income: $1288 Traditional Rental Income: $1711 Airbnb ROI: 1.69% Traditional ROI: 9.13%
372 CARPENTER AVENUE Osteen, FL Under contract-accepting backup offers. âFinish Your Dream Home or Split the Lots and Bu...	3 beds \| 2 baths \| 1,300 sq.ft.	$399,000	Airbnb cash on cash: 5.84% Traditional cash on cash: 4.26% Airbnb Rental Income: $3563 Traditional Rental Income: $2188 Airbnb ROI: 5.84% Traditional ROI: 4.26%
820 CHICKEN FARM ROAD Osteen, FL Looking for country living? Here it is! This 5 beautiful acres in Osteen is a short drive ...	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%
66 EAGLE POINT S Osteen, FL WELCOME TO THE KOVE ESTATE 55+ CO-OP Community Resort Style Living at its finest, all the ...	1 beds \| 1 baths \| 596 sq.ft.	$99,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 8.65% Airbnb Rental Income: $708 Traditional Rental Income: $1357 Airbnb ROI: -1.28% Traditional ROI: 8.65%
804 SWALLOW LANE Osteen, FL RETIRE WITH CONFIDENCE!! Welcome to Kove Estate, a 55+ Co-Op community, a friendly active ...	2 beds \| 2 baths \| 1,220 sq.ft.	$137,500	Airbnb cash on cash: 2.59% Traditional cash on cash: 8.75% Airbnb Rental Income: $1288 Traditional Rental Income: $1698 Airbnb ROI: 2.59% Traditional ROI: 8.75%
76 EAGLE POINT S Osteen, FL LAKE FRONT PROPERTY! - WELCOME TO THE KOVE ESTATE 55+ CO-OP Community Resort Style Living ...	1 beds \| 2 baths \| 654 sq.ft.	$125,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 8.16% Airbnb Rental Income: $708 Traditional Rental Income: $1561 Airbnb ROI: -1.47% Traditional ROI: 8.16%
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.	$145,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 6.75% Airbnb Rental Income: $1288 Traditional Rental Income: $1648 Airbnb ROI: 1.25% Traditional ROI: 6.75%
712 WHIPPOORWILL LANE 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.	$129,900	Airbnb cash on cash: 2.8% Traditional cash on cash: 8.35% Airbnb Rental Income: $1288 Traditional Rental Income: $1578 Airbnb ROI: 2.8% Traditional ROI: 8.35%
79 EAGLE POINT S Osteen, FL Welcome to Kove Estates a 55+ gated and located between Orlando and New Smyrna Beach. This...	2 beds \| 1 baths \| 526 sq.ft.	$89,000	Airbnb cash on cash: 4.36% Traditional cash on cash: 9.28% Airbnb Rental Income: $1288 Traditional Rental Income: $1313 Airbnb ROI: 4.36% Traditional ROI: 9.28%
315 Smith Road Osteen, FL Discover this beautiful 3BR, 2.5BA home offering over 1,700 sqft of comfortable living. Se...	3 beds \| 2 baths \| 1,732 sq.ft.	$725,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 1.81% Airbnb Rental Income: $3563 Traditional Rental Income: $2212 Airbnb ROI: 2.65% Traditional ROI: 1.81%
107 KOVE BOULEVARD Osteen, FL RETIRE WITH CONFIDENCE. HOA is LOW and includes Water/Sewer/Trash Pickup. Kove Estate is a...	1 beds \| 1 baths \| 823 sq.ft.	$139,900	Airbnb cash on cash: -0.96% Traditional cash on cash: 7.75% Airbnb Rental Income: $708 Traditional Rental Income: $1570 Airbnb ROI: -0.96% Traditional ROI: 7.75%
396 URANUS TRAIL Osteen, FL Under contract-accepting backup offers. Peaceful Country Setting with City Access â Oste...	3 beds \| 2 baths \| 1,801 sq.ft.	$590,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 1.93% Airbnb Rental Income: $3563 Traditional Rental Income: $2396 Airbnb ROI: 2.63% Traditional ROI: 1.93%
750 TABATHA DRIVE Osteen, FL Under contract-accepting backup offers. Welcome to your private retreat on just over 10 ac...	3 beds \| 3 baths \| 2,074 sq.ft.	$655,000	Airbnb cash on cash: 1.97% Traditional cash on cash: 1.95% Airbnb Rental Income: $3563 Traditional Rental Income: $2768 Airbnb ROI: 1.97% Traditional ROI: 1.95%
460 OAK STREET Osteen, FL Under contract-accepting backup offers. Tucked away on an oversized corner lot, this beaut...	4 beds \| 2 baths \| 1,684 sq.ft.	$365,000	Airbnb cash on cash: 4.67% Traditional cash on cash: 5.03% Airbnb Rental Income: $2852 Traditional Rental Income: $2311 Airbnb ROI: 4.67% Traditional ROI: 5.03%
330 ENTERPRISE OSTEEN ROAD Osteen, FL Under contract-accepting backup offers. Meticulously Maintained and move in ready! This ch...	2 beds \| 2 baths \| 1,152 sq.ft.	$259,900	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.49% Airbnb Rental Income: $1288 Traditional Rental Income: $1724 Airbnb ROI: 1.07% Traditional ROI: 4.49%
320 OKLAHOMA AVENUE Osteen, FL Under contract-accepting backup offers. Discover the charm of small-town living in this be...	3 beds \| 2 baths \| 1,333 sq.ft.	$295,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 4.93% Airbnb Rental Income: $3563 Traditional Rental Income: $1954 Airbnb ROI: 7.91% Traditional ROI: 4.93%
396 ENTERPRISE OSTEEN ROAD Osteen, FL Enjoy some rural serenity on this 3.64 acre homestead that's between a Super Walmart and a...	4 beds \| 2 baths \| 1,640 sq.ft.	$495,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 3.18% Airbnb Rental Income: $2852 Traditional Rental Income: $2366 Airbnb ROI: 2.8% Traditional ROI: 3.18%
622 RIGGS AVENUE Osteen, FL Welcome to your own private retreat â a stunning 2,061 sq. ft. home with 3 bedrooms 2 ba...	3 beds \| 2 baths \| 2,061 sq.ft.	$548,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.69% Airbnb Rental Income: $3563 Traditional Rental Income: $2491 Airbnb ROI: 3.25% Traditional ROI: 2.69%
1000 PEACH CREEK DRIVE 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.	$410,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 4.01% Airbnb Rental Income: $2852 Traditional Rental Income: $2766 Airbnb ROI: 2.5% Traditional ROI: 4.01%
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.	$179,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 5.27% Airbnb Rental Income: $1288 Traditional Rental Income: $1640 Airbnb ROI: 0.83% Traditional ROI: 5.27%

Real Estate investment in Osteen, FL

There are 22 properties for sale in the city of Osteen . The median list price in Osteen is $224,900 and the average price per square foot is $178. In September 2025, the average monthly cash on cash return in Osteen is 5.00%. The average monthly rental income in Osteen is $1,797.

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

There are 22 investment properties available for sale in Osteen.

In 2025, 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 $1,797.

Your search for investment property begins and ends here

Investment Property for Sale in Osteen, FL

538 MURRAY STREET

Osteen, FL

4 beds | 2 baths | 2,236 sq.ft.

$699,900

Airbnb cash on cash: 1.12%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $2852

Traditional Rental Income: $2475

Airbnb ROI: 1.12%

Traditional ROI: 1.56%

723 RIVER RUN ROAD

Osteen, FL

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

$799,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $3563

Traditional Rental Income: $2204

Airbnb ROI: 2.08%

Traditional ROI: 1.31%

601 PELICAN LANE

Osteen, FL

2 beds | 2 baths | 1,152 sq.ft.

$115,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 9.13%

Airbnb Rental Income: $1288

Traditional Rental Income: $1711

Airbnb ROI: 1.69%

Traditional ROI: 9.13%

372 CARPENTER AVENUE

Osteen, FL

3 beds | 2 baths | 1,300 sq.ft.

$399,000

Airbnb cash on cash: 5.84%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3563

Traditional Rental Income: $2188

Airbnb ROI: 5.84%

Traditional ROI: 4.26%

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%

66 EAGLE POINT S

Osteen, FL

1 beds | 1 baths | 596 sq.ft.

$99,000

Airbnb cash on cash: -1.28%

Traditional cash on cash: 8.65%

Airbnb Rental Income: $708

Traditional Rental Income: $1357

Airbnb ROI: -1.28%

Traditional ROI: 8.65%

804 SWALLOW LANE

Osteen, FL

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

$137,500

Airbnb cash on cash: 2.59%

Traditional cash on cash: 8.75%

Airbnb Rental Income: $1288

Traditional Rental Income: $1698

Airbnb ROI: 2.59%

Traditional ROI: 8.75%

76 EAGLE POINT S

Osteen, FL

1 beds | 2 baths | 654 sq.ft.

$125,000

Airbnb cash on cash: -1.47%

Traditional cash on cash: 8.16%

Airbnb Rental Income: $708

Traditional Rental Income: $1561

Airbnb ROI: -1.47%