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
445 S STATE ROAD 415 Osteen, FL Exceptional 5+ acre property located just off SR-415 with excellent access and strong pote...	4 beds \| 4 baths \| 2,654 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.17% Airbnb Rental Income: $null Traditional Rental Income: $3671 Airbnb ROI: N/A Traditional ROI: 3.17%
326 ENTERPRISE OSTEEN ROAD Osteen, FL Set on over 4 fully usable acres in Osteen, this custom-built estate offers a rare combina...	4 beds \| 3 baths \| 3,112 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $3776 Airbnb ROI: N/A Traditional ROI: 2.7%
723 RIVER RUN ROAD Osteen, FL Discover exceptional country living on this 10-acre AG-zoned property in Osteen, FL featur...	3 beds \| 2 baths \| 1,728 sq.ft.	$699,999	Airbnb cash on cash: 3.07% Traditional cash on cash: 2.29% Airbnb Rental Income: $4155 Traditional Rental Income: $2763 Airbnb ROI: 3.07% Traditional ROI: 2.29%
812 SWALLOW LANE Osteen, FL COMPLETELY RENOVATED!! MOVE IN READY!! Kove Estate, a 55+ Co-Op community, friendly active...	2 beds \| 2 baths \| 1,492 sq.ft.	$205,000	Airbnb cash on cash: 7.87% Traditional cash on cash: 4.24% Airbnb Rental Income: $3128 Traditional Rental Income: $1712 Airbnb ROI: 7.87% Traditional ROI: 4.24%
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.	$136,900	Airbnb cash on cash: 9.03% Traditional cash on cash: 9.42% Airbnb Rental Income: $2295 Traditional Rental Income: $1775 Airbnb ROI: 9.03% Traditional ROI: 9.42%
155 11TH AVENUE Osteen, FL Spectacular Opportunity â Live, Work & Play on 1.6 Acres! Step into the epitome of Flori...	3 beds \| 2 baths \| 1,665 sq.ft.	$765,000	Airbnb cash on cash: 3.22% Traditional cash on cash: 2.52% Airbnb Rental Income: $4155 Traditional Rental Income: $2769 Airbnb ROI: 3.22% Traditional ROI: 2.52%
1312 Peach Creek Drive Osteen, FL NO BANK NEEDED! Approx. $14,000 down & est. payments from $3,250/mo. Seller financing, own...	4 beds \| 2 baths \| 1,950 sq.ft.	$379,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2971 Airbnb ROI: N/A Traditional ROI: 5.22%
140 11TH AVENUE Osteen, FL ***Inquire about $7,500 seller incentive to buyer plus additional incentive if buyer uses ...	3 beds \| 2 baths \| 1,483 sq.ft.	$352,000	Airbnb cash on cash: 8.51% Traditional cash on cash: 6.26% Airbnb Rental Income: $4155 Traditional Rental Income: $2532 Airbnb ROI: 8.51% Traditional ROI: 6.26%
144 11TH AVENUE Osteen, FL ***Inquire about $7,500 seller incentive to buyer plus additional incentive if buyer uses ...	3 beds \| 2 baths \| 1,483 sq.ft.	$352,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 6.29% Airbnb Rental Income: $4155 Traditional Rental Income: $2542 Airbnb ROI: 8.5% Traditional ROI: 6.29%
132 11TH AVENUE Osteen, FL ***Inquire about $7,500 seller incentive to buyer plus additional incentive if buyer uses ...	3 beds \| 2 baths \| 1,483 sq.ft.	$352,000	Airbnb cash on cash: 8.5% Traditional cash on cash: 6.29% Airbnb Rental Income: $4155 Traditional Rental Income: $2545 Airbnb ROI: 8.5% Traditional ROI: 6.29%
136 11TH AVENUE Osteen, FL ***Inquire about $7,500 seller incentive to buyer plus additional incentive if buyer uses ...	3 beds \| 2 baths \| 1,483 sq.ft.	$352,000	Airbnb cash on cash: 8.47% Traditional cash on cash: 6.47% Airbnb Rental Income: $4155 Traditional Rental Income: $2613 Airbnb ROI: 8.47% Traditional ROI: 6.47%
70 & 71 EAGLE POINT S Osteen, FL KOVE ESTATES - 55+ ACTIVE COMMUNITY - WATERFRONT & AFFORDABLE - DOUBLE WATERFRONT LOT- Per...	2 beds \| 2 baths \| 1,084 sq.ft.	$199,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 1.95% Airbnb Rental Income: $3128 Traditional Rental Income: $1240 Airbnb ROI: 8.18% Traditional ROI: 1.95%
2598 ENTERPRISE OSTEEN ROAD Osteen, FL THERE IS NO OTHER LIKE THIS ONE. IT'S A CUSTOM-BUILT HOME FROM ONE OF THE BEST BUILDERS AR...	3 beds \| 2 baths \| 1,825 sq.ft.	$595,500	Airbnb cash on cash: 4.18% Traditional cash on cash: 3.04% Airbnb Rental Income: $4155 Traditional Rental Income: $2639 Airbnb ROI: 4.18% Traditional ROI: 3.04%
1501 ASHBY CREEK ROAD Osteen, FL TRUE OUTDOOR LIVING, 25 SECLUDED ACRES, 4 CAR DETACHED GARAGE, PRIVATE POND, SOLAR (fully ...	3 beds \| 2 baths \| 1,344 sq.ft.	$449,000	Airbnb cash on cash: 6.15% Traditional cash on cash: 3.73% Airbnb Rental Income: $4155 Traditional Rental Income: $2259 Airbnb ROI: 6.15% Traditional ROI: 3.73%
1018 Peach Creek Drive Osteen, FL Welcome to your dream home in Osteen, Florida! This nearly brand new four bedroom, two bat...	4 beds \| 2 baths \| 1,950 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $2350 Airbnb ROI: N/A Traditional ROI: 3.96%
1395 MAYTOWN ROAD Osteen, FL Escape to Your Private Almost 5-Acre Country Retreat Discover the perfect balance of se...	3 beds \| 3 baths \| 2,063 sq.ft.	$700,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.64% Airbnb Rental Income: $4155 Traditional Rental Income: $2764 Airbnb ROI: 3.42% Traditional ROI: 2.64%
171 River Oaks Drive Osteen, FL LISTED BELOW APPRAISED VALUE!!! Luxury country living awaits on 5 pristine acres in this n...	3 beds \| 3 baths \| 2,250 sq.ft.	$975,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 1.1% Airbnb Rental Income: $4155 Traditional Rental Income: $2776 Airbnb ROI: 1.64% Traditional ROI: 1.1%
531 Remick Street Osteen, FL This townhome is a 4 bedroom, 2.5 baths and 2 car garage, all built with concrete block co...	4 beds \| 3 baths \| 1,758 sq.ft.	$305,490	Airbnb cash on cash: N/A Traditional cash on cash: 6.88% Airbnb Rental Income: $null Traditional Rental Income: $2368 Airbnb ROI: N/A Traditional ROI: 6.88%
558 Remick Street Osteen, FL This townhome is a 4 bedroom, 2.5 baths and 2 car garage, all built with concrete block co...	4 beds \| 3 baths \| 1,758 sq.ft.	$320,490	Airbnb cash on cash: N/A Traditional cash on cash: 6.51% Airbnb Rental Income: $null Traditional Rental Income: $2368 Airbnb ROI: N/A Traditional ROI: 6.51%
3078 Blue Bonnet Lane Osteen, FL Built in 2023 this immaculately maintained 3-bedroom, 2-bath home with a spacious 2 car ga...	3 beds \| 2 baths \| 1,330 sq.ft.	$324,900	Airbnb cash on cash: 8.01% Traditional cash on cash: 3.95% Airbnb Rental Income: $4155 Traditional Rental Income: $2034 Airbnb ROI: 8.01% Traditional ROI: 3.95%
1104 Peach Creek Drive Osteen, FL Welcome to 1104 Peach Creek Drive, where modern living meets the peaceful charm of Osteen....	3 beds \| 2 baths \| 1,330 sq.ft.	$319,900	Airbnb cash on cash: 8.22% Traditional cash on cash: 4.05% Airbnb Rental Income: $4155 Traditional Rental Income: $2019 Airbnb ROI: 8.22% Traditional ROI: 4.05%

Real Estate investment in Osteen, FL

There are 23 properties for sale in the city of Osteen . The median list price in Osteen is $324,900 and the average price per square foot is $216. In July 2026, the average monthly cash on cash return in Osteen is 6.00%. The average monthly rental income in Osteen is $2,368.

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

There are 23 investment properties available for sale in Osteen.

The ROI for Short-Term is higher than the Long-Term in Osteen with average rental income of $4,155.

Your search for investment property begins and ends here

Investment Property for Sale in Osteen, FL

445 S STATE ROAD 415

Osteen, FL

4 beds | 4 baths | 2,654 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.17%

Airbnb Rental Income: $null

Traditional Rental Income: $3671

Airbnb ROI: N/A

Traditional ROI: 3.17%

326 ENTERPRISE OSTEEN ROAD

Osteen, FL

4 beds | 3 baths | 3,112 sq.ft.

$800,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $3776

Airbnb ROI: N/A

Traditional ROI: 2.7%

723 RIVER RUN ROAD

Osteen, FL

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

$699,999

Airbnb cash on cash: 3.07%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $4155

Traditional Rental Income: $2763

Airbnb ROI: 3.07%

Traditional ROI: 2.29%

812 SWALLOW LANE

Osteen, FL

2 beds | 2 baths | 1,492 sq.ft.

$205,000

Airbnb cash on cash: 7.87%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $3128

Traditional Rental Income: $1712

Airbnb ROI: 7.87%

Traditional ROI: 4.24%

107 KOVE BOULEVARD

Osteen, FL

1 beds | 1 baths | 823 sq.ft.

$136,900

Airbnb cash on cash: 9.03%

Traditional cash on cash: 9.42%

Airbnb Rental Income: $2295

Traditional Rental Income: $1775

Airbnb ROI: 9.03%

Traditional ROI: 9.42%

155 11TH AVENUE

Osteen, FL

3 beds | 2 baths | 1,665 sq.ft.

$765,000

Airbnb cash on cash: 3.22%

Traditional cash on cash: 2.52%

Airbnb Rental Income: $4155

Traditional Rental Income: $2769

Airbnb ROI: 3.22%

Traditional ROI: 2.52%

1312 Peach Creek Drive

Osteen, FL

4 beds | 2 baths | 1,950 sq.ft.

$379,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.22%

Airbnb Rental Income: $null

Traditional Rental Income: $2971

Airbnb ROI: N/A

Traditional ROI: 5.22%

140 11TH AVENUE

Osteen, FL

3 beds | 2 baths | 1,483 sq.ft.

$352,000

Airbnb cash on cash: 8.51%

Traditional cash on cash: 6.26%

Airbnb Rental Income: $4155

Traditional Rental Income: $2532

Airbnb ROI: 8.51%