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

separator

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: 1.05% Traditional cash on cash: 3.17% Airbnb Rental Income: $2852 Traditional Rental Income: $3671 Airbnb ROI: 1.05% 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: 0.57% Traditional cash on cash: 2.7% Airbnb Rental Income: $2852 Traditional Rental Income: $3776 Airbnb ROI: 0.57% 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: 2.32% Traditional cash on cash: 2.29% Airbnb Rental Income: $3563 Traditional Rental Income: $2763 Airbnb ROI: 2.32% Traditional ROI: 2.29%
807 SWALLOW LANE Osteen, FL RETIRE WITH CONFIDENCE!! Welcome to Kove Estate, a 55+ Co-Op community, a friendly active...	2 beds \| 2 baths \| 1,368 sq.ft.	$144,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 9.45% Airbnb Rental Income: $1288 Traditional Rental Income: $2077 Airbnb ROI: 0.81% Traditional ROI: 9.45%
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: -0.02% Traditional cash on cash: 4.24% Airbnb Rental Income: $1288 Traditional Rental Income: $1712 Airbnb ROI: -0.02% 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: -1.04% Traditional cash on cash: 9.42% Airbnb Rental Income: $708 Traditional Rental Income: $1775 Airbnb ROI: -1.04% 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: 2.53% Traditional cash on cash: 2.52% Airbnb Rental Income: $3563 Traditional Rental Income: $2769 Airbnb ROI: 2.53% Traditional ROI: 2.52%
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.	$162,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 9.35% Airbnb Rental Income: $1288 Traditional Rental Income: $2140 Airbnb ROI: 1.23% Traditional ROI: 9.35%
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: 3.03% Traditional cash on cash: 5.22% Airbnb Rental Income: $2852 Traditional Rental Income: $2971 Airbnb ROI: 3.03% 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: 7.01% Traditional cash on cash: 6.26% Airbnb Rental Income: $3563 Traditional Rental Income: $2532 Airbnb ROI: 7.01% 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: 7.01% Traditional cash on cash: 6.29% Airbnb Rental Income: $3563 Traditional Rental Income: $2542 Airbnb ROI: 7.01% 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: 7.01% Traditional cash on cash: 6.29% Airbnb Rental Income: $3563 Traditional Rental Income: $2545 Airbnb ROI: 7.01% 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: 6.98% Traditional cash on cash: 6.47% Airbnb Rental Income: $3563 Traditional Rental Income: $2613 Airbnb ROI: 6.98% 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: 0.06% Traditional cash on cash: 1.95% Airbnb Rental Income: $1288 Traditional Rental Income: $1240 Airbnb ROI: 0.06% 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: 3.29% Traditional cash on cash: 3.04% Airbnb Rental Income: $3563 Traditional Rental Income: $2639 Airbnb ROI: 3.29% 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: 4.97% Traditional cash on cash: 3.73% Airbnb Rental Income: $3563 Traditional Rental Income: $2259 Airbnb ROI: 4.97% Traditional ROI: 3.73%
511 FLAMINGO LANE Osteen, FL COMPLETELY RENOVATED!! MOVE IN READY!! Welcome to Kove Estates in Osteen! This beautifully...	2 beds \| 2 baths \| 1,114 sq.ft.	$122,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 11.68% Airbnb Rental Income: $1288 Traditional Rental Income: $1943 Airbnb ROI: 2.68% Traditional ROI: 11.68%
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: 3.49% Traditional cash on cash: 3.96% Airbnb Rental Income: $2852 Traditional Rental Income: $2350 Airbnb ROI: 3.49% Traditional ROI: 3.96%
2563 Sheffield Osteen, FL Charming Move-In Ready Home on an Expansive Lot â NO HOA!! Discover this beautifully m...	3 beds \| 2 baths \| N/A	$309,900	Airbnb cash on cash: 7.66% Traditional cash on cash: 5.59% Airbnb Rental Income: $3563 Traditional Rental Income: $2176 Airbnb ROI: 7.66% Traditional ROI: 5.59%
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: 2.67% Traditional cash on cash: 2.64% Airbnb Rental Income: $3563 Traditional Rental Income: $2764 Airbnb ROI: 2.67% 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: 1.1% Traditional cash on cash: 1.1% Airbnb Rental Income: $3563 Traditional Rental Income: $2776 Airbnb ROI: 1.1% Traditional ROI: 1.1%
749 N SR 415 Osteen, FL RARE OPPORTUNITY!! Welcome to this fully renovated, owner-occupied COMMERCIALLY ZONED sin...	3 beds \| 2 baths \| 1,040 sq.ft.	$395,000	Airbnb cash on cash: 5.69% Traditional cash on cash: 2.83% Airbnb Rental Income: $3563 Traditional Rental Income: $1723 Airbnb ROI: 5.69% Traditional ROI: 2.83%
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: 6.25% Traditional cash on cash: 6.88% Airbnb Rental Income: $2852 Traditional Rental Income: $2368 Airbnb ROI: 6.25% 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: 5.91% Traditional cash on cash: 8% Airbnb Rental Income: $2852 Traditional Rental Income: $2817 Airbnb ROI: 5.91% Traditional ROI: 8%
575 Remick Street Osteen, FL This community offers townhomes with 4 bedrooms, 2.5 baths and 2 car garage, all built wit...	4 beds \| 3 baths \| 1,758 sq.ft.	$304,990	Airbnb cash on cash: 6.26% Traditional cash on cash: 6.89% Airbnb Rental Income: $2852 Traditional Rental Income: $2368 Airbnb ROI: 6.26% Traditional ROI: 6.89%

Real Estate investment in Osteen, FL

There are 25 properties for sale in the city of Osteen . The median list price in Osteen is $320,490 and the average price per square foot is $219. 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 25 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 $2,368.

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: 1.05%

Traditional cash on cash: 3.17%

Airbnb Rental Income: $2852

Traditional Rental Income: $3671

Airbnb ROI: 1.05%

Traditional ROI: 3.17%

326 ENTERPRISE OSTEEN ROAD

Osteen, FL

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

$800,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2852

Traditional Rental Income: $3776

Airbnb ROI: 0.57%

Traditional ROI: 2.7%

723 RIVER RUN ROAD

Osteen, FL

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

$699,999

Airbnb cash on cash: 2.32%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $3563

Traditional Rental Income: $2763

Airbnb ROI: 2.32%

Traditional ROI: 2.29%

807 SWALLOW LANE

Osteen, FL

2 beds | 2 baths | 1,368 sq.ft.

$144,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 9.45%

Airbnb Rental Income: $1288

Traditional Rental Income: $2077

Airbnb ROI: 0.81%

Traditional ROI: 9.45%

812 SWALLOW LANE

Osteen, FL

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

$205,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $1288

Traditional Rental Income: $1712

Airbnb ROI: -0.02%

Traditional ROI: 4.24%

107 KOVE BOULEVARD

Osteen, FL

1 beds | 1 baths | 823 sq.ft.

$136,900

Airbnb cash on cash: -1.04%

Traditional cash on cash: 9.42%

Airbnb Rental Income: $708

Traditional Rental Income: $1775

Airbnb ROI: -1.04%

Traditional ROI: 9.42%

155 11TH AVENUE

Osteen, FL

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

$765,000

Airbnb cash on cash: 2.53%

Traditional cash on cash: 2.52%

Airbnb Rental Income: $3563

Traditional Rental Income: $2769

Airbnb ROI: 2.53%

Traditional ROI: 2.52%

314 LAKEVIEW DRIVE

Osteen, FL

2 beds | 2 baths | 1,526 sq.ft.

$162,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 9.35%

Airbnb Rental Income: $1288

Traditional Rental Income: $2140

Airbnb ROI: 1.23%