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
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: 0.14% Traditional cash on cash: 2.7% Airbnb Rental Income: $2472 Traditional Rental Income: $3776 Airbnb ROI: 0.14% Traditional ROI: 2.7%
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.	$130,000	Airbnb cash on cash: -3.34% Traditional cash on cash: 10.54% Airbnb Rental Income: $637 Traditional Rental Income: $2077 Airbnb ROI: -3.34% Traditional ROI: 10.54%
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: -2.81% Traditional cash on cash: 4.24% Airbnb Rental Income: $637 Traditional Rental Income: $1712 Airbnb ROI: -2.81% 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: -3.19% Traditional cash on cash: 9.42% Airbnb Rental Income: $368 Traditional Rental Income: $1775 Airbnb ROI: -3.19% Traditional ROI: 9.42%
155 11TH Avenue Osteen, FL Spectacular Opportunity - Live, Work & Play on 1.6 Acres! Step into the epitome of Florida...	3 beds \| 2 baths \| 1,665 sq.ft.	$765,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.52% Airbnb Rental Income: $2668 Traditional Rental Income: $2769 Airbnb ROI: 1.49% 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: -2.27% Traditional cash on cash: 9.35% Airbnb Rental Income: $637 Traditional Rental Income: $2140 Airbnb ROI: -2.27% Traditional ROI: 9.35%
1312 Peach Creek Drive Osteen, FL 2024 built 4 bedroom in Osteen with a real path to ownership. Seller financing and owner f...	4 beds \| 2 baths \| 1,950 sq.ft.	$349,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 5.75% Airbnb Rental Income: $2472 Traditional Rental Income: $2971 Airbnb ROI: 2.4% Traditional ROI: 5.75%
2598 ENTERPRISE OSTEEN Road Osteen, FL Virtually Staged. Price reduction! This exceptional, custom-built home stands in a class o...	3 beds \| 2 baths \| 1,825 sq.ft.	$525,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.57% Airbnb Rental Income: $2668 Traditional Rental Income: $2639 Airbnb ROI: 2.34% Traditional ROI: 3.57%
232 MEADOW LARK Drive Osteen, FL Welcome to resort-style living in Kove Estates, a sought-after 55+ co-op community offerin...	3 beds \| 2 baths \| 1,849 sq.ft.	$169,000	Airbnb cash on cash: 8.58% Traditional cash on cash: 11.38% Airbnb Rental Income: $2668 Traditional Rental Income: $2486 Airbnb ROI: 8.58% Traditional ROI: 11.38%
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.	$430,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.94% Airbnb Rental Income: $2668 Traditional Rental Income: $2259 Airbnb ROI: 3.38% Traditional ROI: 3.94%
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: -1.93% Traditional cash on cash: 11.68% Airbnb Rental Income: $637 Traditional Rental Income: $1943 Airbnb ROI: -1.93% Traditional ROI: 11.68%
1395 MAYTOWN Road Osteen, FL Escape to Your Private Almost 5-Acre Country Retreat Discover the perfect balance of seren...	3 beds \| 3 baths \| 2,063 sq.ft.	$690,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.69% Airbnb Rental Income: $2668 Traditional Rental Income: $2764 Airbnb ROI: 1.56% Traditional ROI: 2.69%
171 River Oaks Drive Osteen, FL LISTED $148K BELOW APPRAISED VALUE!!Luxury country living awaits on 5 pristine acres in th...	3 beds \| 3 baths \| 2,250 sq.ft.	$949,999	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.15% Airbnb Rental Income: $2668 Traditional Rental Income: $2776 Airbnb ROI: 0.31% Traditional ROI: 1.15%
749 N SR 415 Osteen, FL RARE OPPORTUNITY!! Welcome to this fully renovated, owner-occupied COMMERCIALLY ZONED sing...	3 beds \| 2 baths \| 1,040 sq.ft.	$395,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 2.83% Airbnb Rental Income: $2668 Traditional Rental Income: $1723 Airbnb ROI: 3.67% 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: 5.15% Traditional cash on cash: 6.88% Airbnb Rental Income: $2472 Traditional Rental Income: $2368 Airbnb ROI: 5.15% 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: 4.86% Traditional cash on cash: 6.51% Airbnb Rental Income: $2472 Traditional Rental Income: $2368 Airbnb ROI: 4.86% Traditional ROI: 6.51%
3078 Blue Bonnet Lane Osteen, FL SELLERS ARE MOTIVATED and open to helping with closing costs with reasonable offer! BUYER ...	3 beds \| 2 baths \| 1,330 sq.ft.	$310,000	Airbnb cash on cash: 4.18% Traditional cash on cash: 4.18% Airbnb Rental Income: $2668 Traditional Rental Income: $2034 Airbnb ROI: 4.18% Traditional ROI: 4.18%
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.	$306,900	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.26% Airbnb Rental Income: $2668 Traditional Rental Income: $2019 Airbnb ROI: 4.32% Traditional ROI: 4.26%
938 BLUE HERON Boulevard Osteen, FL WELCOME to 938 Blue Heron Blvd. Kove Estates a premier 55+ community in Osteen Fl. Updated...	2 beds \| 2 baths \| 1,152 sq.ft.	$162,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 8.39% Airbnb Rental Income: $637 Traditional Rental Income: $1746 Airbnb ROI: -0.69% Traditional ROI: 8.39%
301 LAKEVIEW Drive Osteen, FL Welcome to this beautifully remodeled manufactured home in the desirable 55+ CO-OP communi...	2 beds \| 2 baths \| 1,194 sq.ft.	$195,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 6.99% Airbnb Rental Income: $637 Traditional Rental Income: $1681 Airbnb ROI: -0.24% Traditional ROI: 6.99%
541 REMICK Street Osteen, FL Priced To Sell well below appraised value! Your completed, move-in ready End Unit represen...	3 beds \| 3 baths \| 1,758 sq.ft.	$299,987	Airbnb cash on cash: 4.28% Traditional cash on cash: 5.41% Airbnb Rental Income: $2668 Traditional Rental Income: $2353 Airbnb ROI: 4.28% Traditional ROI: 5.41%
680 WILD ACRES Road Osteen, FL If you've dreamed of owning acreage along a winding dirt road with a peaceful country feel...	4 beds \| 2 baths \| 2,052 sq.ft.	$430,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 3.75% Airbnb Rental Income: $2472 Traditional Rental Income: $2231 Airbnb ROI: 2.86% Traditional ROI: 3.75%

Real Estate investment in Osteen, FL

There are 26 properties for sale in the city of Osteen . The median list price in Osteen is $299,987 and the average price per square foot is $214. In October 2026, the average monthly cash on cash return in Osteen is 6.00%. The average monthly rental income in Osteen is $2,109.

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

There are 26 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 $2,109.

Your search for investment property begins and ends here

Investment Property for Sale in Osteen, FL

326 ENTERPRISE OSTEEN ROAD

Osteen, FL

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

$800,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $2472

Traditional Rental Income: $3776

Airbnb ROI: 0.14%

Traditional ROI: 2.7%

807 SWALLOW Lane

Osteen, FL

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

$130,000

Airbnb cash on cash: -3.34%

Traditional cash on cash: 10.54%

Airbnb Rental Income: $637

Traditional Rental Income: $2077

Airbnb ROI: -3.34%

Traditional ROI: 10.54%

812 SWALLOW Lane

Osteen, FL

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

$205,000

Airbnb cash on cash: -2.81%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $637

Traditional Rental Income: $1712

Airbnb ROI: -2.81%

Traditional ROI: 4.24%

107 KOVE Boulevard

Osteen, FL

1 beds | 1 baths | 823 sq.ft.

$136,900

Airbnb cash on cash: -3.19%

Traditional cash on cash: 9.42%

Airbnb Rental Income: $368

Traditional Rental Income: $1775

Airbnb ROI: -3.19%

Traditional ROI: 9.42%

155 11TH Avenue

Osteen, FL

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

$765,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 2.52%

Airbnb Rental Income: $2668

Traditional Rental Income: $2769

Airbnb ROI: 1.49%

Traditional ROI: 2.52%

314 LAKEVIEW Drive

Osteen, FL

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

$162,000

Airbnb cash on cash: -2.27%

Traditional cash on cash: 9.35%

Airbnb Rental Income: $637

Traditional Rental Income: $2140

Airbnb ROI: -2.27%

Traditional ROI: 9.35%

1312 Peach Creek Drive

Osteen, FL

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

$349,900

Airbnb cash on cash: 2.4%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $2472

Traditional Rental Income: $2971

Airbnb ROI: 2.4%

Traditional ROI: 5.75%

2598 ENTERPRISE OSTEEN Road

Osteen, FL

3 beds | 2 baths | 1,825 sq.ft.

$525,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $2668

Traditional Rental Income: $2639

Airbnb ROI: 2.34%