Real Estate Investment Properties for Sale in Kissimmee, FL

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

Explore a variety of short-term homes & houses in Kissimmee, FL. Invest wisely with VRBO & Kissimmee, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Windcrest Investment Property for Sale in Kissimmee, FL

Search for Windcrest Investment Property for Sale in Kissimmee, Florida. Browse all of Mashvisor’s Windcrest Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 2,059 Windcrest Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1831 WINDWARD OAKS COURT Kissimmee, FL Welcome to your dream home in the beautiful BellaLago community! This stunning residence a...	5 beds \| 3 baths \| 2,813 sq.ft.	$589,500	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.53% Airbnb Rental Income: $2156 Traditional Rental Income: $3398 Airbnb ROI: 0.27% Traditional ROI: 3.53%
5004 LAGUNA BAY CIRCLE #54 Kissimmee, FL Fabulous condo for sale fully furnished! 3 beds and 2 baths condo located just a few minut...	3 beds \| 2 baths \| 1,220 sq.ft.	$238,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.65% Airbnb Rental Income: $1472 Traditional Rental Income: $1787 Airbnb ROI: -0.68% Traditional ROI: 2.65%
4577 ALBERTO CIRCLE Kissimmee, FL Welcome to Bellavida Resort. This home features 4 bedrooms with 3 full baths and one of th...	4 beds \| 3 baths \| 1,636 sq.ft.	$380,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.81% Airbnb Rental Income: $1735 Traditional Rental Income: $2631 Airbnb ROI: -0.04% Traditional ROI: 3.81%
1737 LEE JANZEN DRIVE Kissimmee, FL PRESTINE KISSIMMEE BAY GOLF AND WATER VIEW POOL HOME, Prepare to be blown away! Golf cours...	3 beds \| 3 baths \| 2,138 sq.ft.	$574,999	Airbnb cash on cash: -0.26% Traditional cash on cash: 3.11% Airbnb Rental Income: $1472 Traditional Rental Income: $2848 Airbnb ROI: -0.26% Traditional ROI: 3.11%
1469 SWAN PLACE Kissimmee, FL One or more photo(s) has been virtually staged. Welcome home to this well maintained 3-bed...	3 beds \| 2 baths \| 1,202 sq.ft.	$244,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 5.8% Airbnb Rental Income: $1472 Traditional Rental Income: $1981 Airbnb ROI: 1.7% Traditional ROI: 5.8%
1822 TROPHY BASS WAY Kissimmee, FL Waterfront home in Shingle Creek Reserve, where Florida living meets comfort and convenien...	4 beds \| 3 baths \| 2,798 sq.ft.	$499,700	Airbnb cash on cash: -0.26% Traditional cash on cash: 3.44% Airbnb Rental Income: $1735 Traditional Rental Income: $2984 Airbnb ROI: -0.26% Traditional ROI: 3.44%
5004 LAGUNA BAY CIRCLE #47 Kissimmee, FL Experience the ultimate Central Florida lifestyle with this exceptional and fully furnishe...	3 beds \| 2 baths \| 1,220 sq.ft.	$269,999	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.6% Airbnb Rental Income: $1472 Traditional Rental Income: $2066 Airbnb ROI: -0.44% Traditional ROI: 3.6%
2713 PEARL COURT Kissimmee, FL This home can be purchased with NO MONEY DOWN!!! Welcome to this beautifully updated 3-bed...	3 beds \| 2 baths \| 1,616 sq.ft.	$384,990	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.74% Airbnb Rental Income: $1472 Traditional Rental Income: $2480 Airbnb ROI: 0.75% Traditional ROI: 4.74%
606 MARKET STREET #240 Kissimmee, FL Welcome home to the ultimate Main Street address in the very heart of "The Town That Disne...	1 beds \| 1 baths \| 640 sq.ft.	$229,999	Airbnb cash on cash: -1.33% Traditional cash on cash: 3.46% Airbnb Rental Income: $678 Traditional Rental Income: $1419 Airbnb ROI: -1.33% Traditional ROI: 3.46%
911 LAKE BERKLEY DRIVE Kissimmee, FL Welcome to 911 Lake Berkley, a beautifully maintained home located in the highly desirable...	4 beds \| 3 baths \| 1,542 sq.ft.	$399,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.68% Airbnb Rental Income: $1735 Traditional Rental Income: $2817 Airbnb ROI: 0.51% Traditional ROI: 4.68%
2239 SANTA LUCIA STREET Kissimmee, FL Centrally located and move-in ready, this 3 bedroom, 2 bath home features an open floor pl...	3 beds \| 2 baths \| 1,059 sq.ft.	$321,497	Airbnb cash on cash: 0.82% Traditional cash on cash: 4.7% Airbnb Rental Income: $1472 Traditional Rental Income: $2210 Airbnb ROI: 0.82% Traditional ROI: 4.7%
2711 Star Grass Circle Kissimmee, FL FOR SALE: - SELLER GIVING CONCESSION TOWARDS CLOSING COST. PLEASE CONTACT FOR MORE DETAILS...	4 beds \| 3 baths \| 2,528 sq.ft.	$420,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $1735 Traditional Rental Income: $2517 Airbnb ROI: -0.6% Traditional ROI: 2.6%
3523 FOREST PARK DRIVE Kissimmee, FL Experience elevated living in this beautifully upgraded two-story home in the prestigious,...	4 beds \| 3 baths \| 2,123 sq.ft.	$578,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 2.4% Airbnb Rental Income: $1735 Traditional Rental Income: $2538 Airbnb ROI: 0.03% Traditional ROI: 2.4%
2521 JASMINE TRACE DRIVE Kissimmee, FL Absolutely stunning and thoughtfully designed, this exceptional home offers the perfect bl...	4 beds \| 3 baths \| 2,658 sq.ft.	$530,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 5.36% Airbnb Rental Income: $1735 Traditional Rental Income: $3698 Airbnb ROI: 0.43% Traditional ROI: 5.36%
8050 KING PALM CIRCLE Kissimmee, FL Welcome to the Guard gated Windsor Palms Resort style Community to escape to paradise. Thi...	4 beds \| 2 baths \| 1,567 sq.ft.	$495,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.9% Airbnb Rental Income: $1735 Traditional Rental Income: $2700 Airbnb ROI: -0.22% Traditional ROI: 2.9%
2310 SILVER PALM DR #104 Kissimmee, FL The Royal Retreat at Windsor Palms: Your Ultimate Orlando Oasis! Prepare to be captivated ...	2 beds \| 2 baths \| 1,022 sq.ft.	$234,900	Airbnb cash on cash: -1.57% Traditional cash on cash: 2.65% Airbnb Rental Income: $1341 Traditional Rental Income: $1865 Airbnb ROI: -1.57% Traditional ROI: 2.65%
2727 SUN KEY PLACE Kissimmee, FL Discover your dream getaway in the stunning Emerald Island Resort! This townhouse is locat...	3 beds \| 3 baths \| 1,291 sq.ft.	$304,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 4.09% Airbnb Rental Income: $1472 Traditional Rental Income: $2202 Airbnb ROI: 0.03% Traditional ROI: 4.09%
2634 CORVETTE LANE Kissimmee, FL Discover Your Dream Getaway in Regal Oaks! This stunning and fully furnished 2-bedroom t...	2 beds \| 3 baths \| 1,350 sq.ft.	$285,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.31% Airbnb Rental Income: $1341 Traditional Rental Income: $2123 Airbnb ROI: -1.14% Traditional ROI: 3.31%
4715 FLAGLER BEACH WAY Kissimmee, FL PRICED BELOW MARKET VALUE â MOTIVATED SELLER â EXCELLENT INVESTMENT OPPORTUNITY Wel...	3 beds \| 3 baths \| 1,286 sq.ft.	$298,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.17% Airbnb Rental Income: $1472 Traditional Rental Income: $2085 Airbnb ROI: 0.44% Traditional ROI: 4.17%
3331 WHITESTONE CIRCLE #201 Kissimmee, FL One or more photo(s) has been virtually staged. BACK ON THE MARKET! Spacious and VERY WEL...	3 beds \| 2 baths \| 1,495 sq.ft.	$240,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 5.02% Airbnb Rental Income: $1472 Traditional Rental Income: $2248 Airbnb ROI: -0.32% Traditional ROI: 5.02%
3032 PARKWAY BOULEVARD #305 Kissimmee, FL Welcome to this beautifully remodeled 2-bedroom, 2-bathroom condo located in the heart of ...	2 beds \| 2 baths \| 937 sq.ft.	$220,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 3.29% Airbnb Rental Income: $1341 Traditional Rental Income: $1728 Airbnb ROI: -0.54% Traditional ROI: 3.29%
3196 STONEHURST CIRCLE Kissimmee, FL WATERFRONT If you're looking for an open-floor plan move-in ready home with a waterfro...	3 beds \| 2 baths \| 1,814 sq.ft.	$430,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.94% Airbnb Rental Income: $1472 Traditional Rental Income: $2310 Airbnb ROI: -0.22% Traditional ROI: 2.94%
763 ROLFE STREET Kissimmee, FL Located in an established Kissimmee neighborhood, this 3-bedroom, 2-bath single-family hom...	3 beds \| 2 baths \| 1,088 sq.ft.	$243,900	Airbnb cash on cash: 1.87% Traditional cash on cash: 6.19% Airbnb Rental Income: $1472 Traditional Rental Income: $2032 Airbnb ROI: 1.87% Traditional ROI: 6.19%
157 POMPANO BEACH DRIVE Kissimmee, FL This stunning furnished townhouse features three spacious bedrooms, two full bathrooms, an...	3 beds \| 3 baths \| 1,286 sq.ft.	$290,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 4.5% Airbnb Rental Income: $1472 Traditional Rental Income: $2085 Airbnb ROI: 0.67% Traditional ROI: 4.5%
2682 MAYAGUANA STREET Kissimmee, FL Beautiful end-unit Townhome located in a gated Community just 2.5 miles from Walt Disney ...	3 beds \| 3 baths \| 1,595 sq.ft.	$293,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 5.41% Airbnb Rental Income: $1472 Traditional Rental Income: $2431 Airbnb ROI: 0.36% Traditional ROI: 5.41%
1410 Celebration Ave #102 Kissimmee, FL Immaculate first floor condo with one car garage, only used as a second home by the owners...	2 beds \| 2 baths \| 1,210 sq.ft.	$360,000	Airbnb cash on cash: -4.07% Traditional cash on cash: -1.17% Airbnb Rental Income: $1341 Traditional Rental Income: $1908 Airbnb ROI: -4.07% Traditional ROI: -1.17%
4722 VERO BEACH PLACE Kissimmee, FL OWNER MOTIVATED â INCOME-GENERATING Townhome in Terra Verde Resort â Just Minutes from...	3 beds \| 3 baths \| 1,286 sq.ft.	$309,900	Airbnb cash on cash: 0.41% Traditional cash on cash: 4.13% Airbnb Rental Income: $1472 Traditional Rental Income: $2124 Airbnb ROI: 0.41% Traditional ROI: 4.13%
2774 ALMATON LOOP #402 Kissimmee, FL Welcome to this fully furnished and well decorated vacation home just minutes from Walt Di...	2 beds \| 2 baths \| 1,081 sq.ft.	$279,000	Airbnb cash on cash: -2.01% Traditional cash on cash: 1.19% Airbnb Rental Income: $1341 Traditional Rental Income: $1769 Airbnb ROI: -2.01% Traditional ROI: 1.19%
3410 OAKMONT COURT Kissimmee, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 3 baths \| 2,741 sq.ft.	$499,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 3.51% Airbnb Rental Income: $1472 Traditional Rental Income: $3093 Airbnb ROI: -0.9% Traditional ROI: 3.51%
2732 OAKWATER DRIVE #101 Kissimmee, FL Welcome to this beautiful 2bedroom and 2 bathroom condo turn key fully furnished. REDUCED ...	2 beds \| 2 baths \| 1,015 sq.ft.	$260,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.36% Airbnb Rental Income: $1341 Traditional Rental Income: $1967 Airbnb ROI: -0.87% Traditional ROI: 3.36%
935 Amy Ridge Ct Kissimmee, FL Beautiful and spacious 3 bedroom 2 bathroom home on over 1/2 acre lot. Light wood laminate...	3 beds \| 2 baths \| 1,656 sq.ft.	$379,990	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.18% Airbnb Rental Income: $1472 Traditional Rental Income: $2347 Airbnb ROI: 0.51% Traditional ROI: 4.18%
304 Grouper Drive Kissimmee, FL Welcome to this 1,809 sq. ft. beautifully maintained 3-bedroom, 2-bathroom home offering c...	3 beds \| 2 baths \| 1,809 sq.ft.	$304,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 5.05% Airbnb Rental Income: $1472 Traditional Rental Income: $2294 Airbnb ROI: 0.66% Traditional ROI: 5.05%
235 INDIAN WELLS AVENUE Kissimmee, FL Live the Resort Life Every Day! This impeccably maintained Palm Island model offers the pe...	2 beds \| 3 baths \| 1,935 sq.ft.	$324,900	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.74% Airbnb Rental Income: $1341 Traditional Rental Income: $2419 Airbnb ROI: -1.14% Traditional ROI: 3.74%
4547 FICUS TREE ROAD Kissimmee, FL Beautifully updated 4-bedroom, 2.5-bath home offering comfort, style, and plenty of space,...	4 beds \| 3 baths \| 2,847 sq.ft.	$397,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 5.79% Airbnb Rental Income: $1735 Traditional Rental Income: $3023 Airbnb ROI: 1.04% Traditional ROI: 5.79%
8519 Bay Lilly Loop Kissimmee, FL Your Perfect Disney-Area Retreat! Welcome to this stunning 3-bedroom, 2.5-bathroom fully ...	3 beds \| 2 baths \| 1,295 sq.ft.	$299,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.87% Airbnb Rental Income: $1472 Traditional Rental Income: $2218 Airbnb ROI: -1.32% Traditional ROI: 2.87%
3100 Parkway Blvd #753 Kissimmee, FL Investors OPORTUNITY, This Condo-Hotel Villas 1BED/1Bath, priced to sell quickly, Short te...	1 beds \| 1 baths \| 524 sq.ft.	$135,000	Airbnb cash on cash: -4.83% Traditional cash on cash: 2.89% Airbnb Rental Income: $678 Traditional Rental Income: $1377 Airbnb ROI: -4.83% Traditional ROI: 2.89%
7681 SIR KAUFMANN COURT Kissimmee, FL Welcome to this beautifully maintained 3-bedroom, 3-bath end-unit townhome featuring a pri...	3 beds \| 3 baths \| 1,440 sq.ft.	$410,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.23% Airbnb Rental Income: $1472 Traditional Rental Income: $2336 Airbnb ROI: -0.15% Traditional ROI: 3.23%
3177 Feltrim Pl #104 Kissimmee, FL Beautiful property in a first floor and open 2-bedroom 2 bath in the Secret Lake Resort Co...	2 beds \| 2 baths \| 1,062 sq.ft.	$205,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.39% Airbnb Rental Income: $1341 Traditional Rental Income: $1883 Airbnb ROI: -0.52% Traditional ROI: 4.39%
7694 INDIAN RIDGE TRAIL S Kissimmee, FL For Sale â Updated 3BR/2BA Home With Conservation View + NEW HOT WATER HEATER Now off...	3 beds \| 2 baths \| 1,535 sq.ft.	$365,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.86% Airbnb Rental Income: $1472 Traditional Rental Income: $2324 Airbnb ROI: 0.11% Traditional ROI: 3.86%
301 Lesesne St Kissimmee, FL Charming 3 bedroom, 2 bathroom home located in the desirable Benita Park community with no...	3 beds \| 2 baths \| 1,375 sq.ft.	$249,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 7.34% Airbnb Rental Income: $1472 Traditional Rental Income: $2277 Airbnb ROI: 2.08% Traditional ROI: 7.34%

Your search for investment property begins and ends here

Windcrest Investment Property for Sale in Kissimmee, FL

1831 WINDWARD OAKS COURT

Kissimmee, FL

5 beds | 3 baths | 2,813 sq.ft.

$589,500

Airbnb cash on cash: 0.27%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2156

Traditional Rental Income: $3398

Airbnb ROI: 0.27%

Traditional ROI: 3.53%

5004 LAGUNA BAY CIRCLE #54

Kissimmee, FL

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

$238,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $1472

Traditional Rental Income: $1787

Airbnb ROI: -0.68%

Traditional ROI: 2.65%

4577 ALBERTO CIRCLE

Kissimmee, FL

4 beds | 3 baths | 1,636 sq.ft.

$380,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $1735

Traditional Rental Income: $2631

Airbnb ROI: -0.04%

Traditional ROI: 3.81%

1737 LEE JANZEN DRIVE

Kissimmee, FL

3 beds | 3 baths | 2,138 sq.ft.

$574,999

Airbnb cash on cash: -0.26%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $1472

Traditional Rental Income: $2848

Airbnb ROI: -0.26%

Traditional ROI: 3.11%

1469 SWAN PLACE

Kissimmee, FL

3 beds | 2 baths | 1,202 sq.ft.

$244,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 5.8%

Airbnb Rental Income: $1472

Traditional Rental Income: $1981

Airbnb ROI: 1.7%

Traditional ROI: 5.8%

1822 TROPHY BASS WAY

Kissimmee, FL

4 beds | 3 baths | 2,798 sq.ft.

$499,700

Airbnb cash on cash: -0.26%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1735

Traditional Rental Income: $2984

Airbnb ROI: -0.26%

Traditional ROI: 3.44%

5004 LAGUNA BAY CIRCLE #47

Kissimmee, FL

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

$269,999

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1472

Traditional Rental Income: $2066

Airbnb ROI: -0.44%

Traditional ROI: 3.6%

2713 PEARL COURT

Kissimmee, FL

3 beds | 2 baths | 1,616 sq.ft.

$384,990

Airbnb cash on cash: 0.75%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $1472

Traditional Rental Income: $2480

Airbnb ROI: 0.75%