Properties For Sale in Kissimmee

Welcome to a truly unparalleled luxury estate, nestled on 5 acres of serene privacy. This custom-built masterpiece, completed in 2009, boasts an impressive 11,138 square feet of meticulously designed living space, where every detail has been thoughtfully curated for the discerning homeowner. A...

Discover a premier investment opportunity in Reunion Resort’s esteemed Bear’s Den community. This custom-designed, ten-bedroom home combines luxurious style, flexible layout, and top-tier amenities, making it ideal for turnkey short-term rentals, corporate retreats, or upscale vacations. Impr...

This elegant and stunning, custom home was built in 2000 by the award-winning builder, ISSA Homes and recently fully renovated to a modern and luxurious standard. No detail was missed, and no expense spared in this one-of-a-kind home which was originally built for the builder himself. The interio...

Unmatched Luxury & Rental Performance in Reunion’s Prestigious Bear’s Den Club! Experience the ultimate in resort-style living in one of the most exceptional vacation rental homes in all of Reunion Resort. This exceptional 7-bedroom residence is positioned on a rare oversized homesite with n...

RARE 9 BEDROOM ***Open 4/14-4/18 Luxury, Legacy and Lifestyle greet you at the private “Bears Den” gate at Reunion Resort. Once inside you will be met by this stunning 9 bedroom 8 ½ bath Reunion Resort Membership property that is equally inviting and LARGE enough to accommodate families with fore...

Custom-Built 2024 Private 5-Acre Estate. High & Dry in Gated Happy Trails. Welcome to a rare opportunity to own this exceptional estate situated on 5 pristine high-and-dry acres, one of the highest elevations within the community. Positioned on a desirable corner lot with dual gated entrances...

One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! This property is not just a home — it’s an experience, a destination, and an incredibly powerful income-producing asset all wrapped into one unforgettable opportunity. Built in 2020 and ...

Experience the pinnacle of resort living and high-yield investment potential at 7936 Jacks Club Court, a stunning 6-bedroom, 6.5-bathroom masterpiece located within the prestigious Bear’s Den enclave at Reunion Resort. Meticulously designed to sleep 14 guests, this fully furnished villa serves as...

One or more photo(s) has been virtually staged. Brand-new custom-built estate offering 4,179 sq ft of living space (5,558 sq ft under roof) on 5 private acres—never lived in! Ideally located in the sought-after acreage community of Happy Trails, just minutes from Celebration, Reunion, and Walt Di...

Exceptional opportunity to acquire a high-income potential property in the exclusive Bear’s Den at Reunion Resort. This 6-bedroom residence is ideally configured to accommodate large groups, making it perfectly suited for short-term rental performance. Located within one of Central Florida’s m...

Welcome to this stunning and well-maintained 12-bedroom, 11-bathroom fully furnished home located in the highly desirable Veranda Palms community! This exceptional property is the perfect opportunity for a primary residence or vacation home. Designed with comfort and functionality in mind, the h...

Stunning 14-bedroom, 11-bathroom corner villa in the heart of Kissimmee! Fully furnished and turnkey, this property features a private pool and spa, 16 Smart TVs, and an expansive open living area with tile floors, large windows overlooking the covered lanai, and a modern dining space with contem...

Reunion Resort Escape: 9BR Whitemarsh Cove Villa—Pool, Theater, & Disney Thrills! To all Investors —welcome to 7638 Whitemarsh Way, your slice of paradise in gated Whitemarsh Cove at Reunion Resort. Nine bedrooms, ten baths, bright open floor plan and vibes—massive living space, chef’s kitch...

Experience luxury and performance in this stunning Reunion Resort home located on one of the community’s deepest lots with panoramic views of the Jack Nicklaus Golf Course. This property stands out as a high-producing short-term rental with strong financial performance and an active Reunion Resor...

Kick back and embrace the laid-back island rhythm at this breezy lakefront retreat in Margaritaville Resort Orlando, perfectly positioned on Parrot Head Place. Wrapped in carefree Key West charm, this home delivers sun-splashed interiors, coastal hues, and a relaxed, barefoot-friendly layout that...

One or more photo(s) has been virtually staged. Come see this rare David Weekley Richmond Model home located in the picturesque town of Celebration, Florida. This spacious home welcomes you onto a charming front porch, built for friends, family, and neighbors to visit as they enjoy a sip of lemon...

One or more photo(s) has been virtually staged. Come see this rare David Weekley Richmond Model home located in the picturesque town of Celebration, Florida. This spacious home welcomes you onto a charming front porch, built for friends, family, and neighbors to visit as they enjoy a sip of lemon...

One or more photo(s) has been virtually staged. Welcome to your dream Oasis!! This exceptional custom home built in 2020, has been designed with every comfort and convenience in mind. Located on a 5-acre lot in the desirable Happy Trails community, you will be impressed from your first glimpse of...

**7 Bedrooms | 8.5 Bathrooms | Lakefront Living at Its Finest** Welcome to your dream home on the lake! This stunning 7-bedroom, 8.5-bathroom house just hit the market and it's everything you've been looking for. Sitting right on the water, you'll enjoy gorgeous sunsets from your backyard ever...

Welcome to 308 Southfield Street, a show-stopping luxury vacation estate located inside the exclusive Encore Resort at Reunion — one of Central Florida’s most sought-after short-term rental communities. Built in 2020 and spanning an impressive 6,351 square feet, this fully furnished 13-bedroom, 1...

Under contract-accepting backup offers. ***NOW OFFERING CREDIT FOR RATE BUYDOWN OR CLOSING COSTS***- SOLD FULLY FURNISHED!! Discover modern elegance and refined luxury in this custom 2021 estate, nestled in the exclusive, lakefront community of Bellalago. Spanning 4,895 sq ft, this 7-bedroom, 5-b...

ENCORE AT REUNION | TURNKEY LUXURY VACATION ESTATE WITH PROVEN INCOME — Built in 2018 and zoned for short-term rentals, this exceptional fully furnished 12-bedroom, 12.5-bathroom estate offers over 6,351 square feet of refined living space in one of Central Florida’s most sought-after resort comm...

Experience luxury, space, and unforgettable entertainment in this stunning home located in Solara Resort. Perfectly designed for family enjoyment or a high-performing short-term rental, this residence blends elegant style with immersive fun. A grand foyer opens to a spacious open-concept layout i...

Under contract-accepting backup offers. PONTOON BOAT NOW INCLUDED! Welcome home to your private water front tropical paradise in guard gated Bellalago with access to Lake Tohopekaliga of the famed Kissimmee chain of lakes including East Lake Toho, & Lakes Cypress & Kissimmee. From the minute you ...