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. Impres...

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...

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...

BREAK IN RENTAL CALENDAR 03/10 and 03/11- OPEN 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 fami...

BACK TO MARKET! MUST SELL! Palatial Estate on 35 Acres w/ Massive Warehouse & Development Approval! A once-in-a-lifetime offering! This is not just land; it's a magnificent 5-bedroom, 5.5-bathroom mansion situated on a massive 35 acre compound, complete with a commercial warehouse. Experience...

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...

Experience modern luxury in this stunning 6-bedroom, 6.5-bathroom home, ideally situated in the exclusive Bear’s Den Club at Reunion Resort. Designed to accommodate up to 14 guests, this residence offers an expansive open-concept living and dining area with a fully equipped kitchen and breakfast ...

In the exclusive Bear’s Den community at Reunion Resort, this luxury Montecito floor plan residence offers an exceptional combination of refined design and strong vacation rental appeal. On a desirable corner lot, the home showcases elegant architectural details, a paver driveway, manicured lands...

This is a GREAT OPPORTUNITY to step into the Bear's Den in a FULLY FURNISHED residential home. It features 6 BR's that are spacious and offer En Suites in all bedrooms and either tile or Luxury Vinyl flooring throughout. The home features a finished MOVIE THEATER as well as Upstairs and Downsta...

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 ho...

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...

WOW! Fun In Paradise Awaits You in this Spectacular Spacious Cottage w/Private Pool & Spa at Margaritaville Resort Orlando! This model features 8 bedrooms all with their own private ensuite bath. The first floor features two bedrooms a gourmet, fully-equipped kitchen with quartz countertops,...

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...

**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...

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...

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...

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...

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...

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 ...

Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Exquisite Luxury Residence in Celebration's Coveted Island Village. Perfectly positioned on a premium corner lot, this meticulously maintained lux...