Homes for Sale Between $2,000,000 to $2,500,000 in Kissimmee, FL

7 Beds ⋅ 7 Baths ⋅ Regal Oak Shores Unit 3 SubDv. ⋅ 34744 Zip Code

Welcome to an extraordinary private lakefront estate on the shores of legendary Lake Tohopekaliga. Situated on nearly three-quarters of an acre at the end of a quiet cul-de-sac, this nearly 8,000 square foot architectural showpiece has been completely reimagined from the ground up with an uncompromising full-scale luxury renovation. Every detail was thoughtfully curated—from the expansive hardwood flooring throughout the main living areas and designer lighting to the stunning chef’s kitchen featuring oversized quartz islands, custom cabinetry, premium appliances, and double built-in ovens designed for effortless entertaining. The home offers an incredible blend of modern sophistication and resort-style living with multiple oversized living spaces, a private fitness studio, dramatic open staircases, soaring ceilings, panoramic lake views, and an expansive screened pool retreat overlooking Lake Toho and a private dock. The upstairs primary suite is truly a sanctuary of its own, featuring an enormous 20x24 bedroom, private balcony with breathtaking sunset views over the water, spa-inspired bath with soaking tub and oversized walk-in shower, and separate his-and-hers custom walk-in closets. With 6 bedrooms, 7 bathrooms, extraordinary entertaining spaces, and luxury finishes throughout, this estate delivers a rare opportunity to own a fully renovated waterfront masterpiece that feels like a private resort while remaining just minutes from Orlando, world-class attractions, and Central Florida’s premier lifestyle amenities.

1890 Saha Court, Kissimmee

$2,500,000

Ambassador Park SubDv. ⋅ 34741 Zip Code

Beautiful 4.417 acre (MOL) lot all clear, high and dry, buildable lot(s). This is great opportunity to purchase a great piece of land located in the heart of Kissimmee. This property is currently zoned High-Density, situated in the most strategic area of Osceola County. Just minutes to Walt Disney World, Orlando International Airport, malls, restaurants, hospitals, resort areas and more. Conveniently located close to major highways such as I-4 and the turnpike accessing transportation routes for commuting or travel. Presents an exceptional opportunity for those seeking to invest. This property is poised to capitalize on the areas booming growth of Osceola County. Don't miss out the chance to own this land. Act now and make it yours.

1500 N Hoagland Boulevard, Kissimmee

$2,500,000

South Semoran Farms Un 2 Unrec SubDv. ⋅ 34744 Zip Code

Property site in close proximity to the ever-growing Austin Tindall Sports Complex! Prime location for future development! This land will only go up as 2 milestones approach, Land Use Study and Boggy Creek Expansion 2026 Presently zoned agricultural. Osceola County is in process of conducting Land Use Study to be complete 5/2025. County is planning to change land use to Community Center, allowing many commercial uses, from restaurants to shopping centers. This is one of the fastest-growing communities which has led to the widening of Boggy Creek Road. Centrally located, minutes to Lake Nona, Medical City, 417, Orlando International Airport, downtown Kissimmee, Buenaventura Lakes and St. Cloud.

4210 Cardinal Lane, Kissimmee

$2,499,000

6 Beds ⋅ 7 Baths ⋅ Reunion West 17th & 18th Fairways Ph 2 SubDv. ⋅ 34747 Zip Code

NEWLY UPDATED IN 2026 WITH AMAZING (75 x 42 ft | 3,150 sq.ft) PRIVATE "PUTT PUTT" MINI GOLF. A feature this large is very unique. This luxury resort home is located in the Bears Den Neighborhood of Reunion Resort with active membership. Open floor plan and offers superb gathering spaces for you and family to enjoy. The backyard area is truly exceptional with seating for all your guests lounge around in the Florida sunshine. Dive into the oversized pool or relax in the hot tube with friends. There is space to significantly extend the pool deck to stand out from the competition. This potential upgrade would likely result in greater rental revenue. Reunion Resort is located just 6 miles from Walt Disney World and centrally located to all the other great attractions in the Orlando area. There is currently $71k of guest bookings in place for 2026. Any future bookings after closing would convey to the new owner should they decide to keep the home in the current vacation rental management program. The popular vacation rental has themed rooms that will make families feel like they’re having a one-of-a-kind getaway. The open living area is a great gathering spot for the family to enjoy each other's company with comfortable seating including a leather sectional overlooking the private pool deck as well as a feature fireplace. The fully equipped kitchen offers a four-seat breakfast bar and a dining table for seating up to twelve for a meal at any time of day. This home can accommodate up to 16 guests, providing plenty of space with two king-sized suites on the bottom floor and an additional king-sized bedroom with a shared family bathroom adjacent. On the second floor, you will find a further king-sized suite, a superhero-themed bedroom with two sets of bunk beds (4x twins) and a connecting bathroom as well as a candy-themed bedroom with two sets of bunk beds (4x twins) and a connecting bathroom. Once you get to the loft area on the second floor, you will be amazed by all its entertainment with a pool, foosball, and air hockey table for plenty of entertainment as well as a video game-themed games room equipped with arcade games and a home theater with a large flat-screen TV. The outdoor deck offers a private swimming pool and spillover spa to enjoy Florida's warm weather as well as a summer kitchen for all your grilling needs and a fire pit. The home gym also allows for some exercise and relaxation while on vacation.

7933 Jacks Club Drive, Reunion

$2,450,000

High Plains SubDv. ⋅ 34744 Zip Code

LOCATION, LOCATION, LOCATION! A Rare Industrial Development Opportunity in Booming Lake Nona area! This rare parcel at almost 2 acres in size unlocks exceptional potential and the property is situated in one of Kissimmee’s most rapidly growing areas. This piece of land has an ideal blend of privacy, peace, and potential. It is a perfect suit for forward-thinking investors and developers as the property is currently zoned for OAC (Open Agriculture and Conversation) and it can transition to Future Land Use (FLU) as Industrial. There is TOTAL FREEDOM with NO HOA restrictions: bring your RVs, boats, storage units, and all your favorite toys ensuring yourself with future development flexibility. Whether you’re looking to entertain, relax, or start your own mini farm, this property has the space and versatility to do it all. Strategically located near key infrastructure including Orlando International Airport, Lake Nona Medical City, Kissimmee’s tourism hotspots, and major highways, this parcel offers both logistical advantage and long-term growth potential. Enjoy the tranquility of rural living without sacrificing convenience. Don’t wait—schedule your private showing today and fall in love with this one-of-a-kind property! This rare gem won’t last long. Come live the life you’ve always imagined, free, connected to nature, and full of possibility. Don’t miss your chance to be part of Central Florida’s next major industrial hub.

4122 High Plains Lane, Kissimmee

$2,450,000

10 Beds ⋅ 10 Baths ⋅ Reunion Ph 1 Prcl 1 Unit 1 SubDv. ⋅ 34747 Zip Code

***Featured on HGTV's Zillow Gone Wild, Season 3 Episode 4 (Florida, Man) — Episode Winner!*** PROPERTY HAS ACTIVE REUNION CLUB MEMBERSHIP! Experience the Ultimate in Luxury and Creativity with this Aviation-Inspired Estate, Known as 'HIGH FLIGHT", Located in Reunion Resort, the Muirfield Model Features 10 Bedrooms and 9 1/2 Bathrooms. Inspired by USAF Combat Rescue Officers and F-22 Pilots, This Residence is Unlike any Other in the Orlando Market. The Property Includes a Rare Full-Scale Retired Puma Military Helicopter with a Custom Simulator, as Well as a 1930s SS Jaguar Equipped with a Racing Simulator. Entertainment Options are Extensive, Including a Private Movie Theater with Sofa Seating, a Game Room with Multiple Flight Simulators, Virtual Reality Games and Two Playstation 5 Consoles, as well as an Entertainment Loft Designed as an Aviation Lounge. Themed Spaces Throughout the Home Include Two Custom-Built Kid’s Bedrooms with Immersive Designs. One Features a Twin/Twin Bunk Bed Setup Situated in the Front End Of An Airplane, Complete with a Cockpit Seating Area. Through the Jack-And-Jill Bathroom, The Second Kid’s Suite Includes Aviation-Inspired Details such as Hanging Led Birds, a Hot Air Balloon Basket with a Small Twin Bed and a Classic Aircraft Design with Four Additional Twin Beds Integrated into the Upper and Lower Wings. Six Master Suites, a Queen Suite and Additional Guest Bedrooms Provide a Variety Of Sleeping Accommodations. The Interior Features an Open Floor Plan with a Fully Equipped Kitchen, Stainless Steel Appliances, an Oversized Island with Seating for Eight and a Formal Dining Room with Seating for Twelve. The Main Living Area Includes a Fireplace, Large Sectional Seating, and Direct Access to the Outdoor Living Space. The Private Pool and Spillover Spa Overlook the Golf Course and are Complemented by Six Loungers, a Covered Lanai, an Outdoor Kitchen with Grill and a Pool Table. Throughout the Home, Authentic Aviation and Military Memorabilia, Pilot Uniforms, and Historical Artifacts Create a Distinctive Environment, with its Unique Design, Extensive Amenities and Prime Location Just Minutes from Disney World Resort and Orlando’s Top Attractions, This Property Offers Exceptional Potential as a Luxury Residence, Investment Property or Vacation Retreat.

1213 Radiant Street, Reunion

$2,299,000

5 Beds ⋅ 5 Baths ⋅ Celebration South Village SubDv. ⋅ 34747 Zip Code

Tucked away on a secluded conservation lot in the heart of Celebration, this extraordinary David Weekley Treefair model is more than a home. It is a work of imagination, artistry, and luxury woven together beneath the Florida sunshine. Once owned by a Disney Imagineer and transformed as only a Disney Imagineer could, this solar-powered estate captures the rare magic of sophisticated design infused with creativity, storytelling, and the beauty of the outdoors brought brilliantly inside. From the moment you enter, the home unfolds like a private boutique resort. Exotic wood flooring, custom wood-paneled walls, dramatic textures, and curated designer finishes create an atmosphere that feels both elevated and deeply inviting. Sunlight pours through expansive walls of windows, illuminating the open living spaces while framing breathtaking views of the sparkling pool and serene conservation beyond. The thoughtfully designed floorplan offers five bedrooms and four-and-a-half bathrooms, including a luxurious downstairs owner’s retreat and a private fifth bedroom suite with full bath and separate entrance from the pool patio, ideal for guests, multigenerational living, or an inspiring creative studio. Formal living (currently used as sitting room) and dining rooms blend elegance with warmth, while the private office features floor-to-ceiling custom built-ins and designer workspace details worthy of a corner office in a luxury magazine spread. At the center of the home, the gourmet chef’s kitchen is a true showpiece. Striking quartz countertops, custom stainless-steel appliances, double ovens, dramatic high-contrast cabinetry, walk-in pantry, oversized cooking island, and a stunning waterfall granite feature create a space equally suited for intimate dinners or lively celebrations. Upstairs, imagination takes center stage with a spectacular 1950s-inspired diner room complete with boomerang countertops, authentic diner booth seating, glossy retro wall finishes, and classic checkerboard floors, a playful nod to vintage Americana wrapped in designer sophistication. Just steps away, the private home theater invites unforgettable movie nights and immersive entertainment experiences. Outside, the atmosphere becomes pure vacation fantasy. The resort-style saltwater pool feels pulled from a luxury island retreat, featuring cascading waterfalls, fire features, fiber-optic lighting, waterslide with faux rock detailing, in-water seating, and lush tropical ambiance throughout. The screened lanai was designed for unforgettable evenings, complete with a fully equipped tiki bar, dual refrigerators, gas grill, custom lighting, firepit gathering spaces, and stunning conservation views that create remarkable privacy and tranquility. Living in Celebration means embracing one of Central Florida’s most beloved and picturesque communities, originally developed by The Walt Disney Company. Residents enjoy charming downtown shops and restaurants, community events year-round, miles of walking and biking trails, scenic parks, golf, highly rated schools, and a lifestyle that feels lifted from a storybook while remaining just minutes from Walt Disney World and Orlando’s world-class attractions. Rarely does a home combine visionary design, luxury living, playful imagination, and resort-style outdoor living so effortlessly. This is not simply a residence. It is an experience.

908 Croton Road, Celebration

$2,299,000

10 Beds ⋅ 10 Baths ⋅ Reunion Phase 1 Parcel 1 Unit 3 SubDv. ⋅ 34747 Zip Code

Luxury 10-Bedroom Golf Front Estate in Reunion Resort. This property comes with the Gold Membership and access to Golf, Water Parks and the Tennis Facilities. – Fully Turnkey Investment Opportunity Welcome to an exceptional 10-bedroom, 9.5-bath luxury estate perfectly positioned on a premium oversized lot backing directly onto the golf course—offering rare privacy and stunning views just off the tee box in Reunion Resort. This fully furnished, turnkey vacation home is designed to impress, combining high-end living with unbeatable income potential. Property Highlights 10 Bedrooms | 9.5 Bathrooms 3 Bedrooms on the ground floor, ideal for multi-generational living 7 Bedrooms upstairs, including multiple en-suites, great kitchen with 2 Refrigerators, 2 Ranges, 2 Microwaves and 2 Dishwashers and there is an upstairs and downstairs laundry rooms. Two luxurious master suites with walk-in showers and a Butler's Pantry. Professionally designed with high-end, luxury furnishings included Entertainment Like No Other This home is built for unforgettable guest experiences: Huge private theater room with luxury electric recliners Custom karaoke stage – a rare and fun showpiece First floor, fully loaded games room 13x19. Upstairs an expansive loft/game area featuring pool table & poker table Three fully themed bedrooms: Moana, Monsters Inc and Minions. Resort-Style Outdoor Living Step outside into your private oasis: Large pool & spa with elegant block pavers Natural gas fire pit for evening relaxation Fully equipped outdoor kitchen No rear neighbors – enjoy peaceful golf course views and total privacy Convenient pool bath (half bath) for outdoor access, there is a 5x19 owners closet. ?? Investment + Lifestyle Whether you’re looking for a high-performing short-term rental or an incredible full-time residence, this home delivers both lifestyle and returns. Located just minutes from Disney and Orlando attractions, homes of this caliber in Reunion Resort are in high demand for luxury vacation rentals. This is a rare opportunity to own one of the most feature-packed, guest-ready homes in one of Central Florida’s premier resort communities.

7442 Gathering Court, Kissimmee

$2,275,000

6 Beds ⋅ 8 Baths ⋅ Reunion West Fairways 17 & 18 Rep SubDv. ⋅ 34747 Zip Code

ACTIVE TRANSFERABLE PLATINUM MEMBERSHIP AVAILABLE for the next owner. From the moment you step through the doors of this SPECTACULAR home you will realize you have found VACATION LUXURY at its finest. Welcome to Nicklaus Manor at Reunion located in the exclusive Bear's Den community at Reunion Resort. This well appointed and meticulously kept 6 Bedroom, 6 Full Bath En suite, and 3 half bath home, is being offered TURN KEY. The Santa Barbara Model boasts high end finishes throughout with an open floor plan that consists of a first floor primary bedroom that includes a HUGE custom walk-in owner's closet with the ability to lock off for privacy as well as additional closet for guests, dual sinks, a large walk-in shower and soaking tub. There is an 2nd en suite guest bedroom on the first floor. The spacious chef's kitchen includes a large island with seating for 4 ppl., an abundance of hardwood cabinets with crown moulding, quartz countertops, stainless JENN-AIR appliances that include a Gas Range, two refrigerators, two dishwashers, convection oven and more. Enjoy quiet meals in the formal dining area with seating for 10 ppl. Adjacent to the dining area is a spacious wet bar area with wine racks, two beverage coolers and additional cabinets for your convenience. Recent enhancements to the home include a converted garage to a state of the art Golf Simulator, two professionally themed children's rooms, decorative accent walls and decor were added throughout the home, and updated movie theater with gaming consoles. The expansive loft area has additional seating, air hockey, pool table, classic arcade game console and a beverage cooler, making this space ideal for both kids and adults to enjoy hours of entertainment. Step outside the loft area to a spacious covered lanai complete with new patio furniture, shuffleboard and an amazing views of the pool deck and the Bear's Den residents only park. The two remaining bedrooms one being an additional primary suite that offers private access to a covered lanai on the second floor. As you step outside to an island oasis enjoy countless hours of enjoyment on your amazing pool deck, featuring a covered lanai with ample seating for family & guests, a lagoon style pool, jacuzzi and beautiful water feature. There is a summer kitchen with a decorative tile backsplash, and a pool half bath just off the lanai. This amazing home is a great opportunity for a vacation rental, second home or primary residence and is walking distance to the Jack Nicklaus clubhouse where the Traditions restaurant and bar is located as well as the Jack Nicklaus Pro Shop. The Bear's Den community features gated security within the gates of Reunion, a fantastic dog park that you can access from your back gate on you pool deck, a sand volleyball court and putting green to practice your game. Reunion Resort is a one of a kind 2300 acre Resort and Golf community that has many amenities including a water park complete with water slides, lazy river, zero entry pools & food and beverage service, 3 award-winning golf courses designed by the legends of golf (Palmer, Watson & Nicklaus), 11 pools throughout the community, mini putt putt golf, world class tennis courts, pickleball courts, playgrounds, dog parks, golf cart & bike rentals and several on-site restaurants to include fine dining. Reunion Resort is located just 6 miles to Disney and the parks, and a short drive to the Orlando Int Airport. STRONG RENTAL INCOME available upon request.

997 Jack Nicklaus Court, Reunion

$2,250,000

20 Beds ⋅ 19 Baths ⋅ Bella Vista Condo SubDv. ⋅ 34741 Zip Code

Bella Vista Condos, is a stabilized 12-unit condominium portfolio located at 409 Fountainhead Circle, Kissimmee, Florida 34741. Units are located in separate buildings inside the apartment complex. Located just 10 miles from Walt Disney World Resort (about a 15 minute drive). This close proximity positions the property to attract a steady rental base from the region’s thriving workforce tied to the tourism, hospitality, and service industries. Additionally, residents benefit from easy access to world-class entertainment, shopping, and dining that make the Kissimmee/Disney corridor one of the most dynamic residential markets in Florida. Built in 1988, Bella Vista Condos consists of 12 individually owned condo units across a larger mid-rise development, totaling 10,652 rentable square feet. The portfolio features a balanced unit mix of 1, 2, and 3-bedroom units. All units are outfitted with central AC and screened-in patios or balconies. Tenants are responsible for electric (separately metered), while water and trash service are included in HOA Fees. Landlord recovers costs via a utility recovery fee. The property sits on a sizable 16.6-acre community, providing residents with open space and shared amenities including a tennis court, swimming pool, playground, and more. The property is also minutes from Downtown Kissimmee, The Loop Shopping Center, and major commuter routes like US-192 and the Florida Turnpike, enhancing convenience for working professionals.

409 Fountainhead Circle, Kissimmee

$2,250,000

24 Beds ⋅ 22 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code

Villa del Sol Condos, is a stabilized 12-unit condominium portfolio located at 2250 N Hoagland Blvd, Kissimmee, Florida 34741. Located just 8 miles (approximately a 15-minute drive) from Walt Disney World Resort, one of the largest tourist attractions in the world. This prime location creates a strong advantage for investors: the ability to attract steady rental demand from the local workforce in the hospitality and tourism industries, or alternatively, capitalize on the thriving short-term rental market to achieve higher returns. Built in 1999, the portfolio consists of 12 individually owned condo units totaling 12,004 square feet, within a larger 35-acre residential development. Each unit features a 2-bedroom layout, with most offering 2 bathrooms and averaging over 1,000 SF. All units include central AC, modern interiors, and access to shared community amenities. Tenants pay for separately metered electric, water and trash services are included in the HOA fees and landlord recovers cost via a utility recovery fee. The property features resort-style amenities including two swimming pools, tennis courts, and other recreational features that enhance tenant satisfaction and retention. Owning a condo portfolio near Disney provides several advantages: consistent tenant demand from hospitality workers, access to millions of annual visitors creating potential for short-term rental revenue, and strong long-term appreciation supported by Orlando’s thriving tourism economy.

2206 Antigua Place, Kissimmee

$2,249,900

8 Beds ⋅ 10 Baths ⋅ Reunion West Village 3a SubDv. ⋅ 34747 Zip Code

Spectacular 8 bed 8.5 bath home in Reunion Resort. Incredible private pool. Fully furnished and ready for move in. Located in the exclusive Eagle Estates community in Reunion Resort. Theme rooms make this a must see home.

1008 Coyote Creek Way, Reunion

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