Kissimmee Real Estate

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

Welcome to your dedicated resource for Homes for Sale Between $2,000,000 to $2,500,000 in Kissimmee, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Kissimmee, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $2,000,000 to $2,500,000 below, or contact a local agent to discuss the details that matters most to your search.

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

1063 Jack Nicklaus Court, Kissimmee
$2,500,000
7 Beds ⋅ 10 Baths ⋅ Reunion West Fairways 17 & 18 SubDv. ⋅ 34747 Zip Code
Exceptional luxury, privacy, and rental appeal await in Reunion Resort’s prestigious Bear’s Den Club. Set on a rare oversized homesite with no rear neighbors and a private park directly behind the property, this fully furnished seven-bedroom residence offers one of the most desirable settings in the community. Professionally designed for unforgettable guest experiences, the home features immersive custom-themed bedrooms, multiple king suites, two creative bunk rooms, a state-of-the-art home theater, a spacious loft with billiards, and a dedicated arcade. The open-concept living area flows seamlessly outdoors to a private pool and spa, covered dining area, and fully equipped summer kitchen—perfect for entertaining and enjoying the Florida sunshine. Located just minutes from Walt Disney World and Orlando’s premier attractions, Bear’s Den offers access to Reunion Resort’s world-class golf courses, dining, tennis, water park, fitness center, and concierge services. An active Reunion Club membership is available, providing immediate access to the resort’s extensive amenities. Whether you’re looking for a luxury vacation retreat or a standout investment property designed to accommodate large groups, this home delivers an exceptional combination of location, entertainment, privacy, and resort living. Be sure to view the video tour!

1063 Jack Nicklaus Court, Kissimmee
1500 N Hoagland Boulevard, 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
8398 Happy Trail, Kissimmee
$2,495,000
4 Beds ⋅ 4 Baths ⋅ Happy Trails Units 1 & 2 Unrec SubDv. ⋅ 34747 Zip Code
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, the property offers enhanced accessibility, privacy, and flexibility for a variety of uses. Ideally located just minutes from Celebration, Reunion, and Walt Disney World, this exceptional property offers the perfect balance of luxury, privacy, and convenience with no HOA. A long, elegant private driveway leads to this impressive residence featuring 4 bedrooms, 3.5 bathrooms, an oversized 3-car garage with EV charging outlet, and a thoughtfully designed open-concept modern floor plan with expansive living spaces throughout. Step inside to experience soaring 14-foot ceilings throughout the entire home, enhanced by tray ceilings in the dining room, living room, and primary suite, along with a striking 16-foot cathedral ceiling in the designer kitchen, creating a bright and dramatic architectural presence. The gourmet kitchen is a true centerpiece, showcasing an oversized island with Italian granite, extensive custom cabinetry, a hidden oversized walk-in pantry, and a seamless connection to the main living and dining areas, ideal for both everyday living and entertaining. The elegant dining room features a stunning double glass-door wine display, while a beautifully designed wet bar with wine cooler adds both style and functionality. The spacious living area is anchored by a modern built-in electric fireplace with custom finishes. The breakfast area is framed by oversized picture windows, offering beautiful views of mature oak trees and the natural landscape, creating a serene, park-like setting. The luxurious primary suite offers a spa-inspired bathroom featuring a freestanding soaking tub positioned beneath a large picture window, a walk-in glass shower, and refined finishes that create a true retreat experience. All additional bedrooms are generously sized and designed for comfort and privacy. Outdoor living is equally impressive, featuring a covered lanai with a fully equipped outdoor kitchen, extensive paved areas, and expansive open acreage surrounded by beautiful mature trees. Zoned for horses, the property offers ample room for a barn, workshop, RV storage, or future additions. Additional features include double-glazed energy-efficient windows, premium modern motorized blinds throughout the entire home, large sliding glass doors, a private water well eliminating monthly water costs, and a seven-zone irrigation system.

8398 Happy Trail, Kissimmee
4122 High Plains Lane, Kissimmee
$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
843 Oak Shadows Road, Celebration
$2,399,000
6 Beds ⋅ 6 Baths ⋅ Celebration East Village SubDv. ⋅ 34747 Zip Code
A rare offering in Celebration’s coveted East Village, this magnificent Issa-built Classical Manor combines timeless architecture, exceptional scale and an enviable setting on an oversized corner homesite overlooking a picturesque park and surrounded by natural preserve. Offering more than 4,600 square feet, 6 bedrooms, 5.5 baths, private office, expansive bonus suite, 3-car garage and resort-style pool and spa, this exceptional residence has also benefited from an impressive collection of thoughtful upgrades. A welcoming front porch opens to interiors rich in architectural detail, complemented by marble flooring throughout the ground level, installed in 2019. Formal living and dining rooms provide an elegant backdrop for entertaining, while the spacious family room creates an inviting heart of the home. The chef’s kitchen is designed for gathering, featuring a Sub-Zero refrigerator (2022), Samsung dual oven (2020) and Samsung dishwasher (2025), all overlooking the outdoor living areas. The first-floor primary suite is a private retreat with French doors to the lanai and pool, two oversized walk-in closets, new carpet (2025) and a beautifully updated bath featuring Carrara marble. All bathrooms were refreshed in 2019 with new flooring, vanities, shower doors and more. An additional first-floor bedroom provides flexibility for guests or multigenerational living, while the private office is ideal for working from home. Upstairs, additional bedrooms and baths offer generous accommodations. The expansive bonus suite above the 3-car garage, with its own full bath and private access, can serve as a guest suite, game room, media room, fitness studio or private living quarters. A dedicated music room features sound treatment, and new ceiling fans have been added in the primary bedroom, living room and two upstairs bedrooms. Major improvements include a new roof by Greenway (2019), three Carrier HVAC systems installed by Ferran (2019), two new water heaters (2019), plus a high-efficiency 5-ton, 19-SEER Trane system serving the living area, installed January 2026. Outside, the screened lanai and oversized heated lagoon-style pool and spa create a true Florida retreat. A pool-area awning and summer kitchen were added in 2021, complete with outdoor grill, cabinetry and washer, creating a superb setting for year-round entertaining. The pool received a new motor and filtration system in 2025. The spacious fenced yard, refreshed front lawn with new sod, oversized corner homesite and 3-car garage provide an uncommon combination of privacy, space and convenience. Celebration offers a lifestyle unlike anywhere else in Central Florida, with scenic pathways, parks and green spaces connecting its distinctive villages. Stroll to Downtown Celebration for lakeside dining, boutiques, community events and the iconic waterfront. Ideally positioned near Walt Disney World Resort, the home also offers convenient access to Orlando International Airport, major roadways, championship golf, medical facilities and Central Florida’s renowned dining, shopping and entertainment. Chandeliers in the dining room and entry foyer do not convey.

843 Oak Shadows Road, Celebration
1051 Jack Nicklaus Court, Kissimmee
$2,299,000
7 Beds ⋅ 8 Baths ⋅ Reunion West Fairways 17 & 18 Rep SubDv. ⋅ 34747 Zip Code
Discover your Florida retreat in the gated community at Reunion Resort, conveniently located near Walt Disney World. This custom-built, 7 bedroom, 7.5 bathroom residence combines an impressive setting with generous space for relaxing, entertaining, and hosting guests. The spacious two-story layout offers room to spread out, while the private in-ground pool, heated spa, and outdoor patio create an inviting setting for enjoying Florida’s sunshine. Spend your days exploring the theme parks, then return home for a refreshing swim or a relaxing evening outdoors. Home layout · Pool and outdoor features The community offers a luxury vacation-home setting within Reunion, with resort offerings that include signature golf courses, dining, recreation. The community amenities set within an established vacation-rental community, this property presents an appealing opportunity for a personal getaway or short-term vacation rental.

1051 Jack Nicklaus Court, Kissimmee
997 Jack Nicklaus Court, Reunion
$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 world class amenities including a waterpark 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, 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
2794 Holiday Woods Drive, Kissimmee
$2,250,000
Acreage & Unrec SubDv. ⋅ 34744 Zip Code
Nearly 6 acres of private waterfront on beautiful East Lake Tohopekaliga (East Lake Toho)—an exceptionally rare opportunity to own one of Central Florida's most unique waterfront properties. Offering direct lake access, majestic oak trees, and an existing residence, this remarkable property is the perfect setting to build your dream waterfront estate, create a private family compound, or secure a one-of-a-kind investment. The existing home provides immediate use while you design your future vision. With no HOA, you'll enjoy the freedom to create the lifestyle you've always imagined, with room for boats, RVs, detached garages, workshops, expansive outdoor living, and more. Whether your vision is a custom waterfront estate, a multi-generational family compound, or exploring future development or rezoning opportunities, this remarkable property offers exceptional flexibility, subject to zoning, county approvals, and buyer due diligence. Enjoy world-class boating and fishing, breathtaking sunsets, abundant wildlife, and the peaceful privacy that only waterfront acreage can provide—all while being just minutes from Lake Nona, Medical City, Orlando International Airport, SR-417, Florida's Turnpike, shopping, dining, and entertainment. Large waterfront parcels of this size in such a prime location rarely come to market. Whether you're looking to build your forever home, create a legacy property for generations to enjoy, or invest in one of Central Florida's most desirable waterfront locations, this is an opportunity that is becoming increasingly difficult to find. Nearly 6 private waterfront acres. No HOA. Endless possibilities. A place to build not just a home—but a legacy.

2794 Holiday Woods Drive, Kissimmee
2794 Holiday Woods Drive, Kissimmee
$2,250,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34744 Zip Code
Nearly 6 acres of private waterfront on beautiful East Lake Tohopekaliga (East Lake Toho)—an exceptionally rare opportunity to own one of Central Florida's most unique waterfront properties. Offering direct lake access, majestic oak trees, and an existing residence, this remarkable property is the perfect setting to build your dream waterfront estate, create a private family compound, or secure a one-of-a-kind investment. The existing home provides immediate use while you design your future vision. With no HOA, you'll enjoy the freedom to create the lifestyle you've always imagined, with room for boats, RVs, detached garages, workshops, expansive outdoor living, and more. Whether your vision is a custom waterfront estate, a multi-generational family compound, or exploring future development or rezoning opportunities, this remarkable property offers exceptional flexibility, subject to zoning, county approvals, and buyer due diligence. Enjoy world-class boating and fishing, breathtaking sunsets, abundant wildlife, and the peaceful privacy that only waterfront acreage can provide—all while being just minutes from Lake Nona, Medical City, Orlando International Airport, SR-417, Florida's Turnpike, shopping, dining, and entertainment. Large waterfront parcels of this size in such a prime location rarely come to market. Whether you're looking to build your forever home, create a legacy property for generations to enjoy, or invest in one of Central Florida's most desirable waterfront locations, this is an opportunity that is becoming increasingly difficult to find. Nearly 6 private waterfront acres. No HOA. Endless possibilities. A place to build not just a home—but a legacy.

2794 Holiday Woods Drive, Kissimmee
1213 Radiant Street, Reunion
$2,250,000
10 Beds ⋅ 10 Baths ⋅ Reunion Ph 1 Prcl 1 Unit 1 SubDv. ⋅ 34747 Zip Code
HUGE PRICE IMPRVOEMENT!! ***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
409 Fountainhead Circle, Kissimmee
$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
2206 Antigua Place, 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
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