Kissimmee, Florida listings for sale

​
$5,900,000 - Kissimmee, FL
8590 Apache Trail Kissimmee, FL - 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. As you enter through the private gate, you are greeted by a stunning family room featuring a handcrafted stone gas fireplace and soaring ceilings that create an inviting atmosphere. The elegant curving marble staircase, adorned with a magnificent Swarovski crystal chandelier, sets the tone for the opulence that awaits. This estate offers 5 spacious bedrooms, each with large walk-in closets and en-suite bathrooms, ensuring comfort and privacy for family and guests alike. The main living areas are enhanced by exquisite woodwork, including a gorgeous dining room and a living room that seamlessly connects to the outdoor oasis through sliding glass doors that open at the corner, perfect for entertaining. Indulge in the ultimate entertainment experience in the media room, complete with luxurious seating and a stunning chandelier commissioned from Tiffany's in New York. The primary suite is a true retreat, featuring a cozy sitting area and an expansive closet. Additional highlights include a gym with a steam room, an office/study/library, and an upstairs game room that overlooks a spacious covered balcony. The outdoor amenities are equally impressive, featuring a large pool with a spa, ample undercover seating, an outdoor kitchen, and tennis courts, all surrounded by lush landscaping and majestic oak trees. The estate also includes a wine cellar, a wet bar with custom woodwork, and coffered ceilings adorned with unique prints. With a 4-car side garage and an attention to detail that is truly one of a kind, this estate is unlike anything you have ever seen. Experience luxury living at its finest—schedule your private tour today and discover the extraordinary lifestyle that awaits you.
2009 | 5 | 7 | 11,138 sqft.
​
$2,950,000 - Kissimmee, FL
1015 Jack Nicklaus Court Kissimmee, FL - This Triple Deck delight is one of the very few true CUSTOM BUILT homes to grace one of Reunion's most sought after addresses- The Bear's Den. Enjoy one of the best outlooks in Reunion from the third-floor deck which can even provide a view to the DISNEY FIREWORKS! Each level of this home was built to ENTERTAIN. Its lofty privacy includes a hot tub, TV screens, and plenty of seating. Another highlight of this home is its game room on the 3rd-floor landing with Playstation 4, Xbox, Fast and Furious Superbikes Race, San Francisco Rush 2049 cat racing machines, and shuffleboard. The home theater has plenty of cushioned seating before a large projector screen. The first two floors contain 8 BEDROOMS that sleep up to 24 people! With an open planned floor plan, the living area is bright and spacious with a large wrap-around sofa before a large wall-mounted TV. The stunning kitchen with stainless steel appliances and granite countertops includes an over-sized double-sink kitchen island. The island counter wraps around a built-in seating area with cushioned benches around a kitchen table. Around the corner you'll find a fine dining table that seats 18 - you're entire party! This home includes two amazing THEMED BEDROOMS kids will love. Each room has two bunk beds (sleep 4) custom made to fit each theme. Whether kids love to zoom through faraway galaxies or live the life of a princess, they will be fully immersed. One upper bunk bed has a secret passage through a slide that takes kids to a secret playroom filled with soft foam blocks. Adults need not worry - alternative access is available! For playtime outdoors, there's a playground only a stonecast away, just behind the home. All of the other bedrooms are King-size with one exception: a room for two with separate Queen-sized beds. All of the rooms have their own TVs and there is an additional gathering room with a large comfy wrap-around sofa before a wall-mounted big-screen TV. The private pool has a spillover spa and the pool deck has plenty of sun loungers. A kids' safety fence is available. The lanai includes a summer kitchen with a BBQ grill. The patio dining table seat 16, and there are a few additional chairs scattered about. This home offers everyone in your family or group the comfort and entertainment that makes a stay in the Orlando area something to boast about. Reserve this beautiful property by booking it as early as possible and it can be part of your next vacation!
2020 | 8 | 9 | 5,827 sqft.
​
$2,925,000 - Kissimmee, FL
942 Jack Nicklaus Court Kissimmee, FL - This is a phenomenal opportunity inside our exclusive Bear's Den subdivision! This beautiful home will make has made a transition from residential home to HIGH RENTAL INCOME in one of the most sought after areas in Reunion. This 8BR CUSTOM BUILD has everything you need for success. 3 Bedrooms downstairs and 5 up accompanied by a perfectly situated & dedicated MOVIE THEATER and MEDIA ROOM. Recent conversion from the 2 car Garage to Entertainment room has greatly enhanced the homes rentability. The lot is exquisite if you like never ending SUNSETS and a fantastic covered lanai with a fully equipped outdoor kitchen and lounge area. FULLY FURNISHED with TRANSFERRABLE MEMBERSHIP and an added bonus with a GOLF CART GARAGE and numerous UPGRADES makes this home a must see for anyone looking to live in Reunion or rent out the home for maximum profit. Begin the day from your Media Room from a dedicated balcony and watch the Sunrise over Disney! Enjoy the day as you swim in the pool or lounge in the GREAT ROOM or have a dinner in the dining room with its 25'ceiling area open to the second floor or finish the day as you gaze out over the incredible back drop of the 18th hole on Reunion's Signature Nicklaus golf course all from the spectacular second level balcony. It's only a short walk away from the Dining, Fitness area, or Practice facilities of the Nicklaus Traditions Clubhouse for convenience. There isn't anything this home lacks! Come and see a perfect home in a perfect area and live out your dream at Reunion Resort. Call today to schedule a showing.
2020 | 8 | 6 | 5,720 sqft.
​
$2,499,000 - Kissimmee, FL
7933 Jacks Club Drive Kissimmee, FL - MOTIVATED SELLER, large price adjustment. 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 are currently $63k of guest bookings in place for 2025. 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.
2023 | 6 | 6 | 4,883 sqft.
​
$2,100,000 - Kissimmee, FL
4121 High Plains Lane Kissimmee, FL - Capitalize on this rare investment opportunity—a prime 3 -acre parcel strategically positioned in Kissimmee's rapidly expanding corridor. Perfect for visionary investors and developers, this property is set to benefit from Osceola County’s thriving business landscape. Currently zoned OAC (Open Agriculture and Conservation), its Future Land Use (FLU) is transitioning to Industrial, pending county and state approval. This shift unlocks a range of development possibilities, including manufacturing facilities, warehouses, logistics hubs, and research complexes. With a strategic location near Orlando International Airport, major highways, Lake Nona Medical City, and Kissimmee’s flourishing tourism industry, this parcel is poised for significant industrial growth. No HOA restrictions and an existing pond provide flexibility for innovative site planning. Whether you're ready to build immediately upon FLU finalization or prefer to cash in for future appreciation, 4121 High Plains Lane offers a unique opportunity to enter Kissimmee’s ever growing industrial market. This is your chance to be part of Osceola County’s dynamic expansion so be sure to schedule your site visit today and secure your place in one of Central Florida’s newest thriving future.
1989 | 3 | 2 | 1,602 sqft.
​
$1,999,000 - Kissimmee, FL
2910 Frontier Drive Kissimmee, FL - Lakefront Luxury on 5 AG-Zoned Acres | 225 Ft on East Lake Toho | No HOA | Near Lake Nona & OIA Up to $10,000 toward buyer’s closing costs with preferred lender. This one-of-a-kind estate offers freedom, privacy, and direct lakefront living, just minutes from Medical City, Orlando International Airport, and Lake Nona’s innovation corridor. Set on 5 agriculturally-zoned acres with 225 feet of shoreline, the property gives you instant access to boating, kayaking, trophy bass fishing, paddleboarding, and peaceful lakefront sunrises, right from your backyard. Inside, enjoy 20-foot ceilings, a formal living room with stunning lake views, and an open layout full of natural light. The remodeled summer kitchen features granite counters, stainless cabinetry, a built-in grill, gas cooktop, and oversized island, ideal for entertaining or everyday luxury. While officially listed as 4 bedrooms, the home lives like 5 thanks to a finished garage conversion with private entrance, perfect for guests, multigenerational living, or a home office. A downstairs den adds even more flexibility for a gym, media room, or playroom. The property itself is a rare find: Grand circular drive under mature oaks Private orchard with over 30 fruit trees, including mango, jackfruit, miracle fruit, loquat, lime, and more Zoned agricultural for horses, livestock, RVs, and gardens Detached 220V utility structure ideal for boats, EVs, or workshop use No HOA restrictions Also featuring a newer roof, three zoned A/C units, and pavered walkways throughout.
1991 | 4 | 4 | 4,664 sqft.
​
$1,950,000 - Kissimmee, FL
8153 Surf Street Kissimmee, FL - 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, stainless steel appliances, & a large island with breakfast bar seating and Frozen Concoction Maker. The second floor features 5 bedrooms including the luxurious primary suite, complete with a private balcony and spa-like ensuite bath with a soaking tub and separate shower. The third floor features a comfortable loft and a separate Game Room w/ Pool Table, Shuffle Board, Air Hockey, Pac Man and Wet Bar. Third floor also features a 675 sq ft Balcony Patio with Spectacular Waterfront Sunset Views. Back downstairs step outside to your own private Lakefront Oasis with a Pool, Heated Spa, a Grill, and Full Cabana Bathroom. The Clubhouse features a beach-style resort pool, St. Somewhere Spa, a gym, playground, splash pad, volleyball court, walking trails, bike rentals, and more. Sunset Walk offers a variety of fantastic restaurants and bars w/live music ,a movie theater and H20 Waterpark. LOCATED MINUTES FROM DISNEY PARKS! Your Perfect opportunity for a primary home, vacation home, or short-term rental.
2020 | 8 | 9 | 4,815 sqft.
​
$1,850,000 - Kissimmee, FL
3088 Parrot Head Place Kissimmee, FL - 'THE BLUE PEARL' is an AMAZING WATERFRONT Cottage with POOL, SPA and GORGEOUS SUNSET VIEWS on Margaritaville Resort Orlando's 'TROPHY ROW'! MOST PREMIER RESORT LOCATION JUST STEPS FROM THE FINS UP BEACH CLUB and OTHER RESORT AMENITIES! FANTASTIC OPPORTUNITY TO OWN ONE of the LARGEST FLOOR PLANS in the Resort and the ONLY MODEL that has 4 BEDROOMS on the FIRST FLOOR! THIS EXTREMELY RARE 4090-C Three-Story Model Features 8 Bedrooms, 9 Full and 2 Half Bathrooms, "BEACH HOUSE" Upgrade Package and a LARGE Patio/Balcony on Second Floor! This BEAUTIFUL Home Features Four En Suite Bedrooms on First Floor, Kitchen with LARGE ISLAND and Windows Facing the Pool Bringing in Tons of Natural Light, Full Size W/D, Living Room with Sliders that Lead to Beautiful Paved Patio, Fenced In Backyard with Covered Area, In-Ground Pool and Spa and Cabana Bath. Second Floor has Four Bedrooms Including a Primary Suite with Large Walk-In Closet, Dual Sinks, Separate Tub and Shower and Balcony Access. The Third Floor Features a Spacious Loft with Two Separate Rooms. One Room in the Loft is Highlighted with a Foosball Game Table and Bubble Hockey Game. Home also has Covered Front Porch, Upgraded 'WOOD' Tile Flooring, QUARTZ Countertops, In-Ceiling Speakers in Living Room that Connects to TV or Phone Via App. Ethan Allen "BEACH HOUSE" Furniture/Housewares Package INCLUDED in List Price! Package Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, Frozen Concoction Maker and SO MUCH MORE! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS! The Time is Now to Start Living the Margaritaville Lifestyle!
2019 | 8 | 10 | 4,092 sqft.
​
$1,795,000 - Kissimmee, FL
3056 Parrot Head Place Kissimmee, FL - 'EASY BREEZY' Cottage on Margaritaville Resort Orlando's 'TROPHY ROW'! EXTREMELY RARE OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT COTTAGES WITH POOL and SPA Plus Your Very Own ELEVATOR ($40k Upgrade)! Home is FULLY HANDICAP ACCESSIBLE. 4131-A Model, 8 Bedrooms, 8 Full Bathrooms and 1 Half Bathroom with IN PARADISE Upgrade Package. This Amazing Home Features Two En Suite Bedrooms on First Floor, Large Kitchen with Tiled Backsplash and Breakfast Bar, Spacious Pantry with CUSTOM SHELVING, Living Room with Sliders that Lead to Beautiful Paved Patio, Fenced In Backyard has Covered Area, Cabana Bath, Outdoor Speakers and 3 TV Hookups, In-Ground Pool and Spa with Spectacular SUNSET VIEWS Over the Lake! Second Floor has Master Suite with Separate Tub and Shower, CUSTOM BUILT CLOSET and Access to Balcony Overlooking Backyard. Three En Suite Bedrooms Complete Second Floor with Hallway Access to the Large Front Balcony. Third Floor has Upgraded Mosaic Tiled Alcoves which Compliment the Stairs leading to a Suite with Separate Tub and Shower, Access to Huge Tiled and COVERED PARTY DECK with Sweeping Lake Views. Loft with Wet Bar is Next to the Eighth Bedroom with Full Bathroom. Home also has Covered Front Porch, Upgraded 'Wood' Tile Flooring, Quartz Countertops, In-Ceiling Speakers in Living Room that Connects to TV or Phone Via App. Awnings Do Not Convey. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS! There's Nothing Like Living the Margaritaville Lifestyle in Paradise!
2018 | 8 | 8 | 4,335 sqft.
​
$1,753,600 - Kissimmee, FL
7438 Excitement Dr Kissimmee, FL - The best all-around investment properties in The Orlando-Kissimee area**CURRENTLY UNDER CONSTRUCTION 102 new units** Enjoy a luxury lifestyle, Live, Vacation, and/or generate income in these fantastic, spacious, no residential or rental restrictions properties, for a limited time we will include an individual, enclosed, covered Garage and a very exclusive Lifetime membership to Reunion Resort and Golf Club which your STR guests can also enjoy, FEATURES: 3 world-class golf courses designed by legends, tennis center, 7 pools, spas, rooftop terrace, fitness center, business center, water park, restaurants, café, bars, and much more!! 5 miles to Disney, and interstate I4, take advantage of this fantastic opportunity at The Crescent At Reunion
2025 | 12 | 8 | 5,312 sqft.