Kissimmee Homes with Pickleball Court(s) Amenities

Kissimmee Homes with Pickleball Court(s) Amenities

Welcome to Kissimmee, a vibrant city located in the sunshine state of Florida! Known for its beautiful weather, endless entertainment options, and close proximity to world-famous theme parks, Kissimmee is a fantastic place to call home.

If you're a fan of staying active and enjoying the outdoors, you'll be pleased to know that many homes in Kissimmee offer pickleball court amenities. Whether you're a seasoned pro or looking to pick up a new hobby, having a pickleball court right in your neighborhood provides endless opportunities for fun and fitness.

Imagine starting your day with a friendly game of pickleball with your neighbors, followed by a relaxing dip in the pool or a leisurely stroll through the community. With homes featuring pickleball courts, staying active and socializing has never been easier.

In Kissimmee, you'll find a diverse range of real estate options, from cozy condos to spacious single-family homes, ensuring that there's something for everyone. So whether you're looking to downsize, upgrade, or invest in a vacation property, Kissimmee has the perfect home for you.

Don't miss out on the opportunity to live in a city that offers the best of Florida living, complete with pickleball court amenities right at your fingertips. Come discover the charm and convenience of Kissimmee – where every day feels like a vacation!

Newest Kissimmee Homes with Pickleball Court(s) Amenities

2 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Ph 2 SubDv. ⋅ 34747 Zip Code

Welcome to the Four Seasons of Orlando's 55+ Community in Kissimmee, Florida just minutes from the Disney Theme Parks. This is a "Sandpiper" Villa with two bedrooms and two full baths plus a bonus room that can be an office or third bedroom. You will enjoy the spacious open concept living with sliders out to your own private heated pool. The caged lanai is extended with plenty of sunshine coming in. The Four Seasons is intertwined within Mystic Dunes Golf Course which makes for an interesting property lay-outs. We have a gate access over to the golf course and can enjoy lunch or dinner at the restaurant. You will also enjoy the two heated pools with a lap lane and hot tub. The clubhouse features a large ballroom, kitchen, game rooms, meeting rooms, gym and excercise room. Come join our community, it sure is a special place to live and minutes to the Disney Parks.

1896 Flora Pass Place, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code

Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code

What's Special: Larger Lot | Flex Room | Pond View | Gourmet Kitchen. New Construction – Ready Now! Welcome to the Ambra at 5676 Nevis Terrace at Esplanade at Westview! The open-concept living area seamlessly connects the great room, spacious kitchen with a large center island, and views of the covered lanai, creating an inviting space for everyday living and entertaining. A formal dining room is conveniently located near the kitchen for special gatherings. At the back of the home, two private primary suites each feature a walk-in closet and en-suite bathroom. A secondary bedroom and full bathroom are situated at the front of the home, while a spacious laundry room just off the garage entry adds everyday convenience. Additional Highlights Include: a bay window in the primary bedroom, a bay window in the second primary bedroom, gourmet kitchen, tray ceiling package, 8' interior doors, and laundry room sink. Photos are for representative purposes only. MLS#O6432452 Experience resort-style living at Esplanade at Westview in Kissimmee! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep Academy of Osceola charter school.

5676 Nevis Terrace, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Esplanade At Westview SubDv. ⋅ 34758 Zip Code

What's Special: Covered Extended Lanai | Pond View | Oversized Garage. New Construction - Model Home Available Now! Welcome to the Pallazio at 4364 Curacao Place in Esplanade at Westview! Blending elegant design with everyday comfort, this thoughtfully crafted home offers a spacious open-concept layout centered around a stunning great room, gourmet kitchen, and casual dining area that flow seamlessly to an expansive outdoor living space. The private primary suite serves as a peaceful retreat, while two secondary bedrooms, a versatile flex room, and formal dining space provide flexibility for work, hosting, or relaxation. With abundant natural gathering spaces and inviting details throughout, this home is designed to make every day feel warm, effortless, and beautifully connected. Additional Highlights Include: upgraded appliance package, 4-foot garage extension and paved back yard. Experience resort-style living at Esplanade at Westview in Kissimmee! This vibrant community offers endless opportunities to stay active, relax, and connect. Unwind by the resort-style pool, sip a drink at the Bahama Bar, or lounge in a private poolside cabana. Stay energized with tennis, pickleball, and bocce ball courts, or enjoy a workout at the state-of-the-art fitness center. Indulge in signature spa services, gather around the firepit with friends, or let your pup play at the bark park. Every day brings new possibilities in this thoughtfully designed community where you can live life to the fullest! Located near the sought-after Bridge-Prep Academy of Osceola charter school. MLS#

4364 Curacao Place, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code

**LIMITED-TIME LAUNCH PRICING — secure this Reunion Grande residence at its introductory price before it returns to market-value pricing after Week 3!** Welcome to Unit #307, a fully furnished 2-bedroom, 2-bath residence offering one of the most compelling features in Reunion: direct, unobstructed views toward Walt Disney World from your own private balcony, where you can take in spectacular Florida sunsets and nightly Disney fireworks. Offering approximately 1,430 square feet, the residence features an open and inviting floor plan with upgraded finishes, crown molding, granite countertops, and a kitchen that flows seamlessly into the living and dining areas. The split-bedroom configuration creates two private bedroom suites with well-appointed bathrooms, making the layout equally suited for personal use, vacationing, or hosting guests. Offered fully furnished and turnkey, #307 is positioned for immediate enjoyment and offers the flexibility of primary, second-home, or vacation-rental use. An active Reunion Resort membership is included and transferable to the new owner, providing access to Reunion's renowned resort lifestyle, including three signature golf courses designed by Arnold Palmer, Tom Watson, and Jack Nicklaus, the multimillion-dollar water park, resort pools, tennis and pickleball, fitness facilities, and additional amenities. Within the Reunion Grande itself, enjoy front desk concierge service, valet parking for members, 7593 Chophouse, a lobby-level sushi bar, Starbucks coffee and gift shop, plus the rooftop restaurant and pool overlooking the surrounding resort and Central Florida skyline. Located just minutes from Walt Disney World and convenient to Orlando's other world-famous attractions, #307 combines location, flexibility, resort amenities, and a view that is difficult to replicate. **With launch pricing available for only the first three weeks, this is the opportunity to act before the property returns to market value.**

7593 Gathering Drive Unit 307, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Reunion Grande Condo SubDv. ⋅ 34747 Zip Code

**LIMITED-TIME LAUNCH PRICING — take advantage of this introductory price before the property returns to market-value pricing after Week 3!** Welcome to Unit #706 at the Reunion Grande, an exceptional opportunity to own a fully furnished, turnkey 2-bedroom, 2-bath residence in the heart of Reunion Resort. Positioned on the 7th floor with desirable east-facing exposure, this spacious 1,430-square-foot condo offers beautiful morning light, elevated resort views, and comfortable shaded afternoons from your private balcony. Inside, an open-concept layout connects the kitchen, dining, and living spaces, while the split-bedroom design provides privacy for owners and guests alike. Offered fully furnished and ready for immediate enjoyment, this residence offers tremendous flexibility as a primary residence, second home, vacation retreat, or short-term rental opportunity. Located inside the iconic Reunion Grande, owners and guests are surrounded by resort-style conveniences including valet parking, front desk concierge service, on-site dining, Starbucks coffee and gift shop, the acclaimed 7593 Chophouse, sushi bar, and an 11th-floor rooftop restaurant and pool offering panoramic views across Central Florida. Beyond the Grande, Reunion Resort encompasses approximately 2,300 acres and is home to three signature championship golf courses, resort pools, dining, fitness and recreation opportunities, and its multimillion-dollar water park. Best of all, you're approximately 6 miles from Walt Disney World with convenient access to Orlando's world-famous attractions and major highways. Whether you're looking for your own Central Florida getaway or a furnished property with vacation-rental flexibility, #706 delivers the location, lifestyle, and versatility Reunion is known for. **The launch price is available for a limited three-week window — don't wait for the price to return to market value.**

7593 Gathering Drive Unit 706, Kissimmee

Reunion Ph 02 Prcl 01 & 1a SubDv. ⋅ 34747 Zip Code

Amazing opportunity to own a fantastic lot on the 3rd hole of the Palmer signature golf course. Land is hard to come by in Reunion these days so purchase while you can. The homesites do not have a time restriction to begin construction immediately so purchase now or for future generations to own. Build for full time residence or vacation home. Great proximity to all the major theme parks especially WALT DISNEY WORLD being just 2 exits away, makes this vacation community a top choice for visitors of all ages. If you are looking to take a few golf swings while on your vacation you can take the challenge on any of the 3 World Class Championship GOLF COURSES designed by Arnold Palmer, Tom Watson And Jack Nicklaus that are located on-site. Reunion offers many onsite restaurants from hamburgers at The Cove to fine dining at Chophouse and everything in between. There are 14 pools in the community including MULTIMILLION DOLLAR WATER PARK with lazy river & water slide.

7632 Excitement Drive, Reunion

3 Beds ⋅ 2 Baths ⋅ Westview Pod B Neighborhood 5 Ph 1 SubDv. ⋅ 34758 Zip Code

Come see this bright and inviting 3-bedroom, 2-bathroom home recently built in 2025 in Kissimmee. This move-in-ready residence blends modern design with everyday comfort, offering an easy, low-maintenance lifestyle just minutes from local shopping, dining, and major roadways. Step onto the covered front porch, an inviting spot for morning coffee, and through the front door into a bright, open-concept living space. The main living and dining areas feature a stylish tray ceiling that adds architectural interest, along with large windows that fill the rooms with natural light. Durable tile flooring runs throughout the main living areas, making cleanup a breeze. The kitchen is a true centerpiece, featuring crisp white cabinetry, sleek stainless-steel appliances, a tile backsplash, and a spacious island with bar seating, perfect for casual meals or entertaining guests. The adjacent dining area comfortably fits a full-size table, and the open flow into the living room makes this home ideal for gatherings with friends and family. The living room invites you through sliding glass doors to the backyard, creating a seamless indoor-outdoor connection. The primary suite offers a peaceful retreat with plush carpet, a ceiling fan, and plenty of natural light, while the second and third bedrooms provide flexible space for guests, family, or a home office. A dedicated large laundry room offers space for a full-size washer and dryer plus built-in shelving for extra storage. The two-car garage offers ample space for parking and storage, and the water softener conveys with the home for added value Outside, the home showcases attractive curb appeal with a paver driveway and walkway, stone accents at the entry, and a well-manicured lawn. Behind the home, unwind on the enclosed, covered lanai overlooking a large backyard and peaceful water view, a perfect spot to relax any time of the day. This home is part of Lennar at Esplanade, a new master-planned community in Kissimmee that welcomes pets, making it a great fit for owners with furry companions. Residents enjoy access to a community pool and clubhouse, a fitness center, dog park plus courts for tennis, pickleball and bocce ball, along with a spa for relaxing after a day of activity. The neighborhood sits close to Highway 17, putting the greater Orlando area within easy reach, and outdoor lovers will appreciate being a short drive from area lakes and nature trails for hiking and exploring, such as the Lake Marion Creek Wildlife Management area. Whether you're a first-time buyer, growing family, or investor, this property checks all the boxes: modern finishes, thoughtful design, and a location that puts you close to everything Central Florida has to offer. With green and energy-efficient construction plus thoughtful finishes throughout, this home offers the comfort of new construction without the wait. Come see the possibilities and make this house your own. Don't miss your chance to own this nearly new home. Schedule your private showing today!

4536 Ochos Rios Place, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Bellalago Ph 6h & 6i SubDv. ⋅ 34746 Zip Code

Vacation every day in this luxury lakefront home, extensively renovated in 2024 and designed for both comfort and style. Enjoy the most beautiful view in the community, creating a serene backdrop for everyday living. The home features new luxury vinyl flooring throughout (2024) and custom built-in cabinetry in the kitchen and hearth room, blending functionality with elegance. The spa-inspired primary bathroom has been completely renovated, offering a private retreat. Perfect for entertaining, the home seamlessly connects indoor and outdoor living with custom folding sliding doors that open to a spacious lanai—ideal for gatherings or relaxing evenings by the water. A dedicated media room provides the perfect setting for family movie nights. Dog lovers will appreciate the thoughtfully designed custom dog wash, adding convenience and luxury for every member of the household. Located in a resort-style community, this home offers the ultimate in lakefront living and lifestyle.

3713 Dockside Dr, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Kindred Ph 2a SubDv. ⋅ 34744 Zip Code

Welcome Home to Kindred living at its finest! Built in 2021, this impressive single-story home features 4 spacious bedrooms, 3 full bathrooms, over 2,100 sq. ft. of beautifully designed open-concept living space, and no rear neighbors! Step inside to an expansive floor plan boasting high ceilings and seamless flow between the living, dining, and chef’s kitchen areas. The open kitchen features modern finishes, a large center island, and plenty of cabinet storage—making it perfect for hosting guests or enjoying family meals. With a 3-full-bathroom layout, this floor plan offers exceptional convenience, ideal for multi-generational living, guests, or a private home office setup with its own dedicated bath. The primary suite serves as a tranquil retreat with a walk-in closet and a spa-like en-suite bathroom. Step outside to your own private backyard retreat with no rear neighbors, featuring a variety of bearing fruit trees including oranges, grapefruit, star fruit, ice cream bananas, and concord grapes. Unbeatable Neighborhood Location: Located directly on Park Side Ave, this home is within easy walking distance to the community Kindred K-8 Elementary school as well as Kindred’s main clubhouse, resort pool, and amenity complex—giving you effortless daily access right out your front door! Beyond the home, enjoy Kindred’s resort-style community amenities, including multiple pools, splash pads, fully equipped fitness centers, sports courts (tennis and sand volleyball), Soccer field, miles of walking trails, tot lots, and a dedicated dog park. Prime Connectivity: Minutes from Neptune Road, US-192, and the Florida Turnpike for smooth daily commutes. Conveniently located near NeoCity (Central Florida’s premier high-tech hub), Lake Tohopekaliga, Lake Nona, and Orlando International Airport (MCO). Schedule your private showing today to experience everything about this home and community!

1621 Park Side Avenue, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Maple Chase At Cypress Woods SubDv. ⋅ 34758 Zip Code

Rare find in this neighborhood. Nestled in the sought-after Maple Chase community within Cypress Woods Poinciana, this stunning 3-bedroom, 2-bathroom home offers 1,876 sq ft on a generous lot — complete with a tranquil water view and no immediate rear neighbors, giving you rare privacy and open space in your backyard. Inside, two living and dining room combinations offer ultimate flexibility — perfect for formal entertaining, a family gathering space, a playroom, or a home office. The spacious layout adapts effortlessly to your lifestyle, with vinyl flooring, and no carpets. The extra-large bedrooms set this home apart, offering ample space for king-sized furniture and room to truly unwind. Minutes from dining, shopping, major highways, and Walt Disney World — this home blends suburban tranquility with Central Florida convenience. Schedule your showing today!

4442 Maple Chase Trail, Kissimmee

4 Beds ⋅ 4 Baths ⋅ Celebration Village Unit 2 SubDv. ⋅ 34747 Zip Code

Welcome to Crescentwood, a truly rare offering in the Main Village of Celebration, a fully reimagined estate set across two homesites, creating a scale and presence seldom found within the community. Thoughtfully renovated with high-end materials and custom finishes throughout, the residence blends timeless architecture with modern luxury in a way that is both refined and highly livable. As you enter, the foyer welcomes you with substantial millwork, curated lighting, and a level of craftsmanship that immediately defines the residence. Formal and casual living spaces are elegantly proportioned, featuring beautiful tile flooring, layered ceiling details with integrated lighting, custom built-ins, French doors and oversized windows that fill the interiors with natural light. A beautiful sitting room framed by eight windows creates an inviting space bathed in natural light throughout the day. At the center of the home, the completely redesigned chef’s kitchen showcases custom Poggenpohl cabinetry, premium integrated appliances, dramatic illuminated stone surfaces, extensive preparation space, and a seamless connection to the adjacent living and dining areas, creating an ideal setting for both entertaining and everyday living. The owner’s suite serves as a luxurious private retreat with a spa-inspired bath finished in striking marble, custom fixtures, and refined architectural detailing. The suite is further enhanced by two walk-in closets, offering exceptional organization and boutique-style functionality. Each secondary bedroom are designed as private ensuite retreats complete with walk-in closets and beautifully updated bathrooms featuring elevated finishes and distinctive design details. The third-story movie room offers a true cinematic experience tucked away as a private entertainment space. Adding to the property’s versatility is a fully upgraded one-bedroom apartment featuring a private entrance, luxurious bath with a freestanding tub and separate shower, eat in space, living room and full-size washer and dryer offering ideal flexibility for guests, extended family or private office space. The main residence includes a two-car garage, while automotive enthusiasts and collectors will especially appreciate the separate temperature controlled oversized three-car garage. Designed with high ceiling height to accommodate vehicle lifts, the space has the potential to house up to six vehicles—an extraordinarily rare amenity within Celebration. The outdoor living experience is equally impressive, featuring a swimming pool and spa surrounded by elegant limestone pavers, summer kitchen, covered entertaining areas, and lush landscaping. A substantial stucco masonry wall encloses the grounds, creating an ultra-private backyard and pool setting rarely found within Celebration’s Main Village. Extensive landscape lighting beautifully illuminates the property and architectural details in the evening, enhancing the estate’s ambiance and presence after sunset. Multiple outdoor gathering spaces further elevate the estate-like atmosphere, creating the feel of a private luxury resort. Crescentwood represents a one-of-one opportunity within Celebration, offering the rarity of a double homesite, a fully renovated luxury residence and a level of finish and scale that is nearly impossible to replicate within the Main Village.

706 Golfpark Drive, Celebration

Start Your Search