Osceola Homes with Pickleball Court(s) Amenities

Osceola Homes with Pickleball Court(s) Amenities

Welcome to Osceola County, Florida, where vibrant communities and endless opportunities await you. Osceola County is a diverse and thriving region located in the heart of the Sunshine State. Known for its beautiful landscapes, rich history, and friendly neighborhoods, Osceola County offers a high quality of life for residents of all ages.

If you're a fan of staying active and enjoying the outdoors, Osceola County is the perfect place for you. Many homes in this area come equipped with pickleball courts, making it easy to stay fit and have fun right in your own backyard. Whether you're a seasoned pro or new to the game, pickleball is a fantastic way to socialize and stay active.

Imagine spending your weekends playing pickleball with friends and neighbors, enjoying the Florida sunshine and creating lasting memories. With homes featuring pickleball court amenities, you can elevate your lifestyle and make the most of your leisure time. Stay active, meet new people, and enjoy all that Osceola County has to offer with homes that cater to your active lifestyle.

Don't miss out on the opportunity to live in a community that values health, wellness, and fun. Explore homes with pickleball court amenities in Osceola County, Florida, and discover the perfect place to call home. Live your best life in Osceola County, where every day is a new adventure waiting to be had.

Newest Osceola Homes with Pickleball Court(s) Amenities

$420,000
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
$569,900
3 Beds ⋅ 3 Baths ⋅ Twin Lakes Ph 2c SubDv. ⋅ 34772 Zip Code
Meticulously Kept, barely lived in Marco Model-3-bedroom, 3-bathroom open & spacious, situated on a corner lot with serene water view, located in the well sought after Del Webb Twin Lakes Active lifestyle 55+ community. As you enter into the oversized front porch, perfect for relaxing. Inside thru the foyer a secondary primary bedroom with a private en-suite bath offers an ideal guest or in-law suite. Adjacent to this is a bonus/flex space, along with a third bedroom, providing versatility to fit your needs. The heart of the home is the great room, where the gourmet kitchen shines with 42" cabinets, Custom Pendant Lights, stainless steel appliances, a built-in oven, microwave, premium cooktop hood, and a natural gas cooktop with 5 burners. A butler’s pantry with shelving makes for a perfect wine or coffee station. Domestic suit with upper cabinets for extra storage. The living & dining room with cam lights, kitchen areas seamlessly flow together, enhanced by abundant natural light. Primary bedroom features tray and light. Walk-in closet with shelves. Step outside from the large sliding glass doors that tuck away to a screen-enclosed Lanai, paradise Outdoor kitchen, Palm Trees privacy and outdoor enjoyment of serene water view. Garage features extra storage in the front of the garage. Amenities include a Resort style pool and Lap Pool, and 3rd pool on the carriage house side, 20,000 square foot Gorgeous Clubhouse, Lots of Activities celebrated in this gorgeous facility, State of the art Fitness Center, Flex room, Tennis Courts, Putting Green, Walking Trails, Pickle Ball Court, Fishing, and Pontoon Boats and Jon boat to use on Live Oak Lake! The community has many active and socializing activities to keep you VERY busy!! Located Central FL close to Lake Nona Medical City, Orlando Intern. Airport, Theme Park, & Beaches. This home is truly must-see!

2699 Midsweet Avenue, St Cloud
$540,000
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
$770,000
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
$325,000
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
$325,000
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
$166,000
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
$299,900
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
$975,000
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
$499,000
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
$579,900
4 Beds ⋅ 4 Baths ⋅ Twin Lakes Ph 2a-2b SubDv. ⋅ 34772 Zip Code
Beautiful Turnkey ready 4-bedroom, 4-bathroom home in the highly sought after Del Webb Twin Lakes 55+ Active lifestyle community. The Marco 2 is a two-story beautiful home with a versatile floor plan. When you step inside, you will be greeted with 10-foot ceilings and upgraded ceramic tile throughout the home. As you enter the kitchen you will be greeted with an upgraded kitchen with stainless steel appliances, convection oven, gas stove, 42" upgraded cabinets, quartz countertops, glass tile backsplash, walk-in pantry and a 10-foot island with upgraded pendant lights that easily seats 6. The Living Room/Dining Room combo has upgraded light fixtures and recess lighting. The sliding glass doors that lead out to the screened porch, open all the way for the ultimate indoor/outdoor Florida living. Out on the screened porch you can sit and enjoy the view of the pond in the back while drinking your morning coffee. The master bedroom has a large walk-in shower with glass doors and a large walk-in closet with a newly installed closet organizing system. There are two more bedrooms on the first floor. Bedroom 2 includes a full bath and a walk-in closet. The 3rd full bath is in the hallway to also be used as a guest bathroom. Bedroom 3 is just down the hall with a nice size closet. Off Bedroom 3 you'll find the office area that is already piped for water if you would like to add a wet bar. The stairs lead up to the second floor where you will find the 4th bedroom and 4th bathroom. This flexible room is currently being used as the owner's media room and office. Amenities include a resort style pool and lap pool, 20,000 square foot Clubhouse, fitness center, tennis courts, putting green, walking trails, pickle ball court, fishing and pontoon boats to use on Live Oak Lake. The community has many active and socializing activities for residents to connect with each other. This versatile home could be a wonderful space for multiple family members or friends who wish to live together. Close to Lake Nona Medical City, Orlando International airport, Theme parks, beaches and downtown Orlando. Call today for your private tour!

2709 Greenlands Street, St Cloud
$649,900
4 Beds ⋅ 4 Baths ⋅ Stoneybrook South Tr K SubDv. ⋅ 33896 Zip Code
WELCOME TO YOUR OWN BUTTERFLY LOVER’S PARADISE IN CHAMPIONSGATE COUNTRY CLUB! Discover this beautifully updated 4-bedroom, 3.5-bath home offering 3,305 square feet of living space, ideally situated on an oversized lot in the desirable Estate section of ChampionsGate Country Club**. Surrounded by thoughtfully designed landscaping that attracts beautiful butterflies, this home offers a peaceful connection to nature right in your own backyard. Step outside to your screened patio and take in the gorgeous pond view with a lighted fountain that creates a spectacular backdrop in the evening. Imagine starting your morning watching butterflies flutter through the landscaping or ending your day listening to the relaxing sound of the fountain as the sun goes down. It’s a tranquil Florida setting that truly needs to be experienced in person. Inside and out, this home has been refreshed and carefully maintained with numerous recent improvements, including fresh interior and exterior paint, new black hardware, a new kitchen single bowl stone sink and a beautiful black matte Moen faucet, new garbage disposal, the kitchen hood was updated to vent outside, new light fixtures throughout, new carpet in the master bedroom and freshly painted cabinetry in the primary bathroom, the front door has a beautiful glass insert to let the FL light shine through! The HVAC system was recently serviced, and an ultraviolet light was installed**, the hot water tank was cleaned, the driveway pavers were recently sealed, and the roof was recently cleaned and inspected. The backyard patio has also been newly screened and includes a new screen door, making it the perfect place to enjoy the beautiful water and fountain views. This home has been meticulously maintained! And the home is only part of what makes living here so special! ChampionsGate Country Club offers an incredible resort-style lifestyle, with a full golf membership and lawn maintenance included in the HOA, 24-hour gated security, cable phone and internet are also included, access to multiple amenity centers, and discounts on food and beverages at community restaurants. If you want to feel like you're on vacation this is the home for you! Whether your perfect day includes golf, tennis, pickleball, bocce ball, sand volleyball, floating along the lazy river, enjoying the water slides, working out, dining with friends, or simply relaxing beside one of the many pools, there is truly something for everyone. All of this is conveniently located near Central Florida’s world-famous theme parks, shopping, dining, and I-4, giving you easy access to everything the Orlando area has to offer. This isn’t simply a home—it’s a lifestyle and a butterfly lover’s paradise! With its oversized Estate-section lot, tranquil pond and lighted fountain views, beautiful butterfly-attracting landscaping, extensive recent improvements, and all the amenities of ChampionsGate Country Club, 1458 Olympic Club Boulevard is one you truly need to see to believe!

1458 Olympic Club Boulevard, Davenport
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