Kissimmee Homes with Tennis Court(s) Amenities

Kissimmee Homes with Tennis Court(s) Amenities

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the excitement of theme parks with the charm of a close-knit community. Nestled just minutes away from the world-famous Walt Disney World Resort, Kissimmee offers a unique lifestyle that caters to families, retirees, and everyone in between. With its warm climate, scenic lakes, and lush green spaces, Kissimmee is not just a place to live; it’s a place to thrive.

One of the standout features of homes in Kissimmee is the availability of properties with tennis court amenities. Imagine stepping outside your back door to find a private tennis court, ready for a friendly match or an invigorating practice session. These homes provide the perfect blend of luxury and leisure, allowing you to enjoy the Florida sunshine while staying active. Whether you’re a seasoned player or just starting out, having a tennis court at home makes it easy to indulge in your passion for the sport.

The community vibe in Kissimmee is enhanced by its numerous parks, recreational facilities, and organized sports leagues, making it an ideal location for tennis enthusiasts. After a day on the court, explore the local dining scene, which offers everything from casual eateries to fine dining, or take a stroll along the picturesque waterfronts.

Investing in a home with tennis court amenities in Kissimmee not only elevates your lifestyle but also positions you in a thriving community that celebrates both leisure and family-friendly activities. Come discover the charm of Kissimmee and find your dream home today!

Newest Kissimmee Homes with Tennis Court(s) Amenities

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 7 SubDv. ⋅ 34747 Zip Code

Welcome to your ultimate vacation retreat, ideally located just 5 miles from Walt Disney World in the highly sought-after Windsor Hills Resort! This beautifully maintained 6-bedroom, 4-bathroom pool home offers the perfect combination of comfort, entertainment, and resort-style living, making it an excellent choice as a second home or high-performing short-term rental investment. The property has been meticulously cared for and features numerous significant upgrades, including luxury vinyl plank flooring throughout (2022), upstairs A/C (2020), downstairs A/C (2022), pool heater (2021), pool motor/pump (2023), pool safety fence (2023), and dishwasher (2026). The home also features a durable tile roof, offering added longevity and value. The main level includes a bedroom and full bathroom, ideal for guests or multi-generational living. Upstairs, you'll find two spacious suites plus three themed guest bedrooms, providing plenty of room for family and vacation guests. The garage has been converted into a fun-filled game room, creating additional entertainment space for all ages. Step outside to your private screened-in pool, the perfect place to relax and enjoy the Florida sunshine. The HOA fee includes lawn service, daily valet trash pickup, internet, and basic cable. Windsor Hills offers outstanding resort amenities, including 24/7 manned gated entry, a resort-style clubhouse and community pool, sports courts, putting green, and more. Conveniently located just minutes from Disney theme parks, major Central Florida attractions, dining, shopping, championship golf courses, airports, and Florida's famous beaches, this is an exceptional opportunity to own a turn-key vacation home in one of Central Florida's most desirable resort communities.

2536 Holtrock Street, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Oakwater Condo Ph 11-14 SubDv. ⋅ 34747 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom fully furnished condo located in the desirable gated Oakwater community, just minutes from Walt Disney World and Central Florida’s most popular attractions. Whether you're searching for a primary residence, second home, or investment opportunity, this inviting condo offers the perfect combination of comfort, convenience, and location. Inside, you’ll find a bright and spacious open-concept living and dining area, a well-equipped kitchen with generous cabinet and counter space, and comfortable bedrooms with plenty of room to unwind. One of the highlights of the home is the private screened balcony overlooking lush tropical landscaping, creating the perfect setting for morning coffee or relaxing in the Florida sunshine. Oakwater offers an impressive collection of resort-style amenities, including a gated entrance, community pool, clubhouse, fitness center, tennis courts, and playground. With shopping, dining, major roadways, and world-famous attractions just minutes away, this condo offers an incredible opportunity to enjoy the best of the Central Florida lifestyle.

2742 Oakwater Drive Unit 104, Kissimmee

8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2b SubDv. ⋅ 34747 Zip Code

Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom, 6-bathroom home spans over 4,000 square feet of space designed for bringing loved ones together. Best of all, it comes fully furnished and turnkey, making it completely move-in or rental-ready from day one. Whether you are looking for a short-term rental investment or a primary residence where family and friends can spread out, this property delivers comfort, luxury, and convenience. From the moment you walk through the front door, the open-concept layout feels welcoming and effortless. The main floor features durable tile flooring throughout the main living areas, centered around a kitchen with rich cabinetry, stone countertops, and a large island where everyone naturally gathers. Just off the main space, slide open the glass doors to your private, screened outdoor oasis, featuring a crystal-clear pool, relaxing spa, and covered brick-paver lanai perfect for outdoor dining and evening relaxation. Thoughtful main-floor planning sets this home apart. The main level includes a private primary bedroom suite, as well as a second full bedroom and guest bathroom—ideal for guests who prefer to avoid stairs or for multi-generational living arrangements. Upstairs and across all bedrooms, you will find newly updated low-maintenance LVP flooring. For added entertainment, the full garage game room comes ready for fun with billiards and air hockey. Beyond the home, the neighborhood offers a complete resort lifestyle. The community amenities include a zero-entry pool with a water slide, lazy river, clubhouse, fitness center, bar and lounge, convenience store, tennis courts, playground, private rentable cabanas and more. The HOA fee simplifies daily living by covering high-speed internet, cable TV, daily trash pick-up, and full lawn maintenance. The location places you close to Central Florida's top attractions. You are approximately 25 minutes from Walt Disney World, minutes from shopping and dining at Posner Park, and close to the dining, shopping, and entertainment options at the Promenade at Sunset Walk, as well as nearby championship golf at ChampionsGate and major roadways like I-4 and US-27. Opportunities like this don't wait long—reach out now to claim your piece of Central Florida resort living today!

1610 Lima Avenue, Kissimmee

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

3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code

Fully Furnished First Floor Condo Near Disney! This beautifully maintained 3 bedroom, 2 bathroom FIRST FLOOR condo in the gated Wyndham Palms Resort Community offers exactly that lifestyle, with the added benefit of being FULLY FURNISHED and APPROVED for SHORT TERM RENTALS and AIRBNB. Whether you are searching for a vacation home, an income producing investment, or a primary residence close to the parks, this property is ready to deliver from day one. The open concept layout centers around a kitchen with STAINLESS STEEL APPLIANCES (2025), flowing easily into the living and dining spaces. NEW LUXURY VINYL PLANK FLOORING, FRESH PAINT, and REPLACED WINDOWS throughout give the home a clean, updated feel, while BRAND NEW LIVING ROOM FURNITURE means it is truly move in ready. The split bedroom design offers privacy for owners and guests alike, and a dedicated office space adds flexibility for remote work or managing your rental. Both bathrooms feature new shower doors for a fresh, modern touch. Imagine mornings on your private patio with coffee in hand, evenings by the resort pool, and easy access to Walt Disney World whenever the mood strikes. Step outside and you are directly across from the clubhouse, where residents enjoy 24 hour guard gated security, a resort style pool, splash pad, jacuzzi, sand volleyball, tennis and basketball courts, a movie theater, game room, and more. Location is everything here. You are minutes from Walt Disney World, Margaritaville Resort Orlando, Island H2O Water Park, Sunset Walk, Celebration, Old Town, championship golf, and Orlando International Airport, with quick access to US 192, SR 429, I 4, and Osceola Parkway. This is more than a condo. It is a chance to own a piece of the Central Florida lifestyle, fully turnkey and ready for you to enjoy

2307 Butterfly Palm Way Unit 104, 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 ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Welcome home! This well-maintained property is located in the desirable Kindred community of Kissimmee and features a thoughtfully designed floor plan that makes excellent use of the living space. The open layout creates a natural flow between the main living areas, offering comfortable spaces for everyday living and entertaining, while the bedrooms provide privacy and flexibility. Step outside and enjoy the screened porch, perfect for relaxing and enjoying the Florida lifestyle. Ideally situated within walking distance of the community clubhouse and school, this home puts everyday convenience close at hand. Enjoy all that Kindred has to offer, including resort-style amenities such as swimming pools, a fitness center, playgrounds, sports courts, walking trails, and more. Conveniently located with easy access to shopping, dining, major roadways, and everything Central Florida has to offer. A wonderful opportunity to enjoy a comfortable home in a vibrant, amenity-rich community!

1702 Walnut Creek Drive, Kissimmee

4 Beds ⋅ 4 Baths ⋅ Celebration Area 5 SubDv. ⋅ 34747 Zip Code

First floor primary bedroom plus upstairs ensuite in desirable Artisan Park. This charming 4-bedroom, 3.5-bath Coastal-style with 2,587 square feet of living space, this home features double front porches and a floor plan designed for comfortable everyday living. The primary suite is conveniently located downstairs, while three additional bedrooms are upstairs, including one with a private bathroom. As you enter the home, you're greeted by a separate dining room and living room, creating a welcoming and traditional entry space. As you continue toward the back of the home, the layout opens into the kitchen and family room, creating a comfortable gathering space for everyday living. The backyard patio provides a great spot for outdoor dining and entertaining, or simply relaxing and enjoying the Florida weather. The home also features fully owned solar panels and a new roof was installed in 2022. Residents of Artisan Park have exclusive access to the private clubhouse, featuring a restaurant and bar, fitness center, and resort-style pool, along with a variety of social events held throughout the month.

1114 Tapestry Drive, Celebration

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code

This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, 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

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