Osceola Homes with Tennis Court(s) Amenities

Osceola Homes with Tennis Court(s) Amenities

Welcome to Osceola County, located in the heart of Kissimmee, Florida! Known for its vibrant community and stunning natural beauty, Osceola County offers a unique blend of urban amenities and outdoor adventures.

If you're a tennis enthusiast looking for the perfect home, Osceola County has a variety of properties with tennis court amenities. Whether you're a beginner or a seasoned pro, having a tennis court at your disposal provides endless opportunities for staying active and enjoying the beautiful Florida weather.

Imagine starting your day with a friendly match on the court, followed by a refreshing dip in your pool or a relaxing evening on your patio. With homes featuring tennis courts, you can elevate your lifestyle and create lasting memories with family and friends.

Osceola County is not just a place to live; it's a place to thrive. From top-rated schools and diverse dining options to exciting entertainment venues and picturesque parks, this county has something for everyone. And with the added luxury of tennis court amenities, you can enjoy a well-rounded lifestyle that combines leisure and wellness.

Discover the perfect home with tennis court amenities in Osceola County and experience the ultimate blend of comfort, convenience, and recreation. Live your best life in this dynamic community where every day is an opportunity for adventure and relaxation.

Newest Osceola Homes with Tennis Court(s) Amenities

$698,000
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
$299,900
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
$655,000
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
$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
$275,000
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
$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
$340,000
3 Beds ⋅ 3 Baths ⋅ Mandalay At Bella Trae SubDv. ⋅ 33896 Zip Code
Virtually Staged. Come tour this spacious end-unit townhome in Bella Trae, a gated community in ChampionsGate! Featuring vaulted ceilings, a neutral color palette, and an open-concept living and dining area, this home offers comfort, privacy, and low-maintenance living. The kitchen features granite countertops and stainless steel appliances, while the first-floor primary suite includes dual sinks, a walk-in shower, and relaxing soaking tub. Also downstairs are a laundry room, powder room, and attached two-car garage. Upstairs, a versatile loft is ideal for a home office or flex space, alongside two guest bedrooms and a full bathroom with dual sinks. Enjoy the enclosed back lanai with no side or rear neighbors for added privacy. Bella Trae HOA dues include lawn care, basic cable, and internet, plus access to resort-style amenities including a zero-entry pool, hot tub, clubhouse, fitness center, tennis courts, putting green, billiards room, and community grills. Ideally located near ChampionsGate shopping and dining, championship golf courses, Orlando attractions, and world-famous theme parks, this Bella Trae townhome combines location, lifestyle, and convenience.

1406 Milledge Lane, Davenport
$379,900
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
$419,900
5 Beds ⋅ 4 Baths ⋅ Stoneybrook South North Prcl Ph 1 SubDv. ⋅ 33896 Zip Code
**MOTIVATED SELLER!** Seller is offering **$1,000 toward Buyer’s closing costs with a full-price offer!** Let’s get to the point—this one checks the boxes! Beautiful, **MODERN, BRIGHT, AND FULLY FURNISHED**, THIS RARE **5-BEDROOM, 4-BATHROOM END-UNIT** OFFERS THE PERFECT COMBINATION OF SPACE, PRIVACY, AND RESORT-STYLE LIVING. Being an END UNIT MEANS MORE PRIVACY, EXTRA NATURAL LIGHT, AND PEACEFUL VIEWS OF THE NATURE BEHIND THE PROPERTY a wonderful bonus when you want to enjoy the resort lifestyle without feeling surrounded. The smart 5-bedroom/4-bathroom layout is especially attractive for larger families, groups, or guests who appreciate having their own space and independence. great condition, stylish modern interiors, and a full range of resort entertainment and amenities, and you have a property that is truly ready to enjoy from day one. The community offers a true resort-style lifestyle, with amenities like golf, tennis courts, a lazy river, water slides, a beach-style pool, spa, fitness center, and more—many of them included in the HOA. The home is currently part of a short-term rental program. There’s plenty more to say… but this home is much better seen in person! Call or text to schedule your private showing.

302 Ocean Course Avenue, Davenport
$875,000
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
$229,999
2 Beds ⋅ 2 Baths ⋅ Promenades At Bellatrae Condo Ph 25 Bldg 48 SubDv. ⋅ 33896 Zip Code
Virtually Staged. This beautifully maintained Spoonbill floor plan offers 1,797 square feet of thoughtfully designed living space and is ideally situated at the end of a quiet cul-de-sac with a west-facing rear exposure overlooking peaceful conservation views. Featuring 2 bedrooms, 2 bathrooms, a versatile den, and an attached 1-car garage, this lightly lived-in second home is move-in ready. The open-concept great room boasts soaring vaulted ceilings, creating a bright and spacious atmosphere that's perfect for entertaining or everyday living. The kitchen is beautifully appointed with granite countertops, stainless steel appliances, upgraded cherry cabinetry, and ample workspace for the home chef. Unwind on the screened lanai as you enjoy tranquil conservation views and watch colorful hot air balloons drift across the evening sky. Bella Trae offers an exceptional, maintenance-free lifestyle with lush landscaping, elegant architecture, and a luxurious amenity center. Residents enjoy access to a resort-style pool, state-of-the-art fitness center, pickleball and tennis courts, and a vibrant calendar of community activities. Conveniently located in Champions Gate, you'll have easy access to premier shopping, dining, golf courses, grocery stores, and major highways including US-27 and I-4, making travel throughout Central Florida effortless.

1218 Bella Cara Court, Davenport
$679,000
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
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