Windsor At Westside Ph 3 Homes with Tennis Court(s) Community Features

Windsor At Westside Ph 3 Homes with Tennis Court(s) Community Features

Welcome to Windsor at Westside Phase 3, a stunning subdivision nestled in the heart of Kissimmee, Florida, in Osceola County. This vibrant community is the epitome of luxury living, offering an array of features that cater to both relaxation and recreation. With its picturesque landscapes and meticulously designed homes, Windsor at Westside is an ideal choice for families, retirees, and anyone seeking a serene yet active lifestyle.

One of the standout features of this community is its impressive selection of homes with tennis courts. Imagine stepping out of your beautifully appointed residence and onto your private court, ready for a friendly match with friends or family. Tennis enthusiasts will appreciate the convenience and accessibility of having this amenity right at their doorstep. The community also boasts a variety of additional recreational facilities, including a sparkling resort-style pool, a state-of-the-art fitness center, and walking trails that wind through lush green spaces.

Beyond the amenities, Windsor at Westside Phase 3 is strategically located near top-rated schools, shopping centers, and dining options, making it easy to enjoy the best of Kissimmee. The proximity to major attractions like Walt Disney World and Universal Studios adds an extra layer of appeal, perfect for those who enjoy the excitement of Florida's entertainment scene.

Whether you’re looking to invest in a vacation home or seeking a permanent residence, Windsor at Westside Phase 3 offers a unique blend of luxury, community, and convenience. Come experience the charm and elegance of this remarkable subdivision, where your dream lifestyle awaits!

Newest Windsor At Westside Ph 3 Homes with Tennis Court(s) Community Features

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code

Fully Furnished 5-Bedroom Townhome with Heated Private Pool in Prime Kissimmee Location Welcome to this exceptional two-story townhome in the heart of Kissimmee, offering the perfect combination of comfort, style, and investment potential. Fully furnished and move-in ready, this beautifully maintained property is an outstanding opportunity for homeowners, vacation home buyers, and investors seeking a high-demand short-term or long-term rental property. Featuring 5 spacious bedrooms, 4 full bathrooms, and 1 half bathroom, this home offers an ideal layout for families and guests alike. The elegant primary suite provides a private retreat with a generous walk-in closet and a well-appointed en-suite bathroom. The additional bedrooms feature built-in closets and are thoughtfully designed to maximize comfort and convenience. Adding to the home's appeal, several of the bedrooms showcase fun and creative themed designs that guests of all ages will love, creating a memorable experience and enhancing its rental attractiveness. The open-concept floor plan creates a bright and welcoming atmosphere, seamlessly connecting the spacious living room, dining area, and kitchen. Whether entertaining guests or accommodating larger groups, the expansive living spaces provide both functionality and comfort. The beautiful kitchen is designed to impress, featuring solid wood cabinetry, elegant stone countertops, and a full suite of included appliances. With ample storage and workspace, it is perfectly equipped for everyday living or vacation rental use. Step outside to your own private resort-style retreat. The large heated swimming pool is enclosed within a screened lanai, allowing you and your guests to enjoy Florida’s beautiful weather year-round while maintaining comfort and privacy. This inviting outdoor space is ideal for relaxing, entertaining, or creating unforgettable vacation memories. One of the property's standout features is its access to an incredible, amenity-rich HOA community. Residents and guests enjoy a wide range of resort-style amenities designed to enhance both lifestyle and vacation experiences, adding tremendous value and appeal for owners and renters alike. Ideally located near major roadways, shopping, dining, entertainment, and highly rated schools, this property offers easy access to everything Central Florida has to provide. Its prime location, combined with its fully furnished condition, themed bedrooms, private heated pool, and exceptional community amenities, makes it a highly desirable choice for both personal use and investment purposes. Whether you are looking to expand your real estate portfolio or purchase a turnkey property with outstanding rental potential, this impressive Kissimmee townhome is an opportunity you won't want to miss. Schedule your private showing today and discover the value, versatility, and income potential this remarkable home has to provide

8923 Sydney Avenue, Kissimmee

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code

Just reduced $25,000! PRICED BELOW MARKET VALUE. This fully furnished property with EV station is within walking distance of the clubhouse. Rental-ready 6-bedroom property is priced to move fast and generate income from day one. Located in the newer phase of Windsor at Westside, one of Central Florida's most in-demand short-term rental communities, this turnkey corner-lot pool home is built for out-of-state and international investors seeking a hands-off, high-performing addition to their portfolio. Offering over 3,100 square feet, 6 bedrooms and 4.5 bathrooms, this home sleeps large groups comfortably and is approved for short-term and vacation rental use, a rare combination that keeps demand strong for owners renting on Airbnb, VRBO, and similar platforms. The open floor plan features a chef-style kitchen with stainless steel appliances, a breakfast bar, and abundant counter and cabinet space, flowing directly into the main living and dining areas, ideal for guests, groups, and multi-family stays. The primary suite includes a walk-in closet and a spa-style ensuite with dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms and bathrooms offer flexible sleeping arrangements, making this property equally suited for large families or short-term rental guests booking multiple rooms. Private pool and patio, set on a desirable corner lot with added space and curb appeal. The home is being sold fully furnished, a true turnkey opportunity for investors who want to start generating rental income immediately, with no renovation, staging, or setup required. This home sits within walking distance of one of the community's resort-style pools, and residents enjoy full access to Windsor at Westside's clubhouse, fitness center, game room, basketball court, on-site restaurant, multiple resort pools, a lazy river, and a waterslide. The location is minutes from Central Florida's world-famous attractions, a major draw for renters and a strong long-term value driver for owners.

8936 Prague Way, Kissimmee

5 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code

FULLY FURNISHED | TURNKEY INVESTMENT | RESORT-STYLE COMMUNITY Welcome to this beautiful two-story home located in the highly desirable resort-style community of Windsor at Westside. Featuring 5 spacious bedrooms and 4 full bathrooms, this fully furnished property is move-in ready and perfectly suited as a primary residence, vacation home, or income-producing short-term rental. The home offers a bright and open layout, with a modern kitchen equipped with stainless steel appliances and a breakfast bar, seamlessly connecting to the formal dining area and multiple living spaces—ideal for entertaining family and guests. Large sliding glass doors lead to a private screened-in pool area, providing a relaxing outdoor retreat with added comfort and privacy. Residents and guests enjoy access to outstanding resort-style amenities, including a spectacular pool with lazy river and waterslide, a fully equipped clubhouse with lounge areas, a tiki bar by the pool, fitness center, game room and arcade, as well as sports courts for tennis, basketball, and volleyball, plus a soccer field and playground. The community also features a scenic lake with a pier, a convenience store, and 24-hour gated security. Ideally located just minutes from Walt Disney World Resort, Universal Orlando Resort, and Disney Springs, the property is surrounded by a wide variety of shopping, dining, and entertainment options. This is a fantastic opportunity to own a fully equipped home in one of the most sought-after vacation communities in the area. Schedule your private showing today!

8933 Prague Way, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code

GREAT, GREAT PRICE IMPROVEMENT!! This beautiful home is locate on the third and newest phase of the sought after Windsor at Westside Resort. It boasts 5 bedrooms and 4 bathrooms of pure fun and relaxation! One bedroom and a bathroom are on the first floor, and the other 4 bedrooms, including some thematic, are located on the second floor, just by the family room! The Resort has heated pools, heated jacuzzi, heated lazy river, and a complete tiki bar by the pool complex! This gorgeous home is just waiting to become your next vacation nest!

2429 Dubai Street, Kissimmee

Start Your Search

Brian Scott Smith PA

Before launching his real estate career, Brian Smith spent over a decade in the construction industry, working hands-on with builders throughout Central Florida. That experience gave him an in-depth understanding of the homebuilding process—insight he now brings to his real estate clients, offering a level of expertise that sets him apart from most agents. In 2012, Brian joined his family’s firm, ERA Professional Realty. It was a “sink or swim” environment, and at the time, he wasn’t sure why his parents were so tough on him. Looking back, he’s grateful—they were preparing him for the challenges of a demanding industry, and that foundation shaped the dedicated, knowledgeable agent he is today. Since then, Brian has consistently ranked among the area’s top producers. His success is built on attention to detail, deep market knowledge, and a genuine commitment to client service. He stays current with real estate technology and prides himself on creating a smooth, informed experience for every buyer and seller. Brian has helped countless retirees transition to and from Florida, and he takes particular pride in assisting veterans and seniors through major life changes. In 2015, he was honored as REALTOR® of the Year at ERA Grizzard Real Estate. Today, he continues to list and sell millions of dollars in residential real estate annually and is expanding into commercial properties to serve an even broader range of client needs. A fifth-generation Floridian, Brian was born and raised in Central Florida. His local knowledge runs deep—something clients find to be a true asset when navigating the real estate market. Outside of work, Brian’s greatest pride is being a dad. He enjoys fishing with his son and watching his daughters grow into her own unique spirit. If you’re thinking about making a move, Brian Smith, REALTOR®, is a full-time agent ready to bring hard work, experience, and local expertise to your next real estate transaction.

Learn More

Browse Windsor At Westside Ph 3 Homes by Amenities