Windsor At Westside Ph 2a Homes with Tennis Court(s) Community Features

Windsor At Westside Ph 2a Homes with Tennis Court(s) Community Features

Welcome to Windsor At Westside Phase 2A, a vibrant and inviting community nestled in the heart of Kissimmee, Florida, within beautiful Osceola County. This enchanting subdivision offers a perfect blend of luxury and leisure, making it an ideal destination for families, retirees, and anyone seeking a slice of Florida paradise.

Windsor At Westside Phase 2A is renowned for its stunning homes that embody elegance and comfort. Each residence is thoughtfully designed, featuring modern amenities and spacious layouts that cater to a variety of lifestyles. The community is not just about beautiful homes; it’s a lifestyle that encourages an active and social environment.

One of the standout features of this community is its exceptional tennis courts, perfect for enthusiasts of all skill levels. Whether you’re a seasoned player or just looking to pick up a racket for some fun, the tennis courts provide an excellent venue for exercise and friendly competition. The well-maintained facilities ensure that you can enjoy a game any time of day, surrounded by the lush greenery that characterizes this picturesque neighborhood.

In addition to tennis, Windsor At Westside Phase 2A boasts a range of community amenities designed to enhance your living experience. Residents can take advantage of a sparkling resort-style pool, a state-of-the-art fitness center, and communal spaces that foster connection and camaraderie among neighbors.

Discover the charm of Windsor At Westside Phase 2A, where every day feels like a vacation and community spirit thrives. Embrace the Florida lifestyle in a community that truly has it all!

Newest Windsor At Westside Ph 2a Homes with Tennis Court(s) Community Features

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code

Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.

1844 Gobi Drive, Kissimmee

9 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code

Beautiful 9-bedroom,6-bathroom water-front pool home in the highly sought-after Windsor at Westside resort community. Situated on a premium lot with stunning water view, this fully furnished property is perfect as a luxury vacation retreat or a high-performing short-term rental investment. The spacious open-concept layout offers expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites, one on each floor. Enjoy the Florida lifestyle with your private screened-in pool and hot tub overlooking the pond. This home has been thoughtfully upgraded to enhance the guest experience, including newly installed: *Luxury vinyl plank flooring throughout (no carpet)*, all bedrooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests! Resort-style amenities include a 10,000 sq. ft. clubhouse, resort pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. HOA includes cable, internet, lawn care, and valet trash service. Conveniently located just minutes from Disney, shopping, dining, and major highways. This turn-key property is move-in or rental ready—an opportunity you don’t want to miss!

8811 Macapa Drive, Kissimmee

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code

Fully Furnished Pool and Spa Home. A fantastic choice to be your Vacation Home or Rental Property in the Windsor at Westside Resort! 6 Bedrooms - 4.5 Bathrooms and a Gorgeous Loft. Private Heated Pool and Spa with a great view from your pool deck area. As you step inside, you are greeted by a foyer and entrance high ceiling. The main level features a master bedroom with a bathroom that connects to the pool area, perfect for accommodating guests. A conveniently located half bathroom adds to the overall functionality of this level. Continuing on, you'll discover a spacious and open-concept living area that seamlessly connects the family room, dining area, and kitchen. The kitchen is equipped with stainless steel appliances, abundant counter space, and a breakfast bar, making it a central hub for culinary adventures and social gatherings. Upstairs you will find the large loft with TV, coach and a nice bar table, 1 more en-suite (second master bedroom) and 4 more bedrooms (2 of them Themed Bedrooms) sharing two more bathrooms. This home features a heated private pool/spa, a large covered Lanai with patio furniture and sun loungers, tile roof and furnished. The Windsor at Westside Resort is a Gated Community with a great Clubhouse for vacationers, and features amenities including a lazy river, splash pool, bar, gym, game room and more. This is a great vacation home, very close to other area attractions. Schedule your visit NOW. Stunning Home.

1921 Nice Court, Kissimmee

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

Welcome to the best of Florida resort life! This 8 bedroom 6 bathroom house has all you can ask for and more! Fully furnished, this home is ready for an immediate occupancy, whether you're seeking an ideal AirBNB/Short-Term Rental or a personal vacation/ winter time residence. Airy and bright, the open-concept floor plan connects the living, dining, and kitchen areas, providing the perfect layout. The sliding doors in the family room area lead you directly to the pool patio area, creating a seamless indoor-outdoor living experience. An oversized heated pool with a jacuzzi and large patio space allows for cookouts, pool parties and watching the sunsets. The first-floor primary suite with a private bathroom and direct access to the lanai provides you a great personal space. An additional first-floor bedroom offers flexibility. Upstairs, there are six more spacious bedrooms and a loft space suitable for movie nights or a play area. Located in the luxurious community of Windsor at Westside, you'll have access to a variety of resort-style amenities, including a grand clubhouse, fitness center, lazy river, and more. Theme parks , beaches and shopping are just a short drive away, you'll have endless entertainment options at your fingertips. The HOA covers cable, internet, lawn care, trash, 24 hr security guard for a smooth and worry free life style. Make your appointment today! Equal Opportunity Housing.

8832 Macapa Drive, Kissimmee

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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.

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