Windsor At Westside Homes with Clubhouse Community Features

Windsor At Westside Homes with Clubhouse Community Features

Welcome to Windsor at Westside, a premier subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This enchanting community offers a perfect blend of modern living and resort-style amenities, making it an ideal choice for families, retirees, and vacation home seekers alike.

Windsor at Westside is renowned for its stunning homes, each designed with elegance and comfort in mind. From spacious single-family residences to luxurious townhomes, there’s something to suit every lifestyle. The architectural details and contemporary finishes create inviting spaces that feel like home from the moment you step inside.

One of the standout features of Windsor at Westside is its impressive clubhouse, which serves as the social hub of the community. Residents can enjoy a range of amenities, including a sparkling swimming pool, a state-of-the-art fitness center, and a game room perfect for gatherings with friends and family. The clubhouse also hosts various community events, fostering a sense of camaraderie among neighbors and creating lasting memories.

In addition to the clubhouse, Windsor at Westside boasts beautifully landscaped grounds, walking trails, and recreational areas, providing ample opportunities for outdoor activities and relaxation. With its prime location, residents have easy access to shopping, dining, and world-renowned attractions, making it a convenient and desirable place to call home.

Discover the charm and allure of Windsor at Westside, where community spirit meets luxurious living in the sunny embrace of Kissimmee, Florida. Your dream home awaits!

Newest Windsor At Westside Homes with Clubhouse Community Features

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

Located in one of Central Florida's premier resort communities, this beautifully maintained and fully furnished 5-bedroom, 4-bath pool home offers the perfect blend of comfort, style, and convenience. One of its biggest advantages is its exceptional location within the community—just a short walk to the spectacular clubhouse, allowing you and your guests to easily enjoy all of the resort amenities without needing to drive. Inside, the home features an open-concept floor plan with abundant natural light, creating an inviting space for relaxing or entertaining. The spacious kitchen is the heart of the home, complete with granite countertops, stainless steel appliances, a large center island with seating, and plenty of cabinet space. It flows seamlessly into the dining area and family room before opening to the private screened pool, making indoor-outdoor living effortless. The spacious primary suite offers a peaceful retreat with a large walk-in closet and an ensuite bathroom designed for comfort. Each additional bedroom is generously sized and thoughtfully furnished, providing plenty of room for family and guests. A converted garage game room featuring a pool table, foosball, and air hockey creates the ultimate entertainment space and adds tremendous appeal for vacation rentals. Windsor at Westside is one of the area's most sought-after gated resort communities, featuring a stunning clubhouse with a resort-style pool, lazy river, waterslide, children's splash area, hot tub, fitness center, arcade, sports courts, playground, and the popular Tu Casa Bar & Lounge for poolside dining and drinks. These resort amenities have made the community a favorite destination for vacationers from around the world. Beyond the gates, you'll enjoy an unbeatable location just minutes from Walt Disney World Resort, with easy access to Universal Orlando, SeaWorld, Disney Springs, Margaritaville, Sunset Walk, championship golf courses, countless restaurants, shopping, and major highways that make exploring all of Central Florida simple and convenient. Orlando International Airport is also within an easy drive, making travel effortless for both owners and guests. Whether you're looking for a primary residence, a second home, or a high-performing vacation rental, this home checks every box with its spacious layout, private pool, impressive game room, and one of the best locations in Windsor at Westside—just steps from the community's incredible resort amenities.

8904 Prague Way, Kissimmee

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

Welcome to Windsor at Westside—one of Central Florida's premier resort communities and one of the most sought-after destinations for vacation homeowners and short-term rental investors. This beautifully furnished 4-bedroom, 3.5-bathroom townhome combines exceptional guest appeal with thoughtful upgrades, a private pond view, and a proven rental history. The open-concept floor plan offers a spacious kitchen featuring upgraded quartz countertops, stainless steel appliances, abundant cabinet space, and a large breakfast bar overlooking the dining and living areas, creating the perfect space for entertaining family and guests. Sliding glass doors lead to the covered lanai with a convenient poolside half bath and a private screened-in pool overlooking a tranquil pond, providing a peaceful setting with no direct rear neighbors. The first floor features a spacious guest bedroom and a full bathroom, making it ideal for multigenerational families or guests seeking first-floor accommodations. Upstairs you'll find three additional bedrooms, including a generous primary suite with an en-suite bathroom and walk-in closet. A custom-themed bunk room showcases a hand-painted mural by a local artist, creating a unique and memorable space that guests of all ages will appreciate, while an additional guest bedroom and full bathroom complete the second floor. Beyond its beautiful presentation, this property boasts a proven short-term rental history, making it an outstanding turnkey investment opportunity or vacation home. Residents and guests enjoy access to Windsor at Westside's exceptional resort amenities, including a 10,000-square-foot clubhouse, lagoon-style pool, lazy river, waterslide, splash pad, fitness center, arcade, basketball, volleyball and soccer courts, Tu Casa Bar & Lounge, on-site restaurant and coffee bar, playground, and 24-hour gated security. Ideally located just minutes from Walt Disney World, championship golf courses, shopping, dining, and Orlando's world-famous attractions, this exceptional property offers the perfect combination of location, lifestyle, and investment potential.

8899 Geneve Ct, Kissimmee

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

Welcome to a fantastic investment opportunity in the Windsor at Westside resort community! This fully furnished 5-bedroom, 4-bathroom pool home offers a luxurious living space with great rental potential, perfect for investors. It's an ideal choice for short-term or long-term rental investment or a second home, especially for those looking for a prime location near Disney Parks and other Orlando attractions. Enjoy gatherings and entertainment in the open floor plan, seamlessly blending the living, dining, and kitchen areas. The chef's kitchen features granite countertops and stainless steel appliances. Step outside to the private pool, your oasis in the Florida sun. The main floor has a bedroom and bathroom for guests, while upstairs, the master ensuite and guest bedrooms offer space and privacy. Another bedroom and two guest bedrooms with a shared bathroom provide ample space for everyone. The resort offers amenities like an 8,000 square feet clubhouse, heated pool, lazy river, and spa. Stay connected with poolside wireless internet and enjoy activities like volleyball and basketball. The resort also has a restaurant and bar for your enjoyment. Just minutes from Walt Disney World, Universal Orlando, and Sea World, this home offers endless fun and convenience. Don't miss out on this turn-key dream home!

1857 Nice Court, Kissimmee

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

Welcome to this exceptional 5-bedroom, 4 full bathroom, and 1 half-bathroom home, where luxury, comfort, and entertainment come together perfectly! Located in a highly desirable area, this stunning residence offers an unforgettable experience with spacious living areas and incredible features designed for the ultimate Florida lifestyle. Step inside and discover a thoughtfully designed floor plan with plenty of space for family and guests. One of the highlights of this unique home is the incredible Star Wars-themed bedroom, creating a one-of-a-kind experience that will delight fans of all ages and add a touch of magic to the property. Enjoy your own private backyard oasis featuring a sparkling private pool, perfect for relaxing, entertaining, and enjoying sunny Florida days. Whether hosting gatherings, creating family memories, or simply unwinding after a long day, this outdoor space provides the perfect retreat. With five spacious bedrooms, multiple bathrooms, and an inviting layout, this home delivers the ideal combination of functionality and entertainment. Every detail has been designed to provide comfort, style, and an exceptional living experience. Don’t miss this rare opportunity to own a home that combines luxury living with unique character and resort-style amenities. Schedule your private showing today and experience everything this amazing property has to provides!

2413 Dubai St, Kissimmee

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

Welcome to resort-style living at its finest in the highly sought-after Windsor at Westside Resort! This beautifully maintained 6-bedroom, 4.5-bath pool home is offered fully furnished and turnkey, making it the perfect opportunity for a vacation home, investment property, or even a full-time residence just minutes from Walt Disney World and Central Florida's most popular attractions. Step inside and you'll immediately appreciate the bright, open-concept floor plan designed for gathering and entertaining. The spacious kitchen overlooks the dining and living areas, creating the perfect setting for family meals, celebrations, and relaxing evenings after a day of adventure. The first-floor primary suite offers a peaceful retreat complete with dual vanities, a soaking tub, separate shower, and direct access to the pool area for added convenience. The fun continues in the converted game room, where guests of all ages can enjoy a pool table, air hockey, and gaming stations, creating endless entertainment right at home. Outside, your private screened pool area provides the perfect place to unwind, soak up the Florida sunshine, or enjoy a relaxing evening swim. With no rear neighbors, you'll appreciate the added privacy while enjoying your own personal backyard oasis. Upstairs, a spacious loft serves as a second living and entertainment area, offering plenty of room for movie nights, gaming, or simply spreading out and relaxing. Five additional bedrooms provide comfortable accommodations for family and guests, including a second primary suite and two beautifully themed bedrooms featuring Star Wars and Princess-inspired décor that are sure to delight visitors of all ages. Beyond the home itself, Windsor at Westside offers an exceptional resort experience. This guard-gated community is renowned for its impressive amenities, including a spectacular resort-style pool, lazy river, clubhouse, fitness center, arcade, playground, sports courts, and scenic walking paths surrounding picturesque ponds. Whether you're enjoying a day at the resort or exploring nearby shopping, dining, golf, and world-famous attractions, everything you need is just moments away. Whether you're seeking a personal retreat, a high-demand vacation rental, or a combination of both, this outstanding property delivers the space, location, and amenities that today's buyers are looking for. Don't miss your opportunity to own a piece of paradise in one of Central Florida's premier vacation home communities!

1885 Nice Court, Kissimmee

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

Welcome to your slice of paradise at Windsor at Westside! Fully furnished and Airbnb-ready, this spacious 5-bedroom, 4.5-bath townhome with a private pool is located in one of Greater Orlando’s most sought-after short-term rental communities. Designed to comfortably accommodate 14+ guests, this property is ideal as both a personal getaway and an income-producing investment. The open-concept floorplan creates a bright, inviting atmosphere, enhanced by modern finishes and ample space for gathering and entertaining. Step outside to your private screened-in pool—perfect for unwinding after a day at the parks or enjoying Florida’s year-round sunshine in total privacy. The HOA delivers exceptional value, covering cable, internet, trash removal, lawn care, and 24/7 guard-gated security, offering a truly low-maintenance ownership experience. Residents and guests enjoy access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash zone, hot tub, fitness center, arcade, sports courts, sand volleyball, playground, on-site market and deli, concierge services, and the popular Tu Casa Tiki Bar. Ideally located just minutes from Walt Disney World, with easy access to shopping, dining, and major attractions, this property offers the perfect blend of lifestyle and investment potential. Whether you’re expanding your short-term rental portfolio or searching for a vacation home that pays for itself, this opportunity checks all the boxes. Schedule your private showing today.

2015 Majorca Drive, Kissimmee

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

Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.

8908 Prague Way, 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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