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

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

Welcome to Windsor at Westside, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This community is a perfect blend of luxury and leisure, offering residents an idyllic lifestyle just minutes away from the enchantment of Orlando's world-famous attractions.

Windsor at Westside is renowned for its stunning homes, many of which feature private tennis courts, catering to both seasoned players and casual enthusiasts alike. Imagine stepping out of your backyard and onto your own court, ready for a match with friends or family. The community's commitment to an active lifestyle is further enhanced by its array of amenities, including a state-of-the-art fitness center, a resort-style swimming pool, and lush walking trails that invite you to explore the scenic surroundings.

In addition to its recreational offerings, Windsor at Westside boasts a warm and welcoming atmosphere, perfect for families and individuals seeking a close-knit community. The beautifully designed homes are characterized by their modern architecture and spacious layouts, ensuring that residents enjoy both comfort and style. Whether you're hosting a barbecue on your patio or enjoying a quiet evening in, every moment spent here feels like a retreat.

With its prime location, Windsor at Westside provides convenient access to shopping, dining, and entertainment options, making it easy to enjoy the best that Kissimmee and the greater Orlando area have to offer. Discover the charm of Windsor at Westside, where your dream home awaits amidst a community that celebrates both relaxation and recreation.

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

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

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

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

PRICE REDUCTION — NOW $569,000! TURNKEY 7-BEDROOM VACATION RENTAL | WINDSOR AT WESTSIDE | MINUTES TO DISNEY A $569,000 Opportunity in One of Central Florida's Premier Vacation Rental Resorts! The price has been reduced to $569,000, creating an exciting opportunity to own a fully furnished, actively operating 7-bedroom vacation home in the highly sought-after Windsor at Westside Resort. Welcome to 1861 Nice Court, a spacious 7-bedroom, 5-bathroom home offering 3,281 square feet of living space, a private screened-in pool, themed bedrooms, and everything needed to continue operating as a successful short-term rental. TURNKEY — JUST BRING YOUR INVESTMENT STRATEGY This home was designed specifically with vacationing families and large groups in mind. The open-concept floor plan provides plenty of room for guests to gather, while the modern kitchen with stainless-steel appliances and generous dining area make entertaining easy. Multiple ensuite bedrooms and professionally themed guest rooms add to the vacation experience and give this property the features today's Disney-area guests are looking for. Outside, the private screened-in pool and spacious patio provide the perfect place for guests to relax after a day at the parks. THE RESORT EXPERIENCE GUESTS WANT Windsor at Westside is a premier gated vacation rental community offering an impressive 8,000+ square-foot clubhouse and an extensive list of amenities, including: * Resort-style swimming pool * Lazy river * Waterslide * Fitness center * Tennis courts * Volleyball court * Play and activity areas * Resort activities and entertainment The HOA includes lawn maintenance, internet, cable, and daily valet trash service, helping reduce the day-to-day responsibilities associated with owning a vacation rental. MINUTES FROM THE MAGIC The location is a major advantage. Guests are just minutes from Walt Disney World and close to Margaritaville, Sunset Walk, shopping, dining, golf, and Central Florida's world-famous attractions. For investors, the combination of 7 bedrooms + private pool + resort amenities + proximity to Disney + turnkey furnishings creates a compelling vacation rental package. WHY $569,000 DESERVES YOUR ATTENTION This isn't simply a home—it's an opportunity to own a turnkey vacation rental in one of the most recognizable short-term rental destinations in the country. NEW PRICE: $569,000 7 Bedrooms | 5 Bathrooms 3,281 Sq. Ft. Fully Furnished & Turnkey Active Short-Term Rental Private Screened-In Pool Themed Guest Bedrooms Gated Resort Community Minutes to Walt Disney World Extensive Resort Amenities THE PRICE HAS CHANGED. THE OPPORTUNITY HASN'T. At $569,000, 1861 Nice Court deserves the attention of investors looking for a turnkey Disney-area vacation rental and buyers looking for a spacious vacation home with income-producing potential. If you've been watching the Windsor at Westside market, this is one you won't want to overlook. Schedule your private showing today and take a closer look at what $569,000 can buy you in one of Central Florida's premier vacation rental communities.

1861 Nice Ct, 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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