Windsor At Westside Homes under $500,000

Windsor At Westside Homes under $500,000

Welcome to Windsor at Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This picturesque community offers an idyllic blend of luxury, comfort, and convenience, making it the perfect place to call home.

Windsor at Westside is renowned for its beautiful, modern homes, many of which are available for under $500,000. This affordability does not compromise quality; instead, it provides an exceptional opportunity for families, retirees, and first-time homebuyers to invest in a tranquil yet vibrant community. The homes here boast spacious layouts, contemporary designs, and premium finishes, ensuring that every resident enjoys a stylish and comfortable living experience.

One of the standout features of Windsor at Westside is its resort-style amenities. Residents can take advantage of a stunning clubhouse, a sparkling swimming pool, a state-of-the-art fitness center, and even a lazy river for those sunny Florida days. The community also features well-maintained walking trails, playgrounds, and sports courts, encouraging an active lifestyle for everyone.

Located just a short drive from the excitement of Orlando's world-famous attractions, Windsor at Westside offers a perfect balance of peace and adventure. With easy access to major highways, shopping, dining, and entertainment options are just around the corner.

Discover the charm and convenience of Windsor at Westside, where your dream home awaits at an inviting price. Experience the best of Florida living in a community designed with you in mind!

Newest Windsor At Westside Homes under $500,000

8899 Geneve Ct, Kissimmee
$394,900
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
1857 Nice Court, Kissimmee
$459,000
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
1909 Majorca Drive, Kissimmee
$424,999
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Discover the pinnacle of Florida living in this stunning, fully furnished 5-bedroom, 4.5-bathroom townhome, nestled within the highly sought-after Windsor at Westside resort community. Turnkey and professionally designed, this property is thoughtfully appointed to host large groups in style and comfort—an exceptional opportunity for investors seeking a high-performing short-term rental, or for buyers searching for the ultimate vacation retreat. A standout feature you won't find in most resort homes? Your own private garage—a rare and valuable bonus that offers added convenience, secure storage, and an extra layer of everyday practicality that sets this property apart from the competition. For out-of-state owners and short-term rental investors, this home delivers true peace of mind: a whole-home leak defense system actively monitors for water issues and helps prevent costly damage when you're miles away, while a brand-new refrigerator, washer, and dryer—along with recently replaced smoke detectors throughout—mean fewer maintenance worries down the road. The current owners have also invested in a series of thoughtful upgrades that elevate both comfort and style: sleek, modern light-and-fan fixtures in every bedroom and the loft add a contemporary touch while keeping guests cool and comfortable year-round, and custom-framed mirrors in each bathroom lend a polished, designer finish throughout. Even better, the home is just steps from the clubhouse, resort pool, and full lineup of community amenities—putting the very best of Windsor at Westside right at your doorstep. And when you're ready for quieter moments, step outside to your own private, screened-in pool—a tranquil escape where you can unwind in complete privacy after a day of adventure. As an owner at Windsor at Westside, you and your guests enjoy access to a world-class collection of amenities, including a resort-style main pool with a children's splash pad, a relaxing hot tub, a lazy river, a fully equipped fitness center, an arcade, a kids' activity room, and basketball and volleyball courts. Ideally situated just minutes from Walt Disney World, Universal Studios, and SeaWorld, the home also places you near premier dining, championship golf, and upscale shopping at The Florida Mall and nearby outlet centers. Don't miss your chance to own a slice of paradise in one of Central Florida's most prestigious gated communities—where magical memories and smart investment go hand in hand.

1909 Majorca Drive, Kissimmee
2015 Majorca Drive, Kissimmee
$412,900
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
8944 Sydney Avenue, Kissimmee
$399,900
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mind, this spacious home offers a modern layout perfect for families. Enjoy your own private pool, ideal for relaxing afternoons or entertaining in the Florida sun. The community itself is rich with amenities, including clubhouse access, fitness facilities, resort-style pools, sports courts, playgrounds, and more—ensuring there’s something for everyone to enjoy. Don't miss out on this great opportunitiy! Tour this amazing property today!

8944 Sydney Avenue, Kissimmee
2427 Dubai Street, Kissimmee
$408,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner is this fully furnished 5-bedroom, 4.5-bathroom end unit townhome where luxury meets pure, unadulterated fun. Imagine: sun-kissed mornings by your private, screened-in pool, the cool water shimmering like a sapphire. But hold on, the adventure's just beginning! Picture this: lazy river drifts, piña coladas at the tiki bar, adrenaline-pumping workouts in the cutting-edge gym, and legendary sports court showdowns. This isn't just a home; it's a launchpad to Orlando's magic, where theme park thrills, culinary explosions, and retail therapy await, just minutes away! Sensational financials available on request!

2427 Dubai Street, Kissimmee
8916 Sydney Avenue, Kissimmee
$479,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen and dining area with sliding patio doors in the first floor and also one bedroom. In the second floor you'll find the other bedrooms and a very nice loft area to gatter your guests, family and friends in a private and exclusive area of the home. Property also includes a private pool. This is the perfect home in the most popular resort community that features one of the most amazing Clubhouse Amenities in the area. Just minutes away from world-famous Disney World.

8916 Sydney Avenue, Kissimmee
Start Your Search

How much is your home worth?

Get instant property value now!