Windsor At Westside Homes with Tile Roof

Windsor At Westside Homes with Tile Roof

Welcome to Windsor at Westside, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This picturesque community is designed for those seeking a blend of luxury, comfort, and a touch of Florida’s natural beauty. With its stunning tile-roof homes, Windsor at Westside stands out as a premier destination for families, retirees, and everyone in between.

Each residence in this charming community boasts a distinctive tile roof, not only enhancing the aesthetic appeal but also providing durability and energy efficiency. These homes are thoughtfully designed with open floor plans, spacious living areas, and modern amenities, ensuring that every family can find their perfect oasis. From cozy family gatherings to entertaining friends, the layout of these homes is perfect for creating lasting memories.

Windsor at Westside is more than just a collection of beautiful homes; it’s a lifestyle. Residents enjoy access to a range of amenities, including a resort-style pool, fitness center, and clubhouse, all set against the backdrop of lush landscaping and serene surroundings. The community is conveniently located near shopping, dining, and world-renowned attractions like Walt Disney World, making it an ideal place for both relaxation and adventure.

Whether you’re looking for a vacation home or a permanent residence, Windsor at Westside offers an unparalleled living experience. Discover the charm of this delightful community, where every day feels like a vacation and your dream home awaits!

Newest Windsor At Westside Homes with Tile Roof

8 Beds ⋅ 6 Baths ⋅ O6428715 MLS

Discover an exceptional opportunity to own this beautifully furnished 8-bedroom, 6-bathroom pool home in the highly sought-after GATED resort community of Windsor at Westside.NO REAR NEIGHBORS*NO CARPET, NEW LUXURY VINYL FLOORING* PAID OFF SOLAR PANEL*Offering an ideal blend of luxury, comfort, privacy, and investment potential, this turnkey property is perfectly suited as a primary residence, vacation retreat, or high-performing short-term rental. The thoughtfully designed open floor plan features expansive living and dining areas that flow effortlessly into the well-appointed kitchen, complete with granite countertops, stainless steel appliances, and a large center island. Sliding glass doors lead to the screened lanai, where you'll find a private pool and spa overlooking a peaceful wooded backdrop with *NO REAR NEIGHBORS, providing a rare sense of privacy and a tranquil setting to relax or entertain*. The first floor includes two bedrooms, including a spacious ensuite with direct access to the pool area, while upstairs offers additional guest suites, themed bedrooms, a generous loft, and a dedicated theater room for unforgettable movie nights. Throughout the home, you'll appreciate the low-maintenance flooring with tile and *NEW LUXURY VINYL FLOORING throughout—there is NO CARPET, making the home both stylish and easy to maintain*. A valuable bonus is the* FULLY PAID-OFF SOLAR PANEL SYSTEM installed 2025, valued at approximately $80,000, which can significantly reduce monthly electric costs by an estimated $500+ *while improving long-term energy efficiency. Residents and guests enjoy access to Windsor at Westside's outstanding resort amenities, including a spectacular clubhouse, resort-style pool with lazy river and splash area, fitness center, game room, sports courts, playground, and more. The HOA also includes cable, internet, lawn maintenance, valet trash service, and 24-hour gated security for added convenience. Ideally located just minutes from Walt Disney World, world-class attractions, shopping, dining, golf, and major highways, this move-in-ready home offers the perfect combination of lifestyle, privacy, and exceptional investment value.

8812 Macapa Drive, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6427755 MLS ⋅ 8899 BLDG.

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 ⋅ O6426220 MLS

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 ⋅ S5149758 MLS ⋅ 1909 BLDG.

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

5 Beds ⋅ 5 Baths ⋅ S5148415 MLS ⋅ Windsor At Westside BLDG.

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

7 Beds ⋅ 6 Baths ⋅ O6363676 MLS

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

9 Beds ⋅ 6 Baths ⋅ S5130786 MLS

This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community, the home is ideal for large vacationing groups for investors and for your own pleasure. The open-concept floor plan features multiple living areas, a large upstairs loft/game room, and a modern kitchen with granite countertops, stainless steel appliances, and ample seating. The home includes themed bedrooms, generous sleeping capacity, and stylish furnishings throughout. The private screened-in pool and spa, complete with a covered lanai and outdoor dining area—perfect for relaxing or entertaining. Whether hosting guests or enjoying it personally, this outdoor space adds major rental appeal. Windsor at Westside offers resort-style amenities, including Clubhouse with restaurant and bar, with lazy river and water slide, fitness center, arcade, and sports courts, 24/7 manned security gate. With covered outdoor sitting, hot tub/spa, sand volley, basketball court, walking trails, store/ market place, it is Located only minutes from Walt Disney World! New laminate floors throughout the entire house! Come and take a look today!

2183 Tripoli Ct, Kissimmee

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