Windsor At Westside Homes with Gated Amenities

Windsor At Westside Homes with Gated Amenities

Welcome to Windsor At Westside, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This community is the epitome of modern living, combining luxury with the comfort of a friendly neighborhood atmosphere. Windsor At Westside is not just a place to live; it’s a lifestyle choice, perfect for families, retirees, and everyone in between.

One of the standout features of this remarkable community is its gated amenities, providing residents with both security and peace of mind. As you enter through the elegant gates, you’ll be greeted by beautifully landscaped surroundings that exude charm and sophistication. The community boasts an array of amenities designed to enhance your living experience, including a stunning resort-style pool, a state-of-the-art fitness center, and a clubhouse perfect for social gatherings and events.

The homes within Windsor At Westside are a testament to quality and design, featuring spacious floor plans, modern finishes, and a variety of styles to suit every taste. Whether you’re looking for a cozy retreat or a spacious family home, you’ll find options that cater to your needs. The community’s proximity to major attractions, shopping, and dining makes it an ideal location for those who want to enjoy the best of Florida living.

Experience the charm and allure of Windsor At Westside, where luxury meets convenience in a secure, gated environment. Come explore your dream home in this captivating community today!

Newest Windsor At Westside Homes with Gated Amenities

2105 Malta Terrace, Kissimmee
$699,000
8 Beds ⋅ 6 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Welcome to this stunning 8-bedroom, 6-bathroom vacation home in the highly sought-after Windsor at Westside gated resort community just 2.5 miles from Walt Disney World. This home is perfectly positioned for short-term rental income or a spacious primary residence in the heart of Central Florida's tourist corridor. Inside, you'll find generous living and family room areas ideal for large groups, plus a games room for added entertainment. The home's layout comfortably accommodates multiple families or rental guests with ease. As a resident of Windsor at Westside, owners enjoy access to resort-style amenities including a zero-entry pool with lazy river, water slides and toboggan run, a full-service spa, state-of-the-art fitness center, movie theater, arcade, clubhouse, poolside cabanas, sports courts, volleyball court, playground, and 24-hour concierge service all within a secure, gated community. Located approximately 22 minutes from Disney and Downtown Orlando, 26 minutes from SeaWorld, and 29 minutes from Universal Studios, this property offers the ultimate combination of luxury, convenience, and rental potential. Whether you're an investor seeking strong vacation rental returns or a family wanting a resort lifestyle close to the parks, this home delivers.

2105 Malta Terrace, Kissimmee
8904 Prague Way, Kissimmee
$515,000
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
1857 Nice Court, Kissimmee
$489,000
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
1885 Nice Court, Kissimmee
$559,000
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
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
1861 Nice Ct, Kissimmee
$550,000
7 Beds ⋅ 6 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
INVESTOR ALERT — NOW $550,000! TURNKEY 7-BEDROOM SHORT-TERM RENTAL | WINDSOR AT WESTSIDE | PRIVATE POOL | MINUTES TO DISNEY 7 BEDROOMS. 5+ BATHROOMS. 3,281 SQ. FT. FULLY FURNISHED. NOW $550,000. Investors looking for a large, turnkey vacation rental in the Disney-area market should take a serious look at 1861 Nice Court in Windsor at Westside Resort. This fully furnished 7-bedroom, 5-bathroom home offers 3,281 square feet of living space, a private screened-in pool, themed bedrooms, and a layout designed to accommodate large vacation groups. The property is currently operating as a short-term rental, giving a new owner the opportunity to step into an established vacation-home setup without starting from scratch. INVESTOR-FRIENDLY FEATURES NEW PRICE: $550,000 7 Bedrooms | 5 Bathrooms 3,281 Sq. Ft. Fully Furnished & Turnkey Currently Used as a Short-Term Rental Private Screened-In Pool Themed Guest Bedrooms Spacious floor plan designed for large groups Located in a gated vacation-resort community Minutes from Walt Disney World and Central Florida's major attractions Extensive resort amenities WHY THIS PROPERTY DESERVES A CLOSER LOOK: The combination of seven bedrooms, five bathrooms, a private pool, themed accommodations, and a prime Disney-area location provides the key components vacation-rental investors look for when evaluating a property. Windsor at Westside offers an established resort environment with amenities that appeal to vacation guests, while the home's size and configuration allow it to accommodate larger groups—an important consideration in the Central Florida vacation-rental market. At $550,000, this property gives investors an opportunity to acquire a substantial, fully furnished vacation home in one of the area's established short-term rental communities. Bring your investment strategy and take a closer look at the property, location, furnishings, resort amenities, and overall potential. Schedule your private showing of 1861 Nice Court today.

1861 Nice Ct, Kissimmee
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