Windsor At Westside Homes with Gated Amenities

Windsor At Westside Homes with Gated Amenities

Welcome to Windsor At Westside, a charming subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This vibrant community offers a perfect blend of luxury, comfort, and convenience, making it an ideal choice for families and individuals seeking a serene lifestyle in sunny Florida.

Windsor At Westside is renowned for its exquisite homes that boast modern designs and exceptional craftsmanship. Each residence is thoughtfully designed with spacious layouts, stylish finishes, and ample natural light, ensuring a warm and inviting atmosphere. Whether you’re looking for a cozy retreat or a spacious family home, you’ll find a variety of options to suit your needs.

One of the standout features of Windsor At Westside is its gated amenities, providing an added layer of security and peace of mind for residents. The community is meticulously maintained, offering a sense of exclusivity and tranquility. Residents can enjoy a range of premium amenities, including a resort-style pool, a fully equipped fitness center, and beautifully landscaped common areas perfect for leisurely strolls or family gatherings.

Additionally, Windsor At Westside is conveniently located near major highways, shopping centers, and dining options, making it easy to access everything Kissimmee has to offer. Whether you’re exploring local attractions or enjoying a day at the nearby theme parks, you’ll love the convenience of living in this vibrant community.

Discover the charm of Windsor At Westside, where luxury living meets a welcoming community atmosphere. Your dream home awaits in this idyllic Florida haven!

Newest Windsor At Westside Homes with Gated Amenities

$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

$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

$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

$568,000
7 Beds 6 Baths Windsor At Westside SubDv. 34747 Zip Code
PRICE REDUCTION — NOW $568,000 + $10,000 SELLER CREDIT! TURNKEY 7-BEDROOM VACATION RENTAL | WINDSOR AT WESTSIDE | MINUTES TO DISNEY A $568,000 Opportunity + $10,000 Seller Credit in One of Central Florida's Premier Vacation Rental Resorts! The price has been reduced to $568,000, AND the seller is offering a $10,000 credit to the buyer at closing, creating an even more compelling 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. WHY $568,000 + $10,000 SELLER CREDIT 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: $568,000 PLUS: $10,000 SELLER CREDIT AVAILABLE TO BUYER AT CLOSING 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 JUST GOT BETTER. At $568,000, PLUS a $10,000 seller credit, 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 $568,000 + a $10,000 seller credit can buy you in one of Central Florida's premier vacation rental communities.

1861 Nice Ct, Kissimmee

Start Your Search