Windsor At Westside Real Estate

Windsor At Westside Real Estate

Welcome to Windsor at Westside, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This vibrant community is the perfect blend of luxury and comfort, making it an ideal destination for families, vacationers, and investors alike.

Windsor at Westside boasts a stunning array of single-family homes and townhouses, designed with modern aesthetics and functional layouts. Each residence features spacious living areas, gourmet kitchens, and private outdoor spaces, perfect for entertaining or simply enjoying the warm Florida sunshine. The community is renowned for its upscale amenities, including a resort-style pool, a state-of-the-art fitness center, and a lively clubhouse that hosts a variety of social events throughout the year.

Located just minutes from the world-famous attractions of Walt Disney World, Universal Studios, and SeaWorld, Windsor at Westside offers residents the ultimate convenience. Families will appreciate the proximity to top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

For outdoor enthusiasts, the area is surrounded by lush parks and nature trails, providing ample opportunities for hiking, biking, and enjoying the beautiful Florida weather. Plus, with easy access to major highways, commuting to nearby cities or exploring the stunning Gulf Coast beaches is a breeze.

Whether you’re seeking a permanent residence or a vacation getaway, Windsor at Westside is a community that promises a lifestyle of relaxation, fun, and endless possibilities. Come experience the magic of Kissimmee and discover your dream home today!

Newest Listings in Windsor At Westside

$680,000
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. 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 $200 to $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

Listing courtesy of INTOP REALTY LLC. 407-233-5453
$515,000
5 Beds ⋅ 4 Baths ⋅ 11906546 MLS
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

Listing courtesy of .

$515,000
5 Beds ⋅ 4 Baths ⋅ S5154202 MLS
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

Listing courtesy of LA ROSA REALTY LLC. 321-939-3748
$409,900
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 white 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

Listing courtesy of HOPKEY REALTY. 407-454-1217
$499,000
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

Listing courtesy of RATIO REAL ESTATE, LLC. 305-354-0388
$439,000
5 Beds ⋅ 5 Baths ⋅ O6418129 MLS ⋅ 1 BLDG.
Welcome to this exceptional 5-bedroom, 4 full bathroom, and 1 half-bathroom home, where luxury, comfort, and entertainment come together perfectly! Located in a highly desirable area, this stunning residence offers an unforgettable experience with spacious living areas and incredible features designed for the ultimate Florida lifestyle. Step inside and discover a thoughtfully designed floor plan with plenty of space for family and guests. One of the highlights of this unique home is the incredible Star Wars-themed bedroom, creating a one-of-a-kind experience that will delight fans of all ages and add a touch of magic to the property. Enjoy your own private backyard oasis featuring a sparkling private pool, perfect for relaxing, entertaining, and enjoying sunny Florida days. Whether hosting gatherings, creating family memories, or simply unwinding after a long day, this outdoor space provides the perfect retreat. With five spacious bedrooms, multiple bathrooms, and an inviting layout, this home delivers the ideal combination of functionality and entertainment. Every detail has been designed to provide comfort, style, and an exceptional living experience. Don’t miss this rare opportunity to own a home that combines luxury living with unique character and resort-style amenities. Schedule your private showing today and experience everything this amazing property has to provides!

2413 Dubai St, Kissimmee

Listing courtesy of FLORIDA SCANDI REALTY LLC. 407-982-7224
$559,000
6 Beds ⋅ 5 Baths ⋅ O6415911 MLS
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

Listing courtesy of FLORIDA RESORT REALTY LLC. 305-494-4101
$434,999
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 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

Listing courtesy of TEAM DONOVAN. 407-705-2616
$405,000
5 Beds ⋅ 5 Baths ⋅ O6401749 MLS ⋅ . BLDG.
Welcome to 8900 Sydney Ave in Windsor at Westside, a beautifully positioned end unit 5 bedroom, 4.5 bath townhome offering 2,263 square feet in one of the most sought after vacation home communities near Disney. Originally purchased as the builder’s model, this home stands out from the typical inventory with a brighter, more elevated feel, a desirable end unit location, and interior finishes and furnishings that show far better than many competing townhomes in the community. The cream kitchen, stylish window treatments, upgraded bedroom theming, and strong overall presentation give this property the kind of visual appeal buyers and guests notice right away. Whether you are looking for a personal getaway, a second home, or an income producing vacation property, this townhome offers the combination of location, layout, and resort appeal that today’s buyers want. Windsor at Westside is a gated resort community with a large clubhouse, resort style pool, lazy river, waterslide, fitness center, tiki bar, arcade, and convenient access to the Disney parks, dining, and shopping. With its private pool, popular 5 bedroom layout, and premium end unit positioning, 8900 Sydney Ave is a standout opportunity in a community known for strong guest appeal and resort style living.

8900 Sydney Avenue, Kissimmee

Listing courtesy of KRESSLER REAL ESTATE. 407-864-2184
$412,900
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

Listing courtesy of REALTY ONE GROUP INSPIRATION. 321-233-2300
$570,000
7 Beds ⋅ 6 Baths ⋅ O6363676 MLS
Price Reduction! Turnkey 7-Bedroom Vacation Home in Windsor at Westside – Active Short-Term Rental! Welcome to 1861 Nice Court, a beautifully furnished and actively producing 7-bedroom, 5-bathroom short-term rental located in the sought-after Windsor at Westside Resort. With 3,281 sq ft of living space, this stunning home is designed to impress guests and maximize occupancy—making it the perfect investment property or vacation retreat near the magic of Disney. Step inside to a bright, open-concept layout featuring a spacious living area, modern kitchen with stainless steel appliances, and generous dining space ideal for large families and groups. This home offers multiple ensuite bedrooms and themed guest rooms that delight visitors of all ages and keep bookings strong year-round. The private screened-in pool and patio provide the perfect place to unwind after a day at the parks, offering your guests the relaxation and resort-style experience they’re searching for. Located in the gated, 24-hour resort community of Windsor at Westside, owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities—making ownership truly hassle-free. Just minutes from Walt Disney World, Margaritaville, Sunset Walk, shopping, dining, and major attractions, this property offers strong rental history, excellent future booking potential, and a turnkey setup ready for its next owner. Whether you're looking to expand your STR portfolio or secure a high-performing vacation home, 1861 Nice Court is an exceptional opportunity in one of Central Florida’s premier resort communities.

1861 Nice Ct, Kissimmee

Listing courtesy of EXP REALTY LLC. 888-883-8509
$529,000
6 Beds ⋅ 5 Baths ⋅ O6356954 MLS
Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.

8908 Prague Way, Kissimmee

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122
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