Windsor At Westside Homes for Sale

Windsor At Westside Homes for Sale

Welcome to Windsor at Westside, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This picturesque community is a hidden gem that perfectly blends modern living with the charm of Florida's natural beauty.

Windsor at Westside offers an impressive selection of homes for sale, designed to cater to a variety of lifestyles and preferences. Whether you’re a first-time homebuyer, a growing family, or seeking a vacation retreat, you’ll find a diverse range of floor plans and styles that suit your needs. These beautifully crafted homes feature spacious layouts, contemporary finishes, and ample outdoor spaces that invite relaxation and entertainment.

One of the standout features of Windsor at Westside is its family-friendly atmosphere. Residents enjoy access to a wealth of amenities, including a resort-style pool, state-of-the-art fitness center, and engaging recreational areas that encourage community gatherings. The lush landscaping and serene surroundings create a peaceful environment, while the proximity to major attractions makes it an ideal location for those looking to experience the best of Central Florida.

Conveniently located just minutes from world-renowned theme parks, shopping, and dining options, Windsor at Westside is a prime spot for both residents and vacationers alike. Embrace the Florida lifestyle in this vibrant community where your dream home awaits. Explore our current listings and discover the perfect place to call home in Windsor at Westside today!

Newest Windsor At Westside Homes for Sale

8 Beds ⋅ 6 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

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 $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

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

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

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

7 Beds ⋅ 6 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

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

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

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

9 Beds ⋅ 6 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

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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