Windsor At Westside Homes with Trees/Woods View

Welcome to Windsor At Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community is designed for those who appreciate the perfect blend of modern living and natural beauty. With its lush landscapes and serene surroundings, Windsor At Westside offers a tranquil retreat just moments away from the excitement of Orlando’s world-famous attractions.

One of the standout features of this charming neighborhood is its stunning homes that boast breathtaking views of trees and woods. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature, all while enjoying the comforts of your beautifully designed residence. The thoughtful architecture and spacious layouts of these homes are complemented by the natural beauty that envelops them, creating a perfect harmony between indoor and outdoor living.

Residents of Windsor At Westside enjoy access to a wealth of amenities, including a sparkling community pool, fitness center, and recreational areas, making it an ideal place for families and individuals alike. The community is also conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away.

Whether you’re looking for a permanent residence, a vacation home, or an investment opportunity, Windsor At Westside in Kissimmee offers an irresistible lifestyle that combines comfort, convenience, and the beauty of nature. Come discover your dream home in this enchanting community today!

Newest Windsor At Westside Homes with Trees/Woods View

$680,000

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 $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

$409,900

4 Beds ⋅ 4 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code

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

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