Windsor At Westside Homes with Sidewalk Exterior Features

Windsor At Westside Homes with Sidewalk Exterior Features

Welcome to Windsor at Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This enchanting community offers a perfect blend of modern living and serene surroundings, making it an ideal choice for families, retirees, and anyone seeking a slice of paradise in Central Florida.

Windsor at Westside is renowned for its beautifully designed homes, each featuring charming sidewalk exterior enhancements that encourage a friendly, walkable neighborhood atmosphere. Picture yourself strolling along tree-lined paths, greeting neighbors, and enjoying the Florida sunshine. The community fosters a sense of belonging, where children can play safely outside, and residents can engage in leisurely walks or bike rides.

The homes in Windsor at Westside are thoughtfully crafted with contemporary designs and spacious layouts, catering to a variety of lifestyles. With options ranging from cozy single-family homes to larger residences, there’s something to fit every taste and need. Many properties boast private pools, expansive backyards, and modern amenities, creating perfect spaces for family gatherings and entertaining friends.

Beyond the charming homes, Windsor at Westside offers an array of community amenities, including a resort-style pool, fitness center, and playgrounds, ensuring that residents have everything they need for an active and fulfilling lifestyle. With its prime location, residents enjoy easy access to shopping, dining, and world-famous attractions such as Disney World and Universal Studios.

Discover the beauty and warmth of Windsor at Westside, where your dream home awaits in a community that feels like family. Experience the charm of Kissimmee living today!

Newest Windsor At Westside Homes with Sidewalk Exterior Features

$525,000
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, or income-producing short-term rental. The property is already set up for Airbnb use and is being sold turnkey, allowing for immediate occupancy or continued rental operations. The home offers five bedrooms and four bathrooms, along with a game room and an open, airy floor plan designed for both comfort and functionality. The layout easily accommodates large groups, with multiple spaces to gather or unwind throughout the home. A private first-floor suite provides a quiet retreat, while the kitchen features modern finishes including granite counters and stainless steel appliances. Outdoors, a private pool to create the perfect place to relax at any time of day. Owners and guests enjoy access to a wide range of resort amenities, including a full-service clubhouse, lake and pier, expansive zero-entry pool, water slide, lazy river, splash area, fitness center, sports courts, arcade, and on-site convenience shop. Conveniently positioned near Disney and major attractions, this home combines location, lifestyle, and investment potential in one exceptional opportunity.

2440 Tangier Drive, Kissimmee
$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.NO REAR NEIGHBORS*NO CARPET, NEW LUXURY VINYL FLOORING* PAID OFF SOLAR PANEL*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
$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
$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
$434,999
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
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
$405,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
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
$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
$444,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner is this fully furnished 5-bedroom, 4.5-bathroom end unit townhome where luxury meets pure, unadulterated fun. Imagine: sun-kissed mornings by your private, screened-in pool, the cool water shimmering like a sapphire. But hold on, the adventure's just beginning! Picture this: lazy river drifts, piña coladas at the tiki bar, adrenaline-pumping workouts in the cutting-edge gym, and legendary sports court showdowns. This isn't just a home; it's a launchpad to Orlando's magic, where theme park thrills, culinary explosions, and retail therapy await, just minutes away! Sensational financials available on request!

2427 Dubai Street, Kissimmee
$479,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside SubDv. ⋅ 34747 Zip Code
Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen and dining area with sliding patio doors in the first floor and also one bedroom. In the second floor you'll find the other bedrooms and a very nice loft area to gatter your guests, family and friends in a private and exclusive area of the home. Property also includes a private pool. This is the perfect home in the most popular resort community that features one of the most amazing Clubhouse Amenities in the area. Just minutes away from world-famous Disney World.

8916 Sydney Avenue, Kissimmee
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