Windsor At Westside Ph 1 Homes for Sale

Windsor At Westside Ph 1 Homes for Sale

Welcome to Windsor at Westside Phase 1, a charming subdivision nestled in the heart of Kissimmee, Florida, in Osceola County. This picturesque community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a vibrant lifestyle.

Windsor at Westside is renowned for its stunning homes, featuring contemporary designs and spacious layouts that cater to a variety of lifestyles. Whether you're searching for a cozy retreat or a spacious family residence, you'll find a diverse selection of homes for sale that boast top-notch finishes, open floor plans, and private outdoor spaces perfect for entertaining or relaxing.

The community itself is a haven of amenities, including a resort-style pool, fitness center, and playgrounds, ensuring that residents have everything they need to enjoy an active and fulfilling lifestyle. With beautifully landscaped common areas and friendly neighbors, Windsor at Westside fosters a sense of community that makes it easy to connect and create lasting memories.

Located just minutes away from major attractions, shopping centers, and dining options, residents can easily access the best that Kissimmee has to offer. Plus, with its proximity to Walt Disney World and other theme parks, Windsor at Westside is a prime location for those who enjoy the magic of Florida's entertainment scene.

Explore the homes for sale in Windsor at Westside Phase 1 and discover the perfect place to call home. Embrace the charm, convenience, and community spirit that this delightful neighborhood has to offer!

Newest Windsor At Westside Ph 1 Homes for Sale

$649,000
9 Beds ⋅ 6 Baths ⋅ O6434920 MLS
Welcome to 2135 Tripoli Court, an expansive 9-bedroom, 6-bathroom pool home offering 4,391 square feet in the gated Windsor at Westside Resort. Built in 2016, this spacious residence provides the flexibility and capacity sought by vacationers, investors, and owners who enjoy entertaining. The open-concept living area connects the kitchen, dining space, and gathering areas, while the generous bedroom count and multiple bathrooms gives comfort and privacy throughout the home. Step outside to the private pool and enjoy the Florida lifestyle from your own vacation retreat. Windsor at Westside provides an impressive resort experience featuring a 10,000-square-foot clubhouse, zero-entry resort-style pool, waterslide, lazy river, hot tub, family water playground, fitness center, game room, sports courts, and Tu Casa Bar and Lounge with poolside dining. The community is conveniently located near Walt Disney World, shopping, dining, golf, and Central Florida’s most popular attractions. Whether you are searching for a personal vacation home, second residence, or short-term rental investment, this property combines substantial living space with an amenity-rich resort setting. Schedule your private showing and discover the possibilities at 2135 Tripoli Court.

2135 Tripoli Court, Kissimmee
$675,000
8 Beds ⋅ 6 Baths ⋅ S5151659 MLS
Welcome to 8825 Rhodes Street, 4041sqft beautifully maintained and fully furnished 8-bedroom, 6-bathroom home located within the highly sought-after gated Windsor at Westside Resort community. Designed for comfort, luxury, and entertainment, this spacious property features both upstairs and downstairs living areas, providing plenty of room for family and guests to relax and unwind. The open-concept kitchen showcases elegant granite countertops, ample cabinetry, and plenty of space for gathering and entertaining. Step outside to your private screened-in heated pool and covered lanai, creating the perfect setting for outdoor dining, family gatherings, or weekend BBQs while enjoying Florida's beautiful weather year-round. The converted garage has been transformed into a fun-filled game room, creating an additional entertainment space that guests and family members of all ages will enjoy. Whether you're searching for a primary residence, vacation home, or investment opportunity, this property offers exceptional flexibility and value. Residents enjoy access to all Windsor at Westside Resort amenities through the HOA, including a resort-style pool, clubhouse, fitness center, sports courts, playgrounds, and more. Ideally located approximately 8 miles from Walt Disney World Resort, this home offers convenient access to world-famous attractions, shopping, dining, golf, and major highways while providing the security and lifestyle of one of Central Florida's premier gated resort communities.

8825 Rhodes Street, Kissimmee
$658,000
9 Beds ⋅ 6 Baths ⋅ S5149067 MLS
The largest home on one of the best lots in entire Windsor at Westside resort. This fully furnished/equipped home with private pool deck, is just stone throw away from fabulous clubhouse and resort amenities. Brand new Duralux water proof flooring throughout second floor and ground floor bedrooms. UPGRADED CABINETRY throughout. Large private pool deck, heated pool and spa are ideal for entertaining large group of guests. Wide open game room equipped with wet bar and fridge. Dark granites for kitchen and bathroom counters, stainless steel appliances including two full size french door fridges, 42" cabinets and high ceilings. Windsor at Westside resort features state of art Clubhouse, 24 hour guarded gate, restaurant, bar, scheme park style water park. This home could be your ideal second home or the dream vacation rental investment property you’ve been looking for.

2147 Tripoli Court, Kissimmee
$699,900
7 Beds ⋅ 6 Baths ⋅ S5147600 MLS
7-Bedroom 5.5-Bathroom fully furnished home at Windsor at Westside a Gated Community. Located around 15 minutes from Disney World, Master Bedroom in the First Floor. Resort-Style Community. HOA covers, trash pick-up, lawn care, and grounds maintenance. New Laminate flooring in the Primary Bedroom Downstairs and all the Second Floor in 2026.

2112 Morocco Way, Kissimmee
$580,000
6 Beds ⋅ 5 Baths ⋅ S5147141 MLS
Ideally located in the main section of the highly sought-after Windsor at Westside, just a short distance from the community’s premier entertainment complex and resort amenities. This exceptional pool home presents an outstanding opportunity as a luxury vacation rental, personal retreat, or high-performing investment property. If you are looking for a completely turnkey property, this is the home for you. In only its first year as an active Airbnb this home is already producing strong revenue numbers primarily due to its location and the tens of thousands spent on recent updates. This IS that extremely turnkey home you’ve been looking for. Projections look fantastic and are expected to continue increasing, this property offers immediate and growing income potential. Even better, all future bookings are transferable if the current management company is retained, allowing for a seamless transition and day-one revenue. Inside, the home showcases tens of thousands of dollars in upgrades and custom theming, designed to maximize guest appeal and long-term durability. Featuring all tile and luxury vinyl plank flooring throughout with absolutely no carpet, this home combines style with easy maintenance. The spacious open-concept floor plan flows beautifully from the main living and dining areas to the private screened lanai with pool and spa, creating the ideal space for entertaining and relaxation. The kitchen is fully upgraded with stainless steel appliances, granite countertops, and a large island with seating, while the first-floor primary suite offers privacy and convenience. Upstairs, a generous media and entertainment space provides the perfect setting for movie nights, gaming, and guest enjoyment. Additional bedrooms include a second primary suite, beautifully appointed guest rooms, and professionally themed bunk rooms that elevate the vacation rental experience. Residents and guests enjoy access to one of Central Florida’s premier resort communities, featuring a 5,000-square-foot clubhouse, resort-style pool, lazy river, water slide, fitness center, tennis, basketball, volleyball, soccer field, kids play area, arcade, on-site restaurant, tiki bar, and shop. The HOA covers landscaping, internet, cable, and daily trash service, making ownership easy and hassle-free. Conveniently located near Walt Disney World, shopping, dining, golf, major highways, and Orlando’s top attractions, this property checks every box for both lifestyle and investment performance. Schedule your private showing today and secure one of the strongest opportunities currently available in Windsor at Westside.

2108 Morocco Way, Kissimmee
$540,000
6 Beds ⋅ 5 Baths ⋅ O6358195 MLS
Great, great price improvement!! It is really priced to sell quickly!! Beautiful 6 bedroom 4 1/2 bathroom, hideaway open floor plan on a corner lot in the desirable Windsor at Westside Community. Spacious great room over looking the screened 30 x 20 pool deck with heater pool and heated spa. First and second floor Master Suites. To the second floor is a 19 x 17 Loft, second suite and 4 further bedrooms and 2 bathrooms. This lovely property would make a great family vacation home, an income producing Short Term Rental Home, or even your Primary Residence. Over 3,000 sq ft under air. Luxury features throughout the home including granite counters in the kitchen and bathrooms. Stainless steel appliances, ceramic tile to the first floor and all bathrooms. Energy efficient features include Low E double pane windows, 15 seer A.C system. Located within close proximity to the communities private 8,000 sq ft club house with fitness center, heated pool, heated spa, heated lazy river, tennis courts, and much more. The location of Windsor at Westside is ideal for the attractions, shops, restaurants and much, much more fun! A must purchase!

8956 Rhodes Street, Kissimmee
$610,000
8 Beds ⋅ 6 Baths ⋅ O6289038 MLS
Back on the market due to the buyer’s financing falling through. Welcome to this beautiful vacation home located in the highly sought-after Windsor at Westside community. This stunning property has an open floor plan and features 8 spacious bedrooms and 6 bathrooms, offering ample space for families or groups. The home is perfectly situated with easy access to Disney World® theme parks via the nearby toll road 429, making it an ideal choice for those visiting the magical parks. Additionally, there are a variety of dining and shopping options just a short drive away. The Windsor at Westside community itself is a resort-style retreat, with an array of amenities that will enhance your vacation experience. The incredible 10,000 sq. ft. clubhouse is the perfect spot to relax and unwind, while the community’s lake and pier have serene views and outdoor activities. For ultimate relaxation and fun, enjoy the zero-entry resort-style pool, complete with a thrilling waterslide, lazy river, and a water playground. This home is not just a place to stay; it’s a destination in itself, offering both luxury and convenience. Don’t miss the opportunity to make this dream vacation home yours!

8801 Rhodes Street, Kissimmee
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