Windsor At Westside Ph 1 Homes with Sidewalk Exterior Features

Windsor At Westside Ph 1 Homes with Sidewalk Exterior Features

Welcome to Windsor at Westside Phase 1, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. This charming community offers a perfect blend of modern living and serene surroundings, making it an ideal choice for families, retirees, and anyone looking to enjoy the Florida lifestyle.

Windsor at Westside Phase 1 is characterized by its beautifully designed homes, each featuring stunning architectural details and lush landscaping. One of the standout features of this community is its commitment to walkability; the homes come with delightful sidewalk exterior features that encourage residents to take leisurely strolls through the neighborhood. Imagine evening walks with your family or morning jogs surrounded by friendly neighbors and the natural beauty of Florida’s landscape.

Located in Osceola County, Windsor at Westside is conveniently situated near major highways, making commuting to nearby attractions, shopping centers, and dining establishments a breeze. Just a short drive away, you'll find the excitement of Walt Disney World and other world-renowned theme parks, ensuring that there’s always something fun to do.

In addition to its prime location, Windsor at Westside boasts a range of community amenities, including a sparkling pool, clubhouse, and recreational facilities that foster a sense of community and encourage an active lifestyle. Whether you’re looking to relax by the pool or engage in social activities, this subdivision has something for everyone.

Discover the charm and convenience of Windsor at Westside Phase 1 – where your dream home awaits!

Newest Windsor At Westside Ph 1 Homes with Sidewalk Exterior Features

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

Welcome to 1974 Majorca Drive, located in the highly sought-after resort community of Windsor at Westside, where luxury vacation living meets exceptional investment potential. This home made such an impression on the current owners that they loved the lifestyle so much they ultimately decided to relocate here full time. Their change in plans creates an incredible opportunity for the next owner. Whether you're seeking a high-performing vacation rental, a second home, or a primary residence, this property checks every box. Despite being available for only a short period of time, the home is already producing strong rental revenue through a well-known, low-cost professional management company. Even better, there are numerous future bookings that can be transferred to the new owner when the current management company is retained, providing immediate income potential from day one. Originally intended to remain in the family's portfolio for years to come, the home has undergone several recent improvements and upgrades. Enjoy brand-new furnishings throughout many areas of the home, including a beautifully redesigned primary suite, a stylishly refreshed living room, a newly themed Disney bedroom, and an incredible Harry Potter themed loft and theater room that is sure to be a guest favorite. Additional updates include a brand-new washer and dryer, helping make this property completely turnkey. Step outside and enjoy your own private pool, perfect for relaxing after a day at the parks. Just steps away, the detached garage has been transformed into a dedicated game room, creating the ultimate entertainment space for family and guests. The combination of a private pool and game room significantly enhances both guest appeal and rental performance. The location is outstanding, just minutes from the world-class golf courses of ChampionsGate and Reunion Resort, Walt Disney World, shopping, dining, and major highways that provide convenient access to some of Florida's most beautiful beaches and attractions. As an added bonus, this home is one of the closest properties in Windsor at Westside to the community's renowned entertainment complex and resort amenities, making it especially convenient for owners and guests to enjoy everything the community has to offer. Windsor at Westside is renowned for its incredible resort amenities that attract guests year-round while providing an exceptional lifestyle for residents. Enjoy a resort-style pool, lazy river, splash pad, cabanas, bar and grill, fitness center, basketball, tennis, pickleball, scenic walking and jogging trails, concierge services, organized community events, and the peace of mind that comes with 24/7 live gated and roaming security. If you're looking for a property that offers immediate rental income, extensive upgrades, resort-style amenities, and the flexibility to serve as a vacation home or primary residence, 1974 Majorca Drive deserves a place at the top of your list.

1974 Majorca Drive, Kissimmee

8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

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

4 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

INCOME-PRODUCING OPPORTUNITY in Windsor at Westside, one of Kissimmee’s most sought-after short-term rental communities near Orlando’s world-famous theme parks. Unlike many investment properties in the area, this FULLY FURNISHED and TURNKEY 4-bedroom, 3.5-bath townhome has been primarily owner-used and exceptionally maintained, offering investors and second-home buyers a rare combination of rental potential and pride of ownership. Designed for both guest appeal and long-term durability, the home features a highly functional layout with a private first-floor king suite and full bathroom, ideal for multigenerational stays and vacation guests seeking convenience and privacy. The open-concept living space showcases a modern kitchen with granite countertops, stainless steel appliances, and an oversized island that seamlessly connects to the spacious family room overlooking the private pool area. The covered lanai, complete with a convenient half bath, creates an ideal indoor-outdoor entertainment setting highly desirable in the vacation rental market. Upstairs, a versatile loft provides additional gathering space, complemented by three well-appointed bedrooms and two full bathrooms. This unit offers a one car garage, heated private pool with a pool bathroom and a florida room, and is located within a walking distance from a resort style club house. Whether you are seeking a proven income-producing asset, a second home with rental flexibility, or a well-maintained investment property in a high-demand tourism market, this residence offers exceptional value, location, and long-term potential.

1987 Majorca Drive, Kissimmee

9 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

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

7 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

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

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

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

6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophistication, and excellent investment potential. With 6 bedrooms, 4 full bathrooms, and 1 powder room, the house features a modern open-concept layout, providing spacious, integrated, and well-lit environments. Upon entering, a charming veranda with a garden welcomes you and creates a cozy atmosphere. Inside, you'll find a spacious living room with ceiling fans, integrated with the dining room and kitchen, forming an ideal environment for both everyday life and entertaining guests. Sliding glass doors lead to the outdoor area, where the private pool and covered veranda are located—the perfect space for leisure and relaxation. The kitchen is fully equipped with appliances, wooden cabinets, and a breakfast bar, combining practicality and elegance. The master suite is located on the first floor, offering privacy, a large bathroom, and a walk-in closet. On the second floor are the other five bedrooms—all with closets and carpeting—as well as a spacious loft that can be used as a TV room, game room, or additional living space. The condominium offers a complete resort-style structure, with a clubhouse, swimming pool, gym, volleyball courts, playground, game room, and security, providing leisure and convenience for the whole family. The location is privileged: just 15 minutes from Walt Disney World, close to golf courses, outlets, restaurants, supermarkets, and with easy access to the region's main highways. It is also about 30 minutes from Orlando International Airport, facilitating travel for domestic and international trips. Whether for living or investing in vacation rentals, this is a unique opportunity in one of Florida's most desirable areas.

9013 Rhodes Street, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

Welcome to 8952 Adriatico Lane, a fully furnished 5-bedroom, 4.5-bath townhome in the highly desirable gated community of Windsor at Westside. Offering turnkey luxury, modern upgrades, and a proven history of successful short-term rental performance, this property stands out as an exceptional opportunity for both investors and personal-use buyers. The main level features an open-concept layout with a spacious living area and a well-appointed kitchen complete with granite countertops, stainless steel appliances, and a large central island ideal for gathering. This floor also includes a bedroom and full bathroom, providing convenient accommodations for multi-generational families or high-occupancy rental groups. Sliding glass doors lead to the private, screened-in splash pool and covered lanai, which also includes a dedicated half bathroom for easy poolside access. Upstairs, brand-new carpeting enhances the comfort of the bedrooms and loft area. The floor plan includes a generous primary suite along with additional guest rooms suited for families or vacation rental guests. Recent upgrades include a new dryer and a newly installed EV charging plug. High-quality furnishings and décor are included with the sale, ensuring immediate rental readiness or a seamless second-home transition. Windsor at Westside offers a premier resort lifestyle with an 8,000 sq ft clubhouse, heated zero-entry pool, lazy river, water slide, fitness center, game room, sports courts, on-site dining options, and 24/7 gated security. Cable, internet, lawn care, and trash service are included for a low-maintenance ownership experience. Located approximately 10–12 miles from Magic Kingdom, this home provides quick access to Disney attractions, world-class golf, shopping, and dining. With its prime location, complete furnishing package, community amenities, and strong rental performance, 8952 Adriatico Lane represents exceptional value in one of Central Florida’s most sought-after vacation destinations. Schedule your showing today to experience all that this home and community offer.

8952 Adriatico Lane, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code

Fractional Ownership. Co-Ownership Opportunity in the highly sought-after Windsor at Westside Resort. Offered in 1/13th shares, this is a unique opportunity to enjoy all the benefits of a vacation home with the flexibility and efficiency of co-ownership. This fully furnished five bedroom, four and a half bathroom retreat comfortably accommodates up to 16 guests and is ideally located just minutes from Orlando’s world famous theme parks and attractions. The home blends modern design with resort style amenities, creating the perfect getaway for families and guests alike. On the main level, you will find a private king bedroom and full bathroom, ideal for multi generational stays. The open concept living space features a beautifully designed kitchen with granite countertops, stainless steel appliances, and a large island, all flowing seamlessly into a bright and inviting living room overlooking the private heated pool. Step outside to enjoy the covered lanai and convenient outdoor half bath, perfect for relaxing or entertaining. Upstairs, a spacious loft provides additional living space, along with four more bedrooms and three full bathrooms. Two themed bedrooms, inspired by Frozen and Star Wars, include custom murals and LED lighting for a fun and memorable experience. Contact the listing agent today for additional details.

1995 Majorca Drive, Kissimmee

Start Your Search

Browse Windsor At Westside Ph 1 Homes by Community Extras