Windsor At Westside Ph 1 Real Estate

Windsor At Westside Ph 1 Real Estate

Welcome to Windsor at Westside Phase 1, a stunning community nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This beautifully designed subdivision is the perfect blend of modern living and serene surroundings, making it an ideal choice for families, retirees, and anyone looking to embrace the Florida lifestyle.

Windsor at Westside boasts a variety of luxurious single-family homes, each crafted with meticulous attention to detail and designed to cater to your every need. With spacious floor plans, contemporary finishes, and energy-efficient features, these homes provide both comfort and style. The community is surrounded by lush landscaping and picturesque views, creating a tranquil atmosphere that feels like a retreat from the hustle and bustle of everyday life.

Residents of Windsor at Westside enjoy a wealth of exceptional amenities, including a resort-style pool, a state-of-the-art fitness center, and a clubhouse that serves as the social hub of the community. Children can take advantage of the playground and sports courts, while nature lovers will appreciate the walking trails and green spaces that encourage outdoor activities.

Conveniently located near major highways, Windsor at Westside offers easy access to Orlando's world-renowned attractions, shopping centers, and dining options. Whether you're looking to explore the magic of Disney, enjoy a day at Universal Studios, or simply relax on the nearby beautiful beaches, this community is perfectly positioned for all your adventures.

Discover the charm and convenience of Windsor at Westside Phase 1, where your dream home awaits in a community that truly feels like home.

Newest Listings in Windsor At Westside Ph 1

$390,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
Priced to Sell! Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restaurant & Club House, Pond and Pier and so much more! Those are just the amenities; lets talk about this 5 Bedroom & 5 Bath with a private garage in paradise. You have enough space for the family and some including a theatre area for all to enjoy. Subtle taste of Disney throughout the home and a very nice size kitchen for all to gather. Don't want to stop the fun from the community pool? Well bring it home since you'll have your very own private pool and patio area to enjoy. Its spacious, its clean and comes completely furnished as you see it all you need is the key to make it yours. You can enjoy this home as little or as much as you'd like as short term rental is allowed as well as long term if you'd choose. Want the best of both worlds? Why not leave your vehicle stored in the garage and some personal items in your very own, owners closet's throughout the house. Having too many options is never a bad thing when you either way you are making the right choice. Schedule your next appointment today!

9025 Rhodes Street, Kissimmee
$424,900
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
Welcome to one of the best-located homes in Windsor at Westside Resort! Situated on a premium corner lot and just steps from the clubhouse, this fully furnished 5-bedroom, 4.5-bathroom townhome offers one of the closest walkable locations to the resort’s incredible amenities, making it especially desirable for vacation guests and short-term rental success. Enjoy easy access to the resort-style pool, lazy river, water slides, hot tub, fitness center, arcade, playground, sports courts, tiki bar, and on-site restaurant. Inside, you’ll find a welcoming foyer with a convenient drop zone leading into a bright, open-concept floor plan. The first floor features tile throughout with no carpet, a spacious living and dining area, and a beautifully appointed kitchen with white shaker cabinets, granite countertops, abundant cabinet space, and a large island overlooking the main living area. A first-floor bedroom with a private en suite bathroom offers the perfect setup for guests or multigenerational living. Upstairs features luxury vinyl plank flooring throughout, a spacious loft, laundry room, and four additional bedrooms, including themed Frozen and Mickey Mouse bedrooms with two sets of twin beds. The primary suite offers a king bedroom with a private en suite featuring dual sinks, while an additional queen suite also includes its own private bathroom. Step outside to your private screened-in pool with brick pavers, a covered lanai, and a child safety fence already installed. The detached garage, private driveway, and additional parking directly in front of the home provide plenty of space for owners and guests. The HOA includes cable, internet, valet trash service, lawn maintenance, and access to all of Windsor at Westside’s world-class resort amenities. Whether you’re searching for a primary residence, vacation home, or income-producing short-term rental, this exceptional property offers an unbeatable combination of location, comfort, and resort-style living just minutes from Walt Disney World, shopping, dining, and major highways. Schedule your showing today!

2070 Rome Drive, Kissimmee
$440,000
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
$675,000
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
$416,999
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
$658,000
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
$699,900
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
$399,990
4 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
Welcome to 2022 Majorca Drive, a highly desirable 4-bedroom, 3.5-bathroom townhome located in the Windsor at Westside Resort. Positioned in the preferred Phase 1 of the community, this home sits close to the clubhouse, resort-style lagoon pool, lazy river, bar & lounge, and a full range of premium amenities—an exceptional location that vacation guests consistently look for when booking their stay. Whether used as a personal getaway or an income-producing property, this townhome delivers the perfect combination of comfort, convenience, and resort-style living. Inside, the open-concept layout is ideal for entertaining, featuring a well-equipped kitchen with granite countertops, stainless steel appliances. A convenient outdoor half bathroom enhances the pool area—an extra feature that guests truly appreciate. Each bedroom is thoughtfully furnished to create a relaxing and welcoming atmosphere, making it ideal for vacation stays. Currently operating as a successful full-time short-term rental, the property is fully turnkey and ready to generate income immediately, or to be enjoyed as your own retreat near Orlando’s world-renowned attractions. Windsor at Westside is recognized as one of Central Florida’s premier resort communities. Residents and guests have access to a 10,000 sq. ft. clubhouse, a lagoon-style pool with lazy river and waterslide, fitness center, arcade, volleyball court, poolside Tu Casa bar & lounge, and 24-hour gated security. Ideally located just minutes from Walt Disney World, this property presents a rare opportunity to own one of the best-positioned townhomes in a highly desirable vacation community—offering strong rental potential, excellent guest appeal, and unmatched access to resort amenities. All information provided, including room measurements, is considered reliable but not guaranteed. Buyers and agents are advised to verify all details independently.

2022 Majorca Drive, Kissimmee
$550,000
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
$540,000
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
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
$389,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 1 SubDv. ⋅ 34747 Zip Code
Incredible opportunity in the highly sought-after Windsor at Westside Resort! 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 your own private showing today!

1995 Majorca Drive, Kissimmee
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