Windsor At Westside Townhomes for Sale in Kissimmee - 28 townhouses

Remarks: Fractional Ownership. Co-Ownership Opportunity in the highly sought-after Windsor at Westside Resort. Offered in 1/8 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.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Scott Cohara (407-398-9554)

Remarks: This stunning retreat Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation. With five spacious bedrooms and four and a half bathrooms, offers the perfect blend of comfort and sophistication. As you step inside, you're greeted by an open floor plan that seamlessly integrates the living, dining, and kitchen areas. The kitchen boasts elegant quartz countertops and sleek stainless steel appliances, creating a modern yet inviting atmosphere. The spacious loft upstairs provides an additional living area, perfect for relaxing, entertaining, or even setting up a home office. One of the highlights of this townhouse is the private pool, easily accessible through pool-facing telescopic sliding glass doors. Staying in Windsor at Westside means enjoying world-class amenities. The HOA grants you access to an impressive 8,000 sq ft clubhouse, featuring a lazy river, sports courts, an arcade game room, and more. To make your stay even more effortless, the HOA covers cable, high-speed internet, exterior maintenance, trash pick-up, pest control, and lawn care. Every detail has been thoughtfully curated to ensure your experience is nothing short of extraordinary. This townhouse isn't just a home; it's a lifestyle. Schedule a showing today and take the first step toward making this dream retreat yours.

Listing is courtesy of: AUTHENTIC REAL ESTATE TEAM (407-440-1010)

Listing Agent: Karla Cintra (407-881-7730)

Remarks: 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.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Alexandre Zapparoli (321-444-8701)

Remarks: 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.

Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)

Listing Agent: Paulo Goncalves Ferreira (407-818-0717)

Remarks: Welcome to this 5-bedroom, 4.5-bathroom townhome with private heated pool located in the highly desirable Windsor at Westside — a premier short-term rental community just minutes from major highways, shopping, dining, and Central Florida attractions. This property is a competitive option within the community, featuring a private heated pool and a garage that can be converted into a game room, both highly desirable features for short-term rental performance. The home offers a functional open-concept layout, connecting the living, dining, and kitchen areas. The kitchen includes stainless steel appliances, granite countertops, and ceramic flooring. 1 bedroom on the first floor 4 bedrooms upstairs Spacious loft area Owner’s suite with walk-in closet and private bath Second-floor laundry room Enjoy a private screened-in pool and courtyard, ideal for relaxation and guest use. Community amenities include a resort-style pool, lazy river, clubhouse, fitness center, sports courts, tiki bar, and spa. Zoned for short-term rental, making it suitable for investment and vacation use, or primary residence.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Ciro Noccioli Monteiro Alves (321-442-9680)

Remarks: Just minutes from Disney, this upgraded and fully furnished 4-bedroom, 3.5-bath townhome is the kind of property buyers and investors have been waiting for. Inside, you’ll find newer luxury vinyl flooring throughout, replacing all carpet for a fresh, modern, and easy-to-maintain living space. The home offers a private indoor pool for year-round enjoyment, plus a convenient half bath just outside the pool area, perfect for guests and entertaining. A spacious open loft adds valuable flexibility and can be used as a game room, second living area, or additional guest space. The layout includes a primary suite and Jack-and-Jill bedrooms, making it ideal for personal use, vacation stays, or short-term rental guests. Bright, stylish, and sold fully furnished, this property is ready for immediate enjoyment or rental income potential. Located in a desirable community with great amenities and only minutes from Disney, restaurants, shopping, and Orlando’s top attractions, this home offers location, function, and value all in one.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Sharon Wang (813-951-3122)

Remarks: *** INCOME POTENTIAL *** VACATION HOME FULLY FURNISHED. In Excellent condition and beautifully decorated this 5 Bedroom Townhome with a splash pool has all you need for spending great moments in the Orlando Area or renting it out when not using it. It offers great income potential. Windsor at Westside is a vacation rental community with resort-style amenities featuring a fitness center, a mini market, a restaurant, and bar, a large community pool with a lazy river, a water playground, a playground, a soccer field, sports courts, and a sand volleyball court. 24-hour manned Gated security. Shows beautifully.

Listing is courtesy of: AMERICAN HORIZONS REALTY (407-466-0256)

Listing Agent: Martonio Pinto (407-466-0256)

Remarks: 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. Contact today for your next appointment.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Sergio Palmero (718-915-8957)