Windsor At Westside Townhomes for Sale in Kissimmee - 29 townhouses

Remarks: 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.

Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)

Listing Agent: Laura Teixeira, Pa (941-962-2413)

Remarks: 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!

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: 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 mean one less major appliance to worry about replacing down the road. 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 amenity collection, including a resort-style main pool with children's splash pad, relaxing hot tub, lazy river, fully equipped fitness center, arcade, 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.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: Seller may consider buyer concessions if made in an offer ~ Welcome to opportunity in the GUARD GATED ~ RESORT COMMUNITY of Windsor at Westside – a FULLY FURNISHED ~ TURN KEY 5-bedroom, 4.5-bath PRIVATE POOL townhome that books well as a short-term rental and is ready to generate income from day one! Thoughtfully designed and tastefully decorated, this home feels light, bright, fresh, and truly move-in ready. TILE FLOORS flow throughout the main living areas, complemented by crown molding that elevates the OPEN CONCEPT living and dining spaces. The modern kitchen is both functional and stylish, featuring STAINLESS STEEL APPLIANCES, a tiled backsplash, ample cabinet and counter space, recessed lighting, pantry storage, and a large ISLAND with bar seating under pendant lighting – perfectly positioned to overlook the living and dining areas, making staying connected and entertaining effortless. A built-in drop zone at the foyer adds convenience for guests arriving and departing, while the covered front entry enhances curb appeal. The flexible floor plan includes a MAIN FLOOR BEDROOM & FULL BATH – ideal for multi-generational stays or guests who prefer first-floor accommodations. Upstairs, you will find the generous PRIMARY SUITE, a secondary en-suite bedroom with its own private bath, and additional well-appointed bedrooms and bathrooms designed with comfort and functionality in mind. Step outside to your COVERED PAVER LANAI and PRIVATE SCREENED POOL – a must-have for today’s vacation rental guests – complete with a convenient poolside half bath. Whether guests are soaking up the Florida sunshine poolside or floating the lazy river at the clubhouse, this property delivers the FULL RESORT EXPERIENCE. In addition to your private pool, Windsor at Westside offers a stunning community pool, clubhouse, fitness center, restaurant, game room, and one of the area’s most sought-after lazy rivers – amenities that consistently attract repeat bookings. The 1-car garage adds storage and owner convenience, while the LOW MAINTENANCE townhome lifestyle makes this an easy choice for investors or vacation home/second-home buyers alike. Located just minutes from world-famous theme parks, championship golf courses, premier shopping and dining, and with easy access to US-27 and 192, Windsor at Westside remains one of Kissimmee’s sought-after short-term rental communities. If you have been searching for a well-performing, fully furnished, income-producing vacation home in a true resort-style community – this is the one! Call today for more information and schedule a tour!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Welcome to your ideal vacation home and income-producing property in the highly sought-after Windsor at Westside Resort! This beautifully appointed 4-bedroom, 3.5-bathroom townhome is fully furnished and turnkey, making it perfect for short-term rentals or a personal getaway. Step inside to find stylish décor throughout and an open-concept floor plan designed for comfort and entertaining. The modern kitchen features granite countertops, ample cabinetry, and everything needed for effortless hosting. The spacious living and dining areas flow seamlessly to your private screened-in pool—perfect for relaxing after a day of fun. Upstairs and downstairs sleeping arrangements provide flexibility for guests, while the thoughtfully designed layout ensures privacy and convenience. Enjoy resort-style living with world-class amenities including a stunning clubhouse, resort pool with lazy river, fitness center, tennis courts, playground, and on-site Tiki bar. There’s something for everyone to enjoy! Ideally located just minutes from Central Florida’s top attractions, as well as shopping, dining, and entertainment, this property offers both an exceptional guest experience and strong rental potential. Don’t miss this opportunity to own a slice of paradise in one of the area’s premier vacation communities!

Listing is courtesy of: PROVIDENCE REALTY AND PROPERTY MANAGEMENT LLC (863-512-5238)

Listing Agent: Debbie Bendall (407-922-3035)

Remarks: Welcome to luxurious living in the Windsor at Westside community in Kissimmee, Florida. This exquisite two-story townhome spans 2,263 square feet, offering a generous blend of comfort and style with 5 bedrooms and 4.5 bathrooms. Step inside to discover an open floor plan, perfect for entertaining and family gatherings. The first floor features a convenient bedroom with a full bathroom, catering to both versatile living needs and guest accommodations. The heart of the home opens up to a beautifully decorated, fully furnished interior, where every detail is thoughtfully curated. For those who love outdoor living, the screened-in pool and lanai create an ideal space for relaxation and entertainment. An outdoor half bath brings added convenience, ensuring guests have everything they need while enjoying the Florida sunshine. Currently thriving as a short-term rental, this property offers an incredible investment opportunity, drawing guests with its distinctive charm. The home is in high demand, making viewings a bit challenging, but the experience is truly rewarding when you set foot inside. The Windsor at Westside community is a coveted gated enclave known for its resort-style amenities. Indulge in the heated pool, float along the lazy river, or unwind at the Tiki Bar. For those seeking active recreation, the tennis and basketball courts, along with a fun-filled game room, offer endless enjoyment. Proximity to Walt Disney World Theme Parks adds a magical touch, making this location even more desirable. Embrace a lifestyle where comfort meets leisure in this sought-after Kissimmee townhome. Discover the unique blend of vacation vibes and homey warmth in this exceptional property. Schedule your tour today and experience the essence of Florida living!

Listing is courtesy of: CENTURY 21 EDGE (321-351-2121)

Listing Agent: Gene May Sandobal (321-353-6150)

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: *** 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)