Windsor At Westside Townhomes for Sale in Kissimmee - 14 townhouses

Remarks: Welcome to Windsor at Westside, one of Central Florida’s most desirable short-term vacation communities! Ideally located just minutes from world-famous theme parks, shopping, dining, and entertainment, this stunning 5-bedroom, 4 full bath and 1 half bath home offers the perfect blend of luxury and convenience. Fully furnished and move-in ready, this property is ideal as an income-producing vacation rental or a beautiful second home getaway. Enjoy your own private pool, perfect for relaxing after a day of fun in the sun. The community offers exceptional resort-style amenities, including a lazy river, water playground, cabanas, outdoor fireplace, shaded playground, fitness center, arcade, multi-purpose courts, sand volleyball, Tu Casa Bar & Lounge, event spaces, and a lush sports field. Don’t miss this incredible opportunity to own in a prime location just a short distance from Disney World parks—where comfort, entertainment, and investment potential come together!

Listing is courtesy of: MAGNUS REALTY GROUP LLC (407-286-6042)

Listing Agent: Manuel Minier (407-340-0966)

Remarks: Fully Furnished Turnkey Vacation Rental! This 5-bedroom, 4.5-bathroom vacation retreat is built for both relaxation and revenue—comfortably accommodating up to 16 guests and ready for immediate enjoyment or income potential! Ideally located just minutes from major theme parks, this property blends modern luxury with fun-filled amenities. On the main floor, you'll find a private king bedroom and full bathroom—perfect for multi-generational stays. The open-concept heart of the home features a stylish kitchen with granite countertops, stainless steel appliances, and a large island, flowing seamlessly into a bright, airy living room with views of the private heated pool. Step outside to a covered lanai and convenient outdoor half bath—ideal for entertaining. Upstairs, a spacious loft adds bonus living space, alongside four additional bedrooms and three full bathrooms. Two themed rooms—Frozen and Star Wars—feature custom murals and LED lighting, offering a magical experience for younger guests. Recent upgrades include fresh interior paint, a Nest thermostat, digital door locks, new lighting, plush carpeting, and high-end washer/dryer units. The detached garage provides flexible space for parking, storage, or a future game room or theater conversion. The HOA covers cable, internet, trash, lawn care, and access to resort-style amenities including a clubhouse, arcade,

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

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

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: Welcome to 8851 Geneve Ct in Kissimmee, a fully furnished, turn-key vacation home located in the highly sought-after Windsor at Westside Resort, one of Central Florida’s premier short-term rental communities near Walt Disney World Resort. This income-producing property offers the perfect blend of investment potential and resort-style living. Situated within a gated resort community, residents and guests enjoy world-class amenities including a lazy river, resort-style pool, clubhouse, fitness center, restaurant, playground, and multiple sports courts. The HOA provides exceptional value, covering basic internet and cable, landscaping for the common areas surrounding the unit, daily valet trash service, and full access to the resort’s amenities, including a kids splash pool area, lazy river, basketball and tennis courts, soccer field, volleyball courts, and an additional clubhouse located in Phase 3 of the resort. Security and guest access are well managed with 24/7 guard-gated entry across three guardhouses located throughout the community, additional guards during heavy check-in times, and overnight security rovers. Owners and guests also benefit from the MyQ gate access system, which provides proxy cards for owners and temporary access cards for guests for seamless entry. Ideally located just minutes from Disney and Orlando’s top attractions, with convenient access to U.S. Route 192, State Road 429, and Interstate 4, the home is surrounded by popular shopping, dining, and entertainment options that attract visitors year-round. Being sold completely furnished, this property is move-in ready*and ideal for buyers seeking a vacation home near Disney or a high-performing short-term rental property in Kissimmee’s thriving resort market.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Sofia Lovinsky (407-376-1845)

Remarks: Under contract-accepting backup offers. Welcome to your dream vacation retreat or income-generating investment property! This beautifully appointed 5-bedroom, 4.5-bathroom townhome is located in the highly sought-after Windsor at Westside Resort in Kissimmee, Florida — just minutes from Walt Disney World and Central Florida’s top attractions. Offered fully furnished and turnkey-ready, this spacious home features a modern open-concept layout, stylish finishes, and thoughtful upgrades throughout. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, seamlessly connecting to the dining area and comfortable living room — perfect for entertaining or relaxing after a day at the parks. Each of the five generously sized bedrooms offers plush accommodations, with two en-suite baths for added privacy. The private splash pool and screened lanai create a tranquil outdoor space ideal for family fun or peaceful relaxation. Located in a resort-style, gated community, Windsor at Westside offers unmatched amenities including a luxury clubhouse, lagoon-style pool with lazy river, fitness center, sports courts, arcade, on-site dining, and 24-hour security. Don’t miss your chance to own a piece of paradise in one of Central Florida’s top vacation communities! Schedule your private tour today!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Gabriela Miyamoto (407-800-4385)

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: ***TENANT OCCUPIED*** Discover an exceptional opportunity with this beautiful 4-bedroom, 3.5-bathroom townhome, ideally located just minutes from the Walt Disney World Resort. This 2,102 sq. ft. property, built in 2016, is situated in the desirable, gated Windsor at Westside Community. The townhome includes a private pool and a one-car attached garage. The open floorplan features a kitchen/family room combo, high ceilings, tile and carpet flooring, walk-in closets, and an in-wall pest system. The HOA fees cover internet, cable, ground maintenance, pest control, trash disposal, and exterior maintenance, making it a low-maintenance option for owners. This property is an excellent option for short-term rental/vacation home use, with a minimum lease of just 1-7 days allowed, offering great potential for rental income. It can also be rented as a residencial long term. Residents and guests have access to Windsor at Westside's extensive, 8,000 sq. ft. clubhouse and amenity center, which includes: A resort-style heated pool and spa, Lazy river, Fitness center, Poolside cabanas, On-site store, restaurant, and bar, Sports courts (volleyball, tennis, basketball), Playground and game room. This home offers a perfect blend of a private retreat and resort-style living, with everything needed for a primary residence, second home, or profitable investment property.

Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)

Listing Agent: Danielle Marcondes Franca Viana Silva (407-668-0245)

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)

Remarks: Fantastic spacious fully. furnished 5-Bedroom Town Home in the exciting resort of Windsor at Westside. Nestled in one of the newest resorts in the area near Disney, this beautifully maintained 5-bedroom, 4.5-bathroom town home offers the perfect blend of modern comfort, elegance, and fun decorated kids rooms. Built in 2017 and spanning 2,263 square feet, the property features an open-concept living area, a gourmet kitchen equipped with stainless steel appliances, granite countertops, and a large island ideal for entertaining. Outside, enjoy a private backyard oasis - a spacious deck with a private pool, BBQ, seating area and outdoor TV, perfect for outdoor gatherings. Garage has been converted to a fun fully loaded game room. Conveniently located just minutes from Disney, Universal and other entertainment areas, and schools, this home is ideal for an income generating opportunities, as well as second home or a permanent residence. The stunning 10,000 sq ft Club house features reception desk, Community Pool, Lazy River, Splash zone, Fitness Center, Tiki Bar and Restaurant, Youth activities Center and Arcade room, Security gates manned 24/7. Call and schedule your private tour today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Stani Delcheva (407-405-6815)

Remarks: Welcome to this exceptional 5-bedroom, 4.5-bathroom vacation retreat featuring a private heated pool and outdoor kitchen with gas grill, thoughtfully designed for both refined relaxation and entertaining. This bright corner-unit home is filled with natural light and offers a spacious open-concept layout with ceramic tile throughout. The modern kitchen features stainless steel appliances and overlooks the main living and dining areas. The first floor includes a private bedroom with a full bathroom, ideal for guests or multi-generational living. Upstairs, the expansive primary suite offers an en-suite bathroom, along with a second en-suite bedroom, two additional bedrooms, and a shared full bath. Enjoy Florida living outdoors with a heated pool, pool-area half bath, and outdoor kitchen. A detached garage has been converted into a game room for added entertainment. Located just minutes from world-famous theme parks, this gated resort community offers exceptional amenities, including a resort-style pool with cabanas, lazy river, clubhouse with fitness center, on-site dining, sports courts, playground, and 24/7 security. Conveniently close to golf, shopping, dining, and major attractions. Perfect for families, groups, and vacationers looking for space, comfort, and resort-style fun close to all the action!

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Cassius De Moura (407-989-0007)

Remarks: 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, this stunning retreat 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 granite 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. Imagine unwinding by the poolside or retreating to the screened-in lanai for a serene evening under the stars. 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. Dive into the zero-entry pool or treat yourself to a refreshing spa experience. Family will adore the playground and water slide, while adults can relax with a cocktail at the pool bar or dine at the full-service restaurant. 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. Don’t miss out on the opportunity to own your own piece of paradise. Schedule a showing today and take the first step toward making this dream retreat yours.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Gladys Bezerra (407-701-4034)