Windsor At Westside Homes for Sale in Kissimmee - 48 homes

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: Welcome to your DREAM VACATION HOME in the highly sought-after, Airbnb-friendly resort community of Windsor at Westside. This property comes with strong rental history and over $40,000 in updates to the home which were just done in 2024! This exceptional vacation home stands out for several reason. The prime location of this property, stunning water views, and numerous recent upgrades. Ideally situated just steps from the clubhouse, gym, pool, and restaurant, convenience is at your doorstep. Enjoy water views from the front of the home and multiple rooms inside. Unlike many other short-term rentals on the market this home was recently updated. Recent upgrades include all-new appliances, new luxury flooring, furniture, linens, and more—providing a move-in-ready retreat where all the work has already been done for you! This stunning, FULLY FURNISHED property is perfectly located just 20 minutes from Disney World, 30 minutes from Orlando International Airport, and less than an hour from Florida’s renowned beaches, offering the ultimate convenience for vacationers. This luxurious 3,142 sf, 6-bedroom, 4.5-bathroom home with private pool and hot tub is designed to impress, featuring two master suites and a spacious floor plan. Inside, you'll find a beautifully decorated living space, complemented by an open-concept kitchen equipped with brand new stainless-steel appliances, espresso 42” cabinets, granite countertops, and a recently updated, marble accented island and kitchen floor. Additional updates to the home include stunning, luxury vinyl flooring throughout all bedrooms and the entire upstairs loft, making maintenance a breeze. Carpet, which is only found on the stairs, was also just replaced this year. Other improvements include fresh paint, all new furnishings, linens, flatware, light fixtures, smart televisions, security cameras, Nest thermostats, Schlage locks, and led lights ensuring this home is TURNKEY and ready for guests! The first-floor master suite offers a spacious ensuite with a tub and walk-in shower. Upstairs, the second master suite provides additional privacy, while two themed bedrooms add extra charm and appeal. The expansive loft features a new 85-inch smart TV and a fridge, creating the perfect space for movie nights and relaxation. Step outside to a well-appointed patio with new outdoor furniture, pool alarm for safety, privacy screens for additional relaxation, and a newly added remote-controlled pool heater. Windsor at Westside's features a 10,000 square-foot clubhouse offering a video arcade room, zero-entry heated pool and spa, lazy river, poolside cabanas, tiki bar and restaurant, state-of-the-art fitness center, storefront, and more. You'll also enjoy on-site volleyball, basketball & multi-sport courts, a soccer field, and playground. Included in the HOA dues are landscaping maintenance, internet, cable, pest control, daily valet trash service, and manned security. Windsor at Westside offers a carefree lifestyle that makes this property the ultimate investment opportunity. Seller has also established a great relationship with the booking and property managers making this transition a breeze! Don’t miss the chance to own this incredible vacation home. Schedule you're showing today and start living the Florida dream! Make sure to clink on the Virtual Tour Links for a video of the property as well as a Zillow 3-D Tour!

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Lisa Mahjoub (321-217-9965)

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: Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.

Listing is courtesy of: REAL BROKER LLC (855-450-0442)

Listing Agent: Brian Hamaoui (407-760-0975)

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: 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!

Listing is courtesy of: CELEBRITY GLOBAL REALTY LLC (407-530-9264)

Listing Agent: Valdeci Da Silva Pllc (407-280-2990)