Windsor At Westside Single Family Homes For Sale in Kissimmee - 40 homes

Remarks: Under contract-accepting backup offers. Welcome to the ultimate Florida resort lifestyle! Positioned in the premier gated vacation community of Windsor at Westside Resort- this 8-bedroom, 6-bath lakeview home offers thoughtfully designed living space. This fully furnished, rental-ready home presents an outstanding opportunity for both savvy investors and families seeking a high-performing vacation property just minutes from Walt Disney World, dining, and premier shopping.   Inside, the expansive open-concept design creates a seamless flow between the kitchen, dining, and main living areas — ideal for entertaining large groups. The oversized upstairs loft provides an additional gathering space perfect for movie nights, gaming, or relaxing after long days at the parks. Constructed in 2017, this residence embodies the Florida resort lifestyle. Step outside to your private heated pool and spa, perfectly positioned to capture sweeping lake views — one of the most sought-after settings within the community. Whether hosting guests or enjoying a quiet sunset, the outdoor space delivers both privacy and a true vacation atmosphere. Ownership includes access to Windsor at Westside’s impressive resort amenities, including a grand clubhouse, resort-style pool with lazy river and waterslide, tiki bar, fitness center, arcade, and more — enhancing both guest experience and rental appeal.Whether expanding your investment portfolio or securing a luxury vacation home, this property offers both lifestyle and income potential in one of Central Florida’s top-performing short-term rental communities. Sold fully furnished and rental-ready with future bookings conveying if you keep the rental company. Call for your showing today!

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Katie Bray (407-779-6677)

Remarks: Best priced fully furnished turnkey investment in Windsor at Westside Resort, one of the most sought after short term rental communities near Disney. This spacious 8 bedroom, 6 bathroom vacation home offers strong rental income potential and immediate operation. Features include open concept living area, two owner’s suites on first and second floors, dedicated game room, entertainment loft and private screened pool with spa, ideal for guest satisfaction and high occupancy. Resort amenities include clubhouse, lazy river, heated pool, fitness center, sports courts, restaurant and bar. Prime location near Disney parks, golf, shopping and dining.

Listing is courtesy of: BEKK HOMES LLC (407-342-8012)

Listing Agent: Carlos Selmo (407-342-8012)

Remarks: Don’t miss this amazing opportunity to buy this beautifully 7 bedroom 5 1/2 bathroom FULL FURNISHED POOL HOME in the most desirable resort, fully screened HEATED POOL & SPA, makes it perfect for indoor/outdoor entertaining. Windsor at Westside is gated resort community , one of the favorite desired resort style communities around Orlando and Kissimmee. This community has it all, clubhouse, lake & pier, zero-entry resortstyle pool complete with a waterslide, lazy river, and Kid's water playground, fitness center, volleyball courts, a sundry shop, and a video arcade. This is an ideal location it offers easy access to Disney World® attractions and many others theme parks in the areas. This home sleep up to 14 comfortably and features an open concept floor plan with a large living area. With plenty space spread out for entertaining and relax throughout entire house. The first floor Master Bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances. Heated pool and spa to enjoy it at any time of the day. Don't miss this great opportunity

Listing is courtesy of: DOUBLE PINES REALTY, LLC (954-756-1835)

Listing Agent: Richard Lee (954-756-1835)

Remarks: Location, location!!!!This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft at Windsor at Westside a Gated Community. Enjoy an open-concept kitchen with stainless steel appliances and large island, a first-floor primary suite, and a spacious upstairs loft with 6 Bedrooms and 4 bathrooms Step outside to your private pool with brick pavers, covered patio, and screened lanai This beautiful 7-Bedroom 5.5-Bathroom comes fully furnished to make is turnkey for vacation investment property or simply as second home. Windsor at Westside a Gated Community. Located about 10-15 minutes from Disney World. Owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities Come and see it for yourself!

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Khadija Webber (407-592-2166)

Remarks: Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. There is a master bedroom on the first floor and upstairs you’ll find another spacious master bedroom and additional bedrooms for privacy and comfort. Residents can enjoy world-class resort amenities, including an 8,000 sq. ft. clubhouse, heated pool, lazy river, spa, volleyball and basketball courts, and on-site restaurant and bar. The home is just minutes from Disney Parks and other Orlando attractions.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Eileen Li (407-765-2589)

Remarks: Short Sale. Make your dream a reality. Enjoy this Luxury, conveniently located, Central Florida lifestyle Home. Property can be, and currently is, used as a short-term vacation rental.

Listing is courtesy of: VMY REALTY INC (407-412-4164)

Listing Agent: Eugene Vilkovskiy (407-412-4164)

Remarks: CORNER LOT! Why wait for a new home to be built, when you can buy this fully furnished, turn-key VACATION HOME in the sought-after gated community of Windsor at Westside! Excellent Income Producing SHORT-TERM RENTAL Home. ONLY 10 MINS from Disney Gate! Fully furnished and professionally decorated two-story home with a private pool. This 5 bed/4 bath Winstone model features a spacious great room and kitchen with granite Island, allowing for ample seating and space to entertain. The sliding doors lead to your own private oasis with a covered, screened lanai with pool. One Guest Bedroom/Bath downstairs. Enjoy the myriad benefits of a resort-style community and have a blast! You'll have access to a fantastic clubhouse, a heated pool and spa, wireless internet on the pool deck, a lazy river, a state-of-the-art fitness center, a playground, a game room, and much more - all designed for families to relish for hours! The HOA takes care of landscaping maintenance, provides internet and cable services, and offers daily valet garbage disposal for your convenience. Located just a short distance from Highway 192, this charming short-term rental community provides easy access to major highways like I-4 and US-27. Plus, it's just a stone's throw away from theme parks, attractions, shopping malls, outlets, local restaurants, and grocery stores. Don't miss out on this fantastic opportunity to own a piece of the vacation rental market in the heart of Kissimmee!

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Spacious 5-bedroom, 5.5-bathroom pool home located just 8 miles from Walt Disney World. This open-concept property features a modern kitchen equipped with stainless steel appliances, granite countertops, and a large island overlooking the dining and living areas. The floor plan includes a convenient primary suite on the main level. Upstairs, you will find additional well-appointed en-suite bedrooms, including themed rooms and a master suite. The exterior offers a private, fully screened-in patio with swimming pool. Significant features include high-speed Wi-Fi capability, a dedicated laundry room with full-sized washer and dryer, and keyless entry for seamless access. Situated in a luxury community with easy access to I-4, 192, and local dining, shopping, and grocery stores including Publix and Walmart. Excellent opportunity for a second home, or short-term rental investment. Sold fully furnished and move-in ready.

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

Listing Agent: Alessandra Dale (407-729-6936)

Remarks: 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.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Shawn Huang (512-804-9960)

Remarks: FULLY FURNISHED | TURNKEY INVESTMENT | RESORT-STYLE COMMUNITY Welcome to this beautiful two-story home located in the highly desirable resort-style community of Windsor at Westside. Featuring 5 spacious bedrooms and 4 full bathrooms, this fully furnished property is move-in ready and perfectly suited as a primary residence, vacation home, or income-producing short-term rental. The home offers a bright and open layout, with a modern kitchen equipped with stainless steel appliances and a breakfast bar, seamlessly connecting to the formal dining area and multiple living spaces—ideal for entertaining family and guests. Large sliding glass doors lead to a private screened-in pool area, providing a relaxing outdoor retreat with added comfort and privacy. Residents and guests enjoy access to outstanding resort-style amenities, including a spectacular pool with lazy river and waterslide, a fully equipped clubhouse with lounge areas, a tiki bar by the pool, fitness center, game room and arcade, as well as sports courts for tennis, basketball, and volleyball, plus a soccer field and playground. The community also features a scenic lake with a pier, a convenience store, and 24-hour gated security. Ideally located just minutes from Walt Disney World Resort, Universal Orlando Resort, and Disney Springs, the property is surrounded by a wide variety of shopping, dining, and entertainment options. This is a fantastic opportunity to own a fully equipped home in one of the most sought-after vacation communities in the area. Schedule your private showing today!

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

Listing Agent: Fernanda Pizzamiglio (508-364-4606)

Remarks: Spacious 8-bedroom, 6-bathroom vacation home just minutes from Disney and major attractions. Ideal for short-term rental, investment, or personal use. This well-maintained, fully furnished corner lot property features an open floor plan, fully equipped kitchen, large living and dining areas, and generously sized bedrooms with excellent decoration. Enjoy a private pool and spa, along with outdoor space perfect for relaxation and entertainment. Located in the desirable Windsor at Westside community, offering resort-style amenities including clubhouse, fitness center, and community pool. Zoned for short-term rentals with strong income potential. Conveniently located near shopping, dining, and major highways. Schedule your private showing today.

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

Listing Agent: Antonio Nouer (407-837-6981)

Remarks: Turnkey 8-bedroom, 6-bath fully furnished pool home located in the highly desirable Windsor at Westside Resort. This well-maintained property offers over 4,000 sq ft of living space with a functional and spacious layout ideal for short-term rental use. The home features an open-concept main floor with a large kitchen, breakfast bar, formal dining area, and expansive living room. A first-floor bedroom and full bath provide convenience, along with a rear primary suite offering direct pool access and functioning as a pool bath. The covered lanai overlooks a private setting with no rear neighbors and a pond to the side. Upstairs includes a large loft/game area with projector and gaming stations. The second floor consists of 6 bedrooms and 4 bathrooms, including multiple themed rooms, a Jack-and-Jill bathroom with dual vanities, and additional ensuite configurations. In total, the property offers 3 ensuite bedrooms. The garage has been converted into a game room, enhancing rental appeal. Located just minutes from major theme parks, shopping, and dining. Windsor at Westside offers resort-style amenities including a 10,000 sq ft clubhouse, pool, lazy river, restaurant/bar, fitness center, sports courts, and more. HOA includes gated access, lawn care, daily valet trash service, cable, internet, and full access to amenities. Property has strong rental potential and is being sold fully furnished and ready for immediate use or income production.

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

Listing Agent: Antonio Nouer (407-837-6981)

Remarks: Stunning 8-Bedroom Vacation Home in Windsor at Westside Resort - Perfect for Large Families and Groups! Located just a short drive from all of Orlando’s world-famous theme parks—including Disney, Universal Studios, SeaWorld, and Legoland—this fully furnished 8-bedroom, 6-bathroom vacation home offers the perfect escape for large families or groups looking for luxury and convenience. This spacious home is designed to accommodate many guests with plenty of beds, plenty of room for everyone to relax and unwind. The home features a beautifully appointed interior with a modern design, a fully equipped kitchen, and a large living area. With a range of sleeping arrangements, everyone can have their own space to recharge after a day of adventure. Outside, the fun continues! The home boasts a stunning private pool and spa, ideal for relaxing or entertaining in the Florida sunshine. The covered lanai is the perfect spot for outdoor dining, while the sparkling pool provides a refreshing retreat. Whether you're soaking in the hot tub or lounging by the pool, the outdoor area is designed for ultimate comfort and relaxation. As a resident of Windsor at Westside Resort, you'll have access to the community’s incredible amenities. The 10,000 sq. ft. clubhouse is a hub of activity, offering a state-of-the-art kid’s activity center, a free game room, and a zero-entry resort-style pool complete with a waterslide, lazy river, and kid's water playground—ideal for keeping the little ones entertained for hours. For those looking to relax and unwind, the Tu Casa Bar & Lounge offers poolside dining with a full-service bar featuring your favorite drinks, from frozen cocktails to wine and beer. The resort’s amenities ensure there’s something for everyone, whether you're looking to stay active, relax, or socialize. This vacation home is a turnkey investment, being sold fully furnished and move-in ready—all you need is your clothing! Whether you're looking for a vacation home to enjoy with family and friends or a high-performing vacation rental investment, this home is the ultimate choice. With its prime location and exceptional amenities, Windsor at Westside Resort is a premier destination and a must-see for any investor or vacationer seeking a home away from home. Don't miss out on this incredible opportunity—schedule your showing today! ALL INFORMATION IS INTENDED TO BE ACCURATE IT IS THE BUYER AND BUYERS AGENT'S RESPONSIBILITY TO VERIFY ALL INFORMATION.

Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)

Listing Agent: Eugene Petriella (321-299-8766)

Remarks: Welcome to the best of Florida resort life! This 8 bedroom 6 bathroom house has all you can ask for and more! Fully furnished, this home is ready for an immediate occupancy, whether you're seeking an ideal AirBNB/Short-Term Rental or a personal vacation/ winter time residence. Airy and bright, the open-concept floor plan connects the living, dining, and kitchen areas, providing the perfect layout. The sliding doors in the family room area lead you directly to the pool patio area, creating a seamless indoor-outdoor living experience. An oversized heated pool with a jacuzzi and large patio space allows for cookouts, pool parties and watching the sunsets. The first-floor primary suite with a private bathroom and direct access to the lanai provides you a great personal space. An additional first-floor bedroom offers flexibility. Upstairs, there are six more spacious bedrooms and a loft space suitable for movie nights or a play area.  Located in the luxurious community of Windsor at Westside, you'll have access to a variety of resort-style amenities, including a grand clubhouse, fitness center, lazy river, and more. Theme parks , beaches and shopping are just a short drive away, you'll have endless entertainment options at your fingertips. The HOA covers cable, internet, lawn care, trash, 24 hr security guard for a smooth and worry free life style. Make your appointment today! Equal Opportunity Housing.

Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA:FLORIDA REALTY INVESTMENTS IV (407-207-2220)

Listing Agent: Magdalena Danos, Pll (407-760-9286)

Remarks: This gorgeous professionally decorated 8 Bedrooms/6 Bath single family home with private pool is located in is located in Windsor at Westside Resort one of the most famous resort communities in the Orlando/Kissimmee with easy access to the theme parks, dining and shopping. The home has fully furnished kitchen features upgrades such as stainless steel appliances, granite counter tops, and custom cabinetry. All furniture, decoration and appliances are included. The home can be used for vacation rental, winter home or long term residence. For vacation rental, this home has very beautiful booking history and financial income in the past a few years. Windsor at Westside Resort Amenities and Services include: - 10,000 sq.ft. Clubhouse with State of the Art Fitness Center - Resort style Pool with splash area - Lazy River. The club contains tu Casa Bar and Lounge - Market and Deli - Concierge - Sand Volley Court - Multi purpose court – Small soccer field - Playground.

Listing is courtesy of: ORLANDO REGIONAL PROPERTY MANAGEMENT (407-800-4545)

Listing Agent: Jason Ding (407-808-5589)

Remarks: Under contract-accepting backup offers. Don’t miss this amazing opportunity to buy this beautifully LAKEFRONT 8 bedroom 6 bathroom FULL FURNISHED POOL HOME in the most desirable resort, fully screened HEATED POOL & SPA, makes it perfect for indoor/outdoor entertaining. Windsor at Westside is gated resort community , one of the favorite desired resort style communities around Orlando and Kissimmee. This community has it all, clubhouse, lake & pier, zero-entry resortstyle pool complete with a waterslide, lazy river, and Kid's water playground, fitness center, volleyball courts, a sundry shop, and a video arcade. This is an ideal location it offers easy access to Disney World® attractions and many others theme parks in the areas. This home sleep up to 14 comfortably and features an open concept floor plan with a large living area. With plenty space spread out for entertaining and relax throughout entire house. The first floor Master Bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances. Heated pool and spa to enjoy it at any time of the day. Don't miss this great opportunity

Listing is courtesy of: DOUBLE PINES REALTY, LLC (954-756-1835)

Listing Agent: Richard Lee (954-756-1835)

Remarks: Beautiful 9-bedroom,6-bathroom water-front pool home in the highly sought-after Windsor at Westside resort community. Situated on a premium lot with stunning water view, this fully furnished property is perfect as a luxury vacation retreat or a high-performing short-term rental investment. The spacious open-concept layout offers expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites, one on each floor. Enjoy the Florida lifestyle with your private screened-in pool and hot tub overlooking the pond. This home has been thoughtfully upgraded to enhance the guest experience, including newly installed: *Luxury vinyl plank flooring throughout (no carpet)*, all bedrooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests! Resort-style amenities include a 10,000 sq. ft. clubhouse, resort pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. HOA includes cable, internet, lawn care, and valet trash service. Conveniently located just minutes from Disney, shopping, dining, and major highways. This turn-key property is move-in or rental ready—an opportunity you don’t want to miss!

Listing is courtesy of: YOUR DREAM HOUSE REALTY (440-477-7276)

Listing Agent: Selina Li (440-477-7276)

Remarks: A fantastic choice to be your Vacation Rental Property in the Windsor at Westside, located in Kissimmee Florida! 5 Bedrooms - 4 Bathrooms and your own Private Pool. Welcoming you inside is an amazing open floor concept that combines your living, dining and kitchen areas into one space. Also downstairs you will have an ensuite for your convenience. Upstairs you will find the loft, master bedroom ensuite with a large closet, one more ensuite and two more themed bedrooms and one bathroom. Also the laundry room is conveniently located upstairs. Granite countertops, light color cabinets, stainless steel kitchen appliances, themed bedrooms and much more. This home features a heated, private pool, a covered Lanai and pool deck area. The Windsor at Westside is a resort community and features a large Community pool, Lazy river, splash pool, gym, restaurant and much more. This is a great vacation home, very close to other area attractions.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Zhiming Xu (407-984-0087)

Remarks: 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.

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

Listing Agent: Rosania Taylor (407-580-6137)

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)