Windsor At Westside Homes for Sale in Kissimmee - 77 homes

Remarks: Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: Beautiful fully furnished vacation home located in the highly desirable Windsor at Westside Resort. This property offers an open floor plan, private screened pool and spa, and access to world-class community amenities including clubhouse, resort-style pool, fitness center, playground, and sports courts. Zoned for short-term rental, making it ideal for investors or as a second home. Conveniently located near major highways, shopping, dining, and Orlando’s top attractions. HOA includes cable, internet, lawn care, and resort amenities. Buyer to verify all information, including rental restrictions and HOA requirements.

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

Listing Agent: Paula Maestrini (407-728-2666)

Remarks: This is Windsor at Westside, your new home far from home! This beautiful townhouse features an amazing living room facing the desired pool you crave to see after a day of all the parks fun! INVESTMENT, this is the name of the game, this house has still books to come, which means money in your pocket. Upstairs, you will find 4 bedrooms with decorations ready to go.

Listing is courtesy of: FABIANO DIAS REALTY LLC (689-241-6853)

Listing Agent: Fabiano Dias (689-241-6853)

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: Welcome to your dream vacation and stunning fully furnished 5 bedroom, 4 bathroom pool home located on a corner lot in the highly sought after Windsor at Westside Resort. Perfectly designed for indoor/outdoor entertaining and is excellent income producing short-term rental or a fantastic personal retreat. Designed with lots of space in mind this two story layout and open floor plan is the perfect getaway. The home sleeps up to 14 comfortably and features large living areas with plenty of space for relaxing. The first floor master bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances with a nice island opening to the dining room and living space. Enjoy the gated resort style amenities with the zero entry point pool, water slide, lazy river, and water playground. It boasts a clubhouse, a lake with a pier, fitness center, volleyball courts, sundry shop and video arcade. This is an ideal location as it offers easy access to Disney World attractions and many other theme parks in the area. Welcoming any and all offers.

Listing is courtesy of: BEACHES WITHIN REACHES REALTY (386-864-3154)

Listing Agent: Abby Baker (386-864-3154)

Remarks: Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and revenue-ready, offering a spacious and well-designed floor plan ideal for large families and short-term rental guests. The home features an open-concept main living area, a generous upstairs loft, a 2-car garage, and a private screened-in pool with heated spa for year-round enjoyment. The kitchen offers stainless steel appliances, stone countertops, and a large island with seating, flowing seamlessly into the dining and living spaces. With ample bedrooms—including multiple suites—and thoughtfully designed themed rooms, this residence provides comfort and functionality for owners and guests alike. Located within one of Orlando’s top short-term rental communities, Windsor at Westside offers outstanding resort amenities such as a full-service clubhouse, resort-style pool with lazy river, fitness center, tennis and basketball courts, sand volleyball, arcade, restaurant, and 24-hour gated security. Just minutes from Disney and Central Florida’s world-class attractions, this property is an excellent opportunity for investors or buyers seeking a high-performing vacation retreat.

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Rubens Aranha (407-308-9094)

Remarks: Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functional layout with an open-concept living and dining area, as well as a well-appointed kitchen featuring granite countertops, stainless steel appliances, and a large island for additional workspace. The main floor includes two bedrooms—one of which is an en-suite with direct access to the pool area—along with an additional full bathroom for convenience.Upstairs, you’ll find a true standout feature: your very own cinema room, designed for movie nights and unforgettable moments. A spacious loft offers even more room to relax and enjoy, along with additional bedrooms including a second and a third en-suite and fun themed rooms. The exterior of the home includes a private pool and spa, covered lanai, and patio area with outdoor seating. The pool area provides ample space for relaxation and recreation. Fully furnished and turn key ready. The Windsor at Westside Resort is a Gated Community with a great Clubhouse for vacationers, and features amenities including a lazy river, splash pool, bar, gym, game room and more. This is a great vacation home, very close to other area attractions. Schedule your visit NOW. Stunning Home.

Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)

Listing Agent: Gabriel Silva Andrada (321-666-0301)

Remarks: Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just minutes from Walt Disney World and Central Florida’s top attractions. Designed for comfort, relaxation, and entertaining, this spacious villa is ideal for large families, vacation groups, or short-term rental investment opportunities. The home features an inviting open-concept layout with generous living spaces on both levels, providing plenty of room for everyone to gather and unwind. The upstairs loft offers an additional entertainment area complete with a large TV, comfortable seating, and ample space for movie nights or game days. Step outside to your private west-facing screened lanai where you can enjoy sunny Florida afternoons by the sparkling pool and spa, lounge poolside, or relax under the covered patio while taking in peaceful views. The equipped kitchen includes a breakfast bar, abundant cabinetry, and things needed for meal preparation. Bedroom accommodations include: First-floor primary suite with king bed and private ensuite bath Additional half bath on the main floor Second-floor king suite with ensuite bath Second-floor queen suite with ensuite bath One queen bedroom Two bedrooms with twin beds One bunk room featuring a twin-over-full bunk bed Shared full bathrooms conveniently located between secondary bedrooms All bedrooms include TVs and generous storage space Residents and guests of Windsor at Westside enjoy access to outstanding resort-style amenities, including a lazy river, water slide, resort pool, tiki bar, clubhouse, fitness center, arcade, sports courts, and hot tubs. Conveniently located near Disney World, Universal Studios, SeaWorld, championship golf courses, shopping outlets, dining, and entertainment. Measurements are approximate and should be independently verified. Some furniture has been updated

Listing is courtesy of: CORNERSTONE INTERNATIONAL PROPERTY GROUP LLC (407-334-7497)

Listing Agent: Helen Lei (407-371-1225)

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: 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: 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: 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: 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: 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: 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: 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: 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)