Windsor At Westside Homes for Sale in Kissimmee - 68 homes

Remarks: Under contract-accepting backup offers. A phenomenal vacation rental investment opportunity with great income potential! Discover this prime lot in the vibrant Windsor at Westside, perfectly nestled across from the clubhouse with stunning lake view. This impeccably maintained vacation home is fully furnished with upgraded furniture, including three lavish primary suites and fun themed bedrooms, perfect for large vacation groups. The home boasts newly upgraded luxury vinyl flooring in all bedrooms (NO carpet), sleek granite counter tops in the kitchen and bathrooms, premium stainless steel appliances, and stylish tiles. Dive into relaxation with a private screened pool, paver deck, and covered lanai, backing to a natural pond and conservation area. Energy-smart features like two high-efficiency AC units, LOW-E dual-pane windows, and modern appliances keep it eco-friendly and cost-effective. This guard-gated community dazzles with a 10,000-square-foot resort-style clubhouse with arcade game room, a sparkling heated pool and spa, a meandering lazy river, a thrilling mini water park, a cutting-edge fitness center, a lively tiki bar, and all sorts of sports fields. Landscaping, internet, cable, and daily valet garbage collection are included in the HOA fee. Just minutes from Walt Disney World, premier golf courses, vibrant shopping, the airport, and major attractions, this is your chance to own a slice of paradise for investment or 2nd home! Schedule your exclusive private tour today!

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

Listing Agent: Sherry Wang (484-744-4586)

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: 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: Your Dream Vacation Home—Just Minutes from Disney! Imagine owning a fully furnished 5-bedroom home in one of Kissimmee’s most sought-after resort communities—Windsor at Westside—just minutes from the magic of Disney and the excitement of US-192. Surrounded by restaurants, shops, theme parks, and unforgettable experiences, this could all be yours. The best of both worlds: Enjoy your vacation time with family whenever you want—no more worrying about reservations, availability, or high seasonal rates. Your home will always be ready to create unforgettable memories. And when you're not using it, it becomes a source of income. High returns on Airbnb: Windsor at Westside is a top choice for travelers who value comfort, security, and resort-style amenities. Properties like this offer excellent short-term rental returns, with consistent year-round occupancy thanks to its unbeatable location and full-service infrastructure. Property & community highlights: • 5 spacious bedrooms – perfect for large families or groups • Gated community with 24-hour security • Resort-style clubhouse with pool, lazy river, fitness center, bar, sports courts & more • Fully furnished and move-in ready • Professional vacation rental management available Invest in more than just a home—invest in lifestyle. This property isn’t just real estate. It’s a smart investment, a lifetime of memories, and a source of consistent income. Let’s talk! This might be the opportunity you and your family have been waiting for.

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

Listing Agent: Luciano Real Schroeder (321-304-1550)

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: 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: Welcome to 8900 Sydney Ave in Windsor at Westside, a beautifully positioned end unit 5 bedroom, 4.5 bath townhome offering 2,263 square feet in one of the most sought after vacation home communities near Disney. Originally purchased as the builder’s model, this home stands out from the typical inventory with a brighter, more elevated feel, a desirable end unit location, and interior finishes and furnishings that show far better than many competing townhomes in the community. The white kitchen, stylish window treatments, upgraded bedroom theming, and strong overall presentation give this property the kind of visual appeal buyers and guests notice right away. Whether you are looking for a personal getaway, a second home, or an income producing vacation property, this townhome offers the combination of location, layout, and resort appeal that today’s buyers want. Windsor at Westside is a gated resort community with a large clubhouse, resort style pool, lazy river, waterslide, fitness center, tiki bar, arcade, and convenient access to the Disney parks, dining, and shopping. With its private pool, popular 5 bedroom layout, and premium end unit positioning, 8900 Sydney Ave is a standout opportunity in a community known for strong guest appeal and resort style living.

Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)

Listing Agent: Andre Kressler (407-864-2184)

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: 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 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: Located in the highly sought-after resort-style community of Windsor at Westside, this beautifully maintained and fully furnished 5-bedroom, 4-bathroom townhome offers comfort, functionality, and excellent flexibility for both personal use and investment. The home features an open-concept floor plan with a spacious living and dining area, ideal for entertaining. The kitchen is equipped with modern appliances and ample cabinetry. One bedroom is conveniently located on the first floor, while the remaining bedrooms are upstairs, providing privacy and space for family or guests. Step outside to your private screened-in splash pool, perfect for relaxing after a day in the Orlando area. The property is tastefully decorated and move-in ready, making it suitable as a primary residence, second home, or short-term rental (buyer to verify rental restrictions). Windsor at Westside offers resort-style amenities, including a clubhouse, fitness center, community pool with lazy river, water playground, sports courts, playground, restaurant, and 24-hour gated security. Conveniently located near major highways, shopping, dining, and world-renowned attractions.

Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)

Listing Agent: Bin Cao (407-865-0588)

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: ***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: 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: TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river Kids’ splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

Listing is courtesy of: GOLDEN SUN REALTY INC (407-479-8898)

Listing Agent: Lucia Wu (407-765-2618)

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)