Windsor At Westside Homes for Sale in Kissimmee - 48 homes

Remarks: Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families, multi-generational living, or short-term rental investment, this beautifully maintained home combines comfort, style, and resort-style amenities in a gated community just minutes from Disney and major attractions. The main floor features two generously sized bedrooms, including a primary suite with direct access to the private pool. Upstairs, you'll find five additional themed bedrooms—Harry Potter, Frozen, and Star Wars—plus a large loft that has been transformed into a movie room, perfect for family entertainment. Step outside to enjoy your own screened-in private pool and spa, complete with a child safety fence, offering the ideal setting for relaxation and fun. Residents and guests enjoy full access to world-class amenities, including a lazy river, splash pad, resort-style pools, tennis courts, fitness center, arcade, on-site restaurant, and a clubhouse—all secured with 24-hour gated entry. Conveniently located off US Hwy 192 and Toll Road 429, Windsor at Westside offers quick access to shopping, dining, and the “secret” west entrance to Disney via Western Way. Whether you're searching for a vacation retreat, or a high-performing investment property, this home is move-in ready and offers exceptional value in one of Central Florida’s premier resort communities. Don’t miss your opportunity to own a piece of the magic!

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

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

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: TURN-KEY INVESTMENT OPPORTUNITY! 8-BED LUXURY POOL HOME JUST MINUTES TO DISNEY! Welcome to your ultimate dream vacation home or high-performing short-term rental (Airbnb/VRBO) located in the highly sought-after Windsor community! Perfectly designed to accommodate large groups and multiple families to maximize your rental income. HOME FEATURES: Step inside to a modern, open-concept floor plan with high ceilings that seamlessly connects the fully-equipped chef's kitchen, dining area, and spacious family room. Head outside to your private, screened-in lanai where you will find a sparkling pool and a relaxing SPA—the absolute perfect backyard oasis to unwind after a long day at the theme parks. RESORT-STYLE AMENITIES: Located in a premier, secure gated community, you and your guests will have access to world-class resort amenities. Enjoy the massive luxury clubhouse, resort-style pool, lazy river, fitness center, playground, and more! It truly offers a 5-star resort lifestyle. UNBEATABLE LOCATION: Location is EVERYTHING! Situated in the prime 34747 zip code, you are just a short drive to Walt Disney World, world-class golf courses, and fantastic dining options on Hwy 192. Easy access to major highways and Orlando International Airport (MCO). Whether you are looking to expand your lucrative investment portfolio or seeking the perfect family getaway home, this property checks all the boxes. Properties of this size and in this prime location do not last long—act fast!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Mingke Li (352-973-2303)

Remarks: Short Sale. LOWEST PRICED 7 BEDROOM! Turnkey 7-Bedroom Vacation Home in Windsor at Westside – Active Short-Term Rental! Welcome to 1861 Nice Court, a beautifully furnished and actively producing 7-bedroom, 5-bathroom short-term rental located in the sought-after Windsor at Westside Resort. With 3,281 sq ft of living space, this stunning home is designed to impress guests and maximize occupancy—making it the perfect investment property or vacation retreat near the magic of Disney. Step inside to a bright, open-concept layout featuring a spacious living area, modern kitchen with stainless steel appliances, and generous dining space ideal for large families and groups. This home offers multiple ensuite bedrooms and themed guest rooms that delight visitors of all ages and keep bookings strong year-round. The private screened-in pool and patio provide the perfect place to unwind after a day at the parks, offering your guests the relaxation and resort-style experience they’re searching for. Located in the gated, 24-hour resort community of Windsor at Westside, 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—making ownership truly hassle-free. Just minutes from Walt Disney World, Margaritaville, Sunset Walk, shopping, dining, and major attractions, this property offers strong rental history, excellent future booking potential, and a turnkey setup ready for its next owner. Whether you're looking to expand your STR portfolio or secure a high-performing vacation home, 1861 Nice Court is an exceptional opportunity in one of Central Florida’s premier resort communities.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Michael Steward (386-243-9585)

Remarks: 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: 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: Under contract-accepting backup offers. Experience resort living at its finest in this exceptional 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. Situated on a premium conservation lot, this fully furnished residence is ideal as a luxury vacation retreat or a short-term rental investment. The spacious open-concept layout features expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites—one conveniently located on each floor. Step outside to enjoy the Florida lifestyle with your private screened-in pool and spa, offering serene tree-lined conservation views. Inside, guests will love the two themed bedrooms inspired by Star Wars and Disney Princesses, while the remaining rooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests. Residents and guests have access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. The HOA covers cable, internet, lawn care, and valet trash service for ultimate convenience. Perfectly located just minutes from Disney, shopping, dining, and major highways, this turn-key property is move-in or rental ready—a rare opportunity you don’t want to miss!

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

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

Remarks: Under contract-accepting backup offers. Welcome to this beautiful vacation home located in the highly sought-after Windsor at Westside community. This stunning property has an open floor plan and features 8 spacious bedrooms and 6 bathrooms, offering ample space for families or groups. The home is perfectly situated with easy access to Disney World® theme parks via the nearby toll road 429, making it an ideal choice for those visiting the magical parks. Additionally, there are a variety of dining and shopping options just a short drive away. The Windsor at Westside community itself is a resort-style retreat, with an array of amenities that will enhance your vacation experience. The incredible 10,000 sq. ft. clubhouse is the perfect spot to relax and unwind, while the community’s lake and pier have serene views and outdoor activities. For ultimate relaxation and fun, enjoy the zero-entry resort-style pool, complete with a thrilling waterslide, lazy river, and a water playground. This home is not just a place to stay; it’s a destination in itself, offering both luxury and convenience. Don’t miss the opportunity to make this dream vacation home yours!

Listing is courtesy of: INTOP REALTY LLC (407-233-5453)

Listing Agent: Hanna Zhang (407-601-8668)

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: Under contract-accepting backup offers. Don’t miss this amazing opportunity to buy this beautifully 5 bedroom 4 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: YORK MILLS REALTY LLC (407-620-8528)

Listing Agent: Jin Yao (407-619-9883)

Remarks: Under contract-accepting backup offers. PRICE REDUCED TO SELL – UNBEATABLE OPPORTUNITY! Experience the ultimate in VACATION LIVING OR INVESTMENT POTENTIAL at WINDSOR AT WESTSIDE RESORT, one of Central Florida’s MOST SOUGHT-AFTER DESTINATIONS! This STUNNING 6-BEDROOM, 4.5-BATHROOM TURNKEY HOME is FULLY FURNISHED and ready for immediate enjoyment, featuring TWO MASTER SUITES, A SPACIOUS LOFT, AND A GAME ROOM WITH POOL TABLE & AIR HOCKEY. Recent updates include a NEW AIR HANDLER (2024), BRAND NEW SOFA, AND PATIO FURNITURE, adding comfort and style throughout. The HEATED PRIVATE POOL AND SPA make outdoor entertaining unforgettable, while themed bedrooms like AVENGERS AND MICKEY MOUSE create a magical experience for families and guests. A KING-SIZE MASTER ON THE FIRST FLOOR offers convenience, and the fully equipped kitchen with a dining area for eight is perfect for gathering and entertaining. As part of the resort, enjoy WORLD-CLASS AMENITIES including a ZERO-ENTRY RESORT POOL, LAZY RIVER, INTERACTIVE SPLASH PARK WITH WATER SLIDE, FIRE PIT, TIKI BAR & RESTAURANT, FITNESS CENTER, ARCADE, PLAYGROUND, AND SPORTS COURTS for basketball, tennis, and sand volleyball. Located just 6 MILES FROM WALT DISNEY WORLD® AND 20 MILES FROM UNIVERSAL STUDIOS, this home combines PRIME LOCATION, LUXURY, AND HIGH RENTAL INCOME POTENTIAL, making it a rare opportunity for buyers looking for THE PERFECT VACATION HOME OR INVESTMENT PROPERTY. Don’t miss out – CONTACT US TODAY FOR A PRIVATE SHOWING!

Listing is courtesy of: ORLANDO PRIME HOMES PLLC (978-514-5928)

Listing Agent: Andreia Miguel (978-514-5928)

Remarks: Beautiful vacation home, fully furnished, ready to start your rental business. Kissimmee's most desirable resort communities. Near Disney parks, major roads, restaurants and shops. Clubhouse with resort-style pool, lazy river, gym, bar, sports courts & more. Property is actively used as a short-term rental. Future bookings may convey with the sale. Buyer must honor all existing reservations currently in place after closing. All bookings and rental agreements will be transferred to the new owner.

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

Listing Agent: Andreza Machado (407-988-6639)

Remarks: Welcome to 2112 Rome Dr in Windsor at Westside, a 6 bedroom, 4.5 bathroom private pool home located just 6 miles from Walt Disney World and only a short walk to the community clubhouse. Being this close to the resort amenities adds convenience for guests and owners alike, making it even more attractive for short term rental performance. This fully furnished property is designed for both personal enjoyment and strong rental returns, comfortably accommodating up to 12 guests with a layout that offers space, privacy, and multiple gathering areas. The open concept main level features a fully equipped kitchen with granite countertops, stainless steel appliances, a breakfast bar, and a spacious dining area. Sliding glass doors lead to your private east facing pool and spa, allowing for beautiful morning sun and seamless indoor outdoor living. The covered lanai is a standout feature, complete with outdoor dining, sun loungers, and a built in outdoor kitchen that includes a BBQ grill and sink, creating the perfect setting for entertaining and relaxing between park days. The first floor includes a king suite with an attached bathroom, ideal for guests who prefer main level access. Upstairs, you will find a second king suite with a private bath, 2 additional queen bedrooms, and 2 twin bedrooms including a Mickey themed room that adds strong appeal for vacation guests. A dedicated game room with ping pong and foosball enhances the entertainment experience and further increases rental desirability. Driveway parking for up to 4 vehicles adds convenience, and the location inside Windsor at Westside provides access to one of the area’s most amenity rich resort communities. Owners and guests enjoy a resort style zero entry pool, lazy river, interactive splash park with water slide, tiki bar and restaurant, fitness center, arcade, sand volleyball, basketball and tennis courts, playground, and fire pit areas. Conveniently located near shopping, dining, and major attractions including Universal Studios Florida and SeaWorld Orlando, this property offers the ideal combination of location, layout, and lifestyle. Whether you are seeking a vacation retreat or a high performing short term rental investment, 2112 Rome Dr presents a compelling opportunity inside one of Kissimmee’s most sought after resort communities.

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

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

Remarks: 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: Resort-Style Investment Property Near Disney This fully furnished 5-bedroom, 4.5-bathroom property is an excellent short-term rental investment opportunity, located just 25 minutes from Disney World. Designed to comfortably accommodate up to 10 guests, the home features a king master suite, two queen suites (including one on the ground floor), and two themed bedrooms — one with a castle theme featuring knights and dragons, and another inspired by the magical world of Encanto. The home includes open living spaces, a fully equipped kitchen with stainless steel appliances and granite countertops, as well as in-home laundry. Guests will enjoy the private pool and a dedicated game room with air hockey and foosball for entertainment. Residents and guests also have access to exceptional resort amenities, including a clubhouse, pool and lazy river, jacuzzi, fitness center, and basketball and volleyball courts. Conveniently located near shopping, dining, and everyday essentials, this property is a great opportunity for a short-term rental investment.

Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)

Listing Agent: Stephen Hachey (813-642-6030)

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: 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 your dream Oasis at Windsor at Westside! This professionally decorated, fully furnished 6-bedroom, 4 1/2-bathroom retreat is located just steps from the resort’s clubhouse, placing world-class amenities right at your doorstep. Designed with luxury and comfort in mind, this home boasts two spacious primary suites—one on the main floor and another upstairs—offering ultimate flexibility for guests. You'll love the the open floor plan, upscale furniture, no carpet throughout the home (ideal for easy maintenance and higher booking potential), and a converted garage arcade room for endless family fun. Upstairs, the versatile loft space serves as a movie theater, game room, or a relaxing lounge area. Step outside to your private heated pool and spa, perfect for soaking up the Florida sun year-round. Windsor at Westside offers resort-style living with a 10,000 sq. ft. clubhouse, state-of-the-art fitness center, lazy river, splash area, Tiki Bar, Tu Casa Bar & Lounge, market and deli, arcade, sand volleyball, multipurpose courts, and a playground—everything your guests need for a memorable stay. Location is unbeatable—just minutes from Walt Disney World, 25 minutes away from Epic Universe theme park, and close to shopping, dining, grocery stores, and entertainment. Whether you’re looking for a top-performing short-term rental or a private vacation escape, this home has it all! Call us now for a private tour.

Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)

Listing Agent: Camila Riva (407-765-3656)