Windsor At Westside Ph 1 Homes for Sale in Kissimmee - 14 homes

Remarks: Fully Furnished Turnkey Vacation Rental! This 5-bedroom, 4.5-bathroom vacation retreat is built for both relaxation and revenue—comfortably accommodating up to 16 guests and ready for immediate enjoyment or income potential! Ideally located just minutes from major theme parks, this property blends modern luxury with fun-filled amenities. On the main floor, you'll find a private king bedroom and full bathroom—perfect for multi-generational stays. The open-concept heart of the home features a stylish kitchen with granite countertops, stainless steel appliances, and a large island, flowing seamlessly into a bright, airy living room with views of the private heated pool. Step outside to a covered lanai and convenient outdoor half bath—ideal for entertaining. Upstairs, a spacious loft adds bonus living space, alongside four additional bedrooms and three full bathrooms. Two themed rooms—Frozen and Star Wars—feature custom murals and LED lighting, offering a magical experience for younger guests. Recent upgrades include fresh interior paint, a Nest thermostat, digital door locks, new lighting, plush carpeting, and high-end washer/dryer units. The detached garage provides flexible space for parking, storage, or a future game room or theater conversion. The HOA covers cable, internet, trash, lawn care, and access to resort-style amenities including a clubhouse, arcade,

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

Listing Agent: Scott Cohara (407-398-9554)

Remarks: 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: 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. 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: 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: 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: 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: 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)

Remarks: ***TENANT OCCUPIED*** Discover an exceptional opportunity with this beautiful 4-bedroom, 3.5-bathroom townhome, ideally located just minutes from the Walt Disney World Resort. This 2,102 sq. ft. property, built in 2016, is situated in the desirable, gated Windsor at Westside Community. The townhome includes a private pool and a one-car attached garage. The open floorplan features a kitchen/family room combo, high ceilings, tile and carpet flooring, walk-in closets, and an in-wall pest system. The HOA fees cover internet, cable, ground maintenance, pest control, trash disposal, and exterior maintenance, making it a low-maintenance option for owners. This property is an excellent option for short-term rental/vacation home use, with a minimum lease of just 1-7 days allowed, offering great potential for rental income. It can also be rented as a residencial long term. Residents and guests have access to Windsor at Westside's extensive, 8,000 sq. ft. clubhouse and amenity center, which includes: A resort-style heated pool and spa, Lazy river, Fitness center, Poolside cabanas, On-site store, restaurant, and bar, Sports courts (volleyball, tennis, basketball), Playground and game room. This home offers a perfect blend of a private retreat and resort-style living, with everything needed for a primary residence, second home, or profitable investment property.

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

Listing Agent: Danielle Marcondes Franca Viana Silva (407-668-0245)

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

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

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

Remarks: Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restaurant & Club House, Pond and Pier and so much more! Those are just the amenities; lets talk about this 5 Bedroom & 5 Bath with a private garage in paradise. You have enough space for the family and some including a theatre area for all to enjoy. Subtle taste of Disney throughout the home and a very nice size kitchen for all to gather. Don't want to stop the fun from the community pool? Well bring it home since you'll have your very own private pool and patio area to enjoy. Its spacious, its clean and comes completely furnished as you see it all you need is the key to make it yours. You can enjoy this home as little or as much as you'd like as short term rental is allowed as well as long term if you'd choose. Want the best of both worlds? Why not leave your vehicle stored in the garage and some personal items in your very own, owners closet's throughout the house. Having too many options is never a bad thing when you either way you are making the right choice. Contact today for your next appointment.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Sergio Palmero (718-915-8957)

Remarks: Fantastic spacious fully. furnished 5-Bedroom Town Home in the exciting resort of Windsor at Westside. Nestled in one of the newest resorts in the area near Disney, this beautifully maintained 5-bedroom, 4.5-bathroom town home offers the perfect blend of modern comfort, elegance, and fun decorated kids rooms. Built in 2017 and spanning 2,263 square feet, the property features an open-concept living area, a gourmet kitchen equipped with stainless steel appliances, granite countertops, and a large island ideal for entertaining. Outside, enjoy a private backyard oasis - a spacious deck with a private pool, BBQ, seating area and outdoor TV, perfect for outdoor gatherings. Garage has been converted to a fun fully loaded game room. Conveniently located just minutes from Disney, Universal and other entertainment areas, and schools, this home is ideal for an income generating opportunities, as well as second home or a permanent residence. The stunning 10,000 sq ft Club house features reception desk, Community Pool, Lazy River, Splash zone, Fitness Center, Tiki Bar and Restaurant, Youth activities Center and Arcade room, Security gates manned 24/7. Call and schedule your private tour today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Stani Delcheva (407-405-6815)

Remarks: Welcome to this exceptional 5-bedroom, 4.5-bathroom vacation retreat featuring a private heated pool and outdoor kitchen with gas grill, thoughtfully designed for both refined relaxation and entertaining. This bright corner-unit home is filled with natural light and offers a spacious open-concept layout with ceramic tile throughout. The modern kitchen features stainless steel appliances and overlooks the main living and dining areas. The first floor includes a private bedroom with a full bathroom, ideal for guests or multi-generational living. Upstairs, the expansive primary suite offers an en-suite bathroom, along with a second en-suite bedroom, two additional bedrooms, and a shared full bath. Enjoy Florida living outdoors with a heated pool, pool-area half bath, and outdoor kitchen. A detached garage has been converted into a game room for added entertainment. Located just minutes from world-famous theme parks, this gated resort community offers exceptional amenities, including a resort-style pool with cabanas, lazy river, clubhouse with fitness center, on-site dining, sports courts, playground, and 24/7 security. Conveniently close to golf, shopping, dining, and major attractions. Perfect for families, groups, and vacationers looking for space, comfort, and resort-style fun close to all the action!

Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)

Listing Agent: Cassius De Moura (407-989-0007)

Remarks: Great, great price improvement!! It is really priced to sell quickly!! Beautiful 6 bedroom 4 1/2 bathroom, hideaway open floor plan on a corner lot in the desirable Windsor at Westside Community. Spacious great room over looking the screened 30 x 20 pool deck with heater pool and heated spa. First and second floor Master Suites. To the second floor is a 19 x 17 Loft, second suite and 4 further bedrooms and 2 bathrooms. This lovely property would make a great family vacation home, an income producing Short Term Rental Home, or even your Primary Residence. Over 3,000 sq ft under air. Luxury features throughout the home including granite counters in the kitchen and bathrooms. Stainless steel appliances, ceramic tile to the first floor and all bathrooms. Energy efficient features include Low E double pane windows, 15 seer A.C system. Located within close proximity to the communities private 8,000 sq ft club house with fitness center, heated pool, heated spa, heated lazy river, tennis courts, and much more. The location of Windsor at Westside is ideal for the attractions, shops, restaurants and much, much more fun! A must purchase!

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

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