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$430,000
5 Beds ⋅ 5 Baths ⋅ O6434299 MLS ⋅ 8907 BLDG.
Turnkey 5-Bedroom Townhome – Short-Term Rental Approved! Welcome to this beautifully furnished 5-bedroom, 4.5-bathroom townhome, thoughtfully designed with fun Mickey Mouse and Harry Potter-themed bedroom, perfect for vacationers and investors alike. This move-in-ready property comfortably accommodates up to 12 guests and offers the ideal combination of space, comfort, and entertainment. The open-concept main living area features a modern kitchen with granite countertops, stainless steel appliances, ample cabinetry, and a spacious island perfect for gathering and entertaining. Step outside to your private screened-in pool and patio, an inviting space to relax and unwind after a day at the theme parks. Upstairs, a versatile loft provides additional room for entertainment, lounging, or family time. Guests can enjoy Windsor at Westside’s impressive resort-style amenities, including a clubhouse, resort pool, lazy river, water slide, fitness center, sports courts, game room, and playground—bringing the full vacation-resort experience right to the community.

8907 Sydney Avenue, Kissimmee
$495,000
5 Beds ⋅ 5 Baths ⋅ O6426374 MLS ⋅ N/A BLDG.
Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom home located in the highly sought-after Windsor at Westside Resort in Kissimmee. Whether you're searching for a primary residence, vacation home, or investment property, this home offers the perfect blend of comfort, style, and convenience. The spacious open-concept floor plan features a modern kitchen with granite countertops, stainless steel appliances, and a large island overlooking the living and dining areas. The first-floor primary suite provides privacy and convenience, while the additional bedrooms plenty of space for family and guests. Step outside to your private screened-in pool, perfect for relaxing after a day at the theme parks. Residents and guests enjoy access to resort-style amenities including a clubhouse, fitness center, resort pool, lazy river, waterslide, sports courts, playground, and 24-hour gated security. Ideally located just minutes from Walt Disney World, shopping, dining, golf courses, and major highways, this property offers exceptional convenience for both homeowners and vacation guests. Don't miss this opportunity to own a home in one of Central Florida's premier resort communities.

2417 Dubai Street, Kissimmee
$490,900
5 Beds ⋅ 5 Baths ⋅ B26058583 MLS ⋅ Windsor At Westside BLDG.
This stunning 5-bedroom 4.5-bath townhouse is designed for both guests and owners: a full bedroom and bath downstairs, a private cabana bath, a spacious upstairs loft and thoughtful storage throughout. Neighbor privacy adds an extra layer of comfort rarely found in resort communities. Over $50K in design upgrades elevate the space, including a smart pool control system and noise monitoring for peace of mind. The property is fully turnkey with cleaning and pool teams already in place. This home is ready to go live from day one. Located in a true short-term rental community (28-day max stay, no residential mail), this is a rare opportunity to own in a zone built exclusively for vacation rental performance.

2431 Dubai Street, Kissimmee
$465,000
5 Beds ⋅ 5 Baths ⋅ O6425993 MLS ⋅ 8923 BLDG.
Fully Furnished 5-Bedroom Townhome with Heated Private Pool in Prime Kissimmee Location Welcome to this exceptional two-story townhome in the heart of Kissimmee, offering the perfect combination of comfort, style, and investment potential. Fully furnished and move-in ready, this beautifully maintained property is an outstanding opportunity for homeowners, vacation home buyers, and investors seeking a high-demand short-term or long-term rental property. Featuring 5 spacious bedrooms, 4 full bathrooms, and 1 half bathroom, this home offers an ideal layout for families and guests alike. The elegant primary suite provides a private retreat with a generous walk-in closet and a well-appointed en-suite bathroom. The additional bedrooms feature built-in closets and are thoughtfully designed to maximize comfort and convenience. Adding to the home's appeal, several of the bedrooms showcase fun and creative themed designs that guests of all ages will love, creating a memorable experience and enhancing its rental attractiveness. The open-concept floor plan creates a bright and welcoming atmosphere, seamlessly connecting the spacious living room, dining area, and kitchen. Whether entertaining guests or accommodating larger groups, the expansive living spaces provide both functionality and comfort. The beautiful kitchen is designed to impress, featuring solid wood cabinetry, elegant stone countertops, and a full suite of included appliances. With ample storage and workspace, it is perfectly equipped for everyday living or vacation rental use. Step outside to your own private resort-style retreat. The large heated swimming pool is enclosed within a screened lanai, allowing you and your guests to enjoy Florida’s beautiful weather year-round while maintaining comfort and privacy. This inviting outdoor space is ideal for relaxing, entertaining, or creating unforgettable vacation memories. One of the property's standout features is its access to an incredible, amenity-rich HOA community. Residents and guests enjoy a wide range of resort-style amenities designed to enhance both lifestyle and vacation experiences, adding tremendous value and appeal for owners and renters alike. Ideally located near major roadways, shopping, dining, entertainment, and highly rated schools, this property offers easy access to everything Central Florida has to provide. Its prime location, combined with its fully furnished condition, themed bedrooms, private heated pool, and exceptional community amenities, makes it a highly desirable choice for both personal use and investment purposes. Whether you are looking to expand your real estate portfolio or purchase a turnkey property with outstanding rental potential, this impressive Kissimmee townhome is an opportunity you won't want to miss. Schedule your private showing today and discover the value, versatility, and income potential this remarkable home has to provide

8923 Sydney Avenue, Kissimmee
$409,000
5 Beds ⋅ 5 Baths ⋅ O6421749 MLS ⋅ 8930 BLDG.
UNIQUE OPPORTUNITY AT WINDSOR AT WESTSIDE | PREMIUM CORNER LOT Step into luxury living with this stunning fully furnished 5 bed/4.5 bath pool home located in the highly sought-after, gated vacation community of Windsor at Westside, just minutes from Disney. With a spacious 2,265 SqFt open-concept floor plan, this home offers comfort, style, and functionality for your ideal vacation retreat or primary residence. Upon entering through the welcoming front porch, you'll be immediately struck by the natural light that fills the home, accentuating its beautiful design and layout. The expansive oversized lanai and pool deck provide the perfect space for outdoor relaxation, complete with a large, heated pool, screen enclosure, and attractive brick pavers. A master bedroom on the main floor offers extra privacy and convenience, perfect for families or guests. The kitchen is a chef's dream, outfitted with top-of-the-line stainless steel appliances, including a refrigerator with an ice maker, glass cooktop range, microwave, and dishwasher. The gray granite countertops and extended island with double sinks for ample space for cooking and entertaining, while the open layout connects seamlessly to the dining and living areas, with views of the pool through sliding glass doors. On the Second Floor, there is a spacious loft/game room that offers additional space for entertainment, surrounded by four generously sized bedrooms. The master bedroom is with a walk-in closet and a luxurious bathroom with double vanities, granite counters, and a glass-enclosed shower. Your family will love the specially themed Disney and ocean-style bedrooms, designed to spark their imagination. More importantly, the owner just replaced the brand-new recycled and composite flooring for the whole second floor. Located just minutes from Orlando’s world-renowned theme parks, Windsor at Westside offers a wide range of resort-style amenities: On-site restaurant & coffee bar, Zero-entry pool with a poolside bar, Fitness center, Basketball, soccer, and volleyball courts, Gaming stations, Playground, splash pad, and waterslides. Don’t miss out on this rare opportunity to own a premium corner-lot pool home in a community that has it all. Whether you’re looking for a personal oasis or an investment in vacation property, this home is the perfect blend of luxury and convenience. Schedule your private tour today and make this stunning home your own!

8930 Sydney Avenue, Kissimmee
$495,000
5 Beds ⋅ 5 Baths ⋅ O6419842 MLS ⋅ 2426 BLDG.
Welcome to this beautifully maintained, fully furnished 5-bedroom, 4.5-bath townhome with a private screened pool, located in the highly desirable Windsor at Westside Resort. Built in 2020, this spacious home features an open-concept layout, modern kitchen with solid surface countertops, generous living and dining areas, and a first-floor guest suite. Upstairs offers a spacious primary suite and additional guest bedrooms, making it ideal for large families and vacation guests. Currently operating as a successful short-term rental, this turnkey property presents an exceptional opportunity for investors seeking immediate rental potential or buyers looking for a vacation home in one of Central Florida's premier resort communities. This property may also be acquired as part of a unique turnkey short-term rental investment portfolio. The portfolio includes three established vacation rental properties with proven operational systems, established online presence, verified guest reviews, and documented historical performance. Additional portfolio information is available to qualified buyers upon request. Residents and guests enjoy world-class resort amenities including a 24-hour guard-gated entrance, resort-style pool, lazy river, clubhouse, fitness center, restaurant, sports courts, playground, and more. Conveniently located just minutes from Walt Disney World Resort, Margaritaville, Sunset Walk, championship golf courses, shopping, dining, and major highways. HOA includes cable TV, internet, security, common area maintenance, resort amenities, and professional association management. An outstanding opportunity to own a proven vacation rental property in one of the most sought-after resort communities near Disney.

2426 Tangier Drive, Kissimmee
$524,900
6 Beds ⋅ 5 Baths ⋅ O6414964 MLS
Just reduced $25,000! PRICED BELOW MARKET VALUE. This fully furnished property with EV station is within walking distance of the clubhouse. Rental-ready 6-bedroom property is priced to move fast and generate income from day one. Located in the newer phase of Windsor at Westside, one of Central Florida's most in-demand short-term rental communities, this turnkey corner-lot pool home is built for out-of-state and international investors seeking a hands-off, high-performing addition to their portfolio. Offering over 3,100 square feet, 6 bedrooms and 4.5 bathrooms, this home sleeps large groups comfortably and is approved for short-term and vacation rental use, a rare combination that keeps demand strong for owners renting on Airbnb, VRBO, and similar platforms. The open floor plan features a chef-style kitchen with stainless steel appliances, a breakfast bar, and abundant counter and cabinet space, flowing directly into the main living and dining areas, ideal for guests, groups, and multi-family stays. The primary suite includes a walk-in closet and a spa-style ensuite with dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms and bathrooms offer flexible sleeping arrangements, making this property equally suited for large families or short-term rental guests booking multiple rooms. Private pool and patio, set on a desirable corner lot with added space and curb appeal. The home is being sold fully furnished, a true turnkey opportunity for investors who want to start generating rental income immediately, with no renovation, staging, or setup required. This home sits within walking distance of one of the community's resort-style pools, and residents enjoy full access to Windsor at Westside's clubhouse, fitness center, game room, basketball court, on-site restaurant, multiple resort pools, a lazy river, and a waterslide. The location is minutes from Central Florida's world-famous attractions, a major draw for renters and a strong long-term value driver for owners.

8936 Prague Way, Kissimmee
$428,000
5 Beds ⋅ 5 Baths ⋅ O6414579 MLS ⋅ 2414 BLDG.
Priced to sell! This stunning home sits in the third and newest phase of the sought-after Windsor at Westside Resort, with also a Private Heated Pool. Featuring 5 bedrooms and 4 bathrooms, it offers the perfect blend of fun and relaxation. One bedroom and bathroom are conveniently located on the first floor, while the remaining 4 bedrooms—including some with fun themed designs—are upstairs, just off the family room. The resort amenities include heated pools, a heated jacuzzi, a heated lazy river, and a full tiki bar at the pool complex. Whether you’re looking for a turnkey short-term rental investment or a second home to call your own, this property is zoned for both.

2414 Dubai Street, Kissimmee
$418,000
5 Beds ⋅ 5 Baths ⋅ A4692263 MLS ⋅ N/A BLDG.
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.

2410 Tangier Drive, Kissimmee
$498,000
5 Beds ⋅ 4 Baths ⋅ O6403698 MLS
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!

8933 Prague Way, Kissimmee
$445,000
5 Beds ⋅ 5 Baths ⋅ O6374304 MLS ⋅ 8936 BLDG.
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.

8936 Sydney Avenue, Kissimmee
$568,000
7 Beds ⋅ 6 Baths ⋅ O6347903 MLS
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

2438 Tanger Drive, Kissimmee
$460,000
5 Beds ⋅ 5 Baths ⋅ O6341750 MLS ⋅ No, BLDG.
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.

2402 Dubai Street, Kissimmee
$579,000
7 Beds ⋅ 6 Baths ⋅ O6329265 MLS
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!

8900 Prague Way, Kissimmee
$419,000
5 Beds ⋅ 4 Baths ⋅ O6233761 MLS ⋅ 2428 BLDG.
Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation. With five spacious bedrooms and four and a half bathrooms, this stunning retreat offers the perfect blend of comfort and sophistication. As you step inside, you're greeted by an open floor plan that seamlessly integrates the living, dining, and kitchen areas. The kitchen boasts elegant granite countertops and sleek stainless steel appliances, creating a modern yet inviting atmosphere. The spacious loft upstairs provides an additional living area, perfect for relaxing, entertaining, or even setting up a home office. One of the highlights of this townhouse is the private pool, easily accessible through pool-facing telescopic sliding glass doors. Imagine unwinding by the poolside or retreating to the screened-in lanai for a serene evening under the stars. Staying in Windsor at Westside means enjoying world-class amenities. The HOA grants you access to an impressive 8,000 sq ft clubhouse, featuring a lazy river, sports courts, an arcade game room, and more. Dive into the zero-entry pool or treat yourself to a refreshing spa experience. Family will adore the playground and water slide, while adults can relax with a cocktail at the pool bar or dine at the full-service restaurant. To make your stay even more effortless, the HOA covers cable, high-speed internet, exterior maintenance, trash pick-up, pest control, and lawn care. Every detail has been thoughtfully curated to ensure your experience is nothing short of extraordinary. This townhouse isn't just a home; it's a lifestyle. Don’t miss out on the opportunity to own your own piece of paradise. Schedule a showing today and take the first step toward making this dream retreat yours.

2428 Dubai Street, Kissimmee
$499,000
5 Beds ⋅ 5 Baths ⋅ O6206939 MLS ⋅ Phase 3 BLDG.
GREAT, GREAT PRICE IMPROVEMENT!! This beautiful home is locate on the third and newest phase of the sought after Windsor at Westside Resort. It boasts 5 bedrooms and 4 bathrooms of pure fun and relaxation! One bedroom and a bathroom are on the first floor, and the other 4 bedrooms, including some thematic, are located on the second floor, just by the family room! The Resort has heated pools, heated jacuzzi, heated lazy river, and a complete tiki bar by the pool complex! This gorgeous home is just waiting to become your next vacation nest!

2429 Dubai Street, Kissimmee
$490,000
5 Beds ⋅ 5 Baths ⋅ O6199004 MLS ⋅ 2430 BLDG.
*** 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.

2430 Tangier Drive, Kissimmee