Windsor At Westside Ph 3 Homes under $500,000

Windsor At Westside Ph 3 Homes under $500,000

Welcome to Windsor at Westside Phase 3, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. This exceptional community offers the perfect blend of luxury and affordability, making it an ideal choice for families, retirees, and investors alike.

Windsor at Westside is known for its picturesque surroundings, featuring lush landscapes and beautifully designed homes that exude charm and elegance. The community is strategically located in Osceola County, just a stone's throw away from the excitement of Orlando's world-renowned attractions, including Walt Disney World and Universal Studios. This prime location ensures that residents can enjoy the best of both worlds: a peaceful suburban lifestyle with easy access to urban amenities.

One of the standout features of Windsor at Westside Phase 3 is the availability of stunning homes priced under $500,000. These properties boast modern designs, spacious floor plans, and high-quality finishes, making them perfect for those seeking comfort and style without breaking the bank. From cozy three-bedroom retreats to expansive four-bedroom family homes, there is something for everyone in this community.

Residents can also take advantage of the fantastic amenities that Windsor at Westside has to offer. Enjoy a refreshing dip in the resort-style pool, stay active at the state-of-the-art fitness center, or unwind at the clubhouse, which serves as a hub for social gatherings and community events.

If you’re looking for a place to call home in Kissimmee, Windsor at Westside Phase 3 presents an exceptional opportunity to invest in a thriving community that combines affordability, convenience, and a vibrant lifestyle. Come and discover your dream home today!

Newest Windsor At Westside Ph 3 Homes under $500,000

2433 Dubai Street, Kissimmee
$419,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained 5-bedroom, 4.5-bathroom two-story townhouse located in the sought-after resort community of Windsor at Westside in Kissimmee. The main level welcomes you with a spacious bedroom and full bathroom on the left, followed by a bright and open layout connecting the kitchen, dining area, and living room—perfect for entertaining or relaxing. Sliding doors lead out to the tranquil pool area, ideal for enjoying Florida’s sunny weather year-round. Upstairs, a generous loft provides a comfortable second living space and separates the remaining four bedrooms, including a luxurious primary suite and an additional ensuite bedroom, ensuring comfort and privacy for guests or family members. Windsor at Westside is a gated, amenity-rich community featuring an 8,000 sq. ft. clubhouse, resort-style pool with lazy river and water park, fitness center, restaurant/bar, tennis and basketball courts, sand volleyball, and even a small soccer field. Centrally located just minutes from Disney, golf courses, shopping, dining, and major highways, this townhome is perfect as a short-term rental investment and second home. Don't miss this opportunity to own one of the best-valued homes in a premier resort community!

2433 Dubai Street, Kissimmee
2404 Tangier Drive, Kissimmee
$416,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
Experience elevated Florida living in this beautiful 5-bedroom, 5-bathroom townhome in the sought-after Windsor at Westside community. Featuring a spacious, contemporary layout designed for comfort and effortless entertaining, this exceptional residence offers the perfect blend of style, privacy and resort-inspired living. Ideally located near Orlando's best attractions, dinning, shopping and entertainment, this property is an exceptional opportunity for both personal enjoyment and investment potential.

2404 Tangier Drive, Kissimmee
8907 Sydney Avenue, Kissimmee
$430,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
2417 Dubai Street, Kissimmee
$495,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
8923 Sydney Avenue, Kissimmee
$465,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
2426 Tangier Drive, Kissimmee
$495,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
8936 Prague Way, Kissimmee
$495,000
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
2410 Tangier Drive, Kissimmee
$399,900
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
MAJOR PRICE IMPROVEMENT — TURNKEY, FULLY FURNISHED 5-BEDROOM POOL HOME IN WINDSOR AT WESTSIDE! Welcome to 2410 Tangier Drive, a beautifully maintained and fully furnished 5-bedroom, 4.5-bath townhome offering 2,263 sq. ft. in the highly desirable resort-style community of Windsor at Westside. Whether you are looking for a vacation home, second home, primary residence, or investment opportunity, this property offers exceptional flexibility. The open-concept living and dining area provides plenty of space for family and guests, while the well-equipped kitchen features modern appliances and ample cabinetry. One bedroom is conveniently located on the first floor, with the remaining bedrooms upstairs for added privacy. Step outside to your own private screened and heated splash pool—the perfect place to relax and enjoy the Florida lifestyle. The home is being offered FULLY FURNISHED and MOVE-IN READY, making it especially attractive for buyers looking for a turnkey property without the additional expense and hassle of furnishing a vacation home. Windsor at Westside offers outstanding resort-style amenities including a clubhouse, resort pool with lazy river and waterslide, fitness center, water playground, sports courts, playground, restaurant/bar, and gated security. Conveniently located near Disney and Central Florida’s world-famous attractions, as well as shopping, dining and major highways. Fully Furnished • Private Heated Pool • 5 Bedrooms • 4.5 Baths • 2,263 Sq Ft • Resort Amenities • Excellent Vacation Home & Investment Potential Schedule your private showing today!

2410 Tangier Drive, Kissimmee
8933 Prague Way, Kissimmee
$479,000
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
8936 Sydney Avenue, Kissimmee
$445,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
2402 Dubai Street, Kissimmee
$460,000
5 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
2428 Dubai Street, Kissimmee
$419,000
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 3 SubDv. ⋅ 34747 Zip Code
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
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