Windsor At Westside; Windsor/Westside Real Estate

Windsor At Westside; Windsor/Westside Real Estate

Welcome to Windsor at Westside, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This stunning community is a hidden gem that perfectly blends luxury with comfort, making it an ideal destination for families, vacationers, and those seeking a serene lifestyle close to the excitement of Central Florida.

Windsor at Westside boasts a variety of beautifully designed homes, each reflecting modern architecture and thoughtful layouts. The community features spacious single-family residences with a range of floor plans, ensuring there’s a perfect fit for everyone—from cozy retreats to expansive family homes. Many of these properties come equipped with private pools and outdoor living spaces, encouraging residents to bask in the sunny Florida weather.

Beyond the charming homes, Windsor at Westside offers an array of top-notch amenities. Residents can enjoy a stunning clubhouse, a resort-style swimming pool, a state-of-the-art fitness center, and a lively game room. The community also features sports courts, walking trails, and a children’s playground, making it an ideal spot for families to thrive and create lasting memories.

Located just minutes from the world-renowned attractions of Walt Disney World, Universal Studios, and a plethora of shopping and dining options, Windsor at Westside provides the perfect balance of tranquility and accessibility. Whether you’re looking for a primary residence or a vacation home, this community promises a lifestyle filled with fun, relaxation, and the warmth of Florida living. Discover your dream home in Windsor at Westside today!

Newest Listings in Windsor At Westside; Windsor/Westside

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code

TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Upgraded laminate floor; new dryer/washer (2025); two new king bed and bunkbed Star War theme in loft; Harry Potter theme and Disney Cruise theme in tow rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river plash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between Champions Gate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8904 Sydney Avenue, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code

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

8932 Sydney Avenue, Kissimmee

5 Beds ⋅ 5 Baths ⋅ Windsor At Westside; Windsor/Westside SubDv. ⋅ 34747 Zip Code

TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Newly upgraded laminate floor Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river Kids’ splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!

8942 Sydney Avenue, Kissimmee

Start Your Search

Corey Lott

As a Native Floridian, and with 23 years of experience in Real Estate sales, 13 Years as a Broker, I pride myself in consistently providing exemplary services that I provide my clients. I guide you through the process of selling or buying your NextHome, and make that experience a positive outcome that helps you reach your goals! When you hire me, I am your confidant, your trusted partner, leading you through the sale or purchase of your NextHome with diligence, care, and persistence, as your advocate throughout the transaction and for years to come! I am a Florida Native, a career educator, a Master’s Degree in Leadership, and a Seasoned Real Estate Broker for over 20 years. Coverage Area includes all of Central Florida, Palm Beach, Broward, St. Lucie, Martin, as well as Miami-Dade. My brokerage is a member of Orlando Regional Realtor Associations covering 19 counties, Lake-Sumter, and Beaches MLS.

Learn More

Eric Stalnaker - Realtor

Eric-Stalnaker

I’m here to make your real estate journey not just smooth, but truly rewarding. Whether you’re buying your first home, upgrading, or investing, you deserve an agent who leads with honesty, patience, and care—and that’s exactly what I bring to the table. As a retired elementary school teacher, I know the value of trust, courtesy, and commitment. Just as I once guided my students with dedication, I now guide my clients with that same steady hand—always taking the time to listen, explain, and go the extra mile. With me, you’ll never feel rushed or pressured. Instead, you’ll have a trustworthy partner who ensures you’re informed and confident every step of the way. From navigating the market to negotiating the best deals, I’ll always put your needs first—and our relationship will never end at the closing table. Let’s build more than a transaction. Let’s build a partnership rooted in trust and care. I’d be honored to help you find your place to call home—reach out today, and let’s begin this exciting journey together.

Learn More

Shannon Bass

Looking for an agent who is both committed to your needs and capable of delivering results? Your search ends here - I am a full-time agent who provides top-notch service. With a strong work ethic and a focus on my clients' best interests, I work alongside a team of skilled professionals who know how to get the job done. As a NextHome agent, I prioritize #humansoverhouses and am excited to demonstrate my abilities to you.I am passionate about real estate for a variety of reasons! The excitement of buying or selling a property, the challenge of negotiating deals, the opportunity to help people find their dream homes or investments, and the satisfaction of seeing a project through from start to finish in a constantly changing and dynamic industry are just a few!I serve the Central Florida area specializing in Lake, Sumter, Marion, and Citrus counties. I live in Grand Island, Florida and enjoy helping my friends and neighbors find their next home, first home, or sell their current home! Not ready to buy? I can also help you find a rental!

Learn More

Browse Windsor At Westside; Windsor/Westside Homes by Community Features

Browse Windsor At Westside; Windsor/Westside Homes by Amenities