Windsor At Westside; Windsor/Westside Real Estate

Windsor At Westside; Windsor/Westside Real Estate

Welcome to Windsor at Westside, a stunning subdivision nestled in the heart of Kissimmee, Florida, in Osceola County. This vibrant community is designed for those seeking a perfect blend of luxury, comfort, and convenience, making it an ideal choice for families, vacationers, and retirees alike.

Windsor at Westside boasts a picturesque setting with beautifully landscaped grounds and an array of modern amenities. The community features a stunning clubhouse, a sparkling resort-style pool, and a state-of-the-art fitness center, ensuring that residents have everything they need for a lifestyle of leisure and activity. The thoughtfully designed homes in Windsor at Westside range from spacious townhomes to elegant single-family residences, each showcasing contemporary architecture and high-end finishes.

One of the standout features of Windsor at Westside is its proximity to world-renowned attractions. Just a short drive away, you’ll find the magic of Walt Disney World, Universal Studios, and an array of shopping and dining options that cater to every taste. The community is also conveniently located near major roadways, making it easy to explore the greater Orlando area and all it has to offer.

For those who enjoy outdoor activities, Windsor at Westside is surrounded by stunning natural beauty, with nearby parks and recreation areas perfect for hiking, biking, and enjoying Florida’s sunshine. Whether you’re looking for a permanent residence or a vacation retreat, Windsor at Westside offers a welcoming atmosphere and a lifestyle that truly feels like home. Come discover the charm and allure of this exceptional community today!

Newest Listings in Windsor At Westside; Windsor/Westside

5 Beds ⋅ 5 Baths ⋅ O6413060 MLS ⋅ 2428 BLDG.

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

Listing courtesy of GOLDEN SUN REALTY INC. 4077652618

5 Beds ⋅ 5 Baths ⋅ O6412966 MLS ⋅ 2428 BLDG.

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

Listing courtesy of GOLDEN SUN REALTY INC. 4077652618

5 Beds ⋅ 5 Baths ⋅ O6404821 MLS ⋅ 2428 BLDG.

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

Listing courtesy of GOLDEN SUN REALTY INC. 4077652618

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David Hazellief

David E. Hazellief Broker | CENTURY 21 Hazellief & Prevatt Realty With over 40 years of real estate experience and a lifetime of service to the Okeechobee community, David Hazellief is more than just a broker—he’s a trusted local expert who brings unmatched knowledge, leadership, and dedication to every client relationship. David is a fourth-term Okeechobee County Commissioner, currently serving as Chairman of the Board. His extensive involvement in county planning, housing, and land use gives his clients a unique advantage—especially when it comes to understanding growth patterns, zoning, and investment potential. He’s completed the Florida Association of Counties’ Commissioner Certification Program and serves on numerous local boards, including the Affordable Housing Committee (Chairman), Economic Council of Okeechobee, and the Water Resource Advisory Commission. As owner of Hazellief & Prevatt Realty, H&P Holdings, and Hazellief Family Ranch, David combines deep real estate expertise with a strong agricultural and commercial background. He’s a longtime member of the Okeechobee Chamber of Commerce, Cattleman's Association, Farm Bureau (currently serving as secretary), and the local Board of Realtors. Whether you're buying your first home, expanding your investment portfolio, or looking for acreage, David brings a steady hand, sharp eye, and boots-on-the-ground knowledge to help you make confident decisions. Local roots. Proven leadership. Real results. That’s what you get when you work with David Hazellief.

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Cristie Schmidt

Cristie is a very seasoned Real Estate Agent she brings almost 20 years of Real Estate experience with her. Born in Stuart, Florida this native came from Martin County to Okeechobee County in 1995. She started her Real Estate career in 2008 after the untimely death of her husband. Cristie was the Okeechobee County Board of Realtors Rookie of the year for 2008 and hasn't slowed one iota since. She has been the Top Producer of every office she has worked at since she became licensed. Cristie currently serves as the Vice President of the Okeechobee County Board of Realtors. Cristie also is serving her 4th year on the Board of Directors for Stellar MLS the 3rd largest MLS in the United States. Cristie invites anyone she has met to come see her at her C21 office and anyone she hasn't met please feel free to stop by and introduce yourself, this girl has never met a stranger. Cristie is ready, willing and able to do ALL Real Estate transactions with extensive experience in Residential, short sales, bank owned assets and foreclosures. For honest, relaxed no pressure sales combined with close to 20 years experience call Cristie. Her motto speaks for itself "Doing what I say I will do sometimes more but never less."

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Mark Goodbread

Mark was raised in Okeechobee and graduated from Okeechobee High School in 1985. After graduation from High School Mark attended Texas A&M University to further his education and graduated with a Bachelor of Science degree in Agri-Business in 1992. After graduating college he returned to Okeechobee and worked in the family businesses of a local Real Estate Development Company and the active cattle operation of Goodbread Ranches. Mark has been involved in developing Single Family, Multi-Family and Commercial projects in the area. Mark holds two professional licenses of Florida Licensed General Contractor and Florida Real Estate Broker Associate license. Call Mark as he is over qualified to help you with any type of Real Estate transaction.

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Brad Goodbread

Brad is a Sixth Generation Floridian from a Family of Florida Farmers and Ranchers. He was the President of the Okeechobee High School FFA Chapter his Senior year and Graduated in 1982. After Graduation Brad attended Texas A&M University where he graduated with a Bachelors Degree in Agriculture Economics in 1987 and a Masters Degree in Land Economics Real Estate in 1989. He was a Commercial Real Estate Appraiser in Bryan and Houston, Texas for 6 years before moving back to Florida to help his family in their Ranching and Real Estate Development Businesses. He has been a Licensed Real Estate Salesman since 1988. Recently, he has owned and managed a Trucking Company and is presently in his 3rd term as an elected official as a Commissioner on the Okeechobee County Board of County Commissioners and serves as the 1st Vice Chairman. Brad has also been a Licensed Pilot since 1986.

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