Windsor/Westside-Ph 2a Homes for Sale

Windsor/Westside-Ph 2a Homes for Sale

Welcome to Windsor/Westside-Ph 2a, a vibrant and enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming community is not just a neighborhood; it’s a lifestyle waiting to be embraced.

Windsor/Westside-Ph 2a is renowned for its beautifully designed homes that effortlessly blend modern aesthetics with timeless comfort. Each residence boasts spacious layouts, contemporary finishes, and a variety of floor plans to suit diverse lifestyles. Whether you’re a growing family, a retiree, or looking for a vacation home, you’ll find the perfect match here. Many homes feature open-concept living areas, gourmet kitchens, and private outdoor spaces, ideal for entertaining or simply enjoying the Florida sunshine.

The community itself is a treasure trove of amenities. Residents can take advantage of a stunning clubhouse, a sparkling pool, a well-equipped fitness center, and recreational areas perfect for family gatherings or leisurely strolls. The lush landscaping and serene surroundings create an inviting atmosphere, fostering a strong sense of community among neighbors.

Located just minutes from the excitement of Orlando’s theme parks and attractions, Windsor/Westside-Ph 2a offers the perfect balance of tranquility and adventure. With an array of shopping, dining, and entertainment options nearby, you’ll never run out of things to do.

If you’re looking for homes for sale in this delightful subdivision, you’re in luck! Explore the available listings and discover the opportunity to call Windsor/Westside-Ph 2a your new home. Embrace the charm, comfort, and vibrant lifestyle that this community has to offer!

Newest Windsor/Westside-Ph 2a Homes for Sale

8 Beds ⋅ 6 Baths ⋅ O6429118 MLS

Short Sale. Welcome to your own slice of paradise in the highly sought-after, guard-gated Windsor at Westside Resort! This beautifully updated and fully furnished 8-bedroom, 6-bath home offers over 4,041 square feet of spacious living designed for comfort, entertainment, and unforgettable vacation experiences. The versatile floor plan features a convenient first-floor primary suite, while two upstairs bedrooms include private en-suite baths for added privacy. Enjoy Florida living year-round in your private heated pool and spa, or gather family and guests in the incredible converted game room complete with gaming consoles, a pool table, and driving simulators. Located just minutes from Disney, this exceptional resort home provides access to world-class amenities, including a resort-style pool, lazy river, expansive clubhouse, fitness center, poolside cabana, sand volleyball courts, and tennis courts. Whether you're looking for a vacation retreat, primary residence, or income-producing investment property, this move-in-ready home offers the perfect blend of luxury, location, and resort-style living.

1836 Nice Court, Kissimmee

Listing courtesy of KRESSLER REAL ESTATE. 407-864-2184

7 Beds ⋅ 6 Baths ⋅ O6411765 MLS

Price Improvement!! Welcome to your dream vacation retreat in the highly sought-after Windsor at Westside Resort! This stunning 7-bedroom, 5.5-bath pool home is professionally furnished, beautifully decorated, and completely turnkey—offering everything you need for a successful vacation rental investment, a family getaway, or the perfect combination of both. From the moment you step inside, you'll appreciate the spacious open-concept layout designed for entertaining and relaxation. The fully stocked kitchen features granite countertops, abundant cabinetry, and a large island overlooking the expansive living and dining areas, making it easy to gather with family and friends after a day of fun at the parks. The first-floor primary suite offers a private retreat with direct access to the pool area through the ensuite bathroom—a thoughtful feature that's perfect after an afternoon swim. Step outside and discover your own private oasis, complete with a sparkling screened pool, relaxing hot tub, covered lanai, and the added benefit of no rear neighbors, providing a peaceful setting to enjoy the Florida sunshine year-round. Upstairs, a spacious loft serves as the ultimate entertainment hub, featuring a large-screen viewing area ideal for movie nights, gaming tournaments, or simply unwinding after an exciting day of adventure. The thoughtfully designed split-bedroom floor plan offers plenty of room for multiple families and guests, including two additional ensuite bedrooms and four beautifully themed and/or decorated guest rooms that add an extra touch of magic and fun to every stay. Located within the guard-gated Windsor at Westside Resort, owners and guests enjoy access to world-class amenities centered around the impressive 8,000-square-foot clubhouse. Enjoy dining and drinks at Tu Casa Bar & Lounge, grab essentials at the market and deli, challenge friends in the video arcade, or stay active in the fitness center. Outside, the resort truly shines with its spectacular zero-entry pool, lazy river, water playground with slides, cabanas, tiki bar, volleyball court, and playground. Even better, the HOA includes lawn care and daily valet garbage service, allowing you to spend more time enjoying the resort lifestyle and less time worrying about maintenance. Whether you're searching for a high-performing vacation rental, a second home near Disney, or a luxury retreat for family and friends, this exceptional property checks every box. Just minutes from Walt Disney World, shopping, dining, golf, and Orlando's world-famous attractions, this is your opportunity to own a piece of paradise in one of Central Florida's premier vacation home communities. Schedule your private showing today and experience the Windsor at Westside lifestyle for yourself!

1881 Nice Court, Kissimmee

Listing courtesy of FLORIDA RESORT REALTY LLC. 305-494-4101

7 Beds ⋅ 6 Baths ⋅ O6380867 MLS

Welcome to this beautiful 7 Bed/ 5.5 Bath luxury vacation/investment home with WATERVIEW, nested in one of the most popular resort in Orlando: Windsor at Westside. This Turnkey vacation home comes with high end furnitures and professionally decorated and can easily accommodate up to 15 guests. Some great features of this house include spacious family/dining room combo, variety of game tables in the garage and upstair loft, spacious private pool/hot spa area in screened patio, which make it perfect for family and friends to gather for entertainment. Open kitchen is equipped with high-end cabinetry, granite countertops, and stainless-steel appliances. Spacious master suites on both floors are available to provide more comfort and privacy for owners and guests. The Windsor at Westside Resort provides massive amenities, including 8,000 square feet resort-style clubhouse, resort-style heated pool and spa, wireless internet on the pool deck, lazy river, recreation center, poolside cabana, playground, volleyball, tennis, basketball, game room, restaurant, bar, relaxing lounge area with indoor/outdoor fireplace, TVs and much more... This community is also in close proximity from Disney World and other attractions, like Universal Studios, Sea World, Golf courses, and Shopping Centers.Come check out this luxury and low maintenance vacation home before it slip away. Schedule a private showing today.

1627 Lima Ave, Kissimmee

Listing courtesy of KN PREMIER REALTY, INC. 407-668-8888

7 Beds ⋅ 6 Baths ⋅ O6331125 MLS

New Price! Luxurious 7-Bed, 5.5-Bath Retreat in Windsor at Westside! Nestled on a premium lot in the coveted Windsor at Westside gated community, this fully furnished 7-bedroom, 5.5-bathroom home is perfect for vacations, primary living, or investment, just minutes from Disney. Enjoy a spacious open floor plan with owner’s suites on both floors, a gourmet kitchen featuring stainless steel appliances, 42-inch dark wood cabinets, stone countertops, and a large breakfast bar. The living room seamlessly connects to a vast covered lanai and heated pool with a soothing spa, overlooking a serene conservation area, perfect for soaking up Florida’s sunshine and stunning sunsets. Residents gain access to resort-style amenities, including a clubhouse, heated pool, lazy river, water playground, fitness center, sports courts, games room, on-site store, restaurant, and bar.

1724 Lima Ave, Kissimmee

Listing courtesy of ALLIANCE REAL ESTATE GROUP. 407-375-8680

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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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