Windsor At Westside Ph 2a Homes for Sale

Windsor At Westside Ph 2a Homes for Sale

Welcome to Windsor at Westside Phase 2A, a stunning subdivision nestled in the heart of Kissimmee, Florida. This vibrant community is part of Osceola County and offers an idyllic blend of modern living and natural beauty. With its prime location just minutes from the enchanting attractions of Orlando, residents enjoy the perfect balance of tranquility and excitement.

Windsor at Westside Phase 2A boasts a variety of beautifully designed homes, making it an ideal choice for families, retirees, and everyone in between. Each residence features contemporary architecture, spacious layouts, and high-end finishes that cater to today’s lifestyle. Whether you’re looking for a cozy single-family home or a larger property to accommodate your growing family, you'll find an array of options that suit your needs.

The community itself is designed for leisure and recreation, with a range of amenities that enhance the living experience. Residents can take advantage of the resort-style pool, fitness center, and walking trails, all set against a backdrop of lush landscaping. Perfect for weekend gatherings or relaxing evenings, the clubhouse serves as a hub for social activities and community events.

With homes for sale in Windsor at Westside Phase 2A, now is the perfect time to explore this enchanting neighborhood. Embrace a lifestyle that combines the allure of suburban living with the excitement of nearby attractions. Discover your dream home in this thriving community, where every day feels like a vacation!

Newest Windsor At Westside Ph 2a Homes for Sale

$549,990
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Welcome to this stunning 5-bedroom, 4-bathroom home located in the highly desirable gated community of Windsor at Westside in Kissimmee. This spacious residence offers approximately 2,492 square feet of beautifully designed living space with an open-concept floor plan, perfect for entertaining family and guests. The home features a bright and inviting living area, a modern kitchen with ample cabinetry and counter space, a spacious primary suite, and generously sized bedrooms designed for comfort and privacy. Enjoy the Florida lifestyle with access to the community’s resort-style amenities, including a clubhouse, swimming pool, fitness center, sports courts, and recreational areas. Windsor at Westside is ideally located near world-famous attractions, shopping, dining, major highways, and all that Central Florida has. Whether you are looking for a primary residence, vacation home, or investment opportunity, this property provides the perfect combination of location, space, and resort-style living. Don’t miss the opportunity to own a piece of one of Kissimmee’s most sought-after communities!

1917 Nice Court, Kissimmee
$519,900
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Welcome to the ultimate Florida lifestyle in the highly desirable guard-gated community of winsor at westsite! This stunning, professionally decorated 6 bedroom, 5 bath pool single family house is fully furnished and move-in ready. Located just minutes from Walt Disney World and Central Florida's premier attractions, this property is an absolute dream for a high-performing short-term rental, a family vacation home, or a luxurious primary residence. Step through the front door and be greeted by an expansive, soring cellings that is flooded with natural light. The heart of the home is the gorgeous, fully-equipped kitchen featuring stainless steel appliances, and a large island, which flows seamlessly into the dining and main living areas—perfect for entertaining and gathering after a long day at the theme parks. The luxurious first-floor primary suite serves as your private oasis, boasting a spacious en-suite bathroom with dual vanities, a walk-in shower, and a large soaking tub, plus convenient direct access to the outdoor lanai. Step outside to discover your own private screened-in, heated pool and spa. this outdoor living space offers the perfect blend of privacy and relaxation under the Florida sun. Head upstairs to find a versatile loft space, ideal for movie nights or as a secondary lounge area. The second floor also features generously sized bedrooms, including a second primary suite and beautifully crafted themed bedrooms—designed to transport your youngest guests into another world. Beyond the extraordinary home, the community offers world-class resort amenities. Residents and guests enjoy unlimited access to a spectacular clubhouse, a resort-style pool with a lazy river, water slides, a state-of-the-art fitness center, sports courts, and an on-site restaurant/tiki bar. With its unbeatable location near top-tier shopping, dining, and world-famous theme parks, this property truly has it all. Don't miss your chance to own a turnkey piece of paradise in one of Central Florida's most sought-after resort communities!

1888 Gobi Drive, Kissimmee
$690,000
9 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Welcome to this spectacular 9-bedroom, 6-bathroom fully furnished pool home located in the highly desirable Windsor at Westside Resort! Built in 2018, this spacious two-story residence offers approximately 4,391 square feet of living space, making it an ideal primary residence, vacation home, or income-producing investment. Step inside to an open and inviting floor plan designed for entertaining large groups. The well-appointed kitchen features abundant cabinetry, generous counter space, and overlooks the expansive living and dining areas. Multiple bedrooms, including spacious suites, provide comfort and privacy for family and guests alike. Enjoy Florida living at its finest in your own private screened-in pool and spa, perfect for relaxing after a day at the parks or entertaining outdoors. The home is offered fully furnished, allowing for an effortless move-in or immediate rental opportunity. Located just minutes from Walt Disney World, shopping, dining, golf, and major highways, Windsor at Westside offers outstanding resort-style amenities, including a clubhouse, resort pool with lazy river, fitness center, sports courts, playground, and more, making it one of Central Florida's premier vacation home communities. Don't miss this incredible opportunity to own a spacious, turnkey home in one of Kissimmee's most sought-after resort communities!

1908 Nice Court, Kissimmee
$629,000
8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Welcome to this exceptional 8-bedroom, 6-bathroom resort home in the highly desirable Windsor at Westside community, where stunning pond views, privacy, and resort-style amenities come together to create the ultimate Central Florida retreat. Offered fully furnished and professionally equipped for short-term rentals, this turnkey property is ready for immediate enjoyment or income generation. Designed to accommodate large families and vacation groups, the spacious floor plan features expansive gathering areas, a modern kitchen with granite countertops and stainless-steel appliances, and two primary suites conveniently located on separate floors. Thoughtfully decorated and well-maintained, the home provides a comfortable and inviting atmosphere for owners and guests alike. Step outside to your private screened pool and spa overlooking a serene pond. With no rear neighbors and unobstructed water views, this outdoor oasis offers the perfect setting for relaxing after a day at the attractions. Adding to the home's value and efficiency, solar panels have been installed to help offset electricity costs. The buyer will assume the existing solar lease, which is currently approximately $358/month. Windsor at Westside is one of the area's premier vacation resort communities, featuring a spectacular clubhouse, resort-style pool, lazy river, splash zone, fitness center, arcade, sports courts, playground, and more. HOA dues include cable, internet, lawn maintenance, and valet trash service for added convenience. Ideally located just minutes from Walt Disney World, shopping, dining, golf, and major roadways, this property offers the perfect combination of lifestyle, location, and investment potential. Whether you're searching for a vacation getaway, full-time residence, or income-producing property, this remarkable home is ready to exceed expectations.

1829 Gobi Drive, Kissimmee
$529,000
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Escape to this exceptional vacation retreat located within the popular Windsor at Westside Resort, one of Central Florida’s premier resort communities. Offering 3,142 square feet of thoughtfully designed living space, this spacious home combines comfort, privacy, and convenience just minutes from Orlando’s world-famous attractions. Featuring six generously sized bedrooms and four-and-a-half bathrooms, the home is perfectly suited for large families, groups, or vacation guests. The open-concept floor plan creates an inviting atmosphere for gathering and entertaining, while the fully equipped kitchen serves as the heart of the home. One of the property's standout features is its premium location with no rear neighbors, backing to tranquil green space that provides added privacy and peaceful views. Ample parking further enhances convenience for owners and guests alike. Step outside to your private screened pool and spa, the perfect place to relax after a day spent exploring Walt Disney World, Universal Orlando Resort, shopping, dining, and entertainment destinations nearby. Owners and guests enjoy complimentary access to Windsor at Westside’s outstanding resort amenities, including a resort-style pool, clubhouse, fitness center, sports courts, and recreation areas designed for endless family fun. Whether you're searching for a vacation home, investment property, or personal Florida getaway, this beautifully maintained residence offers the ideal combination of space, privacy, and resort-style living.

1809 Nice Court, Kissimmee
$589,000
7 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just minutes from Walt Disney World and Central Florida’s top attractions. Designed for comfort, relaxation, and entertaining, this spacious villa is ideal for large families, vacation groups, or short-term rental investment opportunities. The home features an inviting open-concept layout with generous living spaces on both levels, providing plenty of room for everyone to gather and unwind. The upstairs loft offers an additional entertainment area complete with a large TV, comfortable seating, and ample space for movie nights or game days. Step outside to your private west-facing screened lanai where you can enjoy sunny Florida afternoons by the sparkling pool and spa, lounge poolside, or relax under the covered patio while taking in peaceful views. The equipped kitchen includes a breakfast bar, abundant cabinetry, and things needed for meal preparation. Bedroom accommodations include: First-floor primary suite with king bed and private ensuite bath Additional half bath on the main floor Second-floor king suite with ensuite bath Second-floor queen suite with ensuite bath One queen bedroom Two bedrooms with twin beds One bunk room featuring a twin-over-full bunk bed Shared full bathrooms conveniently located between secondary bedrooms All bedrooms include TVs and generous storage space Residents and guests of Windsor at Westside enjoy access to outstanding resort-style amenities, including a lazy river, water slide, resort pool, tiki bar, clubhouse, fitness center, arcade, sports courts, and hot tubs. Conveniently located near Disney World, Universal Studios, SeaWorld, championship golf courses, shopping outlets, dining, and entertainment. Measurements are approximate and should be independently verified. Some furniture has been updated

1744 Lima Avenue, Kissimmee
$655,000
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.

1844 Gobi Drive, Kissimmee
$689,000
8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Enjoy breathtaking pond views and exceptional backyard privacy in this stunning 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. This fully furnished residence offers the perfect blend of luxury, comfort, and investment potential, ideal as a vacation retreat or a high-performing short-term rental. The spacious open-concept floor plan features expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites—one conveniently located on each floor for added flexibility. Step outside to your private screened-in pool and spa, where the wide-open pond view creates a peaceful and relaxing setting with no rear neighbors. Inside, the home is tastefully designed with stylish furnishings and quality finishes, creating an inviting space that appeals to a wide range of vacation guests. Residents and guests enjoy access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. The HOA conveniently includes cable, internet, lawn care, and valet trash service. Perfectly located just minutes from Disney, shopping, dining, and major highways, this turn-key property is truly move-in or rental ready — a rare opportunity you don’t want to miss!

8815 Macapa Drive, Kissimmee
$450,000
5 Beds ⋅ 4 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. There is a master bedroom on the first floor and upstairs you’ll find another spacious master bedroom and additional bedrooms for privacy and comfort. Residents can enjoy world-class resort amenities, including an 8,000 sq. ft. clubhouse, heated pool, lazy river, spa, volleyball and basketball courts, and on-site restaurant and bar. The home is just minutes from Disney Parks and other Orlando attractions.

1869 Nice Court, Kissimmee
$735,000
9 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Beautiful 9-bedroom,6-bathroom water-front pool home in the highly sought-after Windsor at Westside resort community. Situated on a premium lot with stunning water view, this fully furnished property is perfect as a luxury vacation retreat or a high-performing short-term rental investment. The spacious open-concept layout offers expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites, one on each floor. Enjoy the Florida lifestyle with your private screened-in pool and hot tub overlooking the pond. This home has been thoughtfully upgraded to enhance the guest experience, including newly installed: *Luxury vinyl plank flooring throughout (no carpet)*, all bedrooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests! Resort-style amenities include a 10,000 sq. ft. clubhouse, resort pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. HOA includes cable, internet, lawn care, and valet trash service. Conveniently located just minutes from Disney, shopping, dining, and major highways. This turn-key property is move-in or rental ready—an opportunity you don’t want to miss!

8811 Macapa Drive, Kissimmee
$510,000
6 Beds ⋅ 5 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Fully Furnished Pool and Spa Home. A fantastic choice to be your Vacation Home or Rental Property in the Windsor at Westside Resort! 6 Bedrooms - 4.5 Bathrooms and a Gorgeous Loft. Private Heated Pool and Spa with a great view from your pool deck area. As you step inside, you are greeted by a foyer and entrance high ceiling. The main level features a master bedroom with a bathroom that connects to the pool area, perfect for accommodating guests. A conveniently located half bathroom adds to the overall functionality of this level. Continuing on, you'll discover a spacious and open-concept living area that seamlessly connects the family room, dining area, and kitchen. The kitchen is equipped with stainless steel appliances, abundant counter space, and a breakfast bar, making it a central hub for culinary adventures and social gatherings. Upstairs you will find the large loft with TV, coach and a nice bar table, 1 more en-suite (second master bedroom) and 4 more bedrooms (2 of them Themed Bedrooms) sharing two more bathrooms. This home features a heated private pool/spa, a large covered Lanai with patio furniture and sun loungers, tile roof and furnished. The Windsor at Westside Resort is a Gated Community with a great Clubhouse for vacationers, and features amenities including a lazy river, splash pool, bar, gym, game room and more. This is a great vacation home, very close to other area attractions. Schedule your visit NOW. Stunning Home.

1921 Nice Court, Kissimmee
$749,000
9 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2a SubDv. ⋅ 34747 Zip Code
Luxury Villa – “Lord of the Manor” – Minutes from Disney Experience elevated comfort and themed luxury at “Lord of the Manor,” a fully renovated 9-bedroom, 6-bathroom villa located just 8 miles from Disney. Designed with both style and function in mind, this spacious property features five king bedrooms, two large living areas, and a dedicated game room with Xbox, air hockey, foosball, and shuffleboard. Unwind in the private pool and spa, or enjoy a movie night in the custom-built theater room. This pet-friendly home has generous gathering spaces and thoughtful amenities throughout, accommodating both relaxation and entertainment with ease. Located just a five-minute walk from the Windsor at Westside Clubhouse, guests have access to premium community amenities including a zero-entry resort pool, waterslide, lazy river,’ splash zone, tiki bar, sand volleyball court, arcade, and more. Additional highlights: Private pool and spa Custom home theater Access to resort clubhouse amenities “Lord of the Manor” is move-in ready and designed for those seeking a high-comfort, high-style getaway experience in the heart of Central Florida.

1940 Nice Court, Kissimmee
Start Your Search