Windsor at Westside

Q: What is the HOA fee for Windsor at Westside?

Please contact Florida Neighborhood Realty for the current HOA fee, payment schedule, and HOA management company contact information. Windsor at Westside's HOA is managed by Castle Group and has historically included lawn and yard maintenance, cable and internet, and daily valet trash removal in addition to security and amenity maintenance.

Q: Is there a CDD fee in Windsor at Westside?

CDD assessments in the 34747 corridor can be complex. Buyers should verify current CDD status for any specific Windsor at Westside property before purchasing. Contact Florida Neighborhood Realty for current CDD information on any specific property.

Q: What floor plans are available in Windsor at Westside?

Townhome plans include the Watermarke (2,102 sq ft) and Castaway (2,263 sq ft) with 4-5 bedrooms. Single-family plans range from the Winstone (5 bed, 2,490 sq ft) to the Clearwater (9 bed, 4,382 sq ft). Every unit includes a private heated screened pool.

About Windsor at Westside Neighborhood

Windsor at Westside is a 592-home, guard-gated resort community located in Kissimmee's 34747 zip code, developed by Pulte Homes beginning in 2015. The community's model center opened at 2105 Malta Terrace off Monaco Boulevard, south of US-192 on the Westside Boulevard and Florence Villa Grove Road corridor. With phases completed through 2019, Windsor at Westside stands as one of the largest and most feature-complete resort communities on Kissimmee's western edge — and one of the highest-profile investments in Pulte's Central Florida vacation portfolio.

The community is divided into townhomes and single-family pool homes with a broad selection of floor plans. The 96 townhomes span two plans — the Watermarke at 2,102 sq ft and the Castaway at 2,263 sq ft — configured with 4–5 bedrooms and 4–4.5 bathrooms, each with a private heated pool and enclosed courtyard area. The 496 single-family homes range from 5-bedroom Winstone plans at 2,490 sq ft up to 9-bedroom Clearwater estates at 4,382 sq ft, covering everything between the Hideaway (6 bed, 3,117 sq ft) and Baymont (8 bed, 4,032 sq ft) configurations. Every home — townhome and single-family alike — comes with a private heated screened pool, paver driveway, barrel tile roof, stainless steel appliances, and granite finishes throughout kitchen and bathrooms.

The physical heart of Windsor at Westside is the 10,000+ sq ft Mediterranean-themed Clubhouse at the community's south end, overlooking a man-made lake where homeowners can fish, kayak, and enjoy sunset views from the community pier. The clubhouse integrates seamlessly with the resort's outdoor waterpark, featuring a zero-entry resort-style pool, waterslide, lazy river, hot tub, and kids' water playground. Inside, the Tu Casa Bar & Lounge serves food and drinks poolside, supported by a full service bar with liquor, beer, wine, and frozen favorites. A state-of-the-art fitness center, video arcade and game room, sundry shop, kids' activity center, and cyber café round out the on-site amenity roster.

Windsor at Westside is fully zoned for short-term vacation rental use, and the vast majority of its homes operate as vacation properties on platforms serving the Disney-area travel market. The HOA, managed by Castle Group, includes lawn and yard maintenance services, cable and internet services, and daily valet trash removal — making the vacation rental management burden significantly lighter for owners. 24-hour guard-gated security ensures the community maintains the quality standards and guest experience expected of a premier Disney-area resort.

📊 Quick Facts

Property Style(s):Townhomes and Single-Family Pool Homes

Home Sizes:2,102–4,382 sq ft (townhomes: 2,102–2,263 sq ft; SFH: 2,490–4,382 sq ft)

Bedrooms:4–5 bedrooms (townhomes); 5–9 bedrooms (SFH)

Year Built:2015–2019 (Pulte Homes)

Total Homes:592 (496 single-family / 96 townhomes)

HOA Fee:Contact us for current fee

CDD Fee:Verify — see our CDD guide

Short-Term Rental:Yes — fully eligible

Distance to Disney:~3.5 miles / 10-min drive via SR-429

🏠 Home Features — Standard Throughout Community

Private heated screened pool on every home and townhome
Barrel tile roof and paver driveway standard
Stainless steel appliances throughout
Granite countertops in kitchen and all bathrooms
Tile showers and premium cabinetry
Open-concept floor plans with large islands and breakfast bars
Generous master suites and walk-in closets
In-unit washer/dryer (most units)
Many garages converted to game rooms or home theaters by owners
Water views or conservation views on select lots

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Windsor at Westside Location & Connections

Windsor at Westside is located in western Kissimmee along the Monaco Boulevard and Florence Villa Grove Road corridor, south of US-192 (W. Irlo Bronson Memorial Hwy) and east of Westside Boulevard. The community's primary entrance provides direct access to SR-429 (Daniel Webster Western Beltway), which is the express route to Walt Disney World's resort entrances approximately 3.5 miles away. The community is bounded by conservation land to its south and west, a community lake and pier at its southern end, and neighboring resort communities along its northern and eastern edges.

The surrounding Westside corridor encompasses some of Central Florida's most recognized resort communities, making Windsor at Westside a natural centerpiece of the vacation-home investment landscape. Direct neighbors include Solara Resort, Murano at Westside, Magnolia at Westside, and Happy Trails.

🏘️ Adjacent Neighborhoods & Areas

Solara Resort — neighboring resort community with waterpark complex
Murano at Westside — modern Westside corridor community to the north
Magnolia at Westside — neighboring residential Westside community
Happy Trails — established Westside corridor neighborhood
Community lake and pier + conservation land — natural southern and western borders

🚗 Detailed Commute Times

Walt Disney World: Approx. 10 minutes (3.5 miles via SR-429)
Universal Orlando: Approx. 30–35 minutes (22–25 miles)
SeaWorld Orlando: Approx. 25 minutes (18 miles)
Disney Springs: Approx. 12–15 minutes (10 miles)
Downtown Orlando: Approx. 35–40 minutes (28 miles)
Lake Nona Medical City: Approx. 35–40 minutes (27 miles)
Cocoa Beach: Approx. 65–75 minutes (63 miles)
UCF Campus: Approx. 40–45 minutes (33 miles)
International Drive: Approx. 20–25 minutes (16 miles)

✈️ Airport Access

Orlando International Airport (MCO): Approx. 30 minutes (25 miles)
Kissimmee Gateway Airport (ISM): Approx. 20 minutes (15 miles)
Orlando Sanford International Airport (SFB): Approx. 55–60 minutes (48 miles)

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Windsor at Westside Amenities & Lifestyle

Windsor at Westside is built around one of the most complete resort amenity packages in the Kissimmee market — a 10,000+ sq ft Mediterranean-themed clubhouse that functions as a genuine resort hub for guests and residents alike. The amenity infrastructure has been deliberately designed to support vacation rental income generation, keeping guests on-property and engaged between theme park visits.

For full-time residents and second-home owners, the community delivers a true resort lifestyle every day of the year. The man-made lake at the community's southern end — accessible from a community pier — adds a distinctly Central Florida waterfront quality to everyday life. The community's HOA manages lawn care, cable, internet, and daily valet trash removal, reducing the maintenance burden on owners and freeing time for genuine enjoyment of the resort amenities.

🏊 Neighborhood Amenities

Amenities found within Windsor at Westside:

10,000+ sq ft Mediterranean-themed Clubhouse with full resort infrastructure
Zero-entry resort-style pool with waterslide, lazy river, hot tub, and kids' water playground
Tu Casa Bar & Lounge — poolside dining with full bar service, food menu, and frozen drinks
State-of-the-art fitness center
Video arcade and game room
Kids' activity center
Sundry shop and cyber café
Community lake with pier for fishing and relaxation
Multi-purpose sports courts (volleyball, basketball, soccer fields)
24-hour guard-gated entry with security
Private heated pools on every home and townhome
HOA-managed lawn and yard maintenance, cable, internet, daily trash valet

🛍️ Shopping & Services

The US-192 corridor immediately north of Windsor at Westside provides comprehensive shopping access — grocery anchors, Target, pharmacy options, and a wide array of national retailers. Outlet shopping is accessible at the Orlando Vineland Premium Outlets and Lake Buena Vista Factory Stores, both within 10–15 minutes. Explore full options at The Loop on John Young Parkway for a broader shopping experience.

For comprehensive shopping information: View our Kissimmee Shopping Guide →

🍽️ Restaurants

Windsor at Westside's own Tu Casa Bar & Lounge provides on-site dining at the clubhouse, but the US-192 corridor outside the gates offers one of the densest dining concentrations in Osceola County — from dinner shows and themed restaurants to Latin cuisine, casual chains, and family dining. Discover Kissimmee's dinner shows and entertainment dining, or explore the city's vibrant Latin cuisine restaurant scene.

For comprehensive restaurant information: View our Kissimmee Restaurants & Dining Guide →

🎭 Arts & Culture

Kissimmee's cultural identity stretches far beyond the resort corridor. Osceola Arts in downtown Kissimmee presents professional live theater, music, and comedy for residents seeking cultural programming. The history of Old Florida is preserved at Pioneer Village at Shingle Creek, and Old Town Kissimmee delivers classic car shows and retro entertainment along the US-192 entertainment corridor.

For comprehensive arts & culture information: View our Kissimmee Arts & Culture Guide →

🏃 Health & Wellness

Windsor at Westside's on-site fitness center serves immediate wellness needs, while the broader Kissimmee area supports residents with major healthcare systems including AdventHealth and HCA Florida Osceola Hospital. Urgent care centers along US-192 provide convenient walk-in access for guests and residents. Learn more about healthcare options in our guide to AdventHealth Kissimmee.

For comprehensive health & wellness information: View our Kissimmee Health & Wellness Guide →

🌳 Parks & Recreation

The community lake and pier provide on-site outdoor recreation for Windsor at Westside residents. Beyond the gates, Shingle Creek Regional Park offers kayaking, hiking, and wildlife observation along the headwaters of the Everglades system. Kissimmee Lakefront Park on Lake Tohopekaliga anchors the downtown waterfront with walking paths, splash pads, and Big Toho Marina access.

For comprehensive parks & recreation information: View our Kissimmee Parks & Recreation Guide →

⚽ Sports & Athletics

Windsor at Westside's multi-purpose sports courts, volleyball courts, and soccer fields provide on-site athletic options. The area's golf options include Falcon's Fire and Oaks National public courses. The Bob Makinson Aquatic Center provides competitive swimming facilities for Osceola County residents.

For comprehensive sports & athletics information: View our Kissimmee Sports & Athletics Guide →

🎉 Fun Things to Do

Windsor at Westside's location delivers unmatched proximity to Central Florida's top entertainment: Walt Disney World is 10 minutes away, Universal Orlando is about 30 minutes, and SeaWorld Orlando is 25 minutes. Disney Springs offers dining, shopping, and entertainment without a park ticket. Locally, Gatorland remains one of Florida's most beloved independent attractions, and Old Town Kissimmee brings classic car culture and family entertainment to the US-192 corridor.

For comprehensive events & activities information: View our Kissimmee Entertainment Guide →

🎓 Schools

Windsor at Westside is served by Osceola County Public Schools. Verify current zoning with the district before purchasing.

Elementary/K-8: Westside K-8 School (verify current assignment)
High: Celebration High School or Tohopekaliga High School (verify current assignment)

⚠️ Publisher note: Osceola County school assignments — especially high school zoning in the western Kissimmee corridor — change frequently. Verify current zoning directly with the Osceola County School District before publishing and before buyer reliance.

For comprehensive school information: View our Kissimmee Schools & Education Guide →

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How Windsor at Westside Compares

Among the major resort communities in Kissimmee's Westside corridor, Windsor at Westside occupies a distinctive position: it is the largest Pulte-built vacation resort in the area, carries the Windsor brand recognition that has driven strong rental demand across Windsor Hills and Windsor Palms, and delivers the most comprehensive on-site amenity package in the corridor outside of newer builds like Solara Resort.

The community's combination of scale, Pulte construction quality, HOA-managed maintenance services, and Disney proximity has positioned Windsor at Westside as one of the top-performing short-term rental communities in Osceola County — consistently cited alongside Windsor Hills and Storey Lake as a benchmark for vacation home investment in the greater Orlando area.

Feature	Windsor at Westside	Windsor Hills	Solara Resort
Builder	Pulte Homes	Pulte Homes	Mattamy Homes
Year Built	2015–2019	2000–2008	2018–present
Total Homes	592	~395	~400+
Home Range	4–9 bedrooms	3–9 bedrooms	4–9 bedrooms
Clubhouse	10,000+ sq ft	Resort waterpark	Large waterpark
Community Lake	Yes — with pier	No	No
Distance to Disney	~3.5 mi / 10 min	~4.5 mi / 12 min	~4 mi / 12 min
HOA Includes	Lawn, cable, internet, trash valet	Basic common area	Varies by phase

💡 Value Proposition: Windsor at Westside delivers the most comprehensive HOA-included services package of any major resort community in the Westside corridor — combining Pulte build quality, 10,000+ sq ft resort amenities, a community lake and pier, and Disney proximity that makes it one of the strongest performing vacation rental communities in Kissimmee.

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Windsor at Westside HOA & CDD Information

Windsor at Westside is managed by Castle Group on behalf of the community's HOA. The HOA structure is notably comprehensive by resort-community standards: HOA fees at Windsor at Westside historically have included lawn and yard maintenance, cable and internet services, and daily valet trash removal — services that significantly reduce the operational burden on vacation rental owners and resident homeowners alike.

The 24-hour guard-gated security, resort amenity maintenance (pool, clubhouse, fitness center), and community management are all covered through the HOA structure. For specific current fee amounts, payment schedules, and any outstanding or anticipated special assessments, please contact us directly — fees and management details change and we verify current information before buyer reliance.

Regarding CDD (Community Development District) fees: buyers should verify the current CDD status for Windsor at Westside before purchase, as resort communities in the 34747 corridor can have overlapping district assessments. Our team can provide current CDD information for any specific property.

💰 HOA Fees & Management Contact

HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company (Castle Group). We can also check for you to see if there are any current or upcoming special assessments.

📋 What HOA Fees Historically Include

24-hour guard-gated security and access management
Lawn and yard maintenance services (historically included)
Cable and internet services (historically included)
Daily valet trash removal (historically included)
Resort amenity maintenance — pool complex, clubhouse, fitness center
Common area landscaping and grounds maintenance
Community insurance for shared structures
Reserve fund contributions

Note: HOA fee inclusions and amounts change. Always verify current scope and cost with the management company before purchase.

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Frequently Asked Questions

What is the HOA fee for Windsor at Westside?

Please contact us for the current HOA fee, payment schedule, and HOA management company contact information. Windsor at Westside's HOA is managed by Castle Group and has historically included lawn and yard maintenance, cable and internet, and daily valet trash removal in addition to standard security and amenity maintenance coverage — making it one of the most comprehensive HOA packages in the Westside corridor.

Is there a CDD fee in Windsor at Westside?

CDD assessments in the 34747 corridor can be complex. Please verify current CDD status for any specific Windsor at Westside property with us before purchasing. Our CDD guide explains how these fees work and what to look for in Osceola County resort communities.

What schools serve Windsor at Westside?

Windsor at Westside is served by Osceola County Public Schools. The primary area school is Westside K-8, with high school zoning in the western corridor historically including Celebration High School and Tohopekaliga High School. Always verify current school assignments directly with the Osceola County School District — boundaries change and our Kissimmee schools guide provides broader district context.

Who built Windsor at Westside?

Windsor at Westside was built by Pulte Homes, beginning in 2015 with construction through approximately 2019. Pulte is the same builder behind Windsor Hills and Windsor Palms — two of Kissimmee's most recognized and best-performing vacation resort communities. Windsor at Westside represents Pulte's largest and most feature-complete resort in the Kissimmee market.

Can Windsor at Westside homes be used as short-term vacation rentals?

Yes. Windsor at Westside is fully zoned for short-term vacation rental use — owners may rent their properties for any duration at any time when they are not personally using them. The vast majority of homes in the community operate as vacation rentals serving the Disney-area travel market. The HOA's included lawn care, cable, internet, and valet trash services further simplify rental management for owners.

How far is Windsor at Westside from Walt Disney World?

Windsor at Westside is approximately 3.5 miles from the Walt Disney World resort boundaries — about a 10-minute drive via SR-429 (Daniel Webster Western Beltway). This is one of the closest residential resort community positions to the Walt Disney World main entrances available in Kissimmee, making it highly competitive for vacation rental demand from Disney-area visitors.

What floor plans are available in Windsor at Westside?

Townhome plans include the Watermarke (2,102 sq ft, 4–5 bed) and Castaway (2,263 sq ft, 4–5 bed). Single-family home plans include the Winstone (5 bed, 2,490 sq ft), Lakeshore (5 bed, 2,587 sq ft), Hideaway (6 bed, 3,117 sq ft), Seashore (7 bed, 3,281 sq ft), Baymont (8 bed, 4,032 sq ft), and Clearwater (9 bed, 4,382 sq ft). Every unit — townhome and single-family — includes a private heated screened pool. Many owners have converted garages to game rooms or home theaters, so resale homes often include additional recreation spaces beyond the standard floor plan.

Does Windsor at Westside have a community lake?

Yes. Windsor at Westside features a man-made community lake positioned at the southern end of the development, where the 10,000+ sq ft clubhouse and resort pool overlook the water. A community pier extends into the lake, providing a scenic spot for fishing, relaxation, and waterfront enjoyment. Homes facing the lake offer water views that add premium value to those lots within the community.