Both communities are within 20 minutes of Disney World. Both are gated 55+. Both are currently active. But Four Seasons is a 557-home boutique K. Hovnanian community in Kissimmee, and Del Webb Oasis is a resort-scale Del Webb in Winter Garden. The overlap in marketing language conceals a substantial difference in what these communities actually are.
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Talk to a Specialist →Four Seasons at Orlando is a 557-home K. Hovnanian 55+ community in Kissimmee, Osceola County, embedded within the Mystic Dunes Resort complex. Golf cart access to Mystic Dunes Golf Club is the signature feature. The 12,000 sq ft clubhouse is modest by Del Webb standards. The community is intimate by design — residents typically know most of their neighbors within the first year.
Del Webb Oasis is a large-scale Del Webb 55+ resort community in Winter Garden, Orange County, built along the western approach to Disney via SR-429. The 27,000+ sq ft Esplanade Club amenity center, resort pools, pickleball complex, and full social programming infrastructure represent the Del Webb premium product. At planned buildout of 3,200+ homes, Oasis will be among the largest 55+ communities in the Orlando metro.
| Cost Variable | Four Seasons at Orlando | Del Webb Oasis |
|---|---|---|
| Home Price Range | $350K–$650K | $420K–$800K+ |
| HOA Fee | ~$265/month | ~$310–$355/month |
| County Tax Rate | Osceola 0.93% | Orange 0.87% |
| Tax on $480K Home (after homestead) | ~$3,900/yr (~$325/mo) | ~$3,655/yr (~$305/mo) |
| Golf | Golf cart to Mystic Dunes — separate membership | No on-site golf |
| CDD | Verify per parcel | Active — verify before closing |
| Community Scale | 557 homes (complete) | 3,200+ homes (active build) |
| Est. All-In Monthly (excl. CDD) | ~$800–$850/month | ~$870–$950/month |
Orange County's 0.87% rate beats Osceola's 0.93%. On a $480K home, Orange County saves approximately $288/year before exemptions compared to Osceola. Over 20 years that is $5,760. Del Webb Oasis's higher HOA partially offsets this, but the county tax advantage is structural and permanent. It is one concrete financial argument in Oasis's favor that most comparisons overlook.
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Choose Four Seasons at Orlando if: You want boutique scale and a community where you will know your neighbors. You play golf and the Mystic Dunes access has genuine value for your lifestyle. You prefer K. Hovnanian's traditional floor plan style. The Kissimmee location works for your daily life pattern. Budget sensitivity makes the lower entry price and HOA meaningful.
Choose Del Webb Oasis if: You want the Del Webb brand, scale, and social infrastructure. A 27,000+ sq ft amenity center with full resort programming matters to you. You are comparing communities based on the depth and quality of amenity investment. The western Orange County location and SR-429 Disney access works better for your geographic needs. You are comfortable with an active-construction community that will evolve over the next 5–8 years.
Del Webb Oasis is still actively building. Buyers in early phases are purchasing into a community that will look substantially different in 5 years. The amenity center may not be complete, landscaping is immature, and neighbors are all newcomers simultaneously. This is a preference variable, not a flaw — but it is different from buying into the established Four Seasons community where the culture and neighbor relationships are already formed.
| Four Seasons at Orlando | Del Webb Oasis | |
|---|---|---|
| Walt Disney World | ~15 min (US-192) | ~15–20 min (SR-429) |
| Orlando International Airport | ~35 min | ~30 min via FL-417/SR-429 |
| AdventHealth Kissimmee | ~20 min | ~25 min |
| AdventHealth Winter Garden | ~35 min | ~10 min |
| Downtown Orlando | ~40 min I-4 | ~25 min SR-429/I-4 |
Del Webb Oasis has a meaningful location advantage for everyday Orlando-area access — closer to downtown Orlando, AdventHealth Winter Garden, and airport access via the western beltway. Four Seasons has marginally better Disney proximity and the Kissimmee-corridor infrastructure for daily errands.
We can run the full all-in cost comparison for your specific budget and help you figure out which community's trade-offs align with how you actually plan to retire.
Connect with a specialist who knows this market from the inside — real cost math, honest community comparisons, and what's actually happening right now. Every agent is personally vetted by the Nova55Living founder.
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