Skip to content
Editorial illustration of a Central Florida residential street lined with single-story stucco homes, palms, trimmed shrubs and landscaped lawns.

55+ living in Kissimmee

Four Seasons at Orlando homes for sale and 55+ community guide

View Four Seasons at Orlando homes for sale. Compare villas, detached homes and maintenance needs to focus your shortlist.

Browse Four Seasons at Orlando properties by price

Search price ranges within this area while keeping the property criteria for this page.

Four Seasons at Orlando area-wide market snapshot

All property types in this area. Inventory and asking prices are area-wide; the property searches above may use narrower criteria.

For sale now
20
Median asking price
$452,500

Recent sales near Four Seasons at Orlando

46 properties sold within half a mile in the last 12 months · median $386,000

Homes and ownership choices

We help you compare Four Seasons at Orlando homes for sale across villas and detached houses in this Kissimmee 55+ community. We assess the actual floor plan, outdoor space and lot setting alongside maintenance responsibilities and the recreation you want to use. Historical builder designs provide context, while the property's current condition and terms guide your purchase comparison.

A closer look at the community amenities

These facilities describe ways to enjoy community life, not a measure of any home’s value. Check current access and operations for amenities you plan to use.

  • Clubhouse

    The documented clubhouse brings several shared indoor spaces together.

  • Pool and spa

    A pool and spa are part of the documented amenity campus.

  • Fitness center

    The clubhouse plans include a fitness center for owners interested in an on-site workout space.

  • Craft and gathering spaces

    A craft room and ballroom provide documented spaces for hobbies and gatherings.

  • Outdoor courts

    The amenity plans show bocce, pickleball and tennis courts.

  • Café and bar spaces

    Café and bar spaces are documented, but current food and beverage service is not established.

Kissimmee location and neighboring golf

Four Seasons at Orlando sits in Kissimmee, in Osceola County, beside Mystic Dunes Golf Club. That setting may appeal if you enjoy having a golf course nearby, but Mystic Dunes is a public course with its own playing and membership arrangements. Buying a home next door does not establish that golf is included in community ownership. Think about the location in terms of the trips and activities that matter to you, and check the arrangements for any course access you expect to use.

Check the current occupancy documents

K. Hovnanian’s published terms for its Four Seasons homes call for at least one occupant aged 55 or older and no permanent resident under 19. Those terms are a useful starting point, but the community’s current recorded declaration and any amendments govern the details you need for a purchase. Ask the homeowners association for those documents before making plans for other household members or guests. Do not assume that a general age-restricted housing provision creates an exception for your household.

HOA, club and district costs

Four Seasons at Orlando has a homeowners association, and the community lies within the Windward Community Development District. The district’s adopted FY2027 budget separates operating assessments from debt-service funds, but a district-wide budget cannot tell you what a particular home owes. Request the association’s current budget and fee schedule, find out which services dues cover, and ask whether any club charges apply. For a home you are considering, review its address-specific district assessment and property tax record rather than relying on a community-wide estimate.

Top Villas Intelligence

Know what a home will earn before you buy

Create a free account to see projected rental revenue, ownership costs and operating yield on every eligible listing.

Sample: $118,400 gross rental revenue at 74% projected occupancy, $61,900 operating income and a 7.2% operating yield, with high confidence.

What to weigh as an owner

May suit you if

  • A documented clubhouse and recreation campus offer places to exercise, spend time outdoors and gather with neighbors.
  • Mystic Dunes Golf Club is next to the community and offers public playing arrangements.
  • The published 55+ occupancy terms describe a residential setting for buyers seeking an age-restricted community.

Check before deciding

  • Shared amenities sit alongside association dues and address-specific district assessments; check any applicable club charges too.
  • Golf playing or membership arrangements are separate from owning a home in the community.
  • Review the current recorded occupancy documents against your household and guest plans.

New construction or resale?

A historical builder inventory sheet confirms that new homes were marketed at Four Seasons at Orlando, not that any remain available. If you are considering a new home, establish current builder availability and examine the proposed home and its applicable documents. For a resale, pay particular attention to condition, layout, lot position and any work you would want to undertake. Neither route should be judged by the older inventory sheet’s offerings or prices. Compare actual properties and their ownership terms before deciding which better fits your plans.

Verify rental rules before planning any letting

If you might let a home when you are not using it, establish the rules before you buy. The current rental restrictions for Four Seasons at Orlando have not been verified, and neither the community’s amenities nor its Kissimmee location establishes permission for short-term stays. Request the association’s current declaration, amendments and applicable rental policies, then check how they apply to the particular property and your intended use. Make the decision on documented rules, not on assumptions drawn from other communities.

Four Seasons at Orlando FAQs: location, homes and community life

Four Seasons at Orlando FAQs: costs and buying decisions

Explore other 55+ communities

If you are still deciding which setting fits, our Florida and Orlando 55+ community guides can help you organize a broader search. The Villages, Trilogy Orlando, Solivita, Del Webb Oasis in Winter Garden and Del Webb Sunbridge are other names you may want to investigate. Compare each community on its own location, home choices, current documents and ownership costs rather than assuming its amenities or rules match Four Seasons at Orlando. Narrowing down what matters most to you will make individual property comparisons more useful.

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find Four Seasons at Orlando homes for sale with Gaby

Tell me your budget and plans for the home. I'll help you compare Four Seasons at Orlando homes for sale, weigh villas, detached homes and maintenance needs, and identify the details to resolve before you choose.

Find a home that fits your plans

If Four Seasons at Orlando interests you, ask us to help you identify the documents and property details worth checking before you decide. We can help you frame questions about occupancy, association costs and a particular home’s condition. This page does not provide a live search filtered to Four Seasons at Orlando, so general search results should not be read as confirmed community matches. Explore properties for sale, then verify the location and governing documents of any home that catches your eye.

Browse homes for sale