55+ Communities for Sale in 34786

Browse All 55+ Active Adult Homes for Sale in 34786 Windermere FL

5 Beds ⋅ 7 Baths ⋅ Casabella Ph 2 SubDv. ⋅ 34786 Zip Code

EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere, where elegant architecture, exceptional outdoor living, and one of the community’s most desirable lots come together. The true highlight of this property is its exceptional waterfront setting. The lake beautifully surrounds the rear of the home, pool, and outdoor living areas, creating a rare sense of privacy and tranquility. From the expansive covered lanai and upper-level balcony, enjoy breathtaking water views and a peaceful backdrop that makes this property truly special. Featuring two spacious levels and soaring ceilings, this magnificent home offers approximately 5,073 square feet of luxurious living space with 5 bedrooms, all featuring private en-suite bathrooms and walk-in closets. The primary suite is conveniently located on the first floor and offers a spa-inspired bathroom, large windows, and a serene connection to the outdoor surroundings. The gourmet kitchen combines functionality and elegance with modern wood cabinetry, stainless steel appliances, and generous counter space, creating an inviting space for both everyday living and entertaining. The open living areas feature impressive proportions and abundant natural light, perfectly complementing the home's sophisticated Mediterranean-inspired architecture. Step outside to your private resort-style retreat. The expansive outdoor living area features a private pool, heated spa, and spacious gourmet summer kitchen, creating the perfect setting for entertaining guests or enjoying relaxing evenings overlooking the lake. From the elegant façade and impressive two-story design to the spectacular waterfront setting and exceptional outdoor living spaces, this residence offers a rare combination of luxury, privacy, and breathtaking views. Located in Casabella at Windermere, a prestigious gated community known for its spacious homesites and elegant residences, the property is conveniently located near premier shopping, dining, top-rated schools, major roadways, and Orlando’s world-famous attractions. A truly remarkable opportunity to own a one-of-a-kind luxury estate in one of Windermere’s most desirable communities.

3986 Isabella Circle, Windermere

$584,900

4 Beds ⋅ 2 Baths ⋅ Silver Woods Ph 05 SubDv. ⋅ 34786 Zip Code

Windermere Gem: Updated & Move-In Ready! Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully updated home offers an incredible opportunity for homeowners and investors alike, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities. This property has been meticulously maintained, featuring an extensive list of recent high-value upgrades: Recent Upgrades & Features: Brand New Kitchen (March 2026): Fully updated with modern flooring, custom cabinetry, and premium appliances. Comprehensive Pool Refresh (2026): Newly resurfaced pool and deck (Feb 2026), plus a brand-new pool pump and filter (March 2026). New Roof: Installed August 2024. Septic System: Installed January 2018. AC System: Installed 2017. Full House Re-pipe: Completed August 2016. Additional Features: Pool rescreened (2019) and nearby access to community tennis courts. Whether you're looking for a stylish family residence or a high-performing investment property, this home is truly move-in ready.

9011 Chapman Oak Court, Windermere

Start Your Search

34786 has a handful of active 55+ listings on the market at any given time, so inventory here is thin and the good ones move quickly. They run from $584,900 to $899,999, with a median around $742,449. The typical one is about 2,154 square feet with 3 bedrooms. The list below is pulled live from the MLS, so it is current even when this write-up is not.

34786 55+ communities at a glance

Active 55+ listings	a handful
Median list price	$742,449
Price range	$584,900 to $899,999
Median size	2,154 sq ft
Median bedrooms	3
Median year built	1987
Median days on market	82

55+ does not mean everyone has to be 55

This is the part most buyers get wrong. Age restricted communities operate under a federal exemption to the Fair Housing Act, and the exemption has a specific shape.

55+ community	At least 80% of occupied units must have one resident aged 55 or older. The remaining 20% is up to the community, which is how a younger spouse, an adult child, or a caregiver can often live there legally.
62+ community	Every resident must be 62 or older. No 20% allowance. These are far less common and the rule is much harder to work around.
Age restriction on paper only	Some communities market themselves as active adult without being registered under the federal exemption. The marketing and the recorded documents do not always agree.

The MLS carries a single flag for this. The binding rule is in the recorded declaration and the community bylaws, and it is the recorded documents that decide who can live there, who can inherit, and whether the home can be rented. Read them before you write, not after.

34786 55+ homes by price range

$500k-$750k	1
$750k-$1M	1

What to check before you write an offer

What the recorded declaration actually requires, 55+ or 62+, and what the community does with its 20% allowance
Whether a spouse, adult child, or caregiver under the age limit can live there
What the amenity and recreation fees cover, and whether they are separate from any community dues
Rental and occupancy limits, which are usually tighter in age restricted communities
What happens to the age requirement when the home passes to an heir
Whether the community is deed restricted, land leased, or a co-op, because the three finance very differently

Want any of these verified on a specific community? Call or text 407-616-9019 and we will pull the recorded documents.

Frequently asked questions

How many 55+ homes are for sale in 34786?

There are a handful active at any given time. The list on this page comes straight from the MLS and updates on its own.

What do 55+ homes cost in 34786?

The median list price is around $742,449, with the range running $584,900 to $899,999.

Does everyone in a 55+ community have to be 55?

No. Under the federal exemption at least 80% of occupied units need one resident 55 or older, and the community decides what it does with the other 20%. A 62+ community is different - there every resident must meet the age. The recorded documents control, not the listing.

Can a younger spouse live in a 55+ community?

Usually yes in a 55+ community, subject to that community's own rule on the 20% allowance and its minimum age for a second occupant. In a 62+ community, generally no. Check the declaration before you write.

Can you show me 55+ homes in 34786?

Yes. Call or text 407-616-9019 and we will set up showings.