Windermere Homes with 55+ Only

Welcome to Windermere, a charming town nestled in Orange County, Florida. With its picturesque landscapes and serene atmosphere, Windermere is a sought-after destination for those looking to settle down in a peaceful community.

One unique aspect of Windermere is its abundance of homes exclusively for those aged 55 and above. If you're seeking a place where you can enjoy your golden years surrounded by like-minded individuals, Windermere is the perfect choice. With a range of housing options tailored to the needs of older adults, you can find a home that suits your lifestyle and preferences.

Living in a 55+ community in Windermere offers numerous advantages. These neighborhoods often feature amenities such as fitness centers, swimming pools, and social clubs, providing opportunities for active and engaging lifestyles. Additionally, the sense of community and camaraderie among residents in these communities is unparalleled, fostering lasting friendships and a supportive environment.

Windermere itself offers a wealth of recreational activities, including golf courses, parks, and nature trails. The town's proximity to Orlando's vibrant entertainment scene allows residents to easily access world-class dining, shopping, and cultural attractions. Whether you prefer a quiet day by the lake or an adventurous outing to a theme park, Windermere has something for everyone.

If you're ready to embrace the joys of 55+ living in a serene and welcoming community, Windermere should be at the top of your list. Explore the available homes and discover the perfect place to call home in this idyllic corner of Florida.

Newest Windermere Homes with 55+ Only

$3,599,000

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 home offers an incredible opportunity for homeowners, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities. Recent Upgrades & Features: Brand New Kitchen (March 2026): Fully updated with modern flooring, custom cabinetry, and 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, this home is truly move-in ready.

9011 Chapman Oak Court, Windermere

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