Windermere Homes with Maintenance Free Community Extras

Welcome to Windermere, a charming town located in Orange County, Florida. Known for its picturesque landscapes, pristine lakes, and upscale neighborhoods, Windermere offers a serene and luxurious lifestyle for its residents.

If you're looking for homes with maintenance-free community extras, Windermere has plenty to offer. Imagine coming home to a beautifully landscaped neighborhood where all your exterior maintenance tasks are taken care of, allowing you more time to relax and enjoy the Florida sunshine. From lawn care to exterior painting, these communities provide a hassle-free living experience for homeowners.

Whether you're a busy professional, a retiree looking to downsize, or a family seeking a convenient lifestyle, Windermere's homes with maintenance-free community extras are designed to cater to your needs. Enjoy amenities such as community pools, fitness centers, walking trails, and more, all within close proximity to your doorstep.

Experience the best of both worlds in Windermere - a tranquil retreat away from the hustle and bustle, yet with easy access to urban conveniences and attractions. Discover your dream home in Windermere's maintenance-free communities and start living the carefree lifestyle you deserve.

Newest Windermere Homes with Maintenance Free Community Extras

5186 Vardon Drive, Windermere $4,395,000

Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence ...

6 Beds
6 Baths
Isleworth SubDv.
34786 Zip Code

8608 Brookvale Drive, Windermere — 8 $379,900

LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic o...

3 Beds
3 Baths
Lakes/Windermere Lake Reams Twnh SubDv.
34786 Zip Code

Windy Ridge Road, Windermere $4,250,000 ▼

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 158 feet wide and one of four ...

34786 Zip Code

Windy Ridge Road, Windermere $5,250,000 ▲

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 215 feet wide and one of three...

34786 Zip Code

Windy Ridge Road, Windermere $4,750,000 ▲

Exceptional lakefront opportunity to build on one of the most coveted sites along The Butler Chain of Lakes. This prime and elevated lot is 175 feet wide and one of three...

34786 Zip Code

12914 Vennetta Way, Windermere — N/A $379,900 ▼

SELLER OFFERING $5000 FLEXIBLE CONCESSIONS- CAN BE APPLIED TOWARD CLOSING COSTS, RATE BUYDOWNS, PREPAIDS, OR PROPERTY ENHANCEMENTS. NEW ROOF TO BE INSTALLED WITIHIN UPCOM...

3 Beds
3 Baths
Lake Sawyer South Ph 03 SubDv.
34786 Zip Code

4205 Clarice Estates Drive, Windermere image

4205 Clarice Estates Drive, Windermere $2,450,000 ▼

Completely renovated in 2025. State-of-the-art showpiece located in the beautiful Estates at Lake Clarice. This updated residence offers an effortless blend of generous l...

4 Beds
5 Baths
Estates At Lake Clarice SubDv.
34786 Zip Code

7723 Fairgrove Avenue, Windermere — Na $380,000 ▼

Well maintained, move-in ready 3 bedrooms, 2.5 bathrooms townhouse in the Lake Sawyer South community in Windermere. The kitchen features a breakfast bar, granite counte...

3 Beds
3 Baths
Lake Sawyer South Ph 03 SubDv.
34786 Zip Code

1554 Lake Rhea Drive, Windermere $1,275,000 ▼

Price Improvement! Located behind the gates of the prestigious Reserve at Belmere in sought-after Windermere, this exceptional Mediterranean-inspired estate offers a rar...

4 Beds
3 Baths
Reserve At Belmere SubDv.
34786 Zip Code

5151 Latrobe Dr, Windermere $3,800,000 ▼

Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 squ...

4 Beds
5 Baths
Isleworth SubDv.
34786 Zip Code

9725 Chestnut Ridge Drive, Windermere image

9725 Chestnut Ridge Drive, Windermere $5,975,000 ▼

Virtually Staged. Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning a...

7 Beds
7 Baths
Isleworth SubDv.
34786 Zip Code

9721 Carillon Park Drive, Windermere image

9721 Carillon Park Drive, Windermere $4,778,000 ▼

Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe. This extraordinary residence offers 8,305 ...

6 Beds
9 Baths
Keenes Pointe SubDv.
34786 Zip Code