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

12914 Vennetta Way, Windermere — N/A $382,000

Welcome to Berkshire Park, a highly sought-after community where timeless style, everyday comfort, and low-maintenance living come together in the heart of Windermere. Th...

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

5451 Kumquat Loop, Windermere — 5451 $384,900

Very rarly does the end unit, one story townhomes come on the market! For anyone who doesn't want stairs, or master bedroom up - check this one out. Last 4 of these one s...

2 Beds
2 Baths
Summerport Ph 03 SubDv.
34786 Zip Code

8254 Procida Isle Lane, Windermere image

8254 Procida Isle Lane, Windermere $1,050,000

Experience the perfect blend of elegance, comfort, and modern convenience in this exceptional 5-bedroom, 4-bathroom home in the highly sought-after Windermere Isle commun...

5 Beds
4 Baths
Windermere Isle Ph 2 SubDv.
34786 Zip Code

4205 Clarice Estates Drive, Windermere image

4205 Clarice Estates Drive, Windermere $2,550,000

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

9312 Blanche Cove Dr, Windermere $12,350,000

Set along beautiful Lake Blanche within the gates of Isleworth, this extraordinary modern estate is a grand haven of remarkable scale and design. Spanning more than 11,00...

7 Beds
10 Baths
Isleworth 5th Amd SubDv.
34786 Zip Code

1554 Lake Rhea Drive, Windermere $1,350,000 ▼

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 $3,900,000 ▼

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

13525 Gorgona Isle Drive, Windermere image

13525 Gorgona Isle Drive, Windermere $1,089,000 ▼

Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location j...

6 Beds
5 Baths
Windermere Isle SubDv.
34786 Zip Code

9725 Chestnut Ridge Drive, Windermere image

9725 Chestnut Ridge Drive, Windermere $6,000,000 ▼

Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000...

7 Beds
7 Baths
Isleworth SubDv.
34786 Zip Code

4812 Alexandra Garden Court, Windermere image

4812 Alexandra Garden Court, Windermere $3,699,000

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating...

3 Beds
5 Baths
Isleworth SubDv.
34786 Zip Code

9721 Carillon Park Drive, Windermere image

9721 Carillon Park Drive, Windermere $5,000,000 ▼

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