Search All Windermere Real Estate

Orange County, Florida, has a reputation for being exceptional with coveted amenities and high-end residential communities. A fine example is the charming community of Windermere, nestled among the Butler Chain of Lakes. Windermere is home to roughly two thousand, five hundred people in the prestigious Orlando Metro Area. This small bedroom community offers prospective homebuyers the best of both worlds, with a cozy small-town ambiance and high-end exclusive communities in proximity to big-city services, amenities, and attractions. Because of its convenient location, Windermere has experienced consistent growth since 2000.

Originally comprising fewer than two square miles, the town of Windermere was established in 1925. In 2007, it annexed Butler Bay and is therefore slightly larger today. Many others that share the 34786 zip code share Windermere's name, but are considered part of unincorporated West Orange County. Windermere itself has much to offer prospective homebuyers. For example, there are many lovely historic structures in the town, including the Windermere Town Hall and the 1890 Windermere School.

Further contributing to its appeal to homebuyers, Windermere is a family-friendly community served by the Orange County School District and the international and prestigious Windermere Preparatory School. It is in proximity to numerous entertainment, attraction, and recreation destinations and events, including all of the areas theme parks, I-Drive, and the Bay Hill Classic Golf Tournament. Weekly farmers market and monthly food truck night are very popular year-round in historic downtown Windermere.

Real estate in Windermere is surprisingly diverse for such a small community. Homes for sale in Windermere include attached and detached residences of differing ages, architectural styles, and sizes. There are modest Windermere properties with competitive listing prices, and there are sprawling luxury homes in exclusive estate communities in Windermere with listing prices well into the millions. Among Windermere's most noteworthy neighborhoods is the exclusive county club community of Isleworth, nestled on the Butler Chain of Lakes and home to many celebrities and professional sports figures. We would be delighted to answer all of your questions about currently listed properties in Windermere, Florida, so if you would like to learn more, please contact us as soon as it is convenient.

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Newest Windermere Homes & Condos for Sale

11801 Camden Park Drive, Windermere image

11801 Camden Park Drive, Windermere $1,429,000

Welcome to luxury living in the heart of Windermere. This stunning home is nestled in the prestigious GUARD-gated Keene’s Pointe Community, known for multi-million dollar...

5 Beds
3.5 Baths
Keenes Pointe SubDv.
34786 Zip Code

1404 Kelso Boulevard, Windermere $2,800,000

Welcome to Kelso on Lake Butler! Situated on over an acre with approximately 100ft of lake front, this stunning lakefront property offers the perfect blend of luxury and ...

5 Beds
5 Baths
Kelso On Lake Butler SubDv.
34786 Zip Code

13272 Roxboro Road, Windermere $745,000

Discover your dream home in Windermere! Located just a stone's throw from Disney attractions, this beautiful 4-bedroom, 3 and a 1 half -bathroom residence is perfect for ...

4 Beds
3.5 Baths
Lake Sawyer South Ph 01 SubDv.
34786 Zip Code

1703 Roberts Landing Road, Windermere image

1703 Roberts Landing Road, Windermere $1,150,000

Lakefront home on Lake Olivia in highly desired Windermere Florida. Picture yourself entertaining friends on your patio overlooking the lake or step down to your dock and...

4 Beds
3 Baths
Roberts Landing SubDv.
34786 Zip Code

6238 Lake Burden View Drive, Windermere image

6238 Lake Burden View Drive, Windermere $1,750,000

Exquisite, fully renovated residence nestled in the 24-hour guard gated community of Keene’s Pointe. This luxurious 4-bedroom, 4-bathroom home sprawls over 3,512 square f...

4 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

12734 Windermere Isles Place, Windermere image

12734 Windermere Isles Place, Windermere $1,215,300

Welcome to the Isles of Windermere, one of Central Florida's most sought-after neighborhoods. This spacious family residence is just a short stroll from the Lake Butler ...

5 Beds
4 Baths
Isles Windermere SubDv.
34786 Zip Code

14225 Confetti Drive, Windermere — 14225 $430,000

This RARE property offers a 3-bedroom, 2.5-bath townhome with a DETACHED 1-bedroom, 1-bath guest house, located in the highly sought-after Summerport community. The main ...

4 Beds
3.5 Baths
Summerport Ph 04 C E F & G SubDv.
34786 Zip Code

10710 Reams Road, Windermere $500,000

LOCATION, LOCATION, LOCATION!!! Beautiful and cozy residence located in the desirable WINDERMERE area. This single-family - bungalow style home offers four bedrooms, two-...

4 Beds
2.5 Baths
Windermere Trls Ph 1c SubDv.
34786 Zip Code

8797 Peachtree Park Court, Windermere image

8797 Peachtree Park Court, Windermere $584,000

Located just 5 minutes from Walt Disney World, this single-family home puts you right in the middle of the magic! Enjoy a nightly front-row view of Magic Kingdom’s firewo...

3 Beds
2 Baths
Peachtree Park SubDv.
34786 Zip Code

10903 Ledgement Lane, Windermere $917,500

Located in the desirable, gated community of Glenmuir in Windermere, this well-maintained residence offers a blend of comfort and elegance. Featuring four spacious bedroo...

4 Beds
3.5 Baths
Glenmuir Ut 02 51 42 SubDv.
34786 Zip Code

13285 Gorgona Isle Drive, Windermere image

13285 Gorgona Isle Drive, Windermere — O $455,000

Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhouse in the highly desirable Windermere area! Built in 2020, this 1,503 sq ft home is in excellent con...

3 Beds
2.5 Baths
Legado SubDv.
34786 Zip Code

8476 Iron Mountain Trail, Windermere image

8476 Iron Mountain Trail, Windermere — 8476 $450,000

Calling Investors!!! Great Opportunity to own a beautiful 3 bedroom / 2.5 bathroom Townhome in the Community of Windermere Trail, in Orlando, FL!!! This beautiful and wel...

3 Beds
2.5 Baths
Windermere Trails SubDv.
34786 Zip Code

904 Main Street, Windermere $4,850,000

Incredibly Rare Air Conditioned Boathouse that is completely renovated with Apartment, Kitchen and Bathroom - Custom Platform Boat Lift with overhead garage door lends se...

4 Beds
4.5 Baths
Windermere Town SubDv.
34786 Zip Code

11761 Bella Milano Court, Windermere image

11761 Bella Milano Court, Windermere $699,000

For sale is a magnificent home in the very highly sought after Belmere neighborhood. In the famed City of Winderemere live in this beautiful gated community in this stun...

5 Beds
4.5 Baths
Belmere Village G-5 SubDv.
34786 Zip Code

17550 Black Rail Street, Windermere image

17550 Black Rail Street, Windermere $1,325,000

Seller may consider buyer concessions if made in an offer ~ There has never been a more perfect blend of modern luxury and the comforts of home! Welcome to the Enclave, a...

5 Beds
4 Baths
Enclave SubDv.
34786 Zip Code

10652 Reams Road, Windermere $499,000

Experience the enchantment of watching Disney's "Happily Ever After" fireworks from your own home just three miles from Cinderella's Castle. Nestled in the highly desirab...

3 Beds
2.5 Baths
Windermere Trls Ph 1c SubDv.
34786 Zip Code

8243 Procida Isle Lane, Windermere image

8243 Procida Isle Lane, Windermere $950,000

Welcome to 8243 Procida Isle Lane — where luxury meets comfort in every detail. This expansive residence with 5-bedrooms, 4-bathrooms, a stunning pool, and a three car ga...

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

11313 Shandon Park Way, Windermere image

11313 Shandon Park Way, Windermere $1,680,000

Absolutely Fabulous Luxury Home Nestled on a picturesque tree-lined street within the prestigious RESERVE AT BELMERE, a Guard Gated Community. This exceptional residence ...

6 Beds
5 Baths
Reserve At Belmere Ph 2 SubDv.
34786 Zip Code

6719 Valhalla Way, Windermere $4,999,000

Keene's Pointe - 24-hour gated/attended community in highly desired Windermere, Florida. This completely renovated home features formal living and dining rooms, great ro...

4 Beds
5.5 Baths
Keenes Pointe 46/104 SubDv.
34786 Zip Code

2544 Carter Grove Circle, Windermere image

2544 Carter Grove Circle, Windermere $875,000

Incredible opportunity in the established neighborhood of The Manors at Lake Butler. Enjoy a peaceful drive through majestic oaks to your custom home on over half acre l...

5 Beds
3 Baths
Manors At Butler Bay SubDv.
34786 Zip Code

5056 Isleworth Country Club Drive, Windermere image

5056 Isleworth Country Club Drive, Windermere $4,000,000

Experience luxury living in this stunning, modern estate situated on the renowned Isleworth Country Club Golf Course, overlooking the scenic hole 6. This exquisite home o...

4 Beds
4 Baths
Isleworth SubDv.
34786 Zip Code

7336 Penkridge Lane, Windermere $830,000

Seller may consider buyer concessions if made in an offer ~ Welcome to Windermere Sound, a vibrant community just miles from Magic Kingdom for a view of Disney fireworks ...

6 Beds
3.5 Baths
Windermere Sound SubDv.
34786 Zip Code

14276 Desert Haven Street Unit GE, Windermere image

14276 Desert Haven Street Unit GE, Windermere — 3804 $340,000

Welcome to this charming 3-bedroom, 3-bathroom home located in the sought-after Oasis Cove community, just minutes from the magic of Disney World! This beautifully mainta...

3 Beds
2.5 Baths
Oasis Cove Ii At Lakeside Village SubDv.
34786 Zip Code

11668 Black Rail Street, Windermere image

11668 Black Rail Street, Windermere $540,000

This is your chance to own a stunning 3-bedroom, 2.5-bath home in the highly desirable Windermere Landing community. Located on a premium corner lot, this spacious two-st...

3 Beds
2.5 Baths
Windermere Lndgs Ph 02 SubDv.
34786 Zip Code

9016 Reflection Pointe Drive, Windermere image

9016 Reflection Pointe Drive, Windermere $775,000

Windermere Trails! ADORABLE MODERN FARMHOUSE GEM! 4 Bedroom 3 Bath home over 3500 sq ft of living space! The answer is YES, you can see the DISNEY fireworks every night! ...