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.

Our website features the best Windermere real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

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Newest Windermere Homes & Condos for Sale

8216 Tranquility Way Unit 3007, Windermere image

8216 Tranquility Way Unit 3007, Windermere — 3007 $450,000

Indulge in a lifestyle of luxury and comfort at 8216 Tranquility Way, a captivating condo nestled in the heart of Windermere. This meticulously crafted residence spans 2,...

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

11527 Camden Park Drive, Windermere $1,290,000

Located in the high Sough after Jack Nicholaus Golf Community of Keenes Pointe, This amazing remodel house offers an open and air contemporary with lots os natural light!...

5 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

6758 Bridgewater Village Road, Windermere image

6758 Bridgewater Village Road, Windermere $690,000

Welcome to elegance and luxury in the heart of Windermere. This impressive 5-bedroom residence combines a prime location with top-notch amenities, offering an exceptional...

5 Beds
3 Baths
Vineyards/Horizons West Ph 1b SubDv.
34786 Zip Code

2525 Hempel Avenue, Windermere $929,000

Welcome home! This pool home features a private front gate on a ONE-ACRE LOT and boasts over 3000 sq ft with NO HOA. This stunning 4 bedroom, 3.5 bathroom home is surrou...

4 Beds
3.5 Baths
Acreage SubDv.
34786 Zip Code

8760 Peachtree Park Court, Windermere image

8760 Peachtree Park Court, Windermere $950,000

Discover unparalleled comfort and style at 8760 Peachtree Park Ct, a meticulously maintained 4-bedroom, 3.5-bathroom pool home in the heart of Windermere. Boasting a thou...

4 Beds
3.5 Baths
Peachtree Park SubDv.
34786 Zip Code

11353 Evesham Drive, Windermere — N/A $399,000

Welcome to your dream home in the prestigious community of Preston Square in Windermere! This immaculate two-story, 2-bedroom, 2.5-bathroom townhome is a true gem, boasti...

2 Beds
2.5 Baths
Preston Square SubDv.
34786 Zip Code

11312 Fenimore Court, Windermere $1,450,000

Welcome to the epitome of luxury living in the prestigious community of Keene's Pointe in Windermere! This absolutely stunning 5-bedroom, 4-bathroom POND VIEW HOME is a m...

5 Beds
4 Baths
Keenes Pointe Ut 06 50 95 SubDv.
34786 Zip Code

635 Butler Street, Windermere $1,250,000

Welcome to your dream home nestled in the heart of Downtown Windermere, just steps away from Main Street and directly across from the Fernwood Boat Ramp. This stunning th...

3 Beds
3 Baths
Marsh Sub SubDv.
34786 Zip Code

12754 Bideford Avenue, Windermere $650,000

Welcome to your dream home! This meticulously maintained two-story residence is a testament to pride of ownership, offering a perfect blend of comfort and style. As you s...

4 Beds
3.5 Baths
Lakes/Windermere Ph 02a SubDv.
34786 Zip Code

5226 Isleworth Country Club Drive, Windermere image

5226 Isleworth Country Club Drive, Windermere $5,995,000

Located within the gates of the Isleworth Golf and Country Club community, this 7,821 square foot estate presents you with breathtaking views of the 8th fairway and glist...

5 Beds
5.5 Baths
Isleworth SubDv.
34786 Zip Code

5190 Latrobe Drive, Windermere $6,500,000

Spectacular modern property in the Beautiful gated community of Isleworth. Designed with a concrete structure, luxurious finishes, and numerous windows, this residence is...

5 Beds
6.5 Baths
Isle 4th Amd SubDv.
34786 Zip Code

8736 Peachtree Park Court, Windermere image

8736 Peachtree Park Court, Windermere $900,000

Beautifully updated home in Windermere, just minutes from DISNEY WORLD with the perks of nightly fireworks!!! Built in 2017, this modern home on a Premium lot backing to ...

4 Beds
3 Baths
Peachtree Park SubDv.
34786 Zip Code

9922 Brentford Court, Windermere $1,890,000

If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into ...

6 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

11550 Delwick Drive, Windermere $850,000

As you step into this beautiful home, you'll immediately notice the spacious and thoughtfully designed layout. A well-equipped kitchen, gas range, and a beautiful open fl...

5 Beds
3 Baths
Reserve At Belmere Ph 03 51 01 SubDv.
34786 Zip Code

14237 Oasis Cove Boulevard Unit 1806, Windermere image

14237 Oasis Cove Boulevard Unit 1806, Windermere — 14237 $439,000

HOA fee includes Cable TV and Internet *** Experience the BEST water views in the entire Oasis Cove community! Welcome to 14237 Oasis Cove Blvd, Windermere, FL 34786 – a ...

4 Beds
2.5 Baths
Oasis Cove SubDv.
34786 Zip Code

4925 White Bud Court, Windermere $649,900

Introducing 4925 White Bud Ct, an impeccably remodeled haven in the prestigious Windermere community of Florida. This residence has recently undergone an extensive transf...

4 Beds
2.5 Baths
Summerport Ph 5 SubDv.
34786 Zip Code

9025 Balmoral Mews Square, Windermere image

9025 Balmoral Mews Square, Windermere $2,399,999

One or more photo(s) has been virtually staged. UNDER CONSTRUCTION HOUSE WILL BE COMPLETED BY DEC 31!. Step into contemporary elegance inside and out. This 5 Bedroom 3.2...

5 Beds
3.5 Baths
Balmoral SubDv.
34786 Zip Code

8153 Serenity Spring Drive Unit 2107, Windermere image

8153 Serenity Spring Drive Unit 2107, Windermere — 2107 $419,900 ▼

Live the Florida Resort Lifestyle! With cable TV Fast speed internet, water, sewer, trash pickup, exterior grounds maintenance, etc etc This Big and Beautiful unit locat...

4 Beds
2.5 Baths
Oasis Cove 2 At Lakeside Village Condominium Phase SubDv.
34786 Zip Code

8553 Crescendo Avenue, Windermere $524,000

Welcome to the Heart and Soul of Windermere Trails, one of Windermere's most walkable and friendly neighborhoods. This Move-In-Ready Gem is located on a corner lot with r...

3 Beds
2.5 Baths
Windermere Trls SubDv.
34786 Zip Code

4325 Blue Major Drive, Windermere $560,000

This stunning property is a dream come true! With an open main living area and a split-bedroom floorplan, this home offers the perfect blend of space for privacy and qual...

3 Beds
2 Baths
Stillwater Xings Prcl Sc-13 Ph SubDv.
34786 Zip Code

4047 Isabella Circle, Windermere $3,999,000 ▲

This exceptional 2019 luxury property, extensively remodeled in 2021, holds the distinction of being the largest internally in Casabella condominium and the sole Casabell...

6 Beds
7.5 Baths
Casabella Ph 2 SubDv.
34786 Zip Code

6228 Roseate Spoonbill Drive, Windermere image

6228 Roseate Spoonbill Drive, Windermere $1,875,000

Quite motivated owner and willing to give an important discount if home is purchased before end of the year!!!!. More than a home. A happy place with a distinguished sen...

8 Beds
5 Baths
Windermere Lndgs Fd-1 SubDv.
34786 Zip Code

2455 Maguire Road, Windermere $2,600,000

This 4 Bedroom 3 Full & 2 Half Bath Luxurious Lakefront Pool Home also boasts a Separate Home Office and 2nd Floor Bonus Room with Kitchenette and Full Bath having a Balc...

4 Beds
3.5 Baths
Lake Down Estates SubDv.
34786 Zip Code

11433 Arborside Bend Way, Windermere image

11433 Arborside Bend Way, Windermere $675,000

Welcome to this beautiful water view home with four bedrooms and 3 full baths located in the desirable gated community of Glenmuir nestled in the middle of Windermere. As...

4 Beds
3 Baths
Glenmuir 48 39 SubDv.
34786 Zip Code

10821 Bayshore Dr, Windermere $6,490,000

One or more photo(s) has been virtually staged. Under Construction. Stunning custom lakefront home located on Lake Down, one of the famed Butler Chain of Lakes in Winderm...