Windermere Homes for Sale

Orange County has a stunning reputation for its high-end communities that provide exceptional amenities to its residents. The Orange County community of Windermere has a population of 2,500 and is located in the Orlando-Kissimmee Metropolitan area. Windermere has the appeal of being a small, safe, cozy town with convenient access to the big city. MAny Windermere residents use the neighborhood as a bedroom town, or in other words a place that residents typically travel outside of to work. Since the year 2000 Windermere has seen significant growth due to its ideal location.

The town of Windermere became established in the year 1925 and was approximately 1.57 square miles but after the annexed community of Butler Bay in 2007, Windermere became slightly larger. Windermere sees a ton of fluctuations in population due to the large number of tourists that travel through to visit Orlando, however, Windermere als benefits from tourists for several reasons. Reason number one: The beautiful historic buildings that line the streets in Windermere making it not only a picturesque place to live and visit but a historically fascinating place as well. For example, The Windermere Town Hall is located on Main street and is also known as the Old Windermere Women’s Club. Another place is the 1890 Windermere School also known as the Armstrong-Parramore House.

Wondering what types of homes are for sale in Windermere? Houses for purchase here vary in size, price, age etc. but come in all forms whether you are looking for a luxurious home or a small simple one. Homes in Windermere can range in price anywhere from $250,000 to over $1 million. The cozy town of Windermere is not only stunning but it is also a wonderful place to raise a family. The Orange County School District provides excellent educators and mentors to guide children through the challenges of a variety of subjects. There is much to be said on the quality and appearance of Windermere but another noteworthy subject is recreation. There are so many community events like art shows and parades that residents are encouraged to attend but there are also a wide variety of activities that all residents and visitors alike can take advantage of. Windermere is extremely close to Butler Bay Recreational Area where visitors may hike, bike, swim and so much more! If you would like more information or help finding a home in Windermere, Florida, please don’t hesitate to contact us today!

Latest Windermere Homes and Condos for Sale

5373 Isleworth Country Club Drive, Windermere image

5373 Isleworth Country Club Drive, Windermere $2,400,000

Sitting majestically along the 17th fairway of Isleworth Golf Course this estate also boasts beautiful views of Lake Louise...the perfect Windermere combination. Step ins...

4 Beds
4 Baths
Isleworth SubDv.
34786 Zip Code

12654 Calderdale Avenue, Windermere image

12654 Calderdale Avenue, Windermere $347,000

Well maintained house in Wickham Park in big corner Lot. Property features 42" solid wood Kitchen cabinets, stainless steel appliances, large master bathroom with double...

3 Beds
2 Baths
Wickham Park SubDv.
34786 Zip Code

6055 Louise Cove Drive, Windermere image

6055 Louise Cove Drive, Windermere $3,400,000

There is almost nothing as beautiful the Butler Chain of Lakes in Windermere. And amongst those lakes, this breathtaking estate sits on the shores of the exquisite Lake L...

5 Beds
5 Baths
Isleworth SubDv.
34786 Zip Code

4071 Isabella Circle, Windermere $2,399,000

Situated in the exclusive gated community of Casabella and only minutes from upscale dining & shopping, world famous attractions, and Butler Chain of Lakes, this property...

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

2006 Bellamere Court, Windermere $1,819,900

Pre-Construction. To be built. Photos are of our Furnished Model (pending sale) next door. Introducing Element Home Builders favorite plan, featuring their paralleled qu...

5 Beds
5 Baths
Bella Vita Estates SubDv.
34786 Zip Code

14368 Desert Haven Street Unit 41, Windermere image

14368 Desert Haven Street Unit 41, Windermere — 4106 $295,000

Welcome home, your "Oasis" awaits you! You won't want to miss your opportunity to reside in the resort style, gated community of Oasis Cove in Windermere. Here you will...

3 Beds
2 Baths
Oasis Cove Ii/Lakeside Village #Xi SubDv.
34786 Zip Code

6378 Southbridge Street, Windermere image

6378 Southbridge Street, Windermere $272,900

Live a peaceful life in this quiet and comfortable townhouse! This home is on a corner lot and backs up into conservation land, giving lush porch views and privacy. This ...

3 Beds
2 Baths
Southbridge Village SubDv.
34786 Zip Code

13549 Gorgona Isle Drive, Windermere image

13549 Gorgona Isle Drive, Windermere $525,000

PREMIER LOCATION! Close to 429, Disney attractions, top rated public and private schools, Hamlin Shops, recreation and dining. This inviting ENERGY STAR Certified home fe...

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

13743 Amelia Pond Drive, Windermere image

13743 Amelia Pond Drive, Windermere $361,500

Lovely home with oversized lot. The Kitchen/Family room combination has the open concept that you are looking for with a bonus room that can be used as an office/den/dini...

3 Beds
2 Baths
Creeks Run SubDv.
34786 Zip Code

11550 Waterstone Loop Drive, Windermere image

11550 Waterstone Loop Drive, Windermere $2,100,000

Set within the luxurious and exclusive guarded community of Waterstone, this contemporary masterpiece combines grandeur and elegance for your enjoyment of living. Spannin...

6 Beds
6 Baths
Waterstone SubDv.
34786 Zip Code

6854 Trellis Vine Loop, Windermere image

6854 Trellis Vine Loop, Windermere $539,900

Check out this gorgeous, well-priced property located in the wonderful community of Windermere! Just minutes to the theme park areas and Downtown Orlando and only five ye...

5 Beds
4 Baths
Windstone SubDv.
34786 Zip Code

13543 Riggs Way, Windermere $420,000

The Windermere lifestyle can now be yours with this immaculately maintained home at Berkshire Park where you will enjoy the walking/running trails, community pool/basketb...

3 Beds
3 Baths
Enclave/Berkshire Park SubDv.
34786 Zip Code

7727 Maslin Street, Windermere — N/A $269,900

**MOVE IN READY WINDERMERE TOWNHOME** **PRIME LOCATION -- DIRECTLY ACROSS FROM COMMUNITY POOL & PARK** **TWO CAR GARAGE** **LARGE FENCED COURTYARD** **WALKING DISTANC...

3 Beds
2 Baths
Wickham Park SubDv.
34786 Zip Code

11842 Gray Rock Trail, Windermere $475,000

Absolutely Gorgeous! Won´t you love too see Magic Kingdom´s fire works from your window? This Stunning home located in Windermere Trails community, can offer you that!!!...

4 Beds
3 Baths
Windermere Trls SubDv.
34786 Zip Code

11792 Hampstead Street, Windermere image

11792 Hampstead Street, Windermere $695,000

TURN KEY OPPORTUNITY AWAITS! Everything you have been looking for but haven't been able to find is waiting for you right now in the Enclave, one of Windermere's newest an...

5 Beds
4 Baths
Enclave SubDv.
34786 Zip Code

7347 Millstone Street, Windermere — Na $265,000

This Windermere two-story home offers a two-car garage. This home is vacant and cleaned regularly.

2 Beds
2 Baths
Lake Burden South Ph I SubDv.
34786 Zip Code

5284 Isleworth Country Club Drive, Windermere image

5284 Isleworth Country Club Drive, Windermere $3,400,000

Poised on Isleworth Country Club Drive overlooking Eagle Pond and the 11th tee, this exquisite estate offers exceptional golf and water views within the gates of Central ...

4 Beds
4 Baths
Isleworth SubDv.
34786 Zip Code

8342 Boyla Court, Windermere $699,000

This is your opportunity to build your WATER FRONT dream home on one of the last buildable lots in the Keene's Pointe Community. This beautiful lakefront lot on a privat...

Keenes Pointe SubDv.
34786 Zip Code

Windermere $474,900

This one owner home is spotless. This home is loaded with upgrades both inside and outside. Stone elevation on the exterior with tile roof along with a full front porch j...

4 Beds
3 Baths
34786 Zip Code

6432 Deacon Circle, Windermere $8,300,000

This stunning Georgian manor located within the gates of the renowned Isleworth community tastefully intertwines timeless old world charm with modern style. Upon entry, y...

5 Beds
5 Baths
Isleworth 1st Amendment SubDv.
34786 Zip Code

2556 Carter Grove Circle, Windermere image

2556 Carter Grove Circle, Windermere $819,000

HIGHLY DESIRED WINDERMERE COMMUNITY MANORS AT BUTLER BAY! Walk to Windermere Elementary. The quaint Town of Windermere is where residents enjoy friendly small town lifest...

5 Beds
3 Baths
Manors At Butler Bay Ph 02 SubDv.
34786 Zip Code

11009 Hawkshead Court, Windermere $829,000

Discover elegance in this beautiful 4 BR/4.5 bath custom pool home behind the gates of Lake Butler Sound, a 380 acre enclave of exquisite homes in a tranquil Florida wate...

4 Beds
4 Baths
Reserve At Lake Butler Sound SubDv.
34786 Zip Code

13036 Lake Roper Court, Windermere image

13036 Lake Roper Court, Windermere $1,250,000

This stunning completely renovated waterfront home in a gated community features 5 bedrooms and 5 bathrooms on a 1.77-acre lot in the desirable town of Windermere. Situa...

5 Beds
5 Baths
Windermere Pointe At Lake Roper SubDv.
34786 Zip Code

8067 Enchantment Drive Unit 1205, Windermere image

8067 Enchantment Drive Unit 1205, Windermere — 8067 $245,000

BRAND NEW AC AND FRESH INTERIOR PAINT! Make sure to put this one on your MUST SEE list! This 2 bedroom (could be a 3 bedroom by adding a wall in upstairs loft), 2.5 bathr...

2 Beds
2 Baths
Oasis Cove I/Lakeside Village Ph 01 SubDv.
34786 Zip Code

5825 Oxford Moor Boulevard, Windermere image

5825 Oxford Moor Boulevard, Windermere $849,900

Welcome to this Gorgeous 4 bedrooms, 3 full baths and 3 car garage single family home. This amazing property is located on an Oversized Lot in a quiet family friendly gat...