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

1324 Lake Olivia Ln, Windermere $2,495,000

Welcome to stunning lakefront living within the gated community of Lake Oliva Reserve. This custom home by premium builders, Generation Builders, was constructed in 2020 ...

5 Beds
5.5 Baths
Lake Olivia Reserve Rep SubDv.
34786 Zip Code

1566 Lake Rhea Drive, Windermere $1,550,000

LAKE FRONT immaculate custom home is sited directly on Lake Rhea in guard gated Reserve at Belmere. 3 Car Garage with circular paver drive showcases the dramatic fountain...

4 Beds
4 Baths
Reserve At Belmere Ph 02 48 144 SubDv.
34786 Zip Code

6325 Lenox Mill Drive, Windermere $469,900

A Spacious 4 bedroom, 2 bath, Pool Home, Eat-in Kitchen with all New Appliances, Split Floor Plan, Wood & Tile Floors, 2nd Bath has new floor Tile, New Tub & Tile, Scre...

4 Beds
2 Baths
West Point Commons SubDv.
34786 Zip Code

6002 Golden Dewdrop Trail, Windermere image

6002 Golden Dewdrop Trail, Windermere $1,290,000

LOCATION... LOCATION... LOCATION... BEST FIREWORKS VIEW FROM BACKYARD! This gorgeous two-story home with 8 bedrooms and 5 bathrooms has everything you’ve ever wanted in...

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

13486 Sunkiss Loop, Windermere $599,999

*** Multiple Offers. Seller is asking for highest and best by Sunday, 1/16, at 8PM *** This beautifully designed water view Smart Home is located in the highly sought-aft...

4 Beds
2.5 Baths
Summerport Ph 03 SubDv.
34786 Zip Code

5108 Fairway Oaks Drive, Windermere image

5108 Fairway Oaks Drive, Windermere $2,000,000

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Situated on a private, 0.69-acre lot within the desirable main gates of Is...

4 Beds
4 Baths
Isleworth SubDv.
34786 Zip Code

12125 Via Caselli Lane, Windermere image

12125 Via Caselli Lane, Windermere — 12135 $560,000

Pre-Construction. To be built. PRE-CONSTRUCTION/ WILL BE READY IN 30-60 DAYS. Beautiful and bright 5bedroom 4bathroom town-home with pond views, perfect for the close kni...

5 Beds
4 Baths
Royal Estates SubDv.
34786 Zip Code

13166 Kegan Street, Windermere $507,500

Be prepared to fall in love with this spectacular Single-Family home located at the friendly and beautiful Windermere Sounds. This is a charming, spacious and well-kept ...

4 Beds
3.5 Baths
Windermere Sound SubDv.
34786 Zip Code

Windermere $275,000

Live the good life in LAKESIDE AT LAKES OF WINDERMERE split plan condo unit Built by Ahston Woods Home with 3 bedrooms and 2.5 full bathrooms. 42” wood cabinets with cro...

3 Beds
2.5 Baths
Lakeside Villas SubDv.
34786 Zip Code

9033 Woodbreeze Boulevard, Windermere image

9033 Woodbreeze Boulevard, Windermere $509,000

Welcome Home! Come settle down in this highly sought after, quiet community in Windermere. The home has a pool and fireplace so you can enjoy your little slice of Florida...

4 Beds
2 Baths
Silver Woods Ph 01 SubDv.
34786 Zip Code

11562 Amidship Ln Unit 103, Windermere image

11562 Amidship Ln Unit 103, Windermere — Building 1 $359,000

Beautiful Lakeside at Lakes of Windermere condominium - First floor corner unit with screened patio. This FULLY FURNISHED TURN KEY unit offers 3 bedrooms and two baths a...

3 Beds
2 Baths
Lakeside/Lks/Windermere SubDv.
34786 Zip Code

Windermere $1,990,000

The home is located in the well sort after community of Keene's Pointe, the home of Jack Nicklaus Golden Bear Golf community. The community is close to Disney, Universal ...

4 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

2038 Water Key Drive, Windermere $1,195,000

GORGEOUS 5bd / 4.5 bath home in Waterford Pointe, a Premier Community in Windermere. The kitchen opens up into the family room which is great for entertaining. This floor...

5 Beds
4.5 Baths
Reserve At Waterford Pointe Ph 01 SubDv.
34786 Zip Code

9736 Chestnut Ridge Drive, Windermere image

9736 Chestnut Ridge Drive, Windermere $2,092,000

Discover one of the last remaining lakefront home sites in the renowned Isleworth Golf & Country Club. Nestled on a cul-de-sac along the shores of beautiful Lake Bessie, ...

Isleworth SubDv.
34786 Zip Code

9260 Sabal Palm Circle, Windermere image

9260 Sabal Palm Circle, Windermere $445,000

Welcome home to this highly sought Windermere area! Located in a quiet neighborhood with easy access to restaurants and shopping, this home is zoned for A+ schools. As yo...

3 Beds
2 Baths
Silver Woods Ph 01 SubDv.
34786 Zip Code

8249 Procida Isle Lane, Windermere image

8249 Procida Isle Lane, Windermere $648,000

Picture yourself living in one of the Most desirable neighborhoods! This Luxurious 4-bedroom, 3-bathroom home of 2,224 SqFt. ft is located at Windermere Isle Community. T...

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

11940 Lake Butler Boulevard, Windermere image

11940 Lake Butler Boulevard, Windermere $6,995,000

UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300’ SEAWALL. This private, gated lakefront home is set on 2.4 acres in old Windermere, with over 6,500 S...

5 Beds
6.5 Baths
Metcalf Park Rep SubDv.
34786 Zip Code

11035 Schooner Way, Windermere $7,500,000

Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home in the tranquility of the sought after Town of Windermere. Surrounded by the But...

7 Beds
5.5 Baths
Marina Bay Estates SubDv.
34786 Zip Code

925 Main Street, Windermere $740,000

Beautiful house in downtown Windermere, just a short walk to the library and ice cream shop. It's a dream home - come and see! What a Great Opportunity to own the WINDERM...

4 Beds
2.5 Baths
Windermere SubDv.
34786 Zip Code

4333 Isabella Circle, Windermere $2,590,000 ▲

Your DREAM HOME awaits! This Toll Brothers executive home is situated on a generous 2/3 acre lot, ample parking, with a magnificent outdoor entertainment area. As you ent...

6 Beds
7 Baths
Casabella SubDv.
34786 Zip Code

13375 Gorgona Isle Drive, Windermere image

13375 Gorgona Isle Drive, Windermere — Mattamy Homes $420,000

Less than 15 Minutes from theme parks and great shopping, 3 sizable bedrooms, and 2.5 bathrooms combine with generous living space and stylish finishes to make living eas...

3 Beds
2.5 Baths
Legado SubDv.
34786 Zip Code

31 Pine Street, Windermere $2,750,000

Check out video www.31pine.site/mls One lucky buyer will own one of the most desirable lake front lots on the Butler Chain. Boasting well over 500 ft of your own priva...

4 Beds
3 Baths
Windermere Town SubDv.
34786 Zip Code

11049 Bridge House Road, Windermere image

11049 Bridge House Road, Windermere $6,450,000

Presenting a custom-crafted Mediterranean mansion secluded behind its own private gates, perched along the shores of Lake Butler, inside guard-gated Reserve at Lake Butle...

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

6806 Trellis Vine Loop, Windermere image

6806 Trellis Vine Loop, Windermere $540,000

Welcome home to this beautiful 3 BEDROOM LAKE VIEW WINDEREMER HOME .longterm lease till 11/30/2022 . great investment The open spacious floor plan includes a gourmet-sty...

3 Beds
2 Baths
Windstone SubDv.
34786 Zip Code

98 E 10th, Windermere $599,000

RARE OPPORTUNITY TO BRING YOUR BUILDER AND BUILD YOUR DREAM HOME ON A LARGE VACANT HOME SITE IN THE TOWN OF WINDERMERE WITH NO HOA! This large flat, partially wooded, rec...