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

8618 Via Tavoleria Way, Windermere image

8618 Via Tavoleria Way, Windermere — 8618 $364,995

Make your appointment today to view this beautiful 4 bedroom 3 Full baths townhome, located at the beautiful Carrington Community in desirable Windermere Florida while it...

4 Beds
3 Baths
Carrington SubDv.
34786 Zip Code

426 E 6th Avenue, Windermere $516,000

One or more photo(s) has been virtually staged. One or more photo(s) was virtually staged. New Listing! Recently updated 3 bed 2 bath home in Downtown Windermere. Access ...

3 Beds
2 Baths
Jasmine Woods SubDv.
34786 Zip Code

11756 Hampstead Street, Windermere image

11756 Hampstead Street, Windermere $1,150,000

This gorgeous five bedroom, four bath, tow ar garage and a private Blue Moon Pool home offers plenty of space for the whole family. The Chef- inspired gourmet kitchen ov...

5 Beds
4 Baths
Enclave SubDv.
34786 Zip Code

7114 Ventnor Drive, Windermere — 7100 $375,000

Enjoy everything a single family home has but with your exterior maintenance, landscaping, and lawn care all included in this show-stopping townhome in Windermere! HUGE s...

4 Beds
2 Baths
Preston Square SubDv.
34786 Zip Code

11067 Bagley Alley, Windermere $470,000

Welcome to this move-in-ready 4 bedroom, 2.5 bathroom, two-story home in the community of Westside Village in Windemere . This home features an open concept with a living...

4 Beds
2 Baths
Westside Village SubDv.
34786 Zip Code

11267 Rapallo Lane, Windermere $500,000

DEBUT! Stunning WATERFRONT home in the highly desirable GATED Community of BELMERE VILLAGE in Windermere, Florida! The backyard TROPICAL OASIS will take your breath awa...

3 Beds
2 Baths
Belmere Village G2 48 65 SubDv.
34786 Zip Code

520 Haley Drive, Windermere $1,500,000

Highly Sought After Windermere Estate Home on a Large Fully Fenced Acre Lot with Mature Oaks, beautiful landscaping and tons of privacy. This home has been entirely remod...

4 Beds
3 Baths
Crescent Lake Estates SubDv.
34786 Zip Code

13526 Zori Lane, Windermere $610,000

Check out this great pool home in Windermere! This 4 bedroom, 3 bathroom, 3 car garage home is move-in ready for you with beautiful upgrades all throughout. 20' ceilings,...

4 Beds
3 Baths
Providence Ph 02 SubDv.
34786 Zip Code

9542 Kingsbury Court, Windermere $850,000

A must-see in the desirable neighborhood - Windsor Hill. With almost 4,0000 square feet of Living Space, this home features 6 bedrooms, two of which are Master Suites and...

6 Beds
5 Baths
Windsor Hill SubDv.
34786 Zip Code

7422 Bentonshire Avenue, Windermere image

7422 Bentonshire Avenue, Windermere — N/A $299,000

A MUST SEE!!!! Great for investor!!!!!! Tenant in place till May 31st 2022. Unit rents for 1,690 a month. Great tenant since May of 2019. Beautiful and spacious townhome...

2 Beds
2 Baths
Wickham Park 04 05 06 09 10 11 12 01 SubDv.
34786 Zip Code

6869 Thornhill Circle, Windermere $1,375,000

LAKEFRONT! Gorgeous 4 BR, 4.5 BA CUSTOM BUILT, SINGLE STORY, POOL HOME on a wide LAKEFRONT lot on LAKE SAWYER in WINDERMERE. Impeccably maintained and loaded with upgrade...

4 Beds
4 Baths
Lakes Windermere Ph 01 49 108 SubDv.
34786 Zip Code

4345 Saltmarsh Sparrow Drive, Windermere image

4345 Saltmarsh Sparrow Drive, Windermere $669,900

WELCOME HOME! This beautiful 6-bedroom, 5.5-bathroom home is ready for MOVE IN! Split two story floor plan! Convenience first floor office or den with French doors. Plent...

6 Beds
5 Baths
Stillwater Xings Prcl Sc-13 #2 SubDv.
34786 Zip Code

8606 Powder Ridge Trail, Windermere image

8606 Powder Ridge Trail, Windermere $489,000

Find a place to live at the heart of Windermere. Community is situated close to good schools, restaurants and day care and much more. With 4 bedrooms and 2.5 baths, this ...

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

6920 Helmsley Circle, Windermere $410,000

Gorgeous one story home has a great floor plan with a large roomy living and dining room combo. The large eat in kitchen has lots of granite counter space and 42 inch woo...

3 Beds
2 Baths
Preston Square SubDv.
34786 Zip Code

13273 Penshurst Lane, Windermere $560,000

Don't miss the opportunity to live in the desirable community of Windermere Sound. Look no more, this is the property you have been looking for. This beautiful and immacu...

4 Beds
2 Baths
Windermere Sound SubDv.
34786 Zip Code

13125 Casabella Drive, Windermere $3,699,000

Smart Mansion at Casabella. Welcome to the Toll Brothers "The Marcello", a 7,561SF home is fully automated and integrated with Alexa you can control the entire home throu...

5 Beds
5 Baths
Casabella SubDv.
34786 Zip Code

6019 Greatwater Dr, Windermere $3,995,000

Exquisite lakefront masterpiece located in the 24-hour guard-gated community of Keene's Pointe. This home is perfectly positioned on one of the best lakefront lots in the...

6 Beds
6 Baths
Keenes Pointe SubDv.
34786 Zip Code

9007 Legado Drive Unit Lot 37, Windermere image

9007 Legado Drive Unit Lot 37, Windermere — Na $425,490 ▼

Under Construction. FINAL OPPORTUNITIES IN THIS AMAZING COMMUNITY. Windermere, reputed as the most sought-after address in Central Florida, is a Live-Work-Play destinati...

3 Beds
2 Baths
Legado SubDv.
34786 Zip Code

9037 Legado Drive Unit LOT 42, Windermere image

9037 Legado Drive Unit LOT 42, Windermere — Na $435,490 ▼

Under Construction. FINAL OPPORTUNITIES IN THIS AMAZING COMMUNITY. Windermere, reputed as the most sought-after address in Central Florida, is a Live-Work-Play destinati...

3 Beds
2 Baths
Legado SubDv.
34786 Zip Code

12749 Garridan Av, Windermere $492,000

Beautiful house, like new !!! Located in the Wickham Park condo in Windermere, just 10 minutes from Disney, half a mile from Westside Shoppes, close to financial institut...

4 Beds
4 Baths
Wickham Park SubDv.
34786 Zip Code

0000 Reserve Windermere Court, Windermere image

0000 Reserve Windermere Court, Windermere $1,936,000 ▲

Pre-Construction. To be built. The Rio De Janeiro is a fresh take on Element Home Builder's model home with a more modern appeal for today's modern demands. As you approa...

4 Beds
4 Baths
Reserve At Windermere SubDv.
34786 Zip Code

14238 Sonco Avenue, Windermere — Na $329,990

A great townhome!! Located in Windermere. This home offers 2 bedrooms and 2/1 bathroom. Very well maintained with a lot to offer. Great location walking distance to the E...

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

13005 Penshurst Lane, Windermere $490,000

This home has it all – located in the desirable Windermere with a pool and Jacuzzi. Corner-lot backs up to conservation with a water view and is ready to move in immediat...

3 Beds
2 Baths
Lakes/Windermere Ph 03 P & Q SubDv.
34786 Zip Code

11860 Via Lucerna Circle, Windermere image

11860 Via Lucerna Circle, Windermere $575,000

Premium Flag Shaped Extra Private and Super sized with privacy landscaping and numerous palm trees and fruiting trees throughout with a beautiful fire pit in the back yar...

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

1461 Glenheather Drive, Windermere image

1461 Glenheather Drive, Windermere $669,000

This immaculate single story family home is located in guard gated Belmere. The lovely beveled glass double front doors lead to the thoroughly modern yet wonderfully comf...