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

11644 Ashlin Park Boulevard, Windermere image

11644 Ashlin Park Boulevard, Windermere $600,000

This lovely two-story home found in desirable Ashlin Park offers the convenience of a premium location to A- rated schools in Windermere. This home features exquisite upg...

4 Beds
2.5 Baths
Ashlin Park Ph 1 SubDv.
34786 Zip Code

12264 Montalcino Circle, Windermere image

12264 Montalcino Circle, Windermere $6,295,000

A masterpiece of artful design nestled in Windermere, Florida, this one-of-a kind, Lake Burden home immediately transports you to a level of world-class beauty, serenity...

4 Beds
4.5 Baths
Casa Del Lago Rep SubDv.
34786 Zip Code

12224 Mckinnon Road, Windermere $1,799,000

One acre of Windermere lakefront living, with no HOA! This home is situated on Lake Crescent, which is crystal clear and the largest private lake in Windermere. When the ...

4 Beds
4.5 Baths
Butler Bay SubDv.
34786 Zip Code

12846 Langstaff Drive, Windermere — Lake Reams Townhomes $365,000

Rare Lake Reams Townhome in Windermere, Fl. 1380 sq ft, 2 bedroom, 2.5 bath Home on Beautiful Mature Oak Tree Lined Street. 2 Car Garage with Courtyard in between. Ne...

2 Beds
2.5 Baths
Lakes/Windermere-Lk Reams Twnh SubDv.
34786 Zip Code

12856 Strode Lane, Windermere — Lot 244 $430,000

Two story town home in excellent condition and newly painted inside! The kitchen features wood cabinets, granite counter tops, backsplash and a large island. The lighting...

3 Beds
2.5 Baths
Windermere Sound Ph 2 SubDv.
34786 Zip Code

9725 Chestnut Ridge Drive, Windermere image

9725 Chestnut Ridge Drive, Windermere $4,399,000

This home features 6885 square feet of AC living space and 11,000 square feet under roof! The home is situated inside Isleworth, a gated community with 24 hour security b...

5 Beds
6 Baths
Isleworth SubDv.
34786 Zip Code

5507 Worsham Ct, Windermere $5,950,000

This stunning custom estate overlooks the fourteenth green on Isleworth Golf and Country Club, one of the world’s most prestigious private golf club communities. As you c...

5 Beds
5.5 Baths
Isleworth SubDv.
34786 Zip Code

13750 Ancilla Boulevard, Windermere image

13750 Ancilla Boulevard, Windermere — 13750 $359,000

Spacious 2/2 townhome in our desirable summerport community, Featuring spacious open floor design makes this home comforting and cozy. Ceramic tile throughout the home w...

2 Beds
2 Baths
Summerport Ph 03 SubDv.
34786 Zip Code

9247 Legado Drive, Windermere — Mattamy Homes $820,000

Luxury first rental property in Windermere with excellent schools. The property is located in the best and largest lot of the condominium and with a privileged view of th...

4 Beds
2.5 Baths
Legado SubDv.
34786 Zip Code

1810 Westover Reserve Boulevard, Windermere image

1810 Westover Reserve Boulevard, Windermere $999,000

Rare opportunity to own a home in the sought-after gated community of Westover Reserve in the heart of Windermere! An enclave of only 81 homes, this community offers imma...

4 Beds
5 Baths
Westover Reserve Ph 01 SubDv.
34786 Zip Code

11545 Brickyard Pond Lane, Windermere image

11545 Brickyard Pond Lane, Windermere $1,699,765

Magnificent Lakefront home set on a calm cul-de-sac! This spectacular residence treats you to ample privacy, space, and comfort in Windermere. Occupying an oversized 3/4-...

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

12525 Montalcino Circle, Windermere image

12525 Montalcino Circle, Windermere $989,000

ENOUGH LOOKING!! CHECK OUT this Gorgeous POOL home located in the Exclusive GATED Community Casa Del Lago in Windermere. This home has a lovely **courtyard feature** at t...

4 Beds
3.5 Baths
Casa Del Lago Rep SubDv.
34786 Zip Code

8057 Tibet Butler Drive, Windermere image

8057 Tibet Butler Drive, Windermere $1,695,000

THIS HOME IS THE ENTERTAINERS DREAM HOME! Located in the best community of Central Florida, it has a guard gated, golf, tennis and lakefront country club with a Signatur...

4 Beds
4 Baths
Keenes Pointe Unit 2 SubDv.
34786 Zip Code

11444 Misty Oak Alley, Windermere $609,990

Don’t miss out on this absolutely remarkable, MOVE-IN ready home which will accommodate any family's needs. Upon entering the home you are greeted with many upgrades: hig...

4 Beds
2.5 Baths
Ashlin Park Ph 1 SubDv.
34786 Zip Code

11952 Camden Park Drive, Windermere image

11952 Camden Park Drive, Windermere $1,690,000

Welcome to your own private oasis in one of the largest lots at Keene’s Pointe! With plenty of space, both indoor and outdoor, a formal living and dining room, a kitchen ...

5 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

12816 Water Point Boulevard, Windermere image

12816 Water Point Boulevard, Windermere $2,398,000

Stunning Windermere waterfront home located in the guard-gated community of Waterford Pointe. Perfectly positioned on an oversized 1-acre lot, this home was completely re...

5 Beds
3.5 Baths
Waterford Pointe SubDv.
34786 Zip Code

11129 Lake Butler Boulevard, Windermere image

11129 Lake Butler Boulevard, Windermere $799,000

Rare Opportunity to own 1 of the last affordable move in ready homes in Downtown Windermere - Recent sales of new homes are over $2.0 on this street - The Lot is 100 feet...

3 Beds
2 Baths
Wauseon Ridge SubDv.
34786 Zip Code

6005 Down Point Lane, Windermere $2,450,000

JUST LISTED – 6005 Down Point Lane, Windermere – Offered at $2,450,000. Exquisite estate home in Windermere’s private Sunset Bay community, adjacent to Lake Down and Isl...

5 Beds
6.5 Baths
Sunset Bay SubDv.
34786 Zip Code

9306 Blanche Cove Drive, Windermere image

9306 Blanche Cove Drive, Windermere $17,500,000

Sophisticated elegance masterfully packaged into a custom-crafted lakefront mansion built specifically for the ultimate sports enthusiast, situated behind the secured man...

5 Beds
6.5 Baths
Isleworth SubDv.
34786 Zip Code

11237 Camden Park Drive, Windermere image

11237 Camden Park Drive, Windermere $1,200,000

Welcome to your dream home located in the desirable Keene's Pointe community! This updated and upgraded 4 bedroom, 4 bath pool home boasts 3,492 square feet of luxurious ...

4 Beds
4 Baths
Keenes Pointe Unit 7 SubDv.
34786 Zip Code

5139 Isleworth Country Club Dr, Windermere image

5139 Isleworth Country Club Dr, Windermere $7,500,000

With a fabulous location along the front nine of Isleworth’s renowned championship golf course overlooking Hole 3, this expansive estate showcases just under 14,000 squar...

7 Beds
7.5 Baths
Isleworth SubDv.
34786 Zip Code

10430 Birch Tree Lane, Windermere $1,475,000

Now is your opportunity to own a luxurious estate home in the highly sought after Windermere Downs neighborhood! This 6 bedroom, 4.5 bath Brierhill custom-built home sits...

6 Beds
4.5 Baths
Windermere Downs Ph 03 SubDv.
34786 Zip Code

9718 Green Island Cove, Windermere image

9718 Green Island Cove, Windermere $5,999,999

Beautiful lakefront views of Lake Louise set along the renowned Butler Chain of Lakes provide the backdrop for the stunning, modern, newer golf villa. This open concept f...

4 Beds
4.5 Baths
Isleworth SubDv.
34786 Zip Code

7467 Lake Albert Drive, Windermere image

7467 Lake Albert Drive, Windermere $1,799,000

This is a paradise nestled among a conservation area and Lake Burden, with private access to lake Burden which is a 128 acre private lake. This fantastic house boasts 4 ...

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

5110 Honeynut Lane, Windermere $524,900

WINDERMERE - sought after "Want-to-live-in" community of SILVER WOODS. Lovely and well cared for 3 bedroom 2 bath with pool home on a 1/4 acre lot on dead-end Honeynut La...