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

11409 N Camden Commons Drive, Windermere image

11409 N Camden Commons Drive, Windermere $1,100,000

Don't miss out on this home inside the exclusive guard gated community of Keens Pointe and home to the Golden Bear Country Club featuring Jack Nicklaus golf course. This ...

4 Beds
4.5 Baths
Keenes Pointe SubDv.
34786 Zip Code

411 E 6th Avenue, Windermere $899,900

Beautifully updated home in the heart of downtown Windermere on a spacious homesite just a short stroll to Main Street. Nestled among majestic oaks and down a long pavere...

4 Beds
3 Baths
Windermere Rep SubDv.
34786 Zip Code

12842 Jacob Grace Court, Windermere image

12842 Jacob Grace Court, Windermere $1,388,800

Custom Video www.12842jacobgrace.site/mls FIRST TIME EVER OFFERED FOR SALE, original owner and very first lot ever sold in Tildens Grove ! Pride of ownership is self e...

5 Beds
3.5 Baths
Tildens Grove Ph 01 47/65 SubDv.
34786 Zip Code

1825 Windermeredown Place, Windermere image

1825 Windermeredown Place, Windermere $1,295,000

One or more photo(s) has been virtually staged. Gorgeous Executive Estate on over an acre is SUPER SPACIOUS with versatile floor plan where rooms can be repurposed as you...

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

13534 Bramham Lane, Windermere $469,900

* Multiple offers received, Seller has requested Highest and/or Best by 2:00 PM Monday April 4, 2023 * Attention Disney Lovers! On a quiet tree lined street approximatel...

3 Beds
2 Baths
Lakes/Windermere-Peachtree SubDv.
34786 Zip Code

11486 Misty Oak Alley, Windermere $499,900

Beautiful single family home with 3 bedrooms and 2 1/2 baths located in the Ashlin Park Community in Windermere. The kitchen is upgraded with stainless steel appliances....

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

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

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 $599,990 ▼

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

11129 Lake Butler Boulevard, Windermere image

11129 Lake Butler Boulevard, Windermere $849,000 ▲

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

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...