Windermere Real Estate - Search All Windermere Homes & Condos for sale

A highly sought after place to live, Windermere, FL is steeped in a rich history that helps give the town its modern charm.

Founded in 1887, Windermere prides itself on many of its historical sites, from its Town Hall (built from 1922-1924), which began as The Women's Club, to Cal Palmer's office Building (completed in 1911), to the Parramore House, also known as the Historic 1890 Windermere Schoolhouse, which became the first school in the Town of Windermere.

1480 Hempel Avenue, Windermere $930,000

Custom Home Built by Arthur Rutenberg with every upgrade available and proves that Quality never goes out of Style - From the Hand Crafted Iron Entry Doors to the Summer ...

5 Beds
4.5 Baths
Gotha Town SubDv.
34786 Zip Code

10992 Ledgement Lane, Windermere $499,900

***FABULOUS WINDERMERE POOL HOME***Enter the privacy gates of GLENMUIR and appreciate the maturity and class of one of Windermereâ€™s finest neighborhoods. This beautifu...

5 Beds
4.5 Baths
Glenmuir Ut 02 51 42 SubDv.
34786 Zip Code

13314 Roskin Lane, Windermere $425,000

Former Pulte Model Home! Never lived in only used as a vacation home. Gorgeous two story home with enclosed pool and spa. Best-selling Princetown model with large open 2-...

4 Beds
3.5 Baths
Lake Sawyer South Ph 1 SubDv.
34786 Zip Code

8425 Lake Burden Circle, Windermere image

8425 Lake Burden Circle, Windermere $899,000

"Beautiful Spanish Mediterranean Courtyard Home" in the exclusive Keenes Pointe, 24-hour gated community, located by the Lake Butler with ramp access to the Butler Chain ...

5 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

11118 Coniston Way, Windermere $1,950,000

Spanish style and old world charm abound in this magnificent custom Hacienda estate in the guard gated community of Lake Butler Sound. This home has all of the expected l...

5 Beds
6 Baths
Reserve At Lake Butler Sound Unit 02 SubDv.
34786 Zip Code

1632 Lake Rhea Drive, Windermere $949,900

Lakefront, Windermere showstopper for under $1M! This is your rare opportunity to live the lake life in one of Windermere's most sought after communities, The Reserve at ...

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

11850 Waterstone Loop Drive, Windermere image

11850 Waterstone Loop Drive, Windermere $799,000

Welcome to Casa Campano, Silliman custom build home with a unique architecture design. Great open floor plan, perfect for entertainment. Large island kitchen, family dinn...

3 Beds
4 Baths
Waterstone SubDv.
34786 Zip Code

5700 Marleon Drive, Windermere $435,000

One of the last (2) lots of the Lake Cypress community located right next to Windermere Preparatory School. It is a one-way street tranquil neighborhood in the prestige t...

Lake Cypress Cove Ph 03 SubDv.
34786 Zip Code

7930 Jailene Drive, Windermere $429,900

Move in condition! A house you must see! Located in the popular Lake Sawyer South Subdivision of Berkshire Park, this house backs up to a beautiful conservation area. T...

4 Beds
3.5 Baths
Lake Sawyer South Ph 05 SubDv.
34786 Zip Code

6136 Blakeford Drive, Windermere $1,049,900

This elegant European architectural style custom home is beautifully sited for privacy with lovely Golden Bear Club golf course views in guard-gated Keeneâ€™s Pointe Comm...

5 Beds
5.5 Baths
Keenes Pointe SubDv.
34786 Zip Code

5524 Worsham Court, Windermere $1,895,000

Stunning Isleworth custom home features panoramic views of the 15th green with glimpses of Lake Butler in the background. This home was designed for entertaining, from th...

4 Beds
6 Baths
Isleworth SubDv.
34786 Zip Code

9640 Crown Prince Lane, Windermere image

9640 Crown Prince Lane, Windermere $449,500

LOTS OF PRIVACY WITH THIS BEAUTIFUL 4 BEDROOM, SPLIT PLAN ALL OPEN. BRAZILIAN WOOD FLOORING THROUGHOUT FOR EXCEPTIONS OF FOYER AND BATHS,GRANITE COUNTER TOPS THROUGHOUT,...

4 Beds
2 Baths
Windsor Hill SubDv.
34786 Zip Code

5902 Oxford Moor Boulevard, Windermere image

5902 Oxford Moor Boulevard, Windermere $879,000

Exquisitely updated and upgraded in every way! Welcome home to this magnificent Windermere executive home, artfully designed by famed builder, Arthur Rutenberg. The metic...

4 Beds
3.5 Baths
Oxford Moor 47/30 SubDv.
34786 Zip Code

9419 Skiles Court, Windermere $1,120,000

Presenting classic elegance and casual golf course living with majestic water views packed into this beautiful single-story Brentwood masterpiece, situated on a quiet cul...

4 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

11008 Hawkshead Court, Windermere $659,000

Rare Opportunity! Here is the Windermere pool home you have been looking for at a price you won't believe. Perched beautifully on a generous corner lot, flanked by tropic...

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

11007 Ledgement Lane, Windermere $595,000

Location, location, location! This fantastic 4 bed 5 bathroom plus loft home sits on a HUGE lot of almost 3/4 of an acre in a cul de sac overlooking a gorgeous conservati...

4 Beds
5 Baths
Glenmuir Ut 02 51 42 SubDv.
34786 Zip Code

12734 Windermere Isles Place, Windermere image

12734 Windermere Isles Place, Windermere $599,000

THIS AMAZING TWO STORY 4 OR 5 BEDROOM, 4 BATH HOME WITH A 3 CAR GARAGE SITS ON AN OVERSIZED .82 ACRE LOT, IN ISLES OF WINDERMERE. THE EXTERIOR HAS JUST BEEN PAINTED. AMA...

4 Beds
4 Baths
Isles Of Windermere SubDv.
34786 Zip Code

2830 Windsor Hill Drive, Windermere image

2830 Windsor Hill Drive, Windermere $615,000

INCREDIBLE OPPORTUNITY - PRICED TO SELL!!! Located in Windsor Hill, one of Windermere's most sought after communities this unique custom home is situated on just over hal...

5 Beds
5 Baths
Windsor Hill SubDv.
34786 Zip Code

3466 Bay Meadow Court, Windermere $599,000

Exceptional cul-de-sac home set on 1.13 acres in the Town of Windermere, with deeded access to the Butler Chain of Lakes, community tennis courts, and walking distance to...

4 Beds
2.5 Baths
Lake Butler Estates SubDv.
34786 Zip Code

5843 Caymus Loop, Windermere $539,000

This is a 4 bedrooms, 3 bathrooms + Library/Office home that is Ready to Move. It has been recently painted outside and inside. The property is located in the sought afte...