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.

1330 Lake Olivia, Windermere $450,000

Lake Olivia Reserve, a 12 home-site luxury lakefront community, is the last of undeveloped land on the spring fed Lake Olivia. Located within the sought after Windermere ...

Lake Olivia Reserve SubDv.
34786 Zip Code

2006 Roberts Point Drive, Windermere image

2006 Roberts Point Drive, Windermere $1,149,000

POOL HOME PARADISE! Stunning custom built home in the Reserve at Waterford Point with 5 BR, 4f, 2h baths with office, loft, 2 bonus rooms and a 4 car garage on a large lo...

5 Beds
4.5 Baths
Waterford Pointe SubDv.
34786 Zip Code

419 W 1st Avenue, Windermere $450,000

This is a nice 4 bedroom 2 bath home in downtown Windermere.

4 Beds
2 Baths
Windermere Town SubDv.
34786 Zip Code

1978 Windermere Road, Windermere $835,000

Fantastic Opportunity to own this magnificent 5 bedroom / 5 bathroom ensuite home in Windermere! This great home sits on an over sized and beautiful lot! The home feature...

5 Beds
5.5 Baths
Windermere Rural SubDv.
34786 Zip Code

711 Bessie Street, Windermere $975,000

A rare opportunity to own a great waterfront property in the much sought after historic town of Windermere. With over 285’ +/- on pristine Lake Bessie, this artist influ...

3 Beds
3.5 Baths
Windermere Town Rep SubDv.
34786 Zip Code

3636 Lake Buynak Road, Windermere $598,000

Beautiful paradise with sunset views that will take your breath away. Gorgeous Spanish tile flooring throughout, large open rooms that you can easily re-design to make th...

3 Beds
2 Baths
Lake Buynak Estates SubDv.
34786 Zip Code

11761 Vinci Drive, Windermere $1,099,000

Luxury meets comfort in this carefully designed one-story pool home full of details and well-thought-out upgrades. Light and space come together making you fall in love a...

5 Beds
4.5 Baths
Keene's Pointe SubDv.
34786 Zip Code

13456 Bonica Way W, Windermere $850,000

Step into this one story Master Custom Built residence by Hannigan Homes in the highly desirable gated community of Tilden's Grove and you will definitely want to call th...

4 Beds
4 Baths
Tildens Grove SubDv.
34786 Zip Code

5932 Blakeford Drive, Windermere $800,000

Remarkable David Weekly, Chandon model, Elevation F, 5bedroom/5bath golf front pool home in the desirable Keenes Pointe community.

5 Beds
5 Baths
Keenes Pointe SubDv.
34786 Zip Code

9613 Castle Way Drive, Windermere $1,495,000

Poised on almost an acre, this California inspired custom home features the finest quality materials and workmanship throughout. The well thought out floorplan with over...

5 Beds
6.5 Baths
Windsor Hill Reserve SubDv.
34786 Zip Code

12724 Westside Village Loop, Windermere image

12724 Westside Village Loop, Windermere $651,027

Never lived-in former Model now available for Sale as is! This former model home has stunning custom finishes throughout and showcases an inviting pool with a water feat...

4 Beds
3.5 Baths
Westside Village SubDv.
34786 Zip Code

1685 Roberts Landing Road, Windermere image

1685 Roberts Landing Road, Windermere $1,150,000

AMAZING OPPORTUNITY ON PRISTINE LAKE OLIVIA IN WINDERMERE! Don't miss the chance to make this spectacular home yours! This house is brimming with charm, functionality & u...

4 Beds
3 Baths
Roberts Landing SubDv.
34786 Zip Code

11684 Hampstead Street, Windermere image

11684 Hampstead Street, Windermere $580,000

This beautiful and spacious 5 bedroom 4 bath, energy efficient home has lots to offer in the desirable Enclave at Windermere Landing community. Entering the foyer this ho...

5 Beds
4 Baths
Enclave At Windermere Landing SubDv.
34786 Zip Code

1336 Lake Olivia, Windermere $1,950,000

Under Construction - Lake Olivia Reserve, a 12 home-site luxury lakefront community, is the last of undeveloped land on the spring fed Lake Olivia. Located within the sou...

4 Beds
3.5 Baths
Lake Olivia Reserve SubDv.
34786 Zip Code

3407 Wild Myrtle Court, Windermere image

3407 Wild Myrtle Court, Windermere $415,000

Opportunity knocks! This great property located in LAKE BUTLER ESTATES community of Windermere is the perfect area for full time residence. Home set on a lush acre of lan...

4 Beds
3.5 Baths
Lake Butler Ests SubDv.
34786 Zip Code

11450 Claymont Circle, Windermere $549,000

Keene's Pointe - 24 hour gated/attended community in Windermere. You don't want to miss seeing this adorable home featuring 4 bedrooms and 3 baths, formal living and din...

4 Beds
3 Baths
Keenes Pointe SubDv.
34786 Zip Code

6200 Winter Garden Vineland Rd, Windermere image

6200 Winter Garden Vineland Rd, Windermere $469,000

This LANDINGS of LAKE SAWYER home is a CLEAN SLATE and ready for your buyer’s touches! First time ever on the market, this custom-built home features 2336 sq ft with 4 be...

4 Beds
3.5 Baths
Landings At Lake Sawyer SubDv.
34786 Zip Code

8947 Blue Mesa Drive, Windermere $553,500

Must see Windermere property with 6 bedroom and 4 1/2 bathrooms. Boasting two master bedroom, large bonus area, media room, and plenty more. Why build when you can buy n...

6 Beds
4.5 Baths
Windermere Trls Ph 1 SubDv.
34786 Zip Code

6152 Golden Dewdrop Trail, Windermere image

6152 Golden Dewdrop Trail, Windermere $600,000

Amazing opportunity to own a beautiful large home in the desired Windermere Landings community. 8 Bed/5Bath energy efficient home built by Meritage Homes with lots of roo...

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

4083 Isabella Circle, Windermere $1,975,000

Transitional sophistication while offering comfort to enjoy true Florida lifestyle defines this home. Sunlight floods every room of this exceptional 6,987 SqFt, 5 beds, 6...