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.

9078 Overlook Pass Drive, Windermere image

9078 Overlook Pass Drive, Windermere $459,900 ▲

Transitional with a touch of modern flare!!! This inviting open floor plan, FULLY FURNISHED home features 4 Bedrooms, 3 Baths. One is immediately greeted by the modern to...

4 Beds
3 Baths
Windermere Trails SubDv.
34786 Zip Code

11067 Ledgement Lane, Windermere $649,900

Absolutely one of the most unique and amazing houses on the market in Windermere. All you need to do is look at the photos of this home to know exactly what we mean. Th...

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

8439 Eagles Loop Circle, Windermere image

8439 Eagles Loop Circle, Windermere $769,800

KEENES POINTE - A GATED & GUARDED WINDERMERE GOLF AND LAKESIDE COMMUNITY. Lovely 4 Bedroom (ALL BEDROOMS LOCATED ON FIRST FLOOR), 4.5 Bath, Pool/Spa HOME ON BEAUTIFUL PR...

4 Beds
4.5 Baths
Keenes Pointe Ut 06 50 95 SubDv.
34786 Zip Code

4309 Isabella Circle, Windermere $1,750,000

BRAND NEW home, construction just completed. Pictures do not even begin to convey the perfection this home offers. Be prepared to have your breath taken away upon takin...

5 Beds
6.5 Baths
Casabella SubDv.
34786 Zip Code

6854 Trellis Vine Loop, Windermere image

6854 Trellis Vine Loop, Windermere $525,000

LOCATION,LOCATION,LOCATION. SPECTACULAR HOME IN WINDERMERE WITH TWO MASTER SUITES, ONE UPSTAIRS AND ONE DOWNSTAIRS! THIS 2 STORY HOME IS LOADED WITH WARMTH AND CHARM THRO...

5 Beds
4.5 Baths
Windstone SubDv.
34786 Zip Code

13597 Gorgona Isle Drive, Windermere image

13597 Gorgona Isle Drive, Windermere $574,000 ▼

Under Construction. Second image depicts actual color scheme. Unwind from the day with a glass on wine while you relax on your front porch and watch the sunset. This invi...

5 Beds
4.5 Baths
Windermere Isle SubDv.
34786 Zip Code

12023 Sandy Shores Drive, Windermere image

12023 Sandy Shores Drive, Windermere $599,000

Build your dream home on a beautiful canal leading to the Lake Butler chain area! This water facing lot has plenty to offer, both the rear and side canal frontage lead di...

Sandy Shores SubDv.
34786 Zip Code

1457 Belfiore Way, Windermere $714,900

Luxurious Mediterranean Custom Built Home! Your search ends here! Desirable Gated community of Tuscany Ridge in Windermere. Over 4000 sq ft of living space featuring 5...

5 Beds
4.5 Baths
Tuscany Ridge 50 141 SubDv.
34786 Zip Code

47 Pine Street, Windermere $425,000

All Paved Roads Lead to this Beautiful Lot in the heart of Windermere. Enjoy the charm of Olde Windermere at its finest..minutes away from weekly farmer’s market, shoppin...

Windermere SubDv.
34786 Zip Code

1437 Glenwick Drive, Windermere $400,000

Loaded with over $100,000 in recent renovations, this meticulously maintained home sits on a premium lot in a desirable guard gated Windermere community. Stunning wood fl...

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

11043 Ullswater Lane, Windermere $1,295,000

This R L Vogel custom home exudes a spirit of elegance derived from its Southern California architectural influences. Located in guard gated Lake Butler Sound this stunni...

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

13455 Bellaria Circle, Windermere $1,649,000

Well sited on one acre in guard gated Bellaria, this stunning home has been meticulously maintained. The elegant circular drive and fountain enhance the arrival experienc...

5 Beds
5.5 Baths
Bellaria SubDv.
34786 Zip Code

13750 Eden Isle Blvd, Windermere $419,000

This impeccable well maintained Craftsman home located in the cozy community of Eden Isle will leave you breathless. Look no further than your own tropical oasis in the p...

3 Beds
2.5 Baths
Eden Isle Homeowners Association, Inc. SubDv.
34786 Zip Code

6252 Blakeford Drive, Windermere $1,299,000

Take this opportunity to live on the beautiful 18th fairway of the Jack Nicklaus Signature golf course in Keene’s Pointe – an upscale, gated Windermere community. The ho...

5 Beds
4 Baths
Keenes Pointe SubDv.
34786 Zip Code

Windermere $700,000 ▼

REDUCED! Exquisite Mediterranean Estate in Exclusive Tuscany Ridge Gated Subdivision in Windermere!.... within the Olympia High and Thornebrooke Elementary School Distri...

5 Beds
4.5 Baths
34786 Zip Code

11822 Angle Pond Avenue, Windermere image

11822 Angle Pond Avenue, Windermere $525,000

BEAUTIFUL 4 bedroom/3.5 bath POOL home located on a premium corner lot in the desirable Windermere Trails! This home is filled with character and boasts many contemporary...

4 Beds
3.5 Baths
Windermere Trls Ph 1c SubDv.
34786 Zip Code

647 Ridgewood Drive, Windermere $1,195,000

This magnificent Butler Chain property has water on two sides with over 200 ft of shoreline under a canopy of towering oaks. Eastern exposure offers spectacular sunrise v...

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

12943 Holdenbury Lane, Windermere $448,000

Location! Location! Location! Welcome home to Windermere Terrace. This 4 bedroom 3.5 bathroom with MASTER BEDROOM downstairs built by Pulte Homes in 2013 also offers a ...

4 Beds
3.5 Baths
Windermere Terrace SubDv.
34786 Zip Code

1409 Lake Whitney Dr, Windermere $791,400

Located in the guard-gated community of Reserve at Belmere in Windermere, this stunning 4 bedroom, 3 baths, and 2 half bath custom home awaits you. The gorgeously maintai...

4 Beds
3.5 Baths
Reserve At Belmere Ph 2 SubDv.
34786 Zip Code

11249 Macaw Court, Windermere $1,649,000

A rare find in the sought-after golf community of Keenes Pointe with a stunning view of a Golf Course, picturesque sunsets on a lake and a natural pond, all lounging on t...