Orange County

Windermere

About Windermere

Windermere Real Estate Statistics
Total Listings 485
Average Price $1,189,289
Highest Price $23,000,000
Lowest Price $179,900

Windermere FloridaSearch Windermere NeighborhoodsWindermere is part of Orlando’s southwest region that many are familiar with for its amazing attractions and city life. The area is 14 miles southwest of downtown featuring a popular neighborhood for those that want small town living with access to big city living. This original section of Windermere has around 2,855 residents as of 2013 since being established in 1889 and chartered in 1925. 

Downtown Windermere FloridaThe town annexed Butler Bay back in 2007 after trying to annex both this wealthy subdivision and Isleworth. Today, the town covers 1.56 square miles of land, but what is considered "Windermere" and what we have listed as Windermere in this section has grown considerably to the South and West of the original Windermere area. 

For those that love a small town feel next to the best parts of Orlando such as city attractions, the beautiful outdoors, and luxury living, Windermere may be the perfect place to go. Take a look at why many are choosing this neighborhood for their next home.

Windermere Neighborhood Map

Windermere Neighborhood Map

Living in Windermere

Windermere is luxury living with gorgeous estates and luxury homes defining the neighborhood. There are a variety of architectural styles for those with any variety of tastes. You can’t beat the lakefront views that magnify Central Florida’s stunning sunsets and homes on large lots of land that are well-maintained.

Residents of Windermere not only enjoy the natural beauty of the neighborhood, but also the beauty of the lifestyle here, being close to a recreational opportunities, feeling secure with in a gated community, and having a close proximity to Downtown Orlando, perfect for the professional that commutes or the socialite that enjoys big city life.

The trickiest part of living in this otherwise perfect neighborhood is that the downtown area of the community is located between several lakes in the Lake Butler chain on an isthmus which means that navigating through traffic can be a challenge at times.

What makes Windermere Great.

boating on Lake ButlerWindermere is a great place to live, raise a family, enjoy your career, or even choose to retire. It’s truly a great place for all ages and interests, and even a few big name celebrities have called it home at one time. Bubba Watson, Paul Creamer, and Skip Kendall are all professional golfers that call Windermere home, as well as Johnny Damon, a former professional baseball player and Mark Tremonti, a lead guitarist for the band Alter Bridge.

Windermere Farmers MarketPeople are drawn to this luxury neighborhood or its proximity to everything exciting in Downtown Orlando, but the beautiful lakes in Butler Chain of Lakes offers some gorgeous community parks and exciting recreational opportunities. People here love to spend the weekends at stops like Town Square where you’ll find the library and a September 11th Memorial, Palmer Park where you’ll find playgrounds and benches overlooking the lake, Central Park where you’ll find Frisbee golf and a pavilion, and Fernwood Park where you’ll find boat ramps and docks.

Between the family-friendly environment, the access to top-quality public schools, and the rich history from the TImucuan Indians calling this place home in the 1500s until Windermere was incorporated into a town in 1925. It’s truly a great place to invest, to raise your family, and to enjoy the luxury life the Orlando area.

Choose Windermere neighborhood if you like the idea of a great, small, tight-knit community near the amazing Downtown Orlando where life is full of gorgeous views, exciting recreation, and relaxation!

Windermere Homes for Sale

All Listings $100,000 - $200,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 $800,000 - $900,000
$900,000 - $1,000,000 Over $1,000,000
484 Properties Found. Page 1 of 11.
Photo of Listing #O5808308
New Listing

12623 Langstaff Dr, Windermere

$237,500 - 2 Beds, 3 Baths, 1,375 Sf

MLS® # O5808308

Photo of Listing #O5807027
New Listing

7712 Moser Ave, Windermere

$265,000 - 3 Beds, 3 Baths, 1,523 Sf

MLS® # O5807027

Photo of Listing #O5813206
New Listing

13529 Bramham Ln, Windermere

$389,900 - 4 Beds, 4 Baths, 2,599 Sf

MLS® # O5813206

Photo of Listing #O5799664
New Listing

13224 Fossick Rd, Windermere

$449,900 - 4 Beds, 3 Baths, 2,873 Sf

MLS® # O5799664

Photo of Listing #O5801023
New Listing

1324 Whitney Isles Dr, Windermere

$435,000 - 4 Beds, 4 Baths, 2,902 Sf

MLS® # O5801023

Photo of Listing #O5805605
New Listing

8256 Maritime Flag St #107, Windermere

$215,000 - 3 Beds, 2 Baths, 1,455 Sf

MLS® # O5805605

Photo of Listing #O5812503
New Listing

5915 Oxford Moor Blvd, Windermere

$1,049,000 - 5 Beds, 6 Baths, 5,725 Sf

MLS® # O5812503

Photo of Listing #O5813093
New Listing

8430 Lake Burden Cir #2, Windermere

$699,000 - 4 Beds, 4 Baths, 3,566 Sf

MLS® # O5813093

Photo of Listing #O5813123
New Listing

13425 Zori Ln, Windermere

$389,900 - 4 Beds, 3 Baths, 2,616 Sf

MLS® # O5813123

Photo of Listing #T3183205
New Listing

6986 Trellis Vine Loop, Windermere

$459,990 - 4 Beds, 4 Baths, 3,078 Sf

MLS® # T3183205

Photo of Listing #O5800485
New Listing

711 W 2nd Ave, Windermere

$1,550,000 - 1 Beds, 1 Baths, 816 Sf

MLS® # O5800485

Photo of Listing #O5812806
New Listing

1199 Estancia Woods Loop, Windermere

$1,015,085 - 4 Beds, 5 Baths, 4,073 Sf

MLS® # O5812806

Photo of Listing #O5811467
New Listing

6263 Cypress Chase Dr, Windermere

$1,599,000 - 4 Beds, 6 Baths, 5,610 Sf

MLS® # O5811467

Photo of Listing #O5812895
New Listing

1164 Estancia Woods Loop, Windermere

$926,812 - 4 Beds, 5 Baths, 3,832 Sf

MLS® # O5812895

Photo of Listing #O5812929
New Listing

11767 Sprawling Oak Dr, Windermere

$559,000 - 5 Beds, 5 Baths, 3,539 Sf

MLS® # O5812929

Photo of Listing #O5530664
New Listing

953 Lascala Dr, Windermere

$329,000 - 4 Beds, 3 Baths, 2,500 Sf

MLS® # O5530664

Photo of Listing #O5808133
New Listing

7713 Moser Ave, Windermere

$250,000 - 3 Beds, 3 Baths, 1,644 Sf

MLS® # O5808133

Photo of Listing #O5808952
New Listing

13939 Ancilla Blvd, Windermere

$260,000 - 3 Beds, 3 Baths, 1,426 Sf

MLS® # O5808952

Photo of Listing #O5808753
New Listing

11928 Camden Park Dr, Windermere

$549,000 - 4 Beds, 3 Baths, 2,960 Sf

MLS® # O5808753

Photo of Listing #O5810877
New Listing

6414 Merrick Landing Blvd, Windermere

$239,900 - 3 Beds, 3 Baths, 1,387 Sf

MLS® # O5810877

Photo of Listing #O5812462
New Listing

8443 Greenbank Blvd, Windermere

$345,000 - 4 Beds, 3 Baths, 2,420 Sf

MLS® # O5812462

Photo of Listing #O5812696
New Listing

1163 Estancia Woods Loop, Windermere

$936,320 - 4 Beds, 5 Baths, 3,972 Sf

MLS® # O5812696

Photo of Listing #O5799926
New Listing

12543 Cruxbury, Windermere

$234,000 - 2 Beds, 3 Baths, 1,311 Sf

MLS® # O5799926

Photo of Listing #O5806269
New Listing

13770 Bressler Aly, Windermere

$319,999 - 4 Beds, 3 Baths, 2,091 Sf

MLS® # O5806269

Photo of Listing #O5811477
New Listing

13061 Overstreet Rd, Windermere

$395,900 - 4 Beds, 4 Baths, 3,037 Sf

MLS® # O5811477

Photo of Listing #O5812457
New Listing

1375 Glenwick Dr, Windermere

$405,000 - 4 Beds, 3 Baths, 2,606 Sf

MLS® # O5812457

Photo of Listing #O5812339
New Listing

6000 Greatwater Dr, Windermere

$1,450,000 - 6 Beds, 5 Baths, 6,401 Sf

MLS® # O5812339

Photo of Listing #O5812343
New Listing

7414 Bentonshire Ave, Windermere

$255,000 - 3 Beds, 3 Baths, 1,480 Sf

MLS® # O5812343

Photo of Listing #S5015576
New Listing

6149 Blakeford Dr, Windermere

$1,090,000 - 5 Beds, 5 Baths, 4,351 Sf

MLS® # S5015576

Photo of Listing #O5778532
New Listing

13417 Gorgona Isle Dr, Windermere

$282,651 - 3 Beds, 3 Baths, 1,578 Sf

MLS® # O5778532

Photo of Listing #O5796737
New Listing

11874 Water Run Aly, Windermere

$299,900 - 3 Beds, 3 Baths, 1,724 Sf

MLS® # O5796737

Photo of Listing #O5806947
New Listing

8605 Brookvale Dr, Windermere

$232,500 - 3 Beds, 3 Baths, 1,480 Sf

MLS® # O5806947

Photo of Listing #O5809310
New Listing

11325 N Camden Commons Dr, Windermere

$620,000 - 4 Beds, 3 Baths, 3,014 Sf

MLS® # O5809310

Photo of Listing #O5810143
New Listing

5806 Oxford Moor Blvd, Windermere

$869,000 - 5 Beds, 6 Baths, 5,122 Sf

MLS® # O5810143

Photo of Listing #O5800730
New Listing

6443 Crestmont Glen Ln, Windermere

$365,000 - 4 Beds, 4 Baths, 3,080 Sf

MLS® # O5800730

Photo of Listing #O5802927
New Listing

10619 Village Lake Rd, Windermere

$304,900 - 4 Beds, 4 Baths, 1,834 Sf

MLS® # O5802927

Photo of Listing #O5806222
New Listing

11216 Rapallo Ln, Windermere

$449,000 - 4 Beds, 3 Baths, 2,208 Sf

MLS® # O5806222

Photo of Listing #O5805996
New Listing

1922 Hempel Ave, Windermere

$699,900 - 5 Beds, 4 Baths, 3,402 Sf

MLS® # O5805996

Photo of Listing #O5806324
New Listing

14248 Confetti Dr, Windermere

$305,000 - 4 Beds, 4 Baths, 2,132 Sf

MLS® # O5806324

Photo of Listing #O5809597
New Listing

7006 Mapperton Dr, Windermere

$379,000 - 4 Beds, 3 Baths, 2,460 Sf

MLS® # O5809597

Photo of Listing #O5802502
New Listing

6852 Merrick Landing Blvd, Windermere

$425,000 - 3 Beds, 2 Baths, 2,195 Sf

MLS® # O5802502

Photo of Listing #O5811799
New Listing

5155 Sun Palm Dr, Windermere

$409,000 - 4 Beds, 3 Baths, 2,026 Sf

MLS® # O5811799

Photo of Listing #O5812014
New Listing

13815 Beringer St, Windermere

$280,000 - 3 Beds, 3 Baths, 1,912 Sf

MLS® # O5812014

Photo of Listing #O5811435

10403 Down Lakeview Cir, Windermere

$699,900 - 5 Beds, 3 Baths, 3,132 Sf

MLS® # O5811435

Photo of Listing #O5811671

17557 Black Rail St, Windermere

$649,900 - 5 Beds, 4 Baths, 3,910 Sf

MLS® # O5811671

Photo of Listing #O5811110

14077 Ancilla Blvd, Windermere

$290,000 - 3 Beds, 3 Baths, 1,642 Sf

MLS® # O5811110

Photo of Listing #O5810415

1024 Via Tivoli Ct, Windermere

$499,000 - 5 Beds, 5 Baths, 3,036 Sf

MLS® # O5810415

Photo of Listing #O5811326

9025 Outlook Rock Trl, Windermere

$575,000 - 5 Beds, 4 Baths, 4,135 Sf

MLS® # O5811326

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on September 20th, 2019 at 3:30pm CDT.

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