Orange County

Windermere

About Windermere

Windermere Real Estate Statistics
Total Listings 545
Average Price $1,329,329
Highest Price $28,500,000
Lowest Price $175,000

Windermere FloridaWindermere 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
545 Properties Found. Page 1 of 12.
Photo of Listing #O5727975
New Listing

1004 Main St, Windermere

$1,300,000 - 1 Acres

MLS® # O5727975

Photo of Listing #O5767447
New Listing

326 E 5th Ave, Windermere

$390,000 - 3 Beds, 2 Baths, 1,822 Sf

MLS® # O5767447

Photo of Listing #O5771681
New Listing

1335 Kelso Blvd, Windermere

$1,350,000 - 6 Beds, 6 Baths, 7,030 Sf

MLS® # O5771681

Photo of Listing #O5772066
New Listing

9575 Westover Roberts Rd, Windermere

$2,750,000 - 9 Beds, 8 Baths, 8,464 Sf

MLS® # O5772066

Photo of Listing #O5763392
New Listing

13832 Ancilla Blvd, Windermere

$245,000 - 3 Beds, 3 Baths, 1,461 Sf

MLS® # O5763392

Photo of Listing #O5765096
New Listing

12345 Via Derna Pl, Windermere

$275,000 - 4 Beds, 3 Baths, 1,946 Sf

MLS® # O5765096

Photo of Listing #O5769997
New Listing

12933 Emersondale Ave, Windermere

$245,000 - 3 Beds, 3 Baths, 1,480 Sf

MLS® # O5769997

Photo of Listing #O5771645
New Listing

7448 Ripplepointe Way, Windermere

$309,900 - 3 Beds, 3 Baths, 1,881 Sf

MLS® # O5771645

Photo of Listing #O5771828
New Listing

2958 Marquesas Ct #1, Windermere

$824,900 - 5 Beds, 4 Baths, 4,716 Sf

MLS® # O5771828

Photo of Listing #O5772044
New Listing

7513 Colbury Ave, Windermere

$365,000 - 3 Beds, 3 Baths, 2,230 Sf

MLS® # O5772044

Photo of Listing #O5771642
New Listing

11819 Camden Park Dr, Windermere

$620,000 - 5 Beds, 4 Baths, 3,449 Sf

MLS® # O5771642

Photo of Listing #O5764349
New Listing

12922 Calderdale Ave, Windermere

$259,900 - 3 Beds, 3 Baths, 1,561 Sf

MLS® # O5764349

Photo of Listing #O5767770
New Listing

11446 Jasper Kay Ter #206, Windermere

$225,000 - 3 Beds, 2 Baths, 1,455 Sf

MLS® # O5767770

Photo of Listing #O5771263
New Listing

8560 Crescendo Ave, Windermere

$338,000 - 3 Beds, 3 Baths, 2,063 Sf

MLS® # O5771263

Photo of Listing #O5771690
New Listing

6856 Valhalla Way, Windermere

$1,375,000 - 4 Beds, 5 Baths, 5,272 Sf

MLS® # O5771690

Photo of Listing #O5771265
New Listing

13755 Beckman Dr, Windermere

$313,000 - 3 Beds, 3 Baths, 2,113 Sf

MLS® # O5771265

Photo of Listing #O5530664
New Listing

953 Lascala Dr, Windermere

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

MLS® # O5530664

Photo of Listing #O5768756
New Listing

8725 Iron Mountain Trl, Windermere

$575,000 - 5 Beds, 5 Baths, 4,493 Sf

MLS® # O5768756

Photo of Listing #G5013448
New Listing

13852 Caywood Pond Dr, Windermere

$450,000 - 4 Beds, 3 Baths, 2,451 Sf

MLS® # G5013448

Photo of Listing #O5769829
New Listing

6824 Valhalla Way, Windermere

$1,650,000 - 5 Beds, 7 Baths, 5,866 Sf

MLS® # O5769829

Photo of Listing #O5768391
New Listing

1319 Lake Whitney Dr, Windermere

$799,900 - 4 Beds, 5 Baths, 4,222 Sf

MLS® # O5768391

Photo of Listing #O5769308
New Listing

N/A, Windermere

$375,000 - 3 Beds, 3 Baths, 1,888 Sf

MLS® # O5769308

Photo of Listing #O5771416
New Listing

11641 Sprawling Oak Dr, Windermere

$442,500 - 3 Beds, 3 Baths, 2,301 Sf

MLS® # O5771416

Photo of Listing #O5765847
New Listing

9173 Outlook Rock Trl, Windermere

$578,000 - 5 Beds, 4 Baths, 4,087 Sf

MLS® # O5765847

Photo of Listing #O5757182
New Listing

13415 Bonica Way, Windermere

$925,000 - 6 Beds, 5 Baths, 5,526 Sf

MLS® # O5757182

Photo of Listing #S5013300
New Listing

7356 Yoder St, Windermere

$235,000 - 2 Beds, 3 Baths, 1,320 Sf

MLS® # S5013300

Photo of Listing #O5764455
New Listing

8644 Crescendo Ave, Windermere

$449,900 - 4 Beds, 4 Baths, 2,905 Sf

MLS® # O5764455

Photo of Listing #O5765090
New Listing

7764 Rigby St, Windermere

$259,900 - 3 Beds, 3 Baths, 1,505 Sf

MLS® # O5765090

Photo of Listing #O5769882
New Listing

7777 Moser Ave, Windermere

$260,000 - 3 Beds, 3 Baths, 1,670 Sf

MLS® # O5769882

Photo of Listing #O5771036
New Listing

6722 Duncaster St, Windermere

$575,000 - 5 Beds, 5 Baths, 4,085 Sf

MLS® # O5771036

Photo of Listing #O5771056
New Listing

6216 Greatwater Dr #2, Windermere

$1,250,000 - 5 Beds, 6 Baths, 4,208 Sf

MLS® # O5771056

Photo of Listing #O5771077
New Listing

9519 Westover Club Cir, Windermere

$624,900 - 4 Beds, 4 Baths, 3,633 Sf

MLS® # O5771077

Photo of Listing #O5770974
New Listing

5284 Isleworth Country Club Dr, Windermere

$3,750,000 - 4 Beds, 5 Baths, 6,738 Sf

MLS® # O5770974

Photo of Listing #O5771187
New Listing

4126 Blue Major Dr, Windermere

$489,900 - 5 Beds, 4 Baths, 3,355 Sf

MLS® # O5771187

Photo of Listing #O5771048
New Listing

9167 Royal Gate Dr, Windermere

$649,000 - 5 Beds, 4 Baths, 4,717 Sf

MLS® # O5771048

Photo of Listing #S5011027
New Listing

8156 Boat Hook Loop #107, Windermere

$179,000 - 3 Beds, 2 Baths, 1,455 Sf

MLS® # S5011027

Photo of Listing #O5771060
New Listing

2836 Marquesas Ct #1, Windermere

$2,190,000 - 5 Beds, 7 Baths, 6,505 Sf

MLS® # O5771060

Photo of Listing #O5770864
New Listing

11855 Cave Run Ave, Windermere

$479,900 - 4 Beds, 4 Baths, 3,414 Sf

MLS® # O5770864

Photo of Listing #O5765927
New Listing

8690 Brookvale Dr, Windermere

$249,900 - 3 Beds, 3 Baths, 1,500 Sf

MLS® # O5765927

Photo of Listing #O5765088
New Listing

8264 Maritime Flag St #1412, Windermere

$175,000 - 2 Beds, 2 Baths, 1,161 Sf

MLS® # O5765088

Photo of Listing #O5767870
New Listing

2125 Kane Park Way, Windermere

$559,900 - 4 Beds, 3 Baths, 2,743 Sf

MLS® # O5767870

Photo of Listing #O5770100
New Listing

11649 Delwick Dr, Windermere

$564,900 - 4 Beds, 3 Baths, 3,307 Sf

MLS® # O5770100

Photo of Listing #O5770559
New Listing

5348 Isleworth Country Club Dr, Windermere

$1,990,000 - 5 Beds, 6 Baths, 5,412 Sf

MLS® # O5770559

Photo of Listing #O5715186
New Listing

6238 Lake Burden View Dr, Windermere

$899,900 - 4 Beds, 4 Baths, 3,512 Sf

MLS® # O5715186

Photo of Listing #O5763567
New Listing

11330 Winston Willow Ct, Windermere

$699,500 - 5 Beds, 3 Baths, 3,554 Sf

MLS® # O5763567

Photo of Listing #O5764517
New Listing

6024 Roseate Spoonbill Dr, Windermere

$338,000 - 3 Beds, 3 Baths, 2,173 Sf

MLS® # O5764517

Photo of Listing #O5759304

6246 Roseate Spoonbill Dr, Windermere

$500,000 - 4 Beds, 4 Baths, 3,068 Sf

MLS® # O5759304

Photo of Listing #S5013190

8216 Tranquility Way #3007, Windermere

$285,000 - 3 Beds, 3 Baths, 1,875 Sf

MLS® # S5013190

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 March 23rd, 2019 at 7:45pm CDT.

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