Windermere FL Homes For Sale

Windermere is rated by Niche.com as the #14 Windermere FL Real Estatebest suburb to raise a family in Orlando. Find Windermere FL homes for sale and research local real estate market trends. Search new listings, scheduled open houses, recent solds, and price reductions in Windermere. To adjust how your search is displayed, click the gray arrows next to "Sort" to display Windermere homes in Orlando by price, number of bedrooms, or days on market.

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Windermere Homes October 31, 2020
212
Listed
120
Avg. DOM
$305.21
Avg. $ / Sq.Ft.
$1,199,000
Med. List Price
212 Properties
Page 1 of 18
$649,000
Subdivision: Keenes Pointe Ut 04 Sec 31 48 82
5
Beds
4
Baths
3,159
Sq.Ft.
2003
Year Built
1
Day on Site
O5903000
MLS
Keene's Pointe - Gated/24-hour attended community centered around The Golden Bear Club, an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, swimming and dining. This...
$679,000
Subdivision: Keenes Pointe
5
Beds
4
Baths
2,863
Sq.Ft.
2003
Year Built
2
Days on Site
O5827612
MLS
Absolutely stunning home located in Windermere's renowned Keene's Pointe!! This 5 bedroom, 4 bath home is perfect for family living and entertaining. It has been painted inside and outside (2019) ,...
$1,440,000
Subdivision: Reserve At Lake Butler Sound
5
Beds
4F11/2
Baths
5,485
Sq.Ft.
2005
Year Built
3
Days on Site
O5902647
MLS
"Magnificent 5 bedroom, 4.5 bathroom residence in exclusive guard gated Reserve at Lake Butler Sound. MOVE-IN READY. Refurbished and with upgrades throughout complementing many architectural features....
$1,345,000
Subdivision: Waterstone A D E F G H J L
5
Beds
5F21/2
Baths
4,845
Sq.Ft.
2012
Year Built
4
Days on Site
O5902241
MLS
Stunning Butler Chain canal front residence located in the 24-hour guard-gated community of Waterstone. Waterstone is a private gated enclave of 120 homes positioned along the shores of Lake Butler,...
$2,100,000
Subdivision: Keenes Pointe Ut 06 50 95
6
Beds
6F11/2
Baths
5,609
Sq.Ft.
2003
Year Built
4
Days on Site
O5902025
MLS
This absolute immaculate 5,500 + square foot Unnerstall custom built home is located in the most desired Windermere community of Keenes Pointe! Perfectly situated overlooking the 4th hole of the...
$525,000
Subdivision: Windermere Sound Ph 2
5
Beds
3F11/2
Baths
3,954
Sq.Ft.
2016
Year Built
5
Days on Site
O5873786
MLS
Back on the Market! Stunning 5 bedroom home (Plus HUGE Loft) with No Rear Neighbors. This five bedroom home is located in the desirable community of Windermere Sound, and looks out onto a large,...
Open 10/31
2808 Pinnacle Ct Windermere, FL 34786
$829,000
Subdivision: Lake Down Crest
5
Beds
5F21/2
Baths
5,071
Sq.Ft.
1997
Year Built
5
Days on Site
O5902048
MLS
This charming, estate-like property in quaint downtown Windermere has lots to offer. Its Elegance and function is nested and sits on a 1 acre corner lot in the gated community of Lake Down Crest. The...
$499,900
Subdivision: Belmere Vlg G2
5
Beds
4F11/2
Baths
3,036
Sq.Ft.
2002
Year Built
5
Days on Site
S5041789
MLS
Luxury house with private pool & spa! Many top of the line up-grades, it's a 2 story with an outstanding pool and patio area, and tile flooring, including granite and solid surface counters, two...
$795,000
Subdivision: Windermere Town
4
Beds
3
Baths
3,267
Sq.Ft.
1968
Year Built
9
Days on Site
O5901068
MLS
Beautiful 3,267 sq ft., 4 BR (2 master suites), 3 BA, split-plan single story pool home on an oversized corner lot in charming downtown Windermere. A brick paver walkway curves around a majestic old...
$900,000
Subdivision: Keenes Pointe
5
Beds
3F21/2
Baths
4,889
Sq.Ft.
2000
Year Built
10
Days on Site
O5901075
MLS
Auction Property. Custom Luxury built home in a Golf gated/24-hour manned Keene's Pointe community. This two story golf front pool home, boasts 4889 Heated SQ FT, 5 spacious bedrooms, 3 full...
$764,900
Subdivision: Keenes Pointe
4
Beds
4
Baths
2,928
Sq.Ft.
2005
Year Built
10
Days on Site
O5900774
MLS
Come live the Keene's Pointe lifestyle! From famous Halloween parties to the Thanksgiving Turkey Trot there is no better place to live. This fabulously updated 4 bedroom, 4 bath, golf front estate...
$630,000
Subdivision: Keenes Pointe Ut 06 50 95
4
Beds
3
Baths
2,551
Sq.Ft.
2002
Year Built
10
Days on Site
O5897874
MLS
KEENES POINTE Opportunity - Don't wait to schedule your visit!!
This beautiful open floorplan, one story, 4 bed/ 4 bath, three car garage home is located on a small cul-de-sac street and backs...

The Complete Guide That Makes Moving to Windermere, Florida Simple

Central Florida has more to offer than just theme parks. While Disney World attracts nearly 52 million guests annually, the community of Windermere, Florida shouldn't be overlooked.

Located in Orange County, Florida, just 3,000 residents call this picturesque town home, adding to its charm. With close proximity to Orlando and its attractions, residents love the mix of city and suburban life.

With top-rated school systems, luxurious homes, and plenty of amenities, families and retirees are flocking to this developing area. 

Are you ready to join this close-knit town and learn more about what Windermere, Florida has to offer?

Grab your moving check-list and let's get started.

It's All in the Details

Before we get into exactly what makes Windermere one of Florida's most sought-after communities, let's cover exactly where it is and some demographics.

Windermere is located just 9.9 miles (about a 20-minute drive) from Orlando, making it part of the Orlando metropolitan statistical area. 

Windermere was established in 1889 and later redeveloped in 1925, with its biggest expansion occurring in 2007. At this time, Windermere proposed to annex two local subdivisions -- Butler Bay and Isleworth.

Although Isleworth remained independent, Butler Bay was annexed into Windermere with an impressive 90% approval rating. 

Residents of Windermere enjoy a sparse suburban feel and most own their homes outright. With a low crime rate and highly-rated schools, it's a highly sought after area for growing families.

There are also plenty of job opportunities in Windermere and in the local city of Orlando. Windermere residents enjoy a healthy mix of a bustling nightlife, cultural enrichment, and a community-feel. 

Home to several lakes and original dirt roads, both locals and visitors love the quaint atmosphere that this Florida suburb offers. 

Windermere School Systems

If you're a family moving to the Windermere area, the school systems won't disappoint. In fact, they're some of the highest-rated in the state of Florida. All of Windermere's public schools received an A-rating based on reviews.

Elementary school-age children will attend either Windermere Elementary School, Lake Whitney Elementary, and Orlando Science Elementary Charter School.

Charter schools are also a popular option for upper-grade levels. Orlando Science Middle/High Charter School and Olympia High School are both quality establishments for older students.

Windermere residents can also send their children to The New Academy, a private school servicing students Kindergarten through 8th grade. 

Things to Do for Residents of All Ages

Living in Windermere is about more than just going to work and school. With plenty of amenities and things to do, there's truly something for everyone.

Here are just a few of the most notable features in and around Windermere, Florida that make it a desirable place to call home.

Fun for Kids

From theme parks to nature parks, children living in Windermere have plenty of options to stay entertained and active!

Two of the most popular options are, of course, the local theme parks of Disney World and Universal Studios. Located less than 10 miles from Orlando, Windermere residents can plan several day trips or long weekends to these family-friendly theme parks.

Families looking for a more educational experience will love the Titanic: The Artifact Exhibition, also located in Orlando. Ripley's Believe It or Not is another favorite.

When you want to get your kids moving, try the Trapeze Federation or Escapology Escape Rooms.

Fun for Adults

Fun in Windermere isn't just for the kids! Adults will love living here, too. Even the theme parks have nightlife activities for adults.

Disney World's Downtown Disney offers shopping, street entertainment, and plenty of dining options. Universal's Citywalk is another fun-filled nighttime activity for adults and families.

Florida living wouldn't be complete without picturesque beaches. Although Windermere is located in the center of the state, residents can still take advantage of beautiful local beaches.

Windermere isn't far from world-class Cocoa, Daytona, and New Smyrna Beaches. Make it a day for the family or catch some rays with your partner.

Other hidden treasures include local markets and festivals in the nearby cities of Orlando, Mount Dora, and Daytona Beach.

Communities and Housing Options

After you finish a day of fun-filled activities, you'll want to retreat to your gorgeous, comfortable home. With several communities and housing options in Windermere, residents will find something for every taste and budget.

Here are some of the most popular and sought-after communities in Windermere, Florida. 

Butler Lake

The name says it all. If you're looking for lakefront property in or around Windermere, look no further than the Butler Chain of Lakes.

The Butler Lake area is home to eleven gorgeous lakes:

  • Lake Butler
  • Lake Tibet
  • Lake Chase
  • Lake Down
  • Lake Sheen
  • Lake Louise
  • Lake Blanche
  • Lake Isleworth
  • Wauseon Bay
  • Pocket Lake
  • Little Fish Lake

These lakes are known for their quality water and robust animal habitats. 

Sports fans will love knowing that they share a piece of real estate with some of the greats. Shaquille O'Neal, Ken Griffey Jr., and Tiger Woods have all called Butler Lake home.

With breathtaking lakefront views, it's no surprise that the Butler Chain of Lakes is one of Windermere's most popular areas. Residents also credit the small-town feel and natural settings as some of the area's most attractive features. 

Isleworth 

Isleworth is recognized as one of Central Florida's most prestigious private golf club communities.

Spanning over 600 acres, Isleworth is located among the Butler Chain of Lakes and boasts countless amenities and gorgeous estate homes. Residents will enjoy views of either the world-class golf courses, art, or lakes.

In addition to golf, residents have access to tennis and racquetball courts, a fitness center, a spa, and water recreations. Fishing, paddle boarding, and boating are just a few ways residents can enjoy lake life living.

For those who prefer swimming, Isleworth's infinity-edge, resort-style pool features lush daybeds and lake views. Families will love the children's splash pad and nearby poolside grill.

Afterschool youth programs and summer camp are two more amenities that growing families can enjoy for years to come.

The Reserve at Belmere

This fine, residential community offers gated entrances, a clubhouse, and homes that accommodate all tastes and budgets. Homes in The Reserve at Belmere range from $300,000 to $1.5 million. 

Families and retirees flock to this development which offers a lakefront community park and access to private Lake Whitney. Adults can enjoy the world-class fitness center and tennis courts. 

Kids will love the community's playgrounds, fishing pier, and sand volleyball area when they're not attending the A-rated schools of Orange County.

The Reserve at Belmere offers a close, tight-knit community feel where residents know each other's names. The 24/7 guard gate gives residents peace of mind that their homes and loved ones are protected.

Casabella at Windermere

Casabella at Windermere is one of the area's newest luxury communities. This gated community currently offers 79 luxury estate, single-family homes.

Homes are competitively priced, with most in the low millions. Square footage of these homes starts at 5,441, with most having between 4 and 6 bedrooms.

Growing families and retirees alike will love this up-and-coming, gated community. 

The houses of Casabella at Windermere are proudly designed and built exclusively by Toll Brothers. The gated community offers security and amenities for residents and is located less than 20 miles from Orlando.

Casabella at Windermere is also minutes from upscale shopping and dining at the Winter Garden Village, Mall at Millenia, and Restaurant Row. Local activities include time spent on the Butler Chain of Lakes, first-class golfing, and a playground for the kids.

Keene's Point

If you want plenty of homes and communities to choose from, consider Keene's Point. The Keene's Point development started in 1998 and since then, has expanded into one of the areas most sought-after communities.

Keene's Point boasts both natural beauty and luxury living. This upscale community blends quiet, quaint living with timeless beauty. 

Keene's Point has 14 distinct communities that all share an abundance of amenities. Residents have access to world-class golf courses, a swimming pool, nature preserves, tennis courts, an illuminated playground for kids, and The Golden Bear Golf Club.

Just south of Keene's Point you'll find 400 acres of the Tibet-Butler Preserve which houses a bird sanctuary and several endangered species of plants and animals.

Prospective buyers can choose from pre-existing homes or work with one of the community's award-winning builders to create a custom home of your dreams.

Prepare to Call Windermere, Florida Home

Windermere, Florida is quickly becoming one of the most sought-after areas in Central Florida to start a family, retire, or lay roots.

With a combination of world-class golfing and attractions, plus top-rated schools and picturesque lake living options, there's truly something for everyone.

Choose from one of the areas many luxury communities. Most areas are gated with exclusive amenities for residents, protecting both your safety and privacy.