Windermere Florida Homes for Sale

Discover Windermere, Florida: Where Luxury Meets Lake Life

Welcome to Windermere, one of Central Florida’s most prestigious and picturesque communities. Nestled among pristine lakes and rolling hills just 20 minutes from downtown Orlando, Windermere offers an exclusive blend of natural beauty, top-rated schools, and small-town charm that’s increasingly rare in the Sunshine State.

Known for its stunning lakefront estates and tree-lined streets, Windermere has become the address of choice for professionals, families, and those seeking a refined Florida lifestyle. The town’s unique character is defined by its 21 sparkling lakes, including the expansive Butler Chain of Lakes, which provide residents with world-class boating, fishing, and watersports opportunities right in their backyard.

Award-Winning Education

Families are drawn to Windermere’s exceptional educational opportunities. The area is served by highly-rated Orange County Public Schools, including Windermere Elementary and Windermere High School, both consistently earning “A” ratings. The Windermere Preparatory School, a prestigious private institution, offers world-class education from pre-K through 12th grade with an international focus.

Community & Lifestyle

Despite its growth, Windermere maintains its welcoming community spirit. The town center features charming local shops, restaurants, and the beloved town of Windermere hosts regular events throughout the year, including seasonal festivals and the popular farmers market. Residents enjoy easy access to world-renowned theme parks, while the nearby Orange County Parks system offers countless outdoor recreation opportunities.

Whether you’re seeking a waterfront estate, a family-friendly neighborhood, or a luxury golf course community, Windermere delivers an unparalleled Central Florida living experience. At Holiday Realty Florida, we’re proud to help you find your perfect home in this exceptional lakeside paradise.

Sort Option
  • Listing ID
  • Built up Area
  • Price
  • Pictures
  • Add date
  • Featured
Grid
List
Map

9204 Tibet Pointe Cir, Windermere, Florida 34786

Residential For Sale

THE SIMON SIMAAN GROUP
Your stunning Keene’s Pointe custom home by Stonebridge was built for luxurious everyday living and effortless entertaining. The grand first floor features travertine and hardwood floors throughout, a formal living room with gas fireplace and stone mantle, elegant dining room with adjoining dry bar, and a private office with French doors.
$2,450,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,291Sqft

436 E 7th Ave, Windermere, Florida 34786

Residential For Sale

TALENT REALTY SOLUTIONS
Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center.
$2,425,000
4Bedroom(s)
5Bathroom(s)
3,136Sqft

1238 Lake Whitney Dr, Windermere, Florida 34786

Residential For Sale

HOME WISE REALTY GROUP, INC.
Welcome to the exquisite and elegant GUARD GATED COMMUNITY OF Reserve At Belmere. A true luxury Tuscan style luxury home with spectacular views of Lake Whitney . Step into the grand entryway and you will be delighted with the enormous iron chandelier and breathtaking water views that will make you instantly fall in love.
$2,400,000
4Bedroom(s)
6Bathroom(s)
5,266Sqft

409 W 2nd Ave, Windermere, Florida 34786

Residential For Sale

UPSIDE REAL ESTATE INC
Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family.
$2,399,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,688Sqft

6252 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Now it’s your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene’s Pointe. This house with a timeless design inside and out, has five bedrooms (two down and three up), four full bathrooms, three car garage, and incredible outdoor living with renovated pool and brand new pool enclosure.
$2,390,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,287Sqft

3413 Lilas Ct, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Welcome to 3413 Lilas Court, a stunning residence located in the well renowned community of Chaine Du Lac. This exceptional home blends modern luxury with timeless elegance, offering a perfect combination of comfort and style. Upon arrival, you’re greeted by a beautifully landscaped front yard and an inviting exterior that sets the tone for the sophistication within.
$2,300,000
4Bedroom(s)
5Bathroom(s)
5,084Sqft

5909 Oxford Moor Blvd, Windermere, Florida 34786

Residential For Sale

EMPIRE NETWORK REALTY
Under contract-accepting backup offers. Back on the market through no fault of the home - Buyer's financing issue creates a rare second chance for this one-of-a- kind Windermere estate. Welcome to 5909 Oxford Moor Blvd—a beautifully designed, single-story Spanish-style estate on a .56-acre lot with mature landscaping, circular driveway, and tile roof.
$2,299,995
4Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,457Sqft

6134 Keenes Pointe Dr, Windermere, Florida 34786

Residential For Sale

WRA BUSINESS & REAL ESTATE
Welcome to a rare fully furnished opportunity in the heart of Keene’s Pointe, Windermere’s most acclaimed community. This renovated residence, with over 4,400 square feet of living space, has been reimagined to deliver not just a home, but an extraordinary lifestyle where every detail speaks of elegance, comfort, and sophistication.
$2,290,000
4Bedroom(s)
4Bathroom(s)
4,440Sqft

1020 Oakdale St, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Under contract-accepting backup offers. Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space.
$2,200,000
5Bedroom(s)
5Bathroom(s)
3,994Sqft

647 Ridgewood Dr, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.
$2,150,000
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,681Sqft

6036 Greatwater Dr, Windermere, Florida 34786

Residential For Sale

KEENE'S POINTE REALTY
Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course estate home exudes warmth from the gorgeous hardwood floors and abundant natural light.
$2,145,000
4Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,013Sqft

2958 Marquesas Ct, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies Florida luxury living at its finest, where indoor grace meets outdoor serenity.
$2,100,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,716Sqft
434 Results returned.Per Page