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.

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2958 Marquesas Ct, Windermere, Florida 34786

Residential For Sale

DOUGLAS ELLIMAN
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.
$1,885,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,716Sqft

13420 Bonica Way, Windermere, Florida 34786

Residential For Sale

FERRELL REALTY, INC.
Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new AC system in August 2025.
$1,875,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,489Sqft

12001 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

JULIAN PROPERTIES, INC.
Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere.
$1,775,000
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
3,135Sqft

11312 Shandon Park Way, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Welcome to this stunning seven-bedroom, five-bath residence in the exclusive guard-gated community of Reserve at Belmere. This beautifully remodeled home offers 4,902 square feet of living space and a functional two-story layout featuring a spacious family room, formal living and dining areas, and a large kitchen with granite countertops, modern cabinetry and stainless steel appliances.
$1,762,000
7Bedroom(s)
5Bathroom(s)
4,914Sqft

9922 Brentford Ct, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into today, sit down and live, without touching a single thing. This home has not only been renovated from end to end, but also has a three year old new tile roof!! Every square inch of the house feels brand new as you walk thru.
$1,750,000
6Bedroom(s)
4Bathroom(s)
3,894Sqft

311 E 8th Ave, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere.
$1,660,000
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
3,805Sqft

1703 Roberts Landing Rd, Windermere, Florida 34786

Residential For Sale

INTERNATIONAL NETWORK REALTY
This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living.
$1,650,000
4Bedroom(s)
5Bathroom(s)
3,288Sqft

11923 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

JULIAN PROPERTIES, INC.
Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace.
$1,630,000
3Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
2,238Sqft

6222 Lecco Way, Windermere, Florida 34786

Residential For Sale

EMPIRE NETWORK REALTY
Custom Home in Prestigious Waterstone on Lake Butler. This stunning Mizner/Palm Beach–inspired residence offers timeless elegance with stone columns and wrought-iron detailing that welcome you into a private front courtyard—your first outdoor living oasis. Inside, the Grande Room impresses with a fireplace, intricate stone inlays, and a soaring 12-ft stained cypress ceiling.
$1,629,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,967Sqft

11056 Clipper Ct, Windermere, Florida 34786

Residential For Sale

VINTAGE REALTY GROUP LLC
Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the 3rd Bay * Over 1
$1,600,000
5Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
6,375Sqft

11015 Hawkshead Ct, Windermere, Florida 34786

Residential For Sale

CENTURY 21 CARIOTI
REDUCED - Dream home in Windermere! Nestled inside the gates of the luxurious community of Reserve at Lake Sound. Move-in ready home! Tile roof replaced in 2021. Heated area of 3868 sqft built with high quality material and finishing, tall ceilings and travertine floors in the common areas. The refurbishment, done 4 years ago, resulted in adding modern sophistication to the home.
$1,599,000
5Bedroom(s)
5Bathroom(s)
Garage Faces SideParking(s)
3,868Sqft

13124 Filly Ct, Windermere, Florida 34786

Residential For Sale

HOME N OFFICES INTERNATIONAL
Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.
$1,575,000
5Bedroom(s)
3Bathroom(s)
3,300Sqft
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