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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6132 Payne Stewart Dr, Windermere, Florida 34786

Residential Lease For Rent

LPT REALTY, LLC
Isleworth Golf and Country Club opportunity. Located inside the gates of the private and renowned Isleworth Golf & Country Club, this beautifully renovated home is now available. Spanning over 2,800 square feet, this updated home offers 3 bedrooms and 3.5 bathrooms. The thoughtfully designed interior features separate living and family rooms, a separate dining room, and a casual breakfast nook.
$12,000
3Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,848Sqft

5001 Latrobe Dr, Windermere, Florida 34786

Residential Lease For Rent

Q BOUTIQUE SPECIALTY REALTY INC
Available for immediate occupancy. This beautiful, traditional five-bedroom pool home is on a quiet cul-de-sac in Isleworth, Windermere. The traditional brick exterior, grand French doors, and warm mahogany wood floors invite friends and family home. Enjoy views of majestic oaks, the 7th fairway, and Lake Bessie on this half-acre lot.
$12,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,417Sqft

11213 Camden Park Dr, Windermere, Florida 34786

Residential Lease For Rent

S2J REALTY, LLC
Exquisite Modern Living in Keene’s Pointe – Fully Renovated One-Story Luxury Residence - Experience elevated living in this architecturally reimagined home located in the highly sought-after Keene’s Pointe community. Every inch of this property has been meticulously upgraded to reflect timeless elegance, modern design, and exceptional craftsmanship.
$8,750
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,902Sqft

7231 Sangalla Dr, Windermere, Florida 34786

Residential Lease For Rent

VINTAGE REALTY GROUP LLC
WINDERMERE LUXURY LISTING EXCELLENT FLOOR PLAN • GATED COMMUNITY • WINDERMERE LOCATION • RESORT-STYLE BACKYARD • SCREENED POOL • LUXURY FINISHES • TOP-RATED SCHOOLS Live in one of Windermere’s most exclusive gated communities, surrounded by multi-million-dollar lakefront estates.
$8,400
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,835Sqft

9070 Ron Den Ln, Windermere, Florida 34786

Residential Lease For Rent

CORCORAN PREMIER REALTY
Rare opportunity to rent this beautiful Butler chain-of-lakes home, bring your boat and jet skis! This beautifully updated 4-bedroom, 3-bathroom home offers the quintessential Florida lifestyle, with serene water views and exceptional amenities inside and out.
$7,500
4Bedroom(s)
3Bathroom(s)
2,320Sqft

11342 S Camden Commons Dr, Windermere, Florida 34786

Residential Lease For Rent

NOBSKA REAL ESTATE LLC
Welcome to this exquisitely remodeled residence located in the highly coveted gated community of Keene’s Pointe in Windermere. This stunning home blends refined luxury and modern functionality, offering the perfect setting for elegant living and entertaining.
$7,500
6Bedroom(s)
7Bathroom(s)
3,625Sqft

8507 Bowden Way, Windermere, Florida 34786

Residential Lease For Rent

CHARLES RUTENBERG REALTY ORLANDO
One or more photo(s) has been virtually staged. This charming home is nestled on a quiet, tree-lined street inside the highly sought-after gated community of Keene’s Pointe.
$6,500
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,398Sqft

11357 Preserve View Dr, Windermere, Florida 34786

Residential Lease For Rent

MAGNUS REALTY GROUP LLC
Ideally situated on a corner lot within the prestigious, 24-hour guard-gated community of Keene’s Pointe in Windermere, this residence offers the perfect blend of elegance and comfort. Keene’s Pointe is renowned for its exceptional amenities, including fitness facilities, swimming, tennis, golf, and dining, all while being just minutes from Disney, shopping, and fine restaurants.
$6,500
4Bedroom(s)
4Bathroom(s)
3,196Sqft

11503 Camden Park Drive, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY, LLC
This beautiful corner 2 story pool house features "BRAND NEW ROOF", 5 bedrooms and 3.5 baths in the main house plus a full apartment above the 3-car garage. Formal Dining and Living room by the entrance of the house leads to a Beautifull open kitchen with stainless steel appliances, wood cabinets and granite countertop, eat in breakfast nook and family room.
$5,950
5Bedroom(s)
5Bathroom(s)
Garage Faces RearParking(s)
3,029Sqft

307 W 4th Ave, Windermere, Florida 34786

Residential Lease For Rent

MAINFRAME REAL ESTATE
Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees.
$5,900
4Bedroom(s)
3Bathroom(s)
3,190Sqft

12860 Lake Sawyer Ln, Windermere, Florida 34786

Residential Lease For Rent

CROWN REALTY COMPANY
Private LAKEFRONT estate home on that sits on almost 2 acres of land, gated for extreme privacy! Fully furnished with an open floorplan great for families and entertaining. This home features 3 cozy bedrooms with a king, queen, and full bed to accommodate all guests comfortably. Enjoy the convenience of 2 bathrooms, one with a relaxing jetted bathtub.
$5,800
3Bedroom(s)
2Bathroom(s)
1,725Sqft

2113 Grove Point Ln, Windermere, Florida 34786

Residential Lease For Rent

THE FLORIDA LOUNGE REALTY LLC
Discover this stunning rental home located in the Waterford Pointe community on Lake Roberts. Enjoy exclusive access to a private community boat ramp in a serene, gated neighborhood. This beautifully furnished residence features new bamboo flooring, high-end appliances, and elegant décor throughout.
$5,500
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,830Sqft
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