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$624,900
4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
***NEW ROOF IS DONE.***Welcome to this spacious 4-bedroom, 3-bath Victorian-style home in the highly desirable Lakes of Windermere community. Boasting over 3,000 square feet of living space, this beautifully designed home offers an exceptional layout ideal for both everyday living and entertaining. A charming covered front porch and elegant curved staircase create a warm and inviting first impression. The open-concept family room flows seamlessly into the upgraded kitchen, featuring granite countertops, stainless steel appliances, a center island, and abundant cabinet space. The oversized primary suite is conveniently located on the first floor, complete with a spacious walk-in closet and a private ensuite bath. Upstairs, you'll find three generously sized bedrooms and additional full bath accommodations, providing flexibility and comfort for family and guests. Situated on a premium corner lot directly across from a community playground, this home also features a rear-entry attached garage and an ideal location within the neighborhood. Residents of Lakes of Windermere enjoy outstanding amenities, including a community pool, fishing dock, playgrounds, tennis courts, scenic lakes, and recreational areas. The home is also zoned for highly rated A+ schools and is conveniently located just minutes from shopping, dining, major roadways, and Central Florida's world-famous attractions. Don't miss this incredible opportunity to own a beautiful home in one of Windermere's most sought-after communities!

6601 Duncaster Street, Windermere
$1,245,000
6 Beds ⋅ 4 Baths ⋅ Estates At Windermere SubDv. ⋅ 34786 Zip Code
Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable. Inside, soaring ceilings and natural light highlight detailed millwork and thoughtfully designed living spaces that balance character with livability. The kitchen delivers where it counts—gas cooktop, stainless steel appliances, and rich wood cabinetry—anchoring both everyday life and effortless entertaining. Formal and casual spaces connect seamlessly, creating flow without sacrificing definition. The primary suite is privately positioned on the main floor, featuring a recently refreshed, spa-inspired bath. A secondary downstairs bedroom offers flexibility for guests or a true work-from-home setup, while four additional bedrooms upstairs provide the space today’s buyers are searching for. And then—the lot. Set on a rare .63 acres, outdoor living feels like a private retreat. A saltwater pool, lush landscaping, and multiple areas to unwind create a setting that’s equal parts peaceful and functional. It’s the kind of backyard that’s increasingly hard to find in Windermere. Location seals it: gated privacy just minutes from top-rated schools, parks, dining, shopping, farmers markets, hospitals, major highways and everything that makes Windermere one of Central Florida’s most sought-after places to live. Distinctive. Hard to replicate. Worth seeing in person.

2219 Ridgewind Way, Windermere
$1,620,000
5 Beds ⋅ 5 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code
Discover Windermere’s charm and classic style from this stunning Victorian-style pool home, set on a 1-acre lot with no HOA, on one of the most desirable streets. Under the canopy of majestic oaks, this 5-bedroom residence features a dedicated office space and a versatile bonus room ideal for a private apartment or guest suite. A charming wrap-around porch welcomes you into a classic foyer featuring rich wood floors, soaring ceilings, custom millwork, and a graceful grand staircase. Throughout the home, you’ll find exquisite traditional details including dental crown molding, chair rails, and beautifully crafted trim. The spacious formal dining room is filled with natural light and accented by warm wood flooring. The kitchen blends style and function with stainless steel appliances, granite countertops, an island, walk-in pantry, custom cabinetry, and a lovely view of the pool with newly installed screen enclosure. All main living areas are carpet-free, and every bathroom has been thoughtfully updated with travertine flooring, porcelain showers, and marble countertops. The owner’s suite is located upstairs and features bay windows, wood floors, crown molding, and a walk-in closet. Its luxurious bath includes a frameless glass stone shower, dual vanities, and an elegant vessel tub. There’s an added finished and air-conditioned attic playroom above one of the bedrooms for children to explore. Plus the expansive bonus room accessible off the primary bathroom is a spacious and secluded hang out room and offers an optional private entrance leading to the large backyard—complete with a sparkling pool, generous patio space, and room to store a boat. The oversized 3-car garage provides exceptional clearance for larger vehicles, golf carts, and lake toys. Town of Windermere residents have private access available to the Butler Chain via a town boat ramp plus town tennis courts. Home is walking distance to downtown and the weekly farmer’s market, monthly food trucks, and the quaint shopping district.

11449 Lake Butler Boulevard, Windermere
$520,000
4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code
Discover the exceptional potential of this spacious 4-bedroom, 2.5-bathroom Victorian-style home, offering over 3,100 square feet of living space on a desirable corner lot in Windermere. While the property requires some renovation, it presents a unique opportunity for buyers to customize and create their dream residence in a sought-after location. The kitchen offers 42-inch cabinets, and an expansive walk-in pantry, providing ample storage and preparation space. Downstairs primary bedroom features an oversized closet, and a spacious en-suite bathroom with dual sinks, a jetted tub, and a separate shower. Three sizable upper-level bedrooms share a common bathroom. Prime location. Situated in the heart of Windermere, this home is zoned for the highly sought-after Windermere High School. Community features a community pool, tennis courts, a playground, and a dock, This property is ideal for buyers looking to invest in a home with great bones and the opportunity to infuse their personal style. With some TLC, this residence can be transformed into a stunning showcase in one of Windermere's most desirable communities.

12880 Holdenbury Lane, Windermere
$1,600,000
6 Beds ⋅ 5 Baths ⋅ Chaine Du Lac SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. Welcome to your dream home in one of Windermere’s most exclusive communities. This stunning Colonial-style estate spans over 6,000 square feet, set on more than an acre of beautifully maintained land. From the moment you step through the solid wood French doors, elegance and sophistication surround you. The primary suite is a private retreat, boasting a grand spa-like bathroom, while a custom office provides the perfect workspace. With six spacious bedrooms and five full baths, there is ample room for family and guests. Designed for entertainment and relaxation, this home features a cozy media room and a separate game room with a balcony, offering breathtaking views of the pool and lush garden. Step outside to experience the serene atmosphere, where the sparkling pool becomes your personal oasis. This is more than a home—it’s a lifestyle of elegance and exclusivity. Don't miss this rare opportunity to own a piece of luxury in Windermere, FL.

3414 Cocard Court, Windermere
$1,555,000
5 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Beautiful Victorian style home with gorgeous pond and golf views has been nicely updated...and it’s ready for a new family to enjoy!!!! This home is located overlooking the 13th hole in the desirable golf community of Keene's Pointe, home of the Jack Nicklaus designed Golden Bear Club! 24 Hour guard gated community !This home features 5 bedrooms and 5 full baths. Walking into the front door, you will be welcomed by high ceilings, curved stairs with an impressive chandelier and a warm formal and dining area.The chefs size kitchen has been beautifully renovated with top of the line stain steel appliances, a wall oven and a massive island perfect for entertaining. The Primary bedroom is downstairs with a custom designed closet to help organize and a bathroom with a soaking tub and separate shower. Upstairs you will find a very spacious room perfect for a playroom or movie theater and 4 bedrooms with 2 bathrooms. Decorative crown moulding throughout the home. Enjoy swimming in this beautiful pool overlooking the water, and imagine peaceful evenings just sitting on this patio with a glass of wine watching Florida’s beautiful sunsets. "Roof was replaced two years ago, One HVAC Unit was replaced on 2024, Two Gas Water Heaters were replace on 2025"

5939 Blakeford Drive, Windermere