422 ft
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| Address | Bed / Bath | Listing Price |
|---|---|---|
416 MAGNOLIA STREET
Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated.
The family room feels like a cozy t
Living Area:
2115 Sqft.
|
2
Beds,
2
Baths
|
$885,000 |
81 OAKDALE STREET
Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year
Living Area:
4284 Sqft.
|
5
Beds,
5
Baths
|
$2,500,000 |
4818 BREEZY PALMS COURT
MOVE IN FOR THE HOLIDAYS! Don’t miss this Silver Woods jewel box in a super central location! Large corner lot on quiet cul-de-sac. Featuring a FANTASTIC 55x10 screened porch with custom summer kitchen - PERFECT for relaxing and entertaining. Sunny and bright great room plan with vaulted ceiling
Living Area:
1492 Sqft.
|
3
Beds,
2
Baths
|
$535,000 |
299 W 4TH AVENUE
This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, r
Living Area:
2410 Sqft.
|
4
Beds,
3
Baths
|
$895,000 |
9508 Windy Ridge Road
Discover this Perfectly positioned Georgian Estate situated on 12 acres (additional 6 acres available) of lakefront property with meticulously manicured grounds. This walled and gated compound includes approx 614 feet of pristine lake frontage and panoramic views on Lake Down of the Butler Chain of
Living Area:
20865 Sqft.
|
6
Beds,
14
Baths
|
$22,995,000 |
3328 WAX BERRY COURT
One or more photo(s) has been virtually staged. A rare find in the heart of Downtown Windermere! This 4 bedroom, 4 full bath home with an inground pool sits not only on 1 acre but also in a semi-private cul-de-sac with only 8 other homes. You are welcomed by the circular driveway plus rear side entr
Living Area:
2636 Sqft.
|
4
Beds,
4
Baths
|
$975,000 |
2828 INGEBORG COURT
Welcome to this Mediterranean dream home tucked away at the end of a quiet cul-de-sac in Windermere, just steps from beautiful Lake Down. Sitting on over an acre of fenced land, this property is one of the most unique opportunities in the area. From the moment you arrive, the curb appeal stands out
Living Area:
3190 Sqft.
|
5
Beds,
5
Baths
|
$1,225,000 |
4711 JOANNA GARDEN CT
Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally designed interiors, the single-story home seamlessly blends architectural sophistication with i
Living Area:
4089 Sqft.
|
3
Beds,
4
Baths
|
$3,250,000 |
1003 DOWN RESERVE COURT
Welcome to a rare modern estate inside an intimate gated enclave, offering 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom-built masterpiece was designed for those who value privacy, prestige and perfection. Go inside to d
Living Area:
6816 Sqft.
|
6
Beds,
8
Baths
|
$5,499,999 |
4301 DOWN POINT LANE
One or more photo(s) has been virtually staged. EXPERIENCE LUXURY LAKEFRONT LIVING in this one-of-a-kind MEDITERRANEAN-STYLE WATERFRONT HOME with a CUSTOM HEATED POOL—and HOA FREE! Nestled on 3.5 ACRES IN the heart of Windermere, this exceptional residence blends elegance, privacy, and functionali
Living Area:
6834 Sqft.
|
5
Beds,
4
Baths
|
$3,350,000 |
5243 ISLEWORTH COUNTRY CLUB DRIVE
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of p
Living Area:
6424 Sqft.
|
4
Beds,
6
Baths
|
$5,325,000 |
436 E 7TH AVENUE
Seller is Motivated and open to negotiate! 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. The home offers 3,136 sq ft
Living Area:
3136 Sqft.
|
4
Beds,
5
Baths
|
$2,375,000 |
9826 LAUREL VALLEY DRIVE
Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds across a premium homesite on the shores of Lake Butler, where the water is clear, the sandy beach i
Living Area:
7491 Sqft.
|
5
Beds,
6
Baths
|
$5,900,000 |
2 CHASE ROAD
Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Co
Living Area:
3889 Sqft.
|
4
Beds,
5
Baths
|
$3,200,000 |
101 LEE STREET
A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding trees, this home combines comfort, style, and plenty of space for family and friends. The bright, open k
Living Area:
4186 Sqft.
|
5
Beds,
4
Baths
|
$1,550,000 |
9648 MCCORMICK PLACE
Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Bea
Living Area:
4751 Sqft.
|
3
Beds,
4
Baths
|
$3,800,000 |
4812 ALEXANDRA GARDEN COURT
Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picture
Living Area:
4262 Sqft.
|
3
Beds,
5
Baths
|
$3,699,000 |
311 E 8TH AVENUE
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. Imagine waking up to shimmering water views, paddle-boarding before b
Living Area:
3805 Sqft.
|
5
Beds,
4
Baths
|
$1,660,000 |
9731 CHESTNUT RIDGE DRIVE
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers a
Living Area:
4877 Sqft.
|
4
Beds,
4
Baths
|
$3,400,000 |
5036 LATROBE DRIVE
Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and crea
Living Area:
5548 Sqft.
|
5
Beds,
5
Baths
|
$4,900,000 |
7135 HORIZON CIRCLE
TODAY IS THE DAY reduced $96,000! Nestled in the TRUE TOWN of WINDERMERE is this Absolutely stunning, meticulously maintained pool home with TALL CEILINGS and lots of land surrounding on both sides! This HIDDEN GEM has majestic mature oaks on a private .74 ACRE CONSERVATION LOT in QUIET, highly desi
Living Area:
3359 Sqft.
|
4
Beds,
4
Baths
|
$1,449,000 |
109 E 12TH AVENUE
Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida
Living Area:
2791 Sqft.
|
4
Beds,
4
Baths
|
$1,237,000 |
4819 ALEXANDRA GARDEN COURT
Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living an
Living Area:
3745 Sqft.
|
4
Beds,
5
Baths
|
$3,200,000 |
5074 ISLEWORTH COUNTRY CLUB DRIVE
Experience luxury living at its finest in the high end gated community of Isleworth. Nestled on the 6th fairway of Isleworth’s world-renowned golf course, this beautifully redesigned estate offers over 6,900 square feet of exquisite living space, featuring 5 bedrooms and 6.5 bathrooms. Completely
Living Area:
6937 Sqft.
|
5
Beds,
7
Baths
|
$7,995,000 |
5199 LATROBE DRIVE
One or more photo(s) has been virtually staged. Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you
Living Area:
4665 Sqft.
|
5
Beds,
7
Baths
|
$5,494,000 |
111 MAIN STREET
Prime Windermere Location! Fully Renovated and Move-In Ready!
Don’t miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms—perfe
Living Area:
2272 Sqft.
|
3
Beds,
2
Baths
|
$890,000 |
11056 CLIPPER COURT
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 Chai
Living Area:
6375 Sqft.
|
5
Beds,
6
Baths
|
$1,600,000 |
5525 ISLEWORTH COUNTRY CLUB DR
One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interio
Living Area:
9511 Sqft.
|
5
Beds,
6
Baths
|
$14,250,000 |
11002 LAKE BUTLER BOULEVARD
Back on the Market!
Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury
Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more
Living Area:
6248 Sqft.
|
5
Beds,
8
Baths
|
$4,200,000 |
225 MAGNOLIA STREET
LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN
Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakes—a residence that redefines lakefront luxury in the exclusive town of Windermere. Custom-built in 2019, this Mediterranean-inspired esta
Living Area:
5935 Sqft.
|
7
Beds,
11
Baths
|
$4,899,000 |
801 W 2ND AVENUE
Price under appraised value! Experience the epitome of lakefront living on the Butler Chain of Lakes with this exceptional Windermere estate. On one of the area’s desirable streets, this home offers over $350,000 of recent luxurious upgrades, including a new kitchen and fireplace, new windows and
Living Area:
5639 Sqft.
|
5
Beds,
7
Baths
|
$4,150,000 |
409 W 2ND AVENUE
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 fam
Living Area:
4688 Sqft.
|
5
Beds,
5
Baths
|
$2,375,000 |
647 RIDGEWOOD DRIVE
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 Wind
Living Area:
2681 Sqft.
|
3
Beds,
3
Baths
|
$2,150,000 |
11113 LAKE BUTLER BOULEVARD
Welcome to this beautiful, unique and modern home, built less than 3 years ago. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much
Living Area:
4094 Sqft.
|
5
Beds,
6
Baths
|
$2,499,000 |
4200 DOWN POINT LANE
Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudri
Living Area:
14435 Sqft.
|
6
Beds,
9
Baths
|
$10,900,000 |